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Phytochemistry Reviews - Verlag: Springer
'Phytochemistry Reviews'ist eine internationale Zeitschrift mit jährlich drei Ausgaben. Das Journal behandelt aktuelle Themen, von denen einige sich aus den Sitzungen der Europäischen Phytochemischen Gesellschaft ergeben.
Dietary phytochemicals offer protection from oxidative damages and lower the risks of chronic diseases, by complementary and
overlapping action mechanisms. These include antioxidant activity, regulation of gene expression and cell cycle, stimulation
of the immune and hormonal systems and modulation of cell–cell communication. Gap-junction intercellular communication (GJIC)
plays an important role in maintaining tissue homeostasis by allowing the intercellular exchange of ions and regulatory molecules
associated with cell proliferation, differentiation and apoptosis, and by contributing to intracellular signaling. This mechanism
is strictly regulated and abnormal GJIC can result in several pathological conditions. GJIC is deregulated in cancer cells
and reversible GJIC inhibition is strongly related to the promotion phase of carcinogenesis, likely mediated by reactive oxygen
species. Whereas, the reversible inhibition of GJIC is related to the promotion phase of carcinogenicity, enhancers of GJIC
are expected to prevent cancer. Several dietary plant compounds demonstrated the ability to control GJIC at the epigenetic
levels and to prevent GJIC down-regulation by tumor promoting compounds, thus preventing cancers. In this Commentary, a number of reported studies on several phytochemicals in dietary and medicinal plants, which were able to affect GJIC and
their structural proteins, i.e., connexins, in different in vivo and in vitro systems, were examined. The growing evidence,
on the involvement of plant-derived molecules in the modulation of GJIC and in understanding of the specific action mechanisms,
might offer a new perspective of the protective and/or preventive effects of dietary phytochemicals, in addition to possible
chemotherapeutic use.
Content Type Journal Article
Pages 1-23
DOI 10.1007/s11101-012-9235-7
Authors
Antonella Leone, Institute of Science of Food Production, Unit of Lecce (ISPA-Lecce), National Research Council (CNR), Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy
Cristiano Longo, Institute of Science of Food Production, Unit of Lecce (ISPA-Lecce), National Research Council (CNR), Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy
James E. Trosko, Department of Pediatrics and Human Development, Food Safety and Toxicology Center, Center for Integrative Toxicology, Michigan State University, East Lansing, MI, USA
Taxanes form a large family of compounds, the most famous of which is paclitaxel, an effective antitumor drug currently used
against various cancers. First approved for the treatment of ovarian and breast cancer, it was subsequently endorsed for the
treatment of many other cancer pathologies. Originally extracted from the bark of Taxus brevifolia, it has also been found in other Taxus species. Most of the drug for clinical use is currently produced by semi-synthesis, starting from a natural precursor, 10-deacetylbaccatin
III recovered from the needles of Taxus baccata. The yield of paclitaxel and its precursors from yew is very low, and is not sufficient to satisfy the commercial requirements.
Many attempts have been made to explore new paclitaxel-producing species including microorganisms. However, the availability
of paclitaxel and related compounds is still low. The discovery of taxanes in differentiated and undifferentiated tissue of
Corylus avellana suggested that the production of these compounds is not a peculiarity of the genus Taxus, giving hope for the future availability of these compounds. Here we review works aimed at exploring new paclitaxel-producing
organisms with different ecology to Taxus plants. Particular focus has been placed on highlighting the discovery of taxanes in angiosperm plants. Thus, it is conceivable
that, by developing appropriate methodologies, new plant species could be employed for the commercial production of paclitaxel
and other antineoplastic compounds.
Content Type Journal Article
Pages 1-15
DOI 10.1007/s11101-012-9234-8
Authors
Mariangela Miele, Department of Pharmaceutical Sciences, University of Genova, Viale Benedetto XV, 3, 16132 Genoa, Italy
Anna Maria Mumot, Department of Pharmaceutical Sciences, University of Genova, Viale Benedetto XV, 3, 16132 Genoa, Italy
Achille Zappa, Department of Informatics, Systems and Telematics, University of Genoa, Via Opera Pia 13, 16132 Genoa, Italy
Paolo Romano, IRCCS San Martino University Hospital, IST National Cancer Research Institute, Largo R. Benzi, 10, 16132 Genoa, Italy
Laura Ottaggio, IRCCS San Martino University Hospital, IST National Cancer Research Institute, Largo R. Benzi, 10, 16132 Genoa, Italy
This review reports the use of wheat milling by-products for the extraction of high quality oil and vitamin E including our
results on the exploitation of durum wheat bran as a valuable source of important healthful compounds. Wheat oil can be used
as an ingredient in food, pharmaceutical or cosmetic preparations because it contains important bioactive compounds such as
vitamin E, carotenoids and unsaturated fatty acids. Different methods are used for oil recovery from plant materials, such
as solvent extraction, mechanical pressing or the eco-friendly supercritical carbon dioxide (SC-CO2) extraction technology. By using SC-CO2, we obtained an oil from durum wheat (Triticum durum Desf.) bran and optimized the extraction conditions to increase oil and vitamin E yields. Wheat bran, which is composed of
pericarp, aleurone layer and germ, is discarded during the early stages of durum wheat milling processes to obtain a final
product (semolina) that is stable over time. Maximum oil and vitamin E yields were obtained when a durum wheat bran matrix
with particle size of ~30 mesh and a moisture content of 2.6 % was used. The optimal conditions for oil extraction were: 300–350 bar,
60–70 °C, and 4 l min?1 gaseous CO2 flow rate for 1 h. The chemical composition (vitamin E forms, carotenoids, quinones, lipids and fatty acids) of the SC-CO2 extracted oil was analyzed and compared to that of the oil extracted by Soxhlet using hexane as solvent. The findings here
reported highlight the importance of durum wheat bran as a rich source of valuable natural nutrients.
Content Type Journal Article
Pages 1-8
DOI 10.1007/s11101-012-9232-x
Authors
Miriana Durante, Istituto di Scienze delle Produzioni Alimentari—CNR, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy
Marcello S. Lenucci, Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali (Di.S.Te.B.A.), Università del Salento, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy
Leonardo Rescio, Pierre S.r.l., s.s. 476 km 17,650 Zona Industriale, 73013 Galatina, LE, Italy
Giovanni Mita, Istituto di Scienze delle Produzioni Alimentari—CNR, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy
Sofia Caretto, Istituto di Scienze delle Produzioni Alimentari—CNR, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy
Legume seeds are employed as a protein source for animal and human nutrition not only for their nutritional value (high in
protein, lipids and dietary fibre), but also their adaptability to marginal soils and climates. Human consumption of legumes
has been increased in recent years, being regarded as beneficial food ingredients. Legume seeds contain a great number of
compounds which qualify as bioactive compounds with significant potentials benefits to human health. These compounds vary
considerably in their biochemistry and they can be proteins, glycosides, tannins, saponins, alkaloids, etc. Hence, methods
for their extraction, determination and quantification are specific of each compound. They do not appear equally distributed
in all legumes, and their physiological effects are diverse. Some of these compounds are important in plant defence mechanisms
against predators or environmental conditions. Others are reserve compounds, accumulated in seeds as energy stores in readiness
for germination. Processing generally improves the nutrient profile of legume seed by increasing in vitro digestibility of
proteins and carbohydrates and at the same time there are reductions in some antinutritional compounds. Most antinutritional
factors are heat-labile, such as protease inhibitors and lectins, so thermal treatment would remove any potential negative
effects from consumption. On the other hand tannins, saponins and phytic acid are heat stable but can be reduced by dehulling,
soaking, germination and/or fermentation. New directions in bioactive compounds research in the last decade have led to major
developments in our understanding of their role in nutrition. The scientific interest in these compounds is now also turning
to studies of their possible useful and beneficial applications as gut, metabolic and hormonal regulators and as probiotic/prebiotic
agents.
Content Type Journal Article
Pages 1-18
DOI 10.1007/s11101-012-9233-9
Authors
Mercedes Muzquiz, Dep. de Tecnología de Alimentos, SGIT-INIA, 28080 Madrid, Spain
Alejandro Varela, Dep. de Tecnología de Alimentos, SGIT-INIA, 28080 Madrid, Spain
Carmen Burbano, Dep. de Tecnología de Alimentos, SGIT-INIA, 28080 Madrid, Spain
Carmen Cuadrado, Dep. de Tecnología de Alimentos, SGIT-INIA, 28080 Madrid, Spain
Eva Guillamón, Dep. de Tecnología de Alimentos, SGIT-INIA, 28080 Madrid, Spain
Mercedes M. Pedrosa, Dep. de Tecnología de Alimentos, SGIT-INIA, 28080 Madrid, Spain
Plant serine protease inhibitors are defense proteins crafted by nature for inhibiting serine proteases. Use of eco-friendly,
sustainable and effective protein molecules which could halt or slow down metabolism of nutrients in pest would be a pragmatic
approach in insect pest management of crops. The host-pest complexes that we observe in nature are evolutionary dynamic and
inter-depend on other defense mechanisms and interactions of other pests or more generally speaking symbionts with the same
host. Insects have co-evolved and adapted simultaneously, which makes it necessary to investigate serine protease inhibitors
in non-host plants. Such novel serine protease inhibitors are versatile candidates with vast potential to overcome the host
inhibitor-insensitive proteases. In a nutshell exploring and crafting plant serine proteinase inhibitors (PIs) for controlling
pests effectively must go on. Non-host PI seems to be a better choice for coevolved insensitive proteases. Transgenic plants
expressing wound inducible chimaeric PIs may be an outstanding approach to check wide spectrum of gut proteinases and overcome
the phenomenon of resistance development. Thus, this article focuses on an entire array of plant serine protease inhibitors
that have been explored in the past decade, their mode of action and biological implications as well as applications.
Content Type Journal Article
Pages 1-34
DOI 10.1007/s11101-012-9231-y
Authors
Farrukh Jamal, Department of Biochemistry (DST-FIST & UGC-SAP Supported), Dr. Ram Manohar Lohia, Avadh University, Faizabad, 224001 UP, India
Prabhash K. Pandey, Department of Biochemistry (DST-FIST & UGC-SAP Supported), Dr. Ram Manohar Lohia, Avadh University, Faizabad, 224001 UP, India
Dushyant Singh, Department of Biochemistry (DST-FIST & UGC-SAP Supported), Dr. Ram Manohar Lohia, Avadh University, Faizabad, 224001 UP, India
M. Y. Khan, Department of Biotechnology, Babasaheb Bhimrao Ambedkar University, Lucknow, UP, India
In 2009, the Marine Biodiscovery Laboratory was set-up at the Marine Institute with funds from the Marine Institute and the
Beaufort Marine Biodiscovery Research Programme. The Marine Biodiscovery Laboratory has already processed over 130 marine
specimens from coastal zones and from the Deep Sea (?3,000 m) within the Marine Irish Exclusive Economic Zone. Beaufort Biodiscovery
funded taxonomists are involved in species identification and elucidation of evolutionary relationships. The project approach
links sampling, systematics, extraction, microbial metagenomics and biomaterials. The Laboratory consists of approximately
56 m2 including an extraction and a bioassay suite. The Laboratory samples and assesses marine biological diversity geared towards
developing natural products for drug discovery, advanced material applications and bio-medical devices. Samples are tracked
from sample log-into right through to extraction and bioassay using a customised Marine Biodiscovery Database. The extraction
procedure is described along with the anti-bacterial bioassay selected for routine use. The Marine Biodiscovery Database manages
the data generated and links the data collected by the project’s stakeholders to existing biodiversity, genetic and chemical
resources. The system uses in-house developed software tools to merge biodiscovery data collected with other MI resources and
external databases and for the data mining and visualisation of biogeographical, genetic and chemical information aimed at
the identification of potential biodiversity and bioactivity “hotspots”.
Content Type Journal Article
Pages 1-11
DOI 10.1007/s11101-012-9227-7
Authors
Margaret Rae, Ryan Institute, National University of Ireland, Galway, Co. Galway, Ireland
Helka Folch, School of Biological Sciences, Queen’s University Belfast, Belfast, Northern Ireland, UK
Mónica B. J. Moniz, Ryan Institute, National University of Ireland, Galway, Co. Galway, Ireland
Carsten W. Wolff, Ryan Institute, National University of Ireland, Galway, Co. Galway, Ireland
Grace P. McCormack, Ryan Institute, National University of Ireland, Galway, Co. Galway, Ireland
Fabio Rindi, Dipartimento di Scienze della Vita e dell’Ambiente, Universitá Politecnica delle Marche, Ancona, Italy
Mark P. Johnson, Ryan Institute, National University of Ireland, Galway, Co. Galway, Ireland
Marine organisms especially those that live sessile, as sponges, are well known to have specific relationships with a great
variety of microorganisms including bacteria and fungi. As most simple metazoan phylum, the Porifera, which emerged first
during the transition from the non-Metazoa to the Metazoa from the common ancestor, comprise wide arrays of recognition molecules,
both for Gram-negative bacteria and for Gram-positive bacteria as well as for fungi. They react specifically with effector
molecules to inhibit or kill the invading microorganisms. The elicitation and the subsequent effector reactions of the sponges
towards these microbes are outlined. However, besides of the elimination of bacteria and fungi, some of those taxa are kept
as symbionts of the sponges, allowing them, for example, to accumulate the essential element manganese or to synthesize carotinoids.
The sponges produce low-molecular-weight bioactive compounds, secondary metabolites, to eliminate the microorganisms. In addition,
they are armed with cationic antimicrobial peptides allowing them to defend against invasive microorganisms and, in parallel,
to kill or repel also metazoan invaders. The broad range of chemically and functionally different compounds qualifies the
Porifera as the most important animal phylum to be exploited as a source for the isolation of new potential drugs. First molecular
biological strategies have been outlined to obtain those compounds in a sustainable way, by producing them recombinantly.
Content Type Journal Article
Pages 1-22
DOI 10.1007/s11101-012-9226-8
Authors
Xiaohong Wang, National Research Center for Geoanalysis, Chinese Academy of Geological Sciences, 26 Baiwanzhuang Dajie, 100037 Beijing, China
David Brandt, ERC Advanced Grant Research Group at the Institute for Physiological Chemistry, University Medical Center of the Johannes Gutenberg University Mainz, Duesbergweg 6, 55128 Mainz, Germany
Narsinh L. Thakur, Bioorganic Chemistry Group, Chemical Oceanography Division, National Institute of Oceanography, Dona Paula, Goa 403 004, India
Matthias Wiens, ERC Advanced Grant Research Group at the Institute for Physiological Chemistry, University Medical Center of the Johannes Gutenberg University Mainz, Duesbergweg 6, 55128 Mainz, Germany
Renato Batel, Ru?er Boškovi? Institute, Center for Marine Research, Giordano Paliaga 5, HR-52210 Rovinj, Croatia
Heinz C. Schröder, ERC Advanced Grant Research Group at the Institute for Physiological Chemistry, University Medical Center of the Johannes Gutenberg University Mainz, Duesbergweg 6, 55128 Mainz, Germany
Werner E. G. Müller, ERC Advanced Grant Research Group at the Institute for Physiological Chemistry, University Medical Center of the Johannes Gutenberg University Mainz, Duesbergweg 6, 55128 Mainz, Germany
Biochemical pathways involved in the production of marine sponge secondary metabolites remain mostly unknown. The physicochemical
characteristics of the marine environment and the complex structures encountered in marine sponges can explain the lack of
results obtained in the biosynthetic studies on marine organisms. Despite significant structural differences, the question
of the similarity between the terrestrial and marine biosynthetic pathways remains. To increase our level of knowledge on
the sponge metabolic pathways, we developed an experimental protocol using a relatively simple model. Pyrrole imidazole alkaloids
represent a very large and interesting family of sponge alkaloids found in many sponge species worldwide. Using oroidin as
our target metabolite and the common Mediterranean sponge Axinella damicornis, we measured the incorporation of radiolabelled amino acids into secondary metabolites by “feeding” experiment. This in vivo
protocol based on a highly sensitive radioactive detection allowed the identification of the origin of an entire sponge natural
product skeleton for the first time.
Content Type Journal Article
Pages 1-10
DOI 10.1007/s11101-012-9225-9
Authors
Gregory Genta-Jouve, Université de Nice-Sophia Antipolis, Institut de Chimie de Nice, UMR 7272 CNRS, Faculté des Sciences, Parc Valrose, 28, Avenue Valrose, 06108 Nice, France
Olivier P. Thomas, Université de Nice-Sophia Antipolis, Institut de Chimie de Nice, UMR 7272 CNRS, Faculté des Sciences, Parc Valrose, 28, Avenue Valrose, 06108 Nice, France
Development of a designer oilseed crop with improved yield attributes and enhanced nutritional quality for the benefits of
mankind and animal husbandry is now achievable with the combination of genetic engineering and plant breeding. In spite of
their immense importance, the fatty acid profiles of most oilseed crops are imbalanced that necessitate the use of metabolic
engineering strategies to overcome the various shortfalls in order to improve the nutritional quality of these edible oils.
Indian mustard (Brassica juncea L.), being one of the important oilseed crops in Indian subcontinent naturally contains ~50 % nutritionally undesirable very
long chain unsaturated fatty acids (VLCUFAs), e.g. erucic acid (C22:1). For the purpose of nutritional improvement of B. juncea seed oil, several metabolic engineering strategies have been employed to divert the carbon flux from the production of VLCUFAs
to other important fatty acids. Stearic acid, being a saturated but nutritionally neutral fatty acid, is naturally inadequate
in most of the conventional oil seeds. Due to its neutral effect on consumer’s health and as an important industrial ingredient,
increased in planta production of stearic acid in the seed oil not only helps in reduction of production cost but also lessens the trans fatty acid production during commercial hydrogenation process. In this review metabolic engineering strategies to minimize
the VLCUFAs along with increased production of stearic acid in the seed oil of B. juncea are discussed, so that further breeding attempts can be made to improve the nutritionally desirable fatty acid profile in
the suitable cultivars of this important oilseed crop.
Content Type Journal Article
Pages 1-13
DOI 10.1007/s11101-012-9228-6
Authors
Surajit Bhattacharya, Department of Biotechnology, Indian Institute of Technology Kharagpur, Kharagpur, 721302 India
Saheli Sinha, Advanced Laboratory for Plant Genetic Engineering, Advanced Technology Development Center, Indian Institute of Technology Kharagpur, Kharagpur, 721302 India
Prabuddha Dey, Advanced Laboratory for Plant Genetic Engineering, Advanced Technology Development Center, Indian Institute of Technology Kharagpur, Kharagpur, 721302 India
Natasha Das, Department of Biotechnology, Indian Institute of Technology Kharagpur, Kharagpur, 721302 India
Mrinal K. Maiti, Department of Biotechnology, Indian Institute of Technology Kharagpur, Kharagpur, 721302 India
In recent years the discovery of some most important antibiotic compounds obtained by fermenting environmental microbes has
been reported, providing proof that isolation and fermentation of producer strains is a significant approach to decifer novel
structural types of antibiotics. Whereas many microbial taxa and environments have been well investigated in the past (e.g.
soil-borne actinomycetes), the high diversity of microbial populations in certain habitats, e.g. marine sediments, has to
date only been exploited marginally. Myxobacteria, the most prominent class of gliding bacteria, are well known for their
ability to produce structurally intriguing natural products; however, so far no myxobacterial antibiotic has been developed
for clinical use. In our studies, the antibacterial activity of the myxobacterial metabolite corallopyronin A was further
investigated. Feeding studies with labeled precursors allowed to deduce all building blocks for the formation of corallopyronin
A, whereby its biosynthesis from two chains probably connected by a Claisen-type reaction and the incorporation of bicarbonate
into the methyl carbamate functionality can be regarded as unusual characteristics. A trans-AT type mixed PKS/NRPS gene cluster containing a ?-branching cassette was identified as the putative basis for corallopyronin
A biosynthesis in Corallococcus coralloides. Our research also resulted in the cultivation of several unusual marine myxobacteria which produce antibiotically active
molecules.
Content Type Journal Article
Pages 1-10
DOI 10.1007/s11101-012-9224-x
Authors
Alexander Schmitz, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Stephan Felder, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Thomas Höver, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Stefan Kehraus, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Edith Neu, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Friederike Lohr, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Gabriele M. König, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Till F. Schäberle, Institute of Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Phytochemical composition of Hypericum genus has been investigated for many years. In the recent past, studies on the essential oils (EO) of this genus have been
progressing and many of them have reported interesting biological activities. Variations in the EO composition of Hypericum species influenced by seasonal variation, geographic distribution, phenological cycle and type of the organ in which EO are
produced and/or accumulated have also been reported. Although many reviews attributed to the characterization as well as biological
activities of H. perforatum crude extracts have been published, no review has been published on the EO composition and biological activities of Hypericum species until recently (Crockett in Nat Prod Commun 5(9):1493–1506, 2010; Bertoli et al. in Global Sci Books 5:29–47, 2011). In this article, we summarize and update information regarding the composition and biological activities of Hypericum species EO. Based on experimental work carried out in our laboratory we also mention possible biotechnology approaches envisaging
EO improvement of some species of the genus.
Content Type Journal Article
Pages 127-152
DOI 10.1007/s11101-012-9223-y
Authors
Ana P. Guedes, CITAB, Centre for the Research and Technology of Agro-Environmental and Biological Sciences, University of Minho, 4710-057 Braga, Portugal
G. Franklin, CITAB, Centre for the Research and Technology of Agro-Environmental and Biological Sciences, University of Minho, 4710-057 Braga, Portugal
Manuel Fernandes-Ferreira, CITAB, Centre for the Research and Technology of Agro-Environmental and Biological Sciences, University of Minho, 4710-057 Braga, Portugal
Numerous researches have been carried out in Zingiber zerumbet Smith. Since 1944 till date. Z. zerumbet is a monocotyledonous perennial medicinal plant belonging to Zingiberaceae family. It is commonly known as shampoo ginger.
It has many different local names depending on their area of collection and vegetation. It is called as ‘Singkha’ in Manipuri.
Various compounds have been reported to be isolated from Z. zerumbet and they serve a very potent and reliable drug candidate for the various diseases. They have been investigated for its prospects
of effectiveness against number of activities in in vitro as well as in vivo and mechanisms that may be involved in chemo
preventive measures and various pharmaceutical studies.
Content Type Journal Article
Pages 113-125
DOI 10.1007/s11101-011-9222-4
Authors
C. B. Singh, Institute of Bioresources and Sustainable Development, Imphal, 795001 India
Kh. Nongalleima, Institute of Bioresources and Sustainable Development, Imphal, 795001 India
S. Brojendrosingh, Institute of Bioresources and Sustainable Development, Imphal, 795001 India
Swapana Ningombam, S Kula Women College, Nambol, Manipur 795134, India
N. Lokendrajit, Department of Chemistry, Manipur University, Canchipur, 795003 India
L. W. Singh, Department of Chemistry, Manipur University, Canchipur, 795003 India
Plants have a long history as therapeutic tools in the treatment of human diseases and have been used as a source of medicines
for ages. In search of new biologically active natural products, many plants and herbs used in traditional medicine are screened
for natural products with pharmacological activity. In this paper, we present a group of natural products, the sesquiterpene
coumarins isolated from plants, and describe their wide range of biological activity. Sesquiterpene coumarins are found in
some plants of the families Apiaceae (Umbelliferae), Asteraceae (Compositae) and Rutaceae. The coumarin moiety is often umbelliferone
(7-hydroxycoumarin) but scopoletin (7-hydroxy-6-methoxycoumarin) and isofraxidin (7-hydroxy-6,8-dimethoxycoumarin) are also
found. These coumarins are linked to a C15 terpene moiety through an ether linkage. Another group of sesquiterpene coumarins is the prenylated 4-hydroxycoumarins where
the link between the coumarin and the C15 terpene moiety is a C–C-bond at carbon 3 of the coumarin moiety. Finally, the prenyl-furocoumarin-type sesquiterpenoids are
a separate group of sesquiterpene coumarins based on the suggested biosynthetic pathway. Our relatively limited knowledge
on the biosynthesis of sesquiterpene coumarins is reviewed.
Content Type Journal Article
Pages 77-96
DOI 10.1007/s11101-011-9220-6
Authors
Anna Gliszczy?ska, School of Natural Sciences, Linnaeus University, 39281 Kalmar, Sweden
Peter E. Brodelius, School of Natural Sciences, Linnaeus University, 39281 Kalmar, Sweden
Withania somnifera (L.) Dunal (Solanaceae), also known as ashwagandha, is an important medicinal plant that is widely used as a home remedy for several diseases in
the Indian subcontinent and other parts of the world. W. somnifera is a dietary supplement composed of various nutrients, polyphenols and alkaloids that have free radical scavenging capacity,
as well as other chemical constituents that possess anti-inflammatory, antitumor, anti-stress, antioxidant, immunomodulatory,
and rejuvenating properties. The mechanism of action for these properties are not fully understood. W. somnifera also appears to influence the endocrine, cardiopulmonary and central nervous systems. Toxicity studies reveal that W. somnifera can be used without side effects. The findings presented in this review are very encouraging and indicate that this herb
should be studied more extensively to confirm these results and to reveal other potential therapeutic effects.
Content Type Journal Article
Pages 97-112
DOI 10.1007/s11101-011-9221-5
Authors
Nadia Alam, Department of Botany, Rajshahi University, Rajshahi, Bangladesh
Monzur Hossain, Department of Botany, Rajshahi University, Rajshahi, Bangladesh
Md. Ibrahim Khalil, Department of Pharmacology, School of Medical Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian, Kelantan, Malaysia
Mohammed Moniruzzaman, Department of Pharmacology, School of Medical Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian, Kelantan, Malaysia
Siti Amrah Sulaiman, Department of Pharmacology, School of Medical Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian, Kelantan, Malaysia
Siew Hua Gan, Human Genome Centre, School of Medical Sciences, Universiti Sains Malaysia, 16150 Kubang Kerian, Kelantan, Malaysia
Andrographis paniculata (Burm.f) Nees is one of the most popular and important medicinal plant of the Orient, and South East Asia. It finds mention
in various forms in Indian, Chinese, Malay, Thai, Unani, and Japanese systems of medicine. The plant exhibits anti-cancer,
anti-inflammatory, anti-diabetic, anti-hypertensive, anti-venom, cholestatic, hepatoprotective, anti-thrombotic, anti-retroviral,
anti-microbial, anti-pyretic, anti-malarial, anti-oxidant, immunomodulatory, and cardioprotective effects. The major active
principles contributing to biological activity are diterpene lactones, but flavonoids, xanthones and caffeic acid derivatives
also contribute to anti-oxidant, anti-proliferative, anti-atherosclerotic, and anti-malarial effects. As a result of its wide
spectrum of pharmacological activity, almost impeccable safety profile, being a widely cultivated medicinal plant, we have
collected and compiled various facets of this plant. Extensive datamining of the phytochemistry and pharmacology of Andrographis paniculata revealed more than 50 diterpene lactones, 30 flavonoids, 8 quinic acid derivatives, and 4 xanthones. This review contains
information on around 80 isolated compounds, out of which more than half of the compounds have no reported pharmacological
activity. Though there are some good reviews available on Andrographis paniculata, the authors of the earlier reviews focused on one or two aspects of the plant and none have attempted to integrate the available
information on this plant. This provided us the much needed impetus, warranting a full-fledged and complete review on Andrographis paniculata, one of the most popular and important Oriental medicinal plant.
Content Type Journal Article
Pages 39-75
DOI 10.1007/s11101-011-9219-z
Authors
Rammohan Subramanian, Department of Pharmacology, International Medical School (IMS), Management and Science University (MSU), 40100 Shah Alam, Malaysia
Mohd. Zaini Asmawi, Department of Pharmacology, School of Pharmacy, Universiti Sains Malaysia, 11800 Penang, Malaysia
Amirin Sadikun, Department of Pharmaceutical Chemistry, School of Pharmacy, Universiti Sains Malaysia, 11800 Penang, Malaysia
The aim of this review is to highlight updated results on the biologically active saponins from Leguminosae-Mimosoideae. Acacic
acid-type saponins (AATS), is a class of very complex glycosides possessing a common aglycon unit of the oleanane-type (acacic
acid = 3?, 16?, 21? trihydroxy-olean-12-en-28 oic acid), having various oligosaccharide moieties at C-3 and C-28 and an acyl
group at C-21. About sixty molecules of this type have been actively explored in recent years from Leguminosae family, from
a chemical point of view and some fifty were reported to possess cancer related activities. These include cytotoxic/antitumor,
immunomodulatory, antimutagenic, and apoptosis inducing properties and appear to depend on the acylation and esterification
by different moieties at C-21 and C-28 of the acacic acid-type aglycone. One can observe that the (6S) configuration of the outer monoterpenyl moiety (MT) seems more potent in mediating high cytotoxicity than its (6R) isomer. Furthermore, the trisaccharide moiety {?-d-Xylopyranosyl-(1?2)-?-d-Fucopyranosyl-(1?6)- N-Acetamido 2-?-d-Glucopyranosyl-} at C-3, the tetrasaccharide moiety {?-d-Glucopyranosyl-(1?3)-[?-L-Arabinofuranosyl-(1?4)]-?-l-Rhamnopyranosyl-(1?2)-?-d-Glucopyranosyl} at C-28 of the aglycone, and the inner MT hydroxylated at its C-9, having a (6S) configuration can be important substituent patterns for the induction of apoptosis of AATS. Because of their interesting
cytotoxic/apoptosis inducing activity, some AATS can be useful in the search for new potential antitumor agents from Fabaceae.
Furthermore, the sequence 28-O-{Glc-(1?3)-[Araf-(1?4)]-Rha-(1?2)-Glc-Acacic acid}, often encountered in the genera Acacia, Albizia, Archidendron, and Pithecellobium may represent a chemotaxonomic marker of the Mimosoideae subfamily.
Content Type Journal Article
Pages 565-584
DOI 10.1007/s11101-011-9218-0
Authors
Marie-Aleth Lacaille-Dubois, Laboratoire de Pharmacognosie, Uunité de Molécules d’Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D’Arc, BP 87900, 21079 Dijon cedex, France
Dieudonné Emmanuel Pegnyemb, Laboratoire de Pharmacochimie, Département de Chimie Organique, Faculté de Sciences, Université de Yaoundé, BP 812, Yaoundé, Cameroon
Olivier Placide Noté, Laboratoire de Pharmacognosie, Uunité de Molécules d’Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D’Arc, BP 87900, 21079 Dijon cedex, France
Anne-Claire Mitaine-Offer, Laboratoire de Pharmacognosie, Uunité de Molécules d’Intérêt Biologique, UMIB, UPRES EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 bd. Jeanne D’Arc, BP 87900, 21079 Dijon cedex, France
Erratum to: Phenylphenalenone phytoalexins, will they be a new type of fungicide?
Content Type Journal Article
Category Erratum
Pages 13-14
DOI 10.1007/s11101-011-9217-1
Authors
Fernando Echeverri, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Fernando Torres, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Wiston Quiñones, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Gustavo Escobar, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Rosendo Archbold, Facultad de Química Farmaceutica, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Fungi can be found in almost all sorts of habitats competing with an even higher number of other organisms. As a consequence
fungi developed a number of strategies for protection and communication with other organisms. This review focuses on the increasing
number of volatile sesquiterpenes found to be produced by fungal species. The remarkable diversity of this type of volatile
organic compound (VOC) within the kingdom fungi is presented and their benefits for the fungi are discussed. The majority
of these compounds are hydrocarbons comprising several dozens of carbon skeletons. Together with oxygenated sesquiterpenes
they include compounds unique to fungi. Only in recent years the interest shifted from a mere detection and characterization
of compounds to their biological function. This review reveals highly diverse ecological functions including interactions
with bacteria, other fungi, insects and plants. VOCs act as autoinducer, defend against competing species and play essential
roles in attracting pollinators for spreading fungal spores. For many sesquiterpene VOCs sophisticated responses in other
organisms have been identified. Some of these interactions are complex involving several partners or transformation of the
emitted sesquiterpene. A detailed description of ecological functions of selected sesquiterpenes is given as well as their
potential application as marker molecules for detection of mould species. Structures of all described sesquiterpenes are given
in the review and the biosynthetic routes of the most common skeletons are presented. Summarizing, this article provides a
detailed overview over the current knowledge on fungal sesquiterpene VOCs and gives an outlook on the future developments.
Content Type Journal Article
Pages 15-37
DOI 10.1007/s11101-011-9216-2
Authors
Rolf Kramer, Helmholtz Center for Infection Research, Chemical Microbiology, Inhoffenstrasse 7, 38124 Braunschweig, Germany
Wolf-Rainer Abraham, Helmholtz Center for Infection Research, Chemical Microbiology, Inhoffenstrasse 7, 38124 Braunschweig, Germany
Lichens are compound entities of a fungal partner (“mycobiont”) and one or more photosynthetically active algae or cyanobacteria
(“photobionts”). The organisms live in an intimate, symbiotic association which has been classified as a mutualistic or controlled
parasitic relationship. Several metabolites from lichens display unique structures with unknown functions, and only a few
model species have been analysed comprehensively. The complex metabolic interplay between the organisms in lichens is also
incompletely understood. Earlier experiments with 14C-labelled precursors indicated that the photobionts produce from CO2 glucose or sugar alcohols (e.g. ribitol and arabitol) which are then transferred to the mycobionts. In the fungi, these compounds
are believed to be converted into mannitol serving as the carbon and energy source in the downstream metabolic processes.
Recent methodological developments in spectroscopy and “systems biology” now enable a concise analysis of the metabolite profiles,
networks and fluxes by non-targeted quantitative approaches. In this review, we summarize the current knowledge about lichen
metabolism and report on the potential of the advanced methods to reinvestigate lichen chemistry and metabolism on a quantitative
basis.
Content Type Journal Article
Pages 445-456
DOI 10.1007/s11101-011-9215-3
Authors
Wolfgang Eisenreich, Lehrstuhl für Biochemie, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Nihat Knispel, Lehrstuhl für Biochemie, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Andreas Beck, Department of Lichenology and Bryology, Botanische Staatssammlung München, Menzinger Str. 67, 80638 München, Germany
Seaweeds are the primary producers of all aquatic ecosystems. Chemical constituents isolated from diverse classes of seaweeds
exert a wide range of nutritional, functional and biological activities. Unique metabolites of seaweeds possess specific biological
properties that make them potential ingredients of many industrial applications such as functional foods, pharmaceuticals
and cosmeceuticals. Cosmeceuticals of natural origin are becoming more popular than synthetic cosmetics. Hence, the investigation
of new seaweeds derived functional components, a different source of natural products, has proven to be a promising area of
cosmeceutical studies. Brown seaweeds also produce a range of active components including unique secondary metabolites such
as phlorotannins and many of which have specific biological activities that give possibilities for their economic utilization.
Brown seaweeds derived active compounds have been shown various functional properties including, antioxidant, antiwrinkling,
whitening, antiinflammatory and antiallergy. It is well-known that these kind of biological effects are closely associated
with cosmeceutical preparations. This communication reviews the current knowledge on brown seaweeds derived metabolites with
various biological activities and the potential use as cosmeceutical ingredients. It is hoped that the reviewed literature
on multifunctional properties of brown seaweeds will improve access to the seaweed based natural products specially the ability
to incorporate these functional properties in cosmeceutical applications.
Content Type Journal Article
Pages 431-443
DOI 10.1007/s11101-011-9214-4
Authors
W. A. J. P. Wijesinghe, School of Marine Biomedical Sciences, Jeju National University, Jeju, 690-756 Republic of Korea
You-Jin Jeon, School of Marine Biomedical Sciences, Jeju National University, Jeju, 690-756 Republic of Korea
Many Vochysiaceae species, in special Qualea and Vochysia genera, are widely used in folk medicine to treat several diseases. This review describes some aspects of their ethnopharmacology
potential, biological activity and the secondary metabolites reported so far for Vochysiaceae. The chemical constituents of
this family include triterpenoids, steroids and polyphenols like flavonoids and ellagic acid derivatives.
Content Type Journal Article
Pages 413-429
DOI 10.1007/s11101-011-9213-5
Authors
Fausto Carnevale Neto, Department of Organic Chemistry, Chemistry Institute, Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products—NuBBE, São Paulo State University, UNESP, Rua Prof. Francisco Degni s/n, Araraquara, São Paulo 14800-900, Brazil
Alan Cesar Pilon, Department of Organic Chemistry, Chemistry Institute, Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products—NuBBE, São Paulo State University, UNESP, Rua Prof. Francisco Degni s/n, Araraquara, São Paulo 14800-900, Brazil
Dulce Helena Siqueira Silva, Department of Organic Chemistry, Chemistry Institute, Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products—NuBBE, São Paulo State University, UNESP, Rua Prof. Francisco Degni s/n, Araraquara, São Paulo 14800-900, Brazil
Vanderlan da Silva Bolzani, Department of Organic Chemistry, Chemistry Institute, Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products—NuBBE, São Paulo State University, UNESP, Rua Prof. Francisco Degni s/n, Araraquara, São Paulo 14800-900, Brazil
Ian Castro-Gamboa, Department of Organic Chemistry, Chemistry Institute, Nuclei of Bioassays, Biosynthesis and Ecophysiology of Natural Products—NuBBE, São Paulo State University, UNESP, Rua Prof. Francisco Degni s/n, Araraquara, São Paulo 14800-900, Brazil
Secondary plant metabolites, and in particular monoterpenes, have been recognised as potential medicinal agents for centuries.
As such, terpenes have been the focus of a plethora of scientific studies examining various aspects of their bioactivity.
In particular, antimicrobial activity and anticancer potential have been studied extensively. Whilst the antimicrobial and
anticancer activity of terpenes has been demonstrated in vitro, fewer studies have been conducted examining specific aspects
of the mechanisms of antimicrobial action and anticancer efficacy in vivo. The purpose of this review is therefore to examine
recent advances in the areas of antimicrobial and anticancer activity.
Content Type Journal Article
Pages 1-6
DOI 10.1007/s11101-011-9212-6
Authors
Sara J. Greay, Discipline of Microbiology and Immunology (M502), School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, 35 Stirling Hwy, Crawley, WA 6009, Australia
Katherine A. Hammer, Discipline of Microbiology and Immunology (M502), School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, 35 Stirling Hwy, Crawley, WA 6009, Australia
Plants are a rich source of valuable secondary metabolites. Plant cell culture technologies developed in the past as possible
tools for secondary metabolites production. In most cases, for the large scale production of these compounds, production is
too low for commercialization. The cultured cell suspensions being undifferentiated have not gained momentum because of their
instability and non-uniformity of the product formation. Secondary metabolite production is under strict metabolic regulation
and tissue specific localization. Hence the differentiated cultures such as hairy root cultures are widely studied. Agrobacterium rhizogenes causes hairy root disease in plants. Transformed roots produced by A. rhizogenes infection are characterized by high growth rate, genetic stability and growth in hormone free media. These genetically transformed
root cultures can produce amounts of secondary metabolites comparable to that of intact plants. Elicitation of hairy roots
leads to increased production of secondary metabolites and also helps in designing of metabolic traps to allow adsorption
of product, preventing feedback inhibition and protection of metabolites from degradation in the culture media. Permeabilization
and in situ product adsorption result in many fold increase in product yield. T- DNA activation tagging allows overexpressing
the respective gene and increasing the product formation in transformed hairy roots. Recent progress in transgenic research
has opened up the possibility of the metabolic engineering of biosynthetic pathways to produce high-value secondary metabolites.
Metabolic engineering offers promising perspectives to improve yields; however it requires the understanding of the regulation
of the secondary metabolite pathways involved in the regulation of levels of product, enzymes and genes, including aspects
as transport and compartmentation. This article reviews the recent advances in secondary metabolites production in transformed
hairy roots.
Content Type Journal Article
Pages 371-395
DOI 10.1007/s11101-011-9210-8
Authors
Sheela Chandra, Department of Biotechnology, Birla Institute of Technology, Mesra, Ranchi, Jharkhand 835215, India
Ramesh Chandra, Department of Biotechnology, Birla Institute of Technology, Mesra, Ranchi, Jharkhand 835215, India
Chalcone synthase (CHS, EC 2.3.1.74) is a key enzyme of the flavonoid/isoflavonoid biosynthesis pathway. Besides being part
of the plant developmental program the CHS gene expression is induced in plants under stress conditions such as UV light, bacterial or fungal infection. CHS expression
causes accumulation of flavonoid and isoflavonoid phytoalexins and is involved in the salicylic acid defense pathway. This
review will discuss CHS and its function in plant resistance.
Content Type Journal Article
Pages 397-412
DOI 10.1007/s11101-011-9211-7
Authors
T. T. H. Dao, Division of Pharmacognosy, Section Metabolomics, Institute of Biology, Leiden University, Leiden, The Netherlands
H. J. M. Linthorst, Section Plant Cell Physiology, Institute of Biology, Leiden University, Leiden, The Netherlands
R. Verpoorte, Division of Pharmacognosy, Section Metabolomics, Institute of Biology, Leiden University, Leiden, The Netherlands
Quinones are a class of natural and synthetic compounds that have several beneficial effects. Quinones are electron carriers
playing a role in photosynthesis. As vitamins, they represent a class of molecules preventing and treating several illnesses
such as osteoporosis and cardiovascular diseases. Quinones, by their antioxidant activity, improve general health conditions.
Many of the drugs clinically approved or still in clinical trials against cancer are quinone related compounds. Quinones have
also toxicological effects through their presence as photoproducts from air pollutants. Quinones are fast redox cycling molecules
and have the potential to bind to thiol, amine and hydroxyl groups. The aforementioned properties make the analytical detection
of quinones problematic. However, recent advances of the available analytical techniques along with the possibility of using
labeled compound facilitate their detection hence allowing a better understanding of their action. This review summarizes
the current knowledge with respect to the oxido-reductive and electrophilic properties of quinones as well as to the analytical
tools used for their analysis. It includes a general introduction about the physiological, and therapeutical functions of
quinones. A number of studies are reported to cover the chemical reactivity in an attempt to understand quinones as biologically
active compounds. Data ranging from normal analytical methods to study quinones derived from plant or biological matrices
to the use of labeled compounds are presented. The examples illustrate how chemical, biological and analytical knowledge can
be integrated to have a better understanding of the mode of action of the quinones.
Content Type Journal Article
Pages 353-370
DOI 10.1007/s11101-011-9209-1
Authors
Nahed El-Najjar, Division of Pharmaceutical Biology, Faculty of Pharmacy, University of Helsinki, Viikinkaari 5E, P.O. Box 56, 00014 Helsinki, Finland
Hala Gali-Muhtasib, Department of Biology, American University of Beirut, Beirut, Lebanon
Raimo A. Ketola, Center for Drug Research, University of Helsinki, Helsinki, Finland
Pia Vuorela, Pharmaceutical Sciences, Department of Biosciences, Abo Akademi University, Turku, Finland
Arto Urtti, Center for Drug Research, University of Helsinki, Helsinki, Finland
Heikki Vuorela, Division of Pharmaceutical Biology, Faculty of Pharmacy, University of Helsinki, Viikinkaari 5E, P.O. Box 56, 00014 Helsinki, Finland
The genus Garcinia belongs to the family Clusiaceae and has been involved in ayurvedic preparations to medicate various pathophysiological disorders. The bioactive molecules
like hydroxycitric acid (HCA), flavonoids, terpenes, polysaccharides, procyanidines and polyisoprenylated benzophenone derivatives
like garcinol, xanthochymol and guttiferone isoforms have been isolated from the genus Garcinia. The genus has received the attention of pharmaceutical industries due to their immense remedial qualities. The HCA has been
known for its hypolipidemic property. The polyisoprenylated benzophenone and xanthone derivatives are known for their antioxidant,
apoptotic, anti-cancer, anti-inflammatory, anti-bacterial, anti-viral, anti-fungal, anti-ulcer, anti-protozoal, and HAT inhibiting
properties. Future studies on the synthesis of therapeutically important products and their analogs and evaluation of their
safety and efficacy would be of great interest. Though the genus includes more than 300 species, we have made an effort to
conceive the curative qualities of bioactive compounds of selected plants to the best of our knowledge.
Content Type Journal Article
Pages 325-351
DOI 10.1007/s11101-011-9207-3
Authors
M. Hemshekhar, Department of Studies in Biochemistry, University of Mysore, Manasagangothri, Mysore, 570 006 India
K. Sunitha, Department of Studies in Biochemistry, University of Mysore, Manasagangothri, Mysore, 570 006 India
M. Sebastin Santhosh, Department of Studies in Biochemistry, University of Mysore, Manasagangothri, Mysore, 570 006 India
S. Devaraja, PG Department of Biochemistry, Tumkur University, Tumkur, India
K. Kemparaju, Department of Studies in Biochemistry, University of Mysore, Manasagangothri, Mysore, 570 006 India
B. S. Vishwanath, Department of Studies in Biochemistry, University of Mysore, Manasagangothri, Mysore, 570 006 India
S. R. Niranjana, Department of Biotechnology, University of Mysore, Manasagangothri, Mysore, 70006 India
K. S. Girish, Department of Studies in Biochemistry, University of Mysore, Manasagangothri, Mysore, 570 006 India
Phenylphenalenones represent a kind of phytoalexins produced in leaves and rhyzomes of banana and plantains (Musaceae), as
well as in species of other families. These compounds are synthesized in plants by induction with aminoglycosides, or in the
first stages of attack by the pathogenic fungus Mycosphaerella fijensis, a causal agent of the disease known as Black Sigatoka, which reduces banana production. In this paper we report the biosynthesis,
synthesis and antifungal activities of these kinds of compounds and discus the possibility to use phytoalexins inductors as
plant protectants.
Content Type Journal Article
Pages 1-12
DOI 10.1007/s11101-010-9205-x
Authors
Fernando Echeverri, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Fernando Torres, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Wiston Quiñones, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Gustavo Escobar, Instituto de Química, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
Rosendo Archbold, Facultad de Química Farmaceutica, Grupo de Química Orgánica de Productos Naturales-SIU, Universidad de Antioquia, AA 1226 Medellín, Colombia
The understanding of the selection factors that drive chemical diversification of secondary metabolites of constitutive defence
systems in plants, such as pyrrolizidine alkaloids (PAs), is still incomplete. Historically, plants always have been confronted
with microorganisms. Long before herbivores existed on this planet, plants had to cope with microbial pathogens. Therefore,
plant pathogenic microorganisms may have played an important role in the early evolution of the secondary metabolite diversity.
In this review, we discuss the impact that plant-produced PAs have on plant-associated microorganisms. The objective of the
review is to present the current knowledge on PAs with respect to anti-microbial activities, adaptation and detoxification
by microorganisms, pathogenic fungi, root protection and PA induction. Many in vitro experiments showed effects of PAs on
microorganisms. These results point to the potential of microorganisms to be important for the evolution of PAs. However,
only a few in vivo studies have been published and support the results of the in vitro studies. In conclusion, the topics
pointed out in this review need further exploration by carrying out ecological experiments and field studies.
Content Type Journal Article
Pages 127-136
DOI 10.1007/s11101-010-9204-y
Authors
Lotte Joosten, Plant Ecology and Phytochemistry, Institute of Biology, Leiden University, P.O. Box 9505, 2300 RA Leiden, The Netherlands
Johannes A. van Veen, Plant Ecology and Phytochemistry, Institute of Biology, Leiden University, P.O. Box 9505, 2300 RA Leiden, The Netherlands
Plants used in traditional medicine have stood up to the test of time and contributed many novel compounds for preventive
and curative medicine to modern science. India is sitting on a gold mine of well recorded and traditionally well practiced
knowledge of herbal medicine. Specially, plants growing at high altitude in Himalayan pastures are time-honored sources of
health and general well being of local inhabitants. As of today, Himalayan plants are a major contributor to the herbal pharmaceutical
industry both of India and other countries. Plants growing at higher altitudes are subjected to an assault of diverse testing
situations including higher doses of mutagenic UV-radiation, physiological drought, desiccation and strong winds. Plants interact
with stressful environments by physiological adaptation and altering the biochemical profile of plant tissues and producing
a spectrum of secondary metabolites. Secondary metabolites are of special interest to scientists because of their unique pharmacophores
and medicinal properties. Secondary metabolites like polyphenols, terpenes and alkaloids have been reported to possess antimutagenic
and anticancer properties in many studies. The fundamental aspiration of the current review is to divulge the antimutagenic/anticancer
potential of five alpine plants used as food or medicine by the populations living at high altitudes.
Content Type Journal Article
Pages 309-323
DOI 10.1007/s11101-010-9202-0
Authors
Anjana Bhatia, Department of Botany, Hans Raj Mahila Maha Vidyalaya, Jalandhar, India
Saroj Arora, Department of Botanical and Environmental Sciences, Guru Nanak Dev University, Amritsar, 143 005 India
Bikram Singh, Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh 176 061, India
Gurveen Kaur, Department of Botanical and Environmental Sciences, Guru Nanak Dev University, Amritsar, 143 005 India
Avinash Nagpal, Department of Botanical and Environmental Sciences, Guru Nanak Dev University, Amritsar, 143 005 India
Lichens are fungal and algal/cyanobacterial symbioses resulting in the production of specific metabolites. Some of these are
forming an available biomass for phytochemical investigations, including the assessment of biological activities of the isolated
compounds. The alpine or polar region are characterised by highly stressful environmental conditions for many organisms, but
lichens are among the dominating organisms in these habitats. In the performant mutual protective system, lichen fungi often
accumulate high amounts of metabolites with specific physicochemical properties (UV absorbents, hydrophobicity) which help
the lichens to survive. Unique secondary metabolites and polysaccharides have been isolated and tested from these organisms.
Even though this has been tested until now only with a low number of compounds so far, interesting activities have been recorded.
We review here some of the antimicrobial, anti-inflammatory, antiproliferative and antioxidant activities properties described.
Solutions with axenic biotechnological cultivation of each symbiotic partner and particularly the mycobiont to obtain the
lichen secondary metabolites are challenging to overcome the limitations for the supply of these rare compounds. Additionally,
these lichens appear to harbour a diversity of culturable microorganisms from which active compounds have also been isolated
recently.
Content Type Journal Article
Pages 287-307
DOI 10.1007/s11101-010-9201-1
Authors
Joel Boustie, Faculté de Pharmacie, Sciences chimiques de Rennes, équipe PNSCM Produits naturels – Synthèses – Chimie médicinale, UMR CNRS 6226, Université de Rennes 1, Université Européenne de Bretagne, 2 av du Pr. Léon Bernard, 35043 Rennes Cédex, France
Sophie Tomasi, Faculté de Pharmacie, Sciences chimiques de Rennes, équipe PNSCM Produits naturels – Synthèses – Chimie médicinale, UMR CNRS 6226, Université de Rennes 1, Université Européenne de Bretagne, 2 av du Pr. Léon Bernard, 35043 Rennes Cédex, France
Martin Grube, Institut für Pflanzenwissenschaften, Karl-Franzens-Universität Graz, Holteigasse 6, 8010 Graz, Austria
Pyrrolizidine alkaloids are characteristic secondary metabolites of the Asteraceae and some other plant families. They are
especially numerous and diverse in the tribe Senecioneae and form a powerful defense mechanism against herbivores. Studies
into the evolution of pyrrolizidine alkaloid biosynthesis using Senecio species have identified homospermidine synthase as the enzyme responsible for the synthesis of the first specific intermediate.
These studies further indicated that the homospermidine synthase-encoding gene was recruited following gene duplication of
deoxyhypusine synthase and that this occurred independently in several different angiosperm lineages. A review of published
pyrrolizidine alkaloid data shows that the Senecioneae are characterized by a large qualitative and quantitative variation
in pyrrolizidine alkaloid profiles and that these data demonstrate little phylogenetic signal. This suggests that although
the first steps of this pathway are highly conserved, the diversification of secondarily derived pyrrolizidine alkaloids is
extremely plastic.
Content Type Journal Article
Pages 3-74
DOI 10.1007/s11101-010-9184-y
Authors
Dorothee Langel, Biochemische Ökologie und Molekulare Evolution, Botanisches Institut und Botanischer Garten, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany
Dietrich Ober, Biochemische Ökologie und Molekulare Evolution, Botanisches Institut und Botanischer Garten, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany
Pieter B. Pelser, School of Biological Sciences, University of Canterbury, Private Bag 4800, Christchurch, 8140 New Zealand
Since early human history, plants have served as the most important source of medicinal natural products, and even in the
“synthetic age” the majority of lead compounds for pharmaceutical development remain of plant origin. In the marine realm,
algae and seagrasses were amongst the first organisms investigated by marine natural products scientists on their quest for
novel pharmaceutical compounds. Forty years after the pioneering work in the field of marine drug discovery began, the biodiversity
of marine organisms investigated as potential sources of anticancer, anti-inflammatory, and antibiotic compounds has increased
tremendously. Nonetheless, marine plants are still an important source of novel secondary metabolites with interesting biomedical
properties. The present review focuses on the antitumour properties of compounds isolated from marine algae, phytoplankton,
mangroves, seagrasses, or cordgrasses. Compounds produced by marine epi- or endophytic fungi are also discussed.
Content Type Journal Article
Pages 557-579
DOI 10.1007/s11101-010-9200-2
Authors
F. Folmer, Laboratoire de Biologie Moléculaire et Cellulaire de Cancer, Hôpital Kirchberg, 9, rue Edward Steichen, 2540 Luxembourg, Luxembourg
M. Jaspars, Marine Biodiscovery Centre, University of Aberdeen, Meston Walk, Old Aberdeen, AB23 4UE UK
M. Dicato, Laboratoire de Biologie Moléculaire et Cellulaire de Cancer, Hôpital Kirchberg, 9, rue Edward Steichen, 2540 Luxembourg, Luxembourg
M. Diederich, Laboratoire de Biologie Moléculaire et Cellulaire de Cancer, Hôpital Kirchberg, 9, rue Edward Steichen, 2540 Luxembourg, Luxembourg
This paper reports the lecture delivered on the occasion of the “Ceremony of Professional Recognition” to the author at the
6th European Conference on Marine Natural Products (Porto, Portugal, 19–23 July 2009). The most recent results obtained studying
opisthobranchs and diatoms at ICB are presented after a synthetic overview of the most significant moves played during this
exciting 40 years game in the field of Marine Natural Products. In a symbolic manner this career is compared to a chess game.
After the “romantic” opening dedicated to the study of natural black (melanin) and red-brown (phaeomelanins) pigments in the
prestigious group of Rodolfo A. Nicolaus, the research on marine organisms started in 1969 and rapidly led to the characterization
of an impressive number of new compounds exhibiting very unusual structures. Substantially, the “structure hunt” ended with
the publication of a series of alkaloids with absolutely unprecedented structural features: the saraines. Slowly, the scientific
interest shifted “from structure to function”. Opisthobranchs were selected as models to investigate. The majority of the
protective allomones possessed by opisthobranch molluscs are sequestered through the food chain from algae and invertebrates.
However, opisthobranchs were also able to biosynthesize many compounds structurally related to typical molecules possessed
by their prey. These aspects “from function to ecology, to biosynthesis, to evolution” are discussed in detail.
Content Type Journal Article
Pages 547-556
DOI 10.1007/s11101-010-9199-4
Authors
Guido Cimino, Istituto di Chimica Biomolecolare (ICB), Consiglio Nazionale delle Ricerche (CNR), Comprensorio Olivetti, via Campi Flegrei, 34, 80078 Pozzuoli, Napoli, Italy
Natural products play an important role in the development of anticancer drugs. To date, predominantly metabolites from plants
and bacteria served as lead structures for anticancer agents. Fungal metabolites and derivatives thereof are much less investigated
for their potential in cancer therapy. There are, however, some promising candidates derived from fungi in clinical phases
I and II studies. This review gives an overview on the role of natural products in cancer therapy and summarises some of the
latest results of our group in this area.
Content Type Journal Article
Pages 537-545
DOI 10.1007/s11101-010-9198-5
Authors
Hendrik Greve, Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Ietidal E. Mohamed, Department of Botany, University of Khartoum, Khartoum, Sudan
Alexander Pontius, Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Stefan Kehraus, Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Harald Gross, Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Gabriele M. König, Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany
Scientific study of paralytic shellfish poisoning toxins (PSTs) started in the early XXth century. In the 1920s it was understood
the link between the toxicity observed in mussels with certain microalgae species. The poison was eventually purified from
the clam Saxidomus giganteus, taking its name from it: saxitoxin (STX). Along the 1970s and 1980s it was understood that other STX analogues existed,
both in dinoflagellates and bivalves. These were grouped into three major occurring families: the carbamate, N-sulfocarbamoyl and decarbamoyl, depending on the variation of the side chain of the tetrahydropurine core. The deoxydecarbamoyl
family was additionally recognised in the dinoflagellate Gymnodinium catenatum. Chemical research into these STX analogues was conducted worldwide during the 1990s mainly by HPLC with pre- or post-column
oxidation and fluorescence detection. Implementation of fluorescence detection with spectral capabilities and mass spectrometry
detection during the 2000s led to the recognition of new analogues. Metabolites originated by single or double hydroxylation
at C11 position were found in mussels, and later suspected in other bivalves. Designated M1-M4, these present very low fluorescence,
and can only be studied resorting to HILIC-MS. Three hydroxybenzoate analogues were characterised as an important toxin fraction
of the dinoflagellate Gymnodinium catenatum, and named GC1-GC3. Later, many more analogues were suspected: the corresponding N1-hydroxyl variants of GC1-GC3 (GC4-GC6),
di-hydroxybenzoate variants (GC1a-GC6a), and sulphate-benzoate variants (GC1b-GC6b). In bivalves, carbamoylase activity renders
these analogues into decarbamoyl analogues. Other compounds with PST-like characteristics have been detected in bivalves from
Angola, Argentina and Vietnam. Today, the range of naturally occurring STX derivatives, both in marine and freshwater environments,
accounts to more than fifty structural variants. This poses a problem for carrying out food safety analysis based solely in
chemical methods. Fortunately, most modifications to the side chain of the tetrahydropurine core result in diminished toxicity.
Content Type Journal Article
Pages 525-535
DOI 10.1007/s11101-010-9196-7
Authors
Paulo Vale, Instituto Nacional dos Recursos Biológicos/L-IPIMAR (INRB/L-IPIMAR), Av. Brasília, s/n, 1449-006 Lisbon, Portugal
Malaria, a pathology caused by protozoa belonging to the genus Plasmodium, is one of the major threats to global health, with about 300–500 million new clinical cases occurring every year and 1–3
million annual deaths. The recrudescence in the number of fatal cases registered in recent years can be attributed to the
diffusion of multi-drug resistant strains of Plasmodium, which make less effective the limited armamentarium of available drugs. Living organisms are a recognized source of potentially
bioactive molecules and, among them, marine natural products are emerging as one of the most interesting sources to be exploited
for the discovery of new antimalarial compounds. In this article we will report results obtained for a single class of marine
metabolites, namely endoperoxide-containing derivatives. Many of these molecules possess a simple six-membered 1,2-dioxygenated
ring bearing two or three alkyl/aryl groups of different complexity. They can be divided according to the group linked at
one of the two endoperoxide-oxygen bearing carbons: peroxyketal derivatives (methoxy group) or non-peroxyketal derivatives
(methyl/ethyl groups). Molecules belonging to these classes show in vitro antimalarial activity in the nanomolar range on
chloroquine-resistant strains. A number of investigations gave insights into the mechanism of action of these molecules, suggesting
structural changes to optimize their antimalarial activity.
Content Type Journal Article
Pages 515-524
DOI 10.1007/s11101-010-9197-6
Authors
Ernesto Fattorusso, Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli “Federico II”, Via D. Montesano, 49, 80131 Naples, Italy
Orazio Taglialatela-Scafati, Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli “Federico II”, Via D. Montesano, 49, 80131 Naples, Italy
Several theories have been developed to explain why invasive species are very successful and develop into pest species in
their new area. The shifting defence hypothesis (SDH) argues that invasive plant species quickly evolve towards new defence
levels in the invaded area because they lack their specialist herbivores but are still under attack by local (new) generalist
herbivores. The SDH predicts that plants should increase their cheap, toxic defence compounds and lower their expensive digestibility
reducing compounds. As a net result resources are saved that can be allocated to growth and reproduction giving these plants
a competitive edge over the local plant species. We conducted a literature study to test whether toxic defence compounds in
general are increased in the invaded area and if digestibility reducing compounds are lowered. We specifically studied the
levels of pyrrolizidine alkaloids, a toxin which is known for its beneficial and detrimental impact against specialists and
generalists, respectively. Digestibility reducers did not show a clear trend which might be due to the small number of studies
and traits measured. The meta analysis showed that toxic compounds in general and pyrrolizidine alkaloid levels specifically,
increased significantly in the invaded area, supporting the predictions of the SDH that a fast evolution takes place in the
allocation towards defence.
Content Type Journal Article
Pages 99-106
DOI 10.1007/s11101-010-9195-8
Authors
Leonie J. Doorduin, Ecology and Phytochemistry, Institute of Biology, Leiden University, PO Box 9505, 2300 RA Leiden, The Netherlands
Klaas Vrieling, Ecology and Phytochemistry, Institute of Biology, Leiden University, PO Box 9505, 2300 RA Leiden, The Netherlands
The diversity of secondary metabolites (SMs) has been poorly understood from both a mechanistic and a functional perspective.
Hybridization is suggested to contribute to the evolution of diversity of SMs. In this paper we discuss the effects of hybridization
on SMs and herbivore resistance by evaluating the literature and with special reference to our own research results from the
hybrids between Jacobaea vulgaris (syn. Senecio jacobaea) and Jacobaea aquatica (syn. Senecio aquaticus). We also review the possible genetic mechanism which causes the variation of SMs and herbivore resistance in hybrids. Most
SMs in hybrids are present in the parents as well. But hybrids may miss some parental SMs or have novel SMs. The concentration
of parental SMs in hybrids generally is constrained by that in parental plants, but transgressive expression was present in
some hybrids. Hybrids may be as susceptible (resistant) as the parents or more susceptible than the parents, but rarely more
resistant than the parents. However, different hybrid classes (F1, F2, backcrossing and mixed genotypes) show different patterns
in relation to herbivore resistance. The variation in SMs and herbivore resistance occurring in hybrids could be explained
by complicated genetic mechanisms rather than a simple one-gene model. Most previous work in this field only reported mean
trait values for hybrid classes and few studies focused on genotype differences within hybrid classes. Our study in Jacobaea hybrids showed transgressive segregation in most SMs and herbivore resistance. To summarize, our article shows that hybridization
may increase the variation of SMs and affect herbivore resistance, which may partially explain the evolution of chemical diversity
in plants.
Content Type Journal Article
Pages 107-117
DOI 10.1007/s11101-010-9194-9
Authors
Dandan Cheng, Plant Ecology and Phytochemistry Section, Institute of Biology, Leiden University, Sylviusweg 72, 2300 RA Leiden, The Netherlands
Klaas Vrieling, Plant Ecology and Phytochemistry Section, Institute of Biology, Leiden University, Sylviusweg 72, 2300 RA Leiden, The Netherlands
Peter G. L. Klinkhamer, Plant Ecology and Phytochemistry Section, Institute of Biology, Leiden University, Sylviusweg 72, 2300 RA Leiden, The Netherlands
Microorganisms are recognized worldwide as the major source of secondary metabolites with mega diverse structures and promissory
biological activities. However, as yet many of them remain little or under-explored like the microbiota from freshwater aquatic
ecosystems. In the present review, we undertook a recompilation of metabolites reported with pesticidal properties from microalgae
(cyanobacteria and green algae) and fungi, specifically from freshwater aquatic habitats.
Content Type Journal Article
Pages 261-286
DOI 10.1007/s11101-010-9192-y
Authors
Beatriz Hernández-Carlos, Instituto de Recursos, Universidad del Mar, Puerto Ángel, Oaxaca, 70902 México
M. Marcela Gamboa-Angulo, Centro de Investigación Científica de Yucatán, A.C., Unidad de Biotecnología, Calle 43 No. 130, Col. Chuburná, Mérida, Yucatán 97200, México
Pyrrolizidine alkaloids (PAs), mainly those with a 1,2-double bond in the necine base moiety (=1,2-dehydropyrrolizidines),
constitute a class of well studied compounds with respect to their flux through different trophic levels. Plants belonging
to various clades (e.g. Echiteae, Eupatorieae and Senecioneae, Boraginaceae, and Crotalarieae) biosynthesize PAs as N-oxides, generally in the roots, and transport them through the phloem to stems, leaves, and reproductive structures, where
they act as potent deterrents against non-specialist herbivores. On the other hand, PA specialist herbivores (mainly arctiid
moths, danaine and ithomiine butterflies, and some leaf beetles) have become able to overcome this chemical barrier, and to
sequester these alkaloids from their larval host plants or from sources visited by adults, such as flowers and dead or withered
plants. Specialists use PAs for their own benefit as chemical defence against a vast array of predators (e.g. ants, lacewings,
spiders, lizards, birds, and mammals), but some predators are able to feed on PA-insects, by avoiding or physiologically overcoming
PAs present in tissues of the ingested prey. Parasitoids may be affected by PAs, depending on their degree of specialization
in relation to PA-insects. Arctiidae, Danainae and Ithomiinae also use PAs as precursors of sexual pheromones. The effects
of PAs on trophic interactions have been intensely studied over the last four decades, but some open questions remain, and
are discussed, such as the underlying mechanisms that lead to PA diversification, activity of different PA structures, synergism
among PAs and other so-called defensive substances in PA-plants, and the ability to overcome this chemical barrier by predators
and parasitoids.
Content Type Journal Article
Pages 83-98
DOI 10.1007/s11101-010-9191-z
Authors
José Roberto Trigo, Laboratório de Ecologia Química, Departamento de Biologia Animal, Instituto de Biologia, Unicamp, CP 6109, Campinas, SP 13083-970, Brazil
Phytochemistry reviews: special issue on high altitude plants
Content Type Journal Article
Category Editorial
Pages 195-196
DOI 10.1007/s11101-010-9190-0
Authors
Franz Bucar, University of Graz Institute of Pharmaceutical Sciences Universitaetsplatz 4/1 8010 Graz Austria
Simon Gibbons, University of London Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy 29-39 Brunswick Square London WC1N 1AX UK
Biological activity of material whether known in folk medicine or observed in planned screening program has been the starting
point in the drug research. The general pattern is the isolation of active principles, elucidation their structures, followed
by attempts for modulation of its activity potential by chemical modification. Lichens are valuable plant resources and are
used as medicine, food, fodder, perfume, spice, dyes and for miscellaneous purposes throughout the world. Lichens are well
known for the diversity of secondary metabolites that they produce. Compounds isolated from various lichen species have been
reported to display diverse biological activities. Here we review the medicinal efficacy of lichen substances, which intends
to explore the pharmaceutical potential of lichen substances.
Content Type Journal Article
Pages 303-314
DOI 10.1007/s11101-010-9189-6
Authors
Vertika Shukla, Babasaheb Bhimrao Ambedkar (Central) University Department of Environmental Sciences Vidya Vihar, Raebareily Road Lucknow UP 226 025 India
Geeta Pant Joshi, H.N.B. Garhwal University Department of Chemistry Post Box 63 Srinagar Garhwal Uttarakhand 246 174 India
M. S. M. Rawat, H.N.B. Garhwal University Department of Chemistry Post Box 63 Srinagar Garhwal Uttarakhand 246 174 India
The aim of this review is to combine the knowledge of studies on effects of nutrients on pyrrolizidine alkaloids (PAs) in
Senecio with those studies of effects of PAs on herbivores and pathogens in order to predict the effects that nutrients may have
on herbivores and pathogens via changes in PAs. We discuss whether these predictions match with the outcome of studies where
the effect of nutrients on herbivores and insects were measured. PA concentrations in S. jacobaea, S. vulgaris and S. aquaticus were mostly reduced by NPK fertilization, with genotype-specific effects occurring. Plant organs varied in their response
to increased fertilization; PA concentrations in flowers remained constant, while shoot and roots were mostly negatively affected.
Biomass change is probably largely responsible for the change in concentrations. Nutrients affect both the variety and the
levels of PAs in the plant. The reduced PA concentrations after NPK fertilization was expected to benefit herbivores, but
no or negative responses from insect herbivores were observed. Apparently other changes in the plant after fertilization are
overriding the effect of PAs. Pathogens do seem to benefit from the lower PA concentrations after fertilization; they were
more detrimental to fertilized plants than to unfertilized control plants. Future studies should include the effect of each
element of nutrients separately and in combinations in order to gain more insight in the effect of specific nutrients on PA
content in Senecio plants.
Content Type Journal Article
Pages 119-126
DOI 10.1007/s11101-010-9188-7
Authors
W. H. G. Hol, Department of Terrestrial Ecology, Netherlands Institute of Ecology (NIOO-KNAW), Boterhoeksestraat 48, 6666 GA Heteren, The Netherlands
Saponins are natural glycosides which possess a wide range of pharmacological properties including cytotoxic activity. In
this review, the recent studies (2005–2009) concerning the cytotoxic activity of saponins have been summarized. The correlations
between the structure and the cytotoxicity of both steroid and triterpenoid saponins have been described as well as the most
common mechanisms of action.
Content Type Journal Article
Pages 425-474
DOI 10.1007/s11101-010-9183-z
Authors
Irma Podolak, Department of Pharmacognosy, Jagiellonian University, Medical College, Medyczna 9, 30-688 Cracow, Poland
Agnieszka Galanty, Department of Pharmacognosy, Jagiellonian University, Medical College, Medyczna 9, 30-688 Cracow, Poland
Danuta Sobolewska, Department of Pharmacognosy, Jagiellonian University, Medical College, Medyczna 9, 30-688 Cracow, Poland
Pentacyclic triterpenes are abundant in the plant kingdom and have a wide array of pharmacological activities. They also have
insect antifeedant effects and therefore apparently play a role in plant defense. In this paper, we describe the insecticidal
activity of pentacyclic triterpenes of plant origin from different chemical classes on several insect pests (Spodoptera littoralis, Leptinotarsa decemlineata and Myzus persicae), their phytotoxic properties and their selective cytotoxic effects on insect-derived Sf9 and mammalian CHO cells. We also
discuss the role they play in plant defense based on these activities.
Content Type Journal Article
Pages 245-260
DOI 10.1007/s11101-010-9187-8
Authors
Azucena González-Coloma, Instituto de Ciencias Agrarias-CCMA, CSIC, 28016 Madrid, Spain
Carmen López-Balboa, Instituto de Ciencias Agrarias-CCMA, CSIC, 28016 Madrid, Spain
Omar Santana, Instituto de Ciencias Agrarias-CCMA, CSIC, 28016 Madrid, Spain
Matías Reina, Instituto de Productos Naturales y Agrobiología, CSIC, 38206 La Laguna, Tenerife, Canary Islands, Spain
Braulio M. Fraga, Instituto de Productos Naturales y Agrobiología, CSIC, 38206 La Laguna, Tenerife, Canary Islands, Spain
Progress on a total synthesis of the marine natural products, the bryostatins, is reviewed. Following studies aimed at the
synthesis of the 1,16- and 17,27-fragments, procedures for the assembly of the macrocyclic ring of the bryostatins were investigated.
Although ring-closing metathesis was not found to be useful for the synthesis of bryostatins with geminal dimethyl groups
at C18, the modified Julia reaction was found to be useful for the stereoselective formation of the 16,17-double-bond and
led to a synthesis of an advanced macrocyclic intermediate. Several novel synthetic procedures feature in this work.
Content Type Journal Article
Pages 501-513
DOI 10.1007/s11101-010-9186-9
Authors
Anthony P. Green, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL UK
Simon Hardy, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL UK
Alan T. L. Lee, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL UK
Eric J. Thomas, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL UK
Palytoxins are a class of extremely potent non-proteic marine biotoxins, whose main biological target is the Na+/K+-ATPase. Since its isolation in 1971 from samples of Hawaiian Palythoa spp., palytoxin has drawn scientists’ attention from across the world because of its high toxicity, intriguing chemical structural
architecture, and involvement in fascinating ancient Hawaiian folklore. Palytoxins have recently spread also to more temperate
areas, such as the Mediterranean Sea causing severe human intoxications. Over the past years our scientific work has brought
to light the occurrence of new palytoxin analogs by extensive NMR investigation and a new liquid chromatography tandem mass
spectrometry method set up following the Mediterranean toxic outbreaks.
Content Type Journal Article
Pages 491-500
DOI 10.1007/s11101-010-9185-x
Authors
Patrizia Ciminiello, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131 Naples, Italy
Carmela Dell’Aversano, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131 Naples, Italy
Ernesto Fattorusso, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131 Naples, Italy
Martino Forino, Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131 Naples, Italy
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