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Phytochemistry - Verlag: Elsevier
'Phytochemistry' ist eine internationale Zeitschrift für reine und angewandte Chemie Pflanzenchemie, Pflanzenbiochemie und Molekularbiologie.
Publication year: 2012 Source: Phytochemistry, Available online 8 February 2012 Orapun Yodsaoue, Jarinthon Sonprasit, Chatchanok Karalai, Chanita Ponglimanont, Supinya Tewtrakul, ... Chemical investigation of the leaves of the oriental medicinal plantAglaia odorataresulted in the isolation of five compounds: two dolabellane diterpenoids, two dammarane triterpenoids and a protostane triterpenoid, along with twenty known compounds. Their structures were elucidated on the basis of extensive spectroscopic analysis and by comparison of their NMR spectroscopic data with those reported in the literature. The anti-inflammatory activities of all compounds were evaluated as inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Eleven compounds possessed potent nitric oxide inhibitory activity with IC50values ranging from 2.1 to 14.2 ?M, these being better than that of the positive control, indomethacin (IC50 = 14.5 ?M). In addition, three compounds exhibited significant activity against PGE2release with IC50values of 2.6, 16.1 and 23.0 ?M.
Graphical abstract
Chemical investigation of the leaves of the oriental medicinal plantAglaia odorataresulted in the isolation of five compounds: two dolabellane diterpenoids (1,2), two dammarane triterpenoids (6,7) and a protostane triterpenoid (8), along with twenty known compounds. Eleven compounds possessed inhibitory activities against LPS-induced NO production in RAW264.7 cell lines with IC50values ranging from 2.1 to 14.2 ?M). In addition three compounds exhibited significant activity against PGE2release with IC50values of 2.6, 16.1 and 23.0 ?M.
Highlights
? The leaves ofAglaia odoratawere investigated. ? Five compounds of dolabellane, dammarane and protostane classes were isolated. ? The compounds exhibited potential anti-inflammatory activity.
Publication year: 2012 Source: Phytochemistry, Available online 8 February 2012 Manuela E. García, Gloria E. Barboza, Juan C. Oberti, Carla Ríos-Luci, José M. Padrón, ... Three withanolides were isolated from the aerial parts ofJaborosa reflexaPhil.Jaborosa cabreraeBarboza yielded five sativolide withanolides (including jaborosalactones R, S, 38, and 39) and two trechonolide withanolides epimeric at C-23 (trechonolide A and jaborosalactone 32). In addition, five derivatives were obtained by chemical derivatization of jaborosalactone 38, and all compounds were fully characterized by 1D and 2D NMR spectroscopic studies. The in vitro antiproliferative activities of the major natural withanolides and the semisynthetic derivatives were examined against HBL-100, HeLa, SW1573, T-47D, and WiDr human solid tumor cancer cell lines. Some chemotaxonomic considerations are discussed.
Graphical abstract
Several withanolides were isolated and characterized fromJaborosa reflexaandJaborosa cabrerae. In addition, five derivatives were prepared using jaborosalactone 38 as precursor. The antiproliferative activities of natural and semisynthetic derivatives were evaluated against a panel of representative human solid tumor cell lines.
Highlights
? Nine withanolides were isolated fromJaborosa reflexaandJaborosa cabrerae. ? Chemotaxonomic considerations are discussed. ? Five semisynthetic derivatives were obtained. ? The in vitro antiproliferative activities of natural compounds and derivatives were evaluated. ? Structure–activity relationship analysis is consistent with previous studies.
Publication year: 2012 Source: Phytochemistry, Available online 7 February 2012 Abdallah Abu-Mellal, Nooshin Koolaji, Rujee K. Duke, Van H. Tran, Colin C. Duke A prenylated cinnamic acid derivative as well as six prenylated tetrahydroxystilbenes were isolated from the ethyl acetate extract of propolis that originated from Kangaroo Island, Australia. Furthermore, six known stilbenes and two known flavanones were also identified from the same sample. Stilbenes are not common in propolis; therefore, Kangaroo Island propolis is considered a unique type of propolis that is rich in prenylated stilbenes. Stilbene propolis from Kangaroo Island showed a stronger scavenging activity towards DPPH free radical than Brazilian green propolis. This strong activity can be explained by the presence of large number of stilbenes, most of them showed strong free radical scavenging activity.
Graphical abstract
One novel prenylated cinnamic acid derivative and six novel prenylated stilbenes were isolated from the ethyl acetate extract of Kangaroo Island propolis from Australia. The unique sample consisted of approximately 75% (excluding wax) of prenylated stilbenes most of them related to the tetrahydroxystilbene; piceatannol.
Highlights
? A novel cinnamic acid derivative and six novel prenylated stilbenes were isolated from Kangaroo Island propolis. ? Seventy five percent of the total phenolics of Kangaroo Island propolis were prenylated stilbenes. ? High level ofO- andC-prenylation were present in Kangaroo Island propolis. ? Kangaroo Island propolis showed a stronger DPPH free radical scavenging activity than Brazilian green propolis.
Publication year: 2012 Source: Phytochemistry, Available online 9 February 2012 Sheng-Li Niu, Zhan-Lin Li, Feng Ji, Gu-Yue Liu, Nan Zhao, ... Five xanthones, 1,4,5,6-tetrahydroxyxanthone (1) and bracteaxanthones III–VI (2–5) together with twenty-six known compounds (6–31), were isolated from the ethanol extract of the stem bark ofGarcinia bracteata. Their structures were elucidated via spectroscopic analyses. Growth inhibitory activities of these compounds against the human leukaemic HL-60 cell line were measuredin vitro. Compounds7,11, and29exhibited moderate activities with GI50values of 2.8, 3.4, and 3.1 ?M, respectively, and a preliminary structure–activity relationship is discussed.
Graphical abstract
Five new xanthones together with twenty-six known xanthones were isolated from the stem bark ofGarcinia bracteata. The growth inhibitory activities of these compounds were evaluated against human leukaemic HL-60 cell line.
Highlights
? Constituents of stem bark ofGarcinia bracteatawere investigated. ? Thirty one xanthones were isolated from the EtOH extract, five hitherto unknown. ? A hypothetical biosynthetic pathway linking1–4was presumed. ? The growth inhibitory activities of the isolated compounds were measuredin vitro. ? A preliminary structure–activity relationship was discussed.
Publication year: 2012 Source: Phytochemistry, Available online 7 February 2012 Abdallah Abu-Mellal, Nooshin Koolaji, Rujee K. Duke, Van H. Tran, Colin C. Duke A prenylated cinnamic acid derivative as well as six prenylated tetrahydroxystilbenes were isolated from the ethyl acetate extract of propolis that originated from Kangaroo Island, Australia. Furthermore, six known stilbenes and two known flavanones were also identified from the same sample. Stilbenes are not common in propolis; therefore, Kangaroo Island propolis is considered a unique type of propolis that is rich in prenylated stilbenes. Stilbene propolis from Kangaroo Island showed a stronger scavenging activity towards DPPH free radical than Brazilian green propolis. This strong activity can be explained by the presence of large number of stilbenes, most of them showed strong free radical scavenging activity.
Graphical abstract
One novel prenylated cinnamic acid derivative and six novel prenylated stilbenes were isolated from the ethyl acetate extract of Kangaroo Island propolis from Australia. The unique sample consisted of approximately 75% (excluding wax) of prenylated stilbenes most of them related to the tetrahydroxystilbene; piceatannol.
Highlights
? A novel cinnamic acid derivative and six novel prenylated stilbenes were isolated from Kangaroo Island propolis. ? Seventy five percent of the total phenolics of Kangaroo Island propolis were prenylated stilbenes. ? High level ofO- andC-prenylation were present in Kangaroo Island propolis. ? Kangaroo Island propolis showed a stronger DPPH free radical scavenging activity than Brazilian green propolis.
Publication year: 2012 Source: Phytochemistry, Available online 6 February 2012 Wirongrong Kaweetripob, Chulabhorn Mahidol, Vilailak Prachyawarakorn, Hunsa Prawat, Somsak Ruchirawat 5-Formylfurfuryl esters, duabanganals A–D, together with sixteen known compounds, a known 5-formylfurfuryl ester, latifolinal, eight pentacyclic triterpenes, a benzofuran derivative, an ellagic acid derivative, vanillin, ?-sitosterol, ?-sitosterol glucoside, 3-hydroxy-4-methoxycinnamaldehyde, and 5-formylfurfurol, were isolated from the stem bark ofDuabanga grandiflora. The structures of these compounds were elucidated on the basis of spectroscopic analysis. Several of these metabolites were evaluated for cytotoxic activities against six cancer cell lines.
? Isolation of 5-formylfurfuryl esters from stem bark ofDuabanga grandiflora. ? Rare naturally-occurring 5-formylfurfuryl esters. ? Twenty compounds were obtained from the stem bark ofD. grandiflora. ? These compounds could serve as a chemotaxonomic marker forDuabangagenus.
Publication year: 2012 Source: Phytochemistry, Available online 6 February 2012 Bruno Fedrizzi, Graziano Guella, Daniele Perenzoni, Mattia Gasperotti, Domenico Masuero, ... Yellow passion fruit is one of the most well-known tropical fruits and much of its success comes from its typical aroma. Key compounds in explaining yellow passion fruit scent are volatile thiols. These molecules are reported to be present in several fruits and originate from non-volatile precursors. Such free thiols are particularly appreciated in white wines and considerable efforts have been made to try to maximise their production and understand their biosynthesis.Two main precursors have been identified so far:S-glutathionylated andS-cysteinylated precursors, the latter originating in the breaking down of the glycyl and glutamyl moieties of the former. Improving knowledge about this pathway is currently one of the main challenges in the field of aroma chemistry.OnlyS-cysteinylated precursors have been reported in the literature for yellow passion fruit, thus much of the biochemical pathway remains unknown.In this paper a combination of organic synthesis, MS and NMR experiments was developed in order to investigate this pathway in yellow passion fruit. The three missing stages leading to theS-cysteinylated precursor were clearly identified. Both intermediate species betweenS-glutathionyl andS-cysteinyl 3-mercaptohexan-1-ol were found, suggesting that the plant is capable of activating both metabolic routes.The information gained would appear to be crucial for study of this important pathway and for potentially extending this knowledge to other plants, in particular the grapevine.
Graphical abstract
The identification of the missing steps inS-glutathionyl-3-mercaptohexan-1-ol degradation pathways leads to better understanding of the formation of the tropical aroma of yellow passion fruit.
Highlights
? New synthetic strategy for the preparation of Glu-Cys-3MH and Cys-Gly-3MH. ? The three missing stages leading to theS-cysteinylated precursor were identified. ? Two intermediates found betweenS-glutathionyl andS-cysteinyl 3-mercaptohexan-1-ol. ? Demonstrating that the plant is capable of activating both metabolic routes.
Publication year: 2012 Source: Phytochemistry, Available online 6 February 2012 Wirongrong Kaweetripob, Chulabhorn Mahidol, Vilailak Prachyawarakorn, Hunsa Prawat, Somsak Ruchirawat 5-Formylfurfuryl esters, duabanganals A–D, together with sixteen known compounds, a known 5-formylfurfuryl ester, latifolinal, eight pentacyclic triterpenes, a benzofuran derivative, an ellagic acid derivative, vanillin, ?-sitosterol, ?-sitosterol glucoside, 3-hydroxy-4-methoxycinnamaldehyde, and 5-formylfurfurol, were isolated from the stem bark ofDuabanga grandiflora. The structures of these compounds were elucidated on the basis of spectroscopic analysis. Several of these metabolites were evaluated for cytotoxic activities against six cancer cell lines.
? Isolation of 5-formylfurfuryl esters from stem bark ofDuabanga grandiflora. ? Rare naturally-occurring 5-formylfurfuryl esters. ? Twenty compounds were obtained from the stem bark ofD. grandiflora. ? These compounds could serve as a chemotaxonomic marker forDuabangagenus.
Publication year: 2012 Source: Phytochemistry, Available online 6 February 2012 Bruno Fedrizzi, Graziano Guella, Daniele Perenzoni, Mattia Gasperotti, Domenico Masuero, ... Yellow passion fruit is one of the most well-known tropical fruits and much of its success comes from its typical aroma. Key compounds in explaining yellow passion fruit scent are volatile thiols. These molecules are reported to be present in several fruits and originate from non-volatile precursors. Such free thiols are particularly appreciated in white wines and considerable efforts have been made to try to maximise their production and understand their biosynthesis.Two main precursors have been identified so far:S-glutathionylated andS-cysteinylated precursors, the latter originating in the breaking down of the glycyl and glutamyl moieties of the former. Improving knowledge about this pathway is currently one of the main challenges in the field of aroma chemistry.OnlyS-cysteinylated precursors have been reported in the literature for yellow passion fruit, thus much of the biochemical pathway remains unknown.In this paper a combination of organic synthesis, MS and NMR experiments was developed in order to investigate this pathway in yellow passion fruit. The three missing stages leading to theS-cysteinylated precursor were clearly identified. Both intermediate species betweenS-glutathionyl andS-cysteinyl 3-mercaptohexan-1-ol were found, suggesting that the plant is capable of activating both metabolic routes.The information gained would appear to be crucial for study of this important pathway and for potentially extending this knowledge to other plants, in particular the grapevine.
Graphical abstract
The identification of the missing steps inS-glutathionyl-3-mercaptohexan-1-ol degradation pathways leads to better understanding of the formation of the tropical aroma of yellow passion fruit.
Highlights
? New synthetic strategy for the preparation of Glu-Cys-3MH and Cys-Gly-3MH. ? The three missing stages leading to theS-cysteinylated precursor were identified. ? Two intermediates found betweenS-glutathionyl andS-cysteinyl 3-mercaptohexan-1-ol. ? Demonstrating that the plant is capable of activating both metabolic routes.
Publication year: 2012 Source: Phytochemistry, Available online 6 February 2012 Elisabetta Stringano, Christine Hayot Carbonero, Lydia M.J. Smith, Ronald H. Brown, Irene Mueller-Harvey This study investigated 37 diverse sainfoin (Onobrychis viciifoliaScop.) accessions from the EU ‘HealthyHay’ germplasm collection for proanthocyanidin (PA) content and composition. Accessions displayed a wide range of differences: PA contents varied from 0.57 to 2.80 g/100 g sainfoin; the mean degree of polymerisation from 12 to 84; the proportion of prodelphinidin tannins from 53% to 95%, and the proportion oftrans-flavanol units from 12% to 34%. A positive correlation was found between PA contents (thiolyticversusacid–butanol degradation;P < 0.001;R = 0.49). A negative correlation existed between PA content (thiolysis) and mDP (P < 0.05;R = ?0.30), which suggested that accessions with high PA contents had smaller PA polymers. Cluster analysis revealed that European accessions clustered into two main groups: Western Europe and Eastern Europe/Asia. In addition, accessions from USA, Canada and Armenia tended to cluster together. Overall, there was broad agreement between tannin clusters and clusters that were based on morphological and agronomic characteristics.
Graphical abstract
A worldwideOnobrychis viciifoliagermplasm collection was screened for proanthocyanidin (PA) content and composition by thiolysis. PA traits clustered into W. European, E. European/Asian and N. American groups and mirrored the morphological and agronomic clusters. The observed, large variation will enable optimising cultivars for nutritional, environmental and veterinary properties.
Highlights
? Proanthocyanidin contents varied 5-fold amongst diverse sainfoin accessions. ? Mean polymer size varied 7-fold. ? Prodelphinidins ranged from 53% to 95% andtrans-flavanols from 12% to 34%. ? PA traits generated W. European, E. European/Asian and N. American clusters. ? Clusters based on PA traits resembled those based on morphological traits.
Publication year: 2012 Source: Phytochemistry, Available online 30 January 2012 Dolores Asensio, Francesca Rapparini, Josep Peñuelas Previous studies have shown that root colonization by arbuscular mycorrhiza (AM) fungi enhances plant resistance to abiotic and biotic stressors and finally plant growth. However, little is known about the effect of AM on isoprenoid foliar and root content. In this study we tested whether the AM symbiosis affects carbon resource allocation to different classes of isoprenoids such as the volatile nonessential isoprenoids (monoterpenes and sesquiterpenes) and the non-volatile essential isoprenoids (abscisic acid, chlorophylls and carotenoids). By subjecting the plants to stressors such as drought and to exogenous application of JA, we wanted to test their interaction with AM symbiosis in conditions where isoprenoids usually play a role in resistance to stress and in plant defence. Root colonization by AM fungi favoured the leaf production of essential isoprenoids rather than nonessential ones, especially under drought stress conditions or after JA application. The increased carbon demand brought on by AM fungi might thus influence not only the amount of carbon allocated to isoprenoids, but also the carbon partitioning between the different classes of isoprenoids, thus explaining the not previously shown decrease of root volatile isoprenoids in AM plants. We propose that since AM fungi are a nutrient source for the plant, other carbon sinks normally necessary to increase nutrient uptake can be avoided and therefore the plant can devote more resources to synthesize essential isoprenoids for plant growth.
Graphical abstract
Increased carbon demand brought on by AM fungi affected carbon allocation and partitioning between the different classes of isoprenoids. Carbon resources in AM plants were diverted to carotenoids and chlorophylls which serve base plant functions, instead of volatile isoprenoids like mono- and sesquiterpenes, especially under stress conditions.
Highlights
? We analyze the effects of AM symbiosis on plant isoprenoids production. ? AM symbiosis favoured the production of leaf essential isoprenoids. ? AM fungi root colonization caused a decrease in the root isoprenoid content. ? Drought stress and jasmonic acid application affected plant isoprenoid production. ? Overall, these effects might depend on different partitioning between isoprenoids.
Publication year: 2012 Source: Phytochemistry, Available online 30 January 2012 Dolores Asensio, Francesca Rapparini, Josep Peñuelas Previous studies have shown that root colonization by arbuscular mycorrhiza (AM) fungi enhances plant resistance to abiotic and biotic stressors and finally plant growth. However, little is known about the effect of AM on isoprenoid foliar and root content. In this study we tested whether the AM symbiosis affects carbon resource allocation to different classes of isoprenoids such as the volatile nonessential isoprenoids (monoterpenes and sesquiterpenes) and the non-volatile essential isoprenoids (abscisic acid, chlorophylls and carotenoids). By subjecting the plants to stressors such as drought and to exogenous application of JA, we wanted to test their interaction with AM symbiosis in conditions where isoprenoids usually play a role in resistance to stress and in plant defence. Root colonization by AM fungi favoured the leaf production of essential isoprenoids rather than nonessential ones, especially under drought stress conditions or after JA application. The increased carbon demand brought on by AM fungi might thus influence not only the amount of carbon allocated to isoprenoids, but also the carbon partitioning between the different classes of isoprenoids, thus explaining the not previously shown decrease of root volatile isoprenoids in AM plants. We propose that since AM fungi are a nutrient source for the plant, other carbon sinks normally necessary to increase nutrient uptake can be avoided and therefore the plant can devote more resources to synthesize essential isoprenoids for plant growth.
Graphical abstract
Increased carbon demand brought on by AM fungi affected carbon allocation and partitioning between the different classes of isoprenoids. Carbon resources in AM plants were diverted to carotenoids and chlorophylls which serve base plant functions, instead of volatile isoprenoids like mono- and sesquiterpenes, especially under stress conditions.
Highlights
? We analyze the effects of AM symbiosis on plant isoprenoids production. ? AM symbiosis favoured the production of leaf essential isoprenoids. ? AM fungi root colonization caused a decrease in the root isoprenoid content. ? Drought stress and jasmonic acid application affected plant isoprenoid production. ? Overall, these effects might depend on different partitioning between isoprenoids.
Publication year: 2012 Source: Phytochemistry, Available online 28 January 2012 Vanessa G.P. Severino, Patrícia A.C. Braga, Maria Fátima das G.F. da Silva, João B. Fernandes, Paulo C. Vieira, ... The dichloromethane extract from taproots ofHortia oreadicaafforded six limonoids, these are 9,11-dehydro-12?-acetoxyhortiolide A, hortiolide C, 11?-acetoxy-15-deoxy-6-hydroxyhortiolide C, hortiolide D, hortiolide E, 12?-hydroxyhortiolide E, in addition to the known limonoid, guyanin. The dichloromethane extract from stems ofH. oreadicaalso afforded two limonoids 9,11-dehydro-12?-hydroxyhortiolide A and 6-hydroxyhortiolide C. As a result of this study and literature data,Hortiahas been shown to produce highly specialized limonoids that are similar to those from theFlindersia(Flindersioideae). The taxonomy ofHortiahas been debatable, with most authors placing it in the Toddalioideae. Considering the complexity of the isolated limonoids,Hortiadoes not show any close affinity to the genera of Toddalioideae. That is, the limonoids appear to be of little value in resolving the taxonomic situation ofHortia.
Graphical abstract
A study ofHortia oreadicaafforded nine limonoids, whose chemosystematic significance is discussed.
Highlights
? Limonoids of unprecedented structural type were isolated. ? Limonoids were isolated, and their chemotaxonomical significance is discussed. ? Cyclopropanelimonoids were isolated fromHortia oreadica. ? Spirolimonoids were isolated fromH. oreadica. ? The biogenesis of cyclopropane- and spirolimonoids is discussed.
Publication year: 2012 Source: Phytochemistry, Available online 27 January 2012 Duy Hoang Le, Yukiko Takenaka, Nobuo Hamada, Takao Tanahashi Spore-derived mycobionts of the crustose lichenSarcographa tricosawere cultivated on a malt-yeast extract medium supplemented with 10% sucrose. Chemical investigation of the cultivated colonies led to isolation of three eremophilane-type sesquiterpenes, 3-epi-petasol (1), dihydropetasol (2) and sarcographol (3), together with six known eremophilanes and ergosterol peroxide. These structures were elucidated by spectroscopic and chemical methods. This is the first report of eremophilane-type sesquiterpenes from the cultured mycobionts of lichen.
Graphical abstract
Spore-derived mycobionts of the crustose lichenSarcographa tricosawere cultivated on a malt-yeast extract medium supplemented with 10% sucrose. Chemical investigation of the cultivated colonies led to isolation of three eremophilane-type sesquiterpenes, 3-epi-petasol (1), dihydropetasol (2) and sarcographol (3)as well as six known eremophilanes and ergosterol peroxide. Their structures were determined by spectroscopic and chemical methods.
Highlights
? Spore-derived mycobionts of the Vietnamese lichenSarcographa tricosawere cultivated. ? Eremophilane-type sesquiterpenes were isolated from the cultures and their structures were determined. ? This is the first instance of isolation of eremophilane-type sesquiterpenes from lichen mycobionts in culture.
Publication year: 2012 Source: Phytochemistry, Available online 27 January 2012 In A Kim, Bong-Gyu Kim, Mihyang Kim, Joong-Hoon Ahn Hydroxycinnamoyltransferases (HCTs) catalyze the transfer of the cinnamoyl moiety from hydroxycinnamoyl-CoA to various acceptors such as shikimic acid, quinic acid, hydroxylated acid, and glycerol. Four rice HCT homologues (OsHCT1–4) to tobacco HST were cloned, andOsHCT4was expressed inEscherichia colias a glutathioneS-transferase fusion protein. Using the purified recombinant protein and biotransformation techniques, whether OsHCT4 shows hydroxycinnamoyltransferase activity with a variety of acyl group acceptors was investigated. The results of high performance liquid chromatography (HPLC) and mass spectrometry (MS) established that OsHCT4 mediated the trans-esterification of glycerol as well as shikimic acid in the presence of hydroxycinnamoyl-CoA. The structure of the reaction product was determined using nuclear magnetic resonance spectroscopy (NMR).E. colicells co-expressing4CL(4-coumarate:coenzyme A ligase) andOsHCT4convertedp-coumaric acid, ferulic acid, and caffeic acid into the corresponding glycerides. While this conversion is very efficientin vitro, the physiological significant in rice is currently unknown.
Graphical abstract
In vitroassays of OsHCT4 fromOryza sativaestablished that OsHCT4 can efficiently catalyze a transferase reaction using various hydroxycinnamoyl-CoAs, glycerol, and shikimic acid. UsingEscherichia coliharboringOsHCT4and4CL(4-coumarate:coenzyme A ligase), hydroxycinnamoyl glycerols are synthesized. The physiological significance is currently unknown.
Highlights
?OsHCT4was cloned and expressed inEscherichia coli. ? OsHCT4 is proposed to belong to a hitherto unknown class of HCT. ? OsHCT4 uses glycerol as well as shikimic acid as a acyl acceptor. ? UsingE. coliharboringOsHCT4and4CL, hydroxycinnamoyl glycerols were synthesized.
Publication year: 2012 Source: Phytochemistry, Available online 26 January 2012 Jun-Ling Li, Qian-Qian Chen, Qiu-Ping Jin, Juan Gao, Pei-Ji Zhao, ... The traditional Chinese medicinal plant,IsodonL., is remarkably rich in pharmacologically activeent-kaurane diterpenoids of diverse carbon skeletons. In an effort to create a resource for gene discovery and elucidate the biosynthesis ofIsodonent-kaurane diterpenoids, three cDNAs (namedIeCPS1,IeCPS2andIeCPS2a) were isolated putatively encoding copalyl diphosphate synthases fromIsodoneriocalyxleaves. Recombinant proteins ofIeCPS1andIeCPS2were expressed, respectively, inEscherichia coli, and were shown to specifically convert geranylgeranyl diphosphate to copalyl diphosphate as demonstrated by GC–MS analyses. Based on tissue-specific expression and metabolic localization studies, theIeCPS2transcripts were detected in young and mature leaves where the dominantent-kaurane diterpenoid maoecrystal B accumulates, whereas no detectable expression ofIeCPS2was observed in germinating seeds where the gibberellin biosynthetic pathway is usually active. In addition, no evidence for maoecrystal B was found in germinating seeds. On the other hand,IeCPS1transcripts significantly accumulated in germinating seeds as well as in leaves. The biochemical and molecular genetic evidence thus indicated that IeCPS2 is a copalyl diphosphate synthase potentially involved in the biosynthesis ofIsodonditerpenoids in leaves, whileIeCPS1is more probably relevant to gibberellin formation and may, in addition, participate inIsodonent-kaurane diterpenoid production.
Graphical abstract
Recombinant IeCPS2 converts geranylgeranyl diphosphate to copalyl diphosphate.IeCPS2expression occurs inIsodon eriocalyxleaves whereent-kaurane diterpenoids accumulate, this being considered highly relevant to the biosynthesis ofIsodon ent-kauranoids.
Highlights
? Three cDNAs fromI.eriocalyxleaves putatively encoded copalyl diphosphate synthases. ? Recombinant IeCPSs convert geranylgeranyl diphosphate to copalyl diphosphate.? IeCPS2expression occurs in leaves, whereIsodonent-kaurane diterpenoids accumulate. ? Germinating seeds have neither detectableIeCPS2transcripts norIsodonditerpenoids.? IeCPS1is expressed in germinating seeds as well as in leaves.
Publication year: 2012 Source: Phytochemistry, Available online 25 January 2012 Stefan Tresch, Monika Heilmann, Nicole Christiansen, Ralf Looser, Klaus Grossmann The trifluoromethanesulphonanilides mefluidide and perfluidone are used in agriculture as plant growth regulators and herbicides. Despite the fact that mefluidide and perfluidone have been investigated experimentally for decades, their mode of action is still unknown. In this study, we used a cascade approach of different methods to clarify the mode of action and target site of mefluidide and perfluidone. Physiological profiling using an array of biotests and metabolic profiling in treated plants ofLemna paucicostatasuggested a common mode of action in very-long-chain fatty acid (VLCFA) synthesis similar to the known 3-ketoacyl-CoA synthase (KCS) inhibitor metazachlor. Detailed analysis of fatty acid composition inLemnaplants showed a decrease of saturated VLCFAs after treatment with mefluidide and perfluidone. To study compound effects on enzyme level, recombinant KCSs fromArabidopsis thalianawere expressed inSaccharomyces cerevisiae. Enzyme activities of seven KCS proteins from 17 tested were characterized by their fatty acid substrate and product spectrum. For the KCS CER6, the VLCFA product spectrumin vivo, which consists of tetracosanoic acid, hexacosanoic acid and octacosanoic acid, is reported here for the first time. Similar to metazachlor, mefluidide and perfluidone were able to inhibit KCS1, CER6 and CER60 enzyme activitiesin vivo. FAE1 and KCS2 were inhibited by mefluidide only slightly, whereas metazachlor and perfluidone were strong inhibitors of these enzymes with IC50values in ?M range. This suggests that KCS enzymes in VLCFA synthesis are the primary herbicide target of mefluidide and perfluidone.
Graphical abstract
We found that the plant growth-regulating and herbicidal activity of mefluidide or perfluidone is primarily based on the inhibition of distinct KCS isoenzymes in VLCFA synthesis.
Highlights
? The mode of action of mefluidide and perfluidone was studied. ? Physiological and metabolic profiling indicate a primary MoA in VLCFA biosynthesis. ? We have expressed seven active 3-ketoacyl-CoA synthases in anin vivoyeast system. ? Mefluidide and perfluidone inhibit KCS activity in the micro molar range. ? The AtCER6 protein is highly sensitive to compound inhibition.
Publication year: 2012 Source: Phytochemistry, Available online 24 January 2012 Jürgen Breitenbach, Paul D. Fraser, Gerhard Sandmann Carotenoid formation was investigated in wild type and carotenogenic mutants ofBlakeslea trisporaafter mating (?) and (+) strains. The highest yields of carotenoids, especially ?-carotene was observed following mating.In vitroincorporation of geranylgeranyl pyrophosphate into phytoene and ?-carotene corresponded to increased carotenogenesis in the mated strains. Immuno determination of phytoene synthase protein levels revealed that the amounts of this enzyme is concurrent with the increases in carotenoid content. In fungi, phytoene synthase together with lycopene cyclase are encoded by a fusion genecrtYBorcarRAwith two individual domains. These domains were both heterologously expressed in an independent manner and antisera raised against both. These antisera were used, to assess protein levels in mated and non-matedB. trispora. The phytoene synthase domain was detected as an individual soluble protein with a molecular weight of 40 kDa and the lycopene cyclase an individual protein of mass about 30 kDa present in the membrane fraction following sub-cellular fractionation. This result demonstrates a post-translational cleavage of the protein transcribed from a single mRNA into independent functional phytoene synthase and lycopene cyclase.
Graphical abstract
The formation of ?-carotene inBlakeslea trisporais strongly enhanced upon mating of (+) and (?) strains.
Highlights
? Mating of wild type and mutants for high carotene synthesis. ? Correlation ofin vitroincorporation of geranylgeranyl pyrophosphate. ? Levels of phytoene synthase correspond to the degree of carotenogenesis. ? Post-translational cleavage of the phytoene synthase/lycopene cylase fusion protein. ? Immuno detection of individual domains after sub-cellular fractionation.
Publication year: 2012 Source: Phytochemistry, Available online 24 January 2012 Mariana Gil, Mariela Pontin, Federico Berli, Rubén Bottini, Patricia Piccoli This study investigated the terpene profiles as determined by GC–EIMS analysis ofin vitrocultured plants ofVitis viniferaexposed to a “field-like” dose of UV-B (4.75 kJ m d) administered at two different fluence rates (low, 16 h at 8.25 ?W cm, and high 4 h at 33 ?W cm). Low UV-B treatment increased levels of the membrane-related triterpenes sitosterol, stigmasterol and lupeol, more notable in young leaves, suggesting elicitation of a mechanism for grapevine acclimation. By contrast, accumulation of compounds with antioxidant properties, diterpenes ? and ? tocopherol and phytol, the sesquiterpene E-nerolidol and the monoterpenes carene, ?-pinene and terpinolene had maximum accumulation under high UV-B, which was accentuated in mature leaves. Also the levels of the sesquiterpenic stress-related hormone abscisic acid (ABA) increased under high UV-B, although 24 h post irradiation ABA concentrations decreased. Such increments of antioxidant terpenes along with ABA suggest elicitation of mechanism of defense. The adaptative responses induced by relatively low UV-B irradiations as suggested by synthesis of terpenes related with membrane stability correlated with augments in terpene synthase activity.
Graphical abstract
Grape responds to low intensity UV-B by increasing membrane-related triterpenes (1) suggesting acclimation, while under high UV-B treatment they accumulated terpenes with antioxidant properties (2), and the stress-hormone ABA (3), suggesting mechanisms of defense.
Highlights
? We investigated terpenes in grapevines exposed to UV at low and high intensities. ? Low UV-B augmented membrane triterpenes suggesting a mechanism of acclimation. ? High UV-B increased antioxidant terpenes and ABA suggesting mechanism of defense.
Publication year: 2012 Source: Phytochemistry, Available online 24 January 2012 Martine Kos, Benyamin Houshyani, Rafal Wietsma, Patrick Kabouw, Louise E.M. Vet, ... Glucosinolates (GLS) are secondary plant metabolites that as a result of tissue damage, for example due to herbivory, are hydrolysed into toxic compounds that negatively affect generalist herbivores. Specialist herbivores have evolved specific adaptations to detoxify GLS or inhibit the formation of toxic hydrolytic products. Although rarely studied, GLS and their breakdown products may also affect parasitoids. The objectives were to test the effects of GLS in a multitrophic system consisting of the generalist herbivoreSpodoptera exigua, the specialist herbivorePieris rapae, and the endoparasitoidHyposoter ebeninus. Three ecotypes ofArabidopsis thalianathat differ in their GLS composition and concentrations and one transformed line that constitutively produces higher concentrations of aliphatic GLS were used, the latter allowing a direct assessment of the effects of aliphatic GLS on insect performance.Feeding by the generalistS. exiguaand the specialistP. rapaeinduced both higher aliphatic and indole GLS concentrations in theA. thalianaecotypes, although induction was stronger for indole than aliphatic GLS. For both herbivores a negative correlation between performance and aliphatic GLS concentrations was observed. This suggests that the specialist, despite containing a nitrile-specifier protein (NSP) that diverts GLS degradation from toxic isothiocyanates to less toxic nitriles, cannot completely inhibit the formation of toxic GLS hydrolytic products, or that the costs of this mechanism are higher at higher GLS concentrations. Surprisingly, performance of the parasitoid was positively correlated with higher concentrations of aliphatic GLS in the plant, possibly caused by negative effects on host immune responses. Our study indicates that GLS can not only confer resistance against herbivores directly, but also indirectly by increasing the performance of the parasitoids of these herbivores.
Graphical abstract
Our study documents a dual defensive role of glucosinolates: glucosinolates conferred resistance against herbivores directly, and indirectly by increasing the performance of their parasitoids.
Highlights
? Effects of glucosinolates on herbivores and parasitoids. ? Negative correlation of glucosinolates with performance of a generalist herbivore. ? Similar result with a specialist herbivore, despite detoxification mechanism. ? Positive correlation with parasitoid performance, perhaps due to host immune system. ? Our study documents a dual defensive role of glucosinolates.
Publication year: 2012 Source: Phytochemistry, Available online 24 January 2012 Bina Shaheen Siddiqui, Nasima Khatoon, Sabira Begum, Ahsana Dar Farooq, Kehkashan Qamar, ... A pentacyclic triterpene, oleanderocioic acid, two flavonoidal glycosides, quercetin-5-O-[?-l-rhamnopyranosyl-(1 ? 6)]-?-d-glucopyranoside and kaempferol-5-O-[?-l-rhamnopyranosyl-(1 ? 6)-?-d-glucopyranoside, and a cardenolide, oleandigoside, together with 11 known compounds, were isolated from the leaves ofNerium oleander. Their structures were elucidated on the basis of spectroscopic analysis. The growth inhibitory and cytotoxic activities of eight compounds were evaluated against the MCF-7 human breast cancer cell line using a sulforhodamine B assay. Three compounds, oleandrin, odoroside A and B were further assayed using a panel of 57 human cancer cell lines.
Graphical abstract
A triterpene (1), two flavonoidal glycosides (2and3), a cardenolide (4), and 11 known compounds, were isolated fromNerium oleanderleaves (Apocynaceae). Eight compounds were evaluated against the MCF-7 human breast cancer cell line. Three compounds were further assayed using a panel of 57 human cancer cell lines.
Highlights
? Isolation of flavonoids, triterpenes and cardenolides fromNerium oleanderleaves.? Structure elucidation by TOFESIMS and 1D and 2D NMR spectroscopy. ? Cytotoxicity assays of adynerin, oleandrin, odoroside A and B against MCF-7 cells. ? Evaluation of oleandrin, odoroside A and B against 57 cell lines of human cancer. ? First report of cytotoxicity of oleandrin, odoroside A and B against 57 cell lines.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Rui Feng, Zhi Kai Guo, Chun Min Yan, Er Guang Li, Ren Xiang Tan, ... Six flavonoids named cryptogiones A–F, and nine known compounds were isolated from an ethanol extract of stems ofCryptocaryachingii. The structures of the compounds were elucidated by interpretation of comprehensive spectroscopic data and X-ray analysis. A majority of these flavonoids contained an acetic acid/lactone moiety, a possible taxonomic marker. Anti-inflammatory effects of the compounds were evaluated using in vitro assays. At 20 ?M concentration, three compounds significantly inhibited TNF?-induced NF-?B activation and LPS-induced IL-1? expression.
Graphical abstract
Six new flavonoids, cryptoginone A–F, together with nine known compounds were isolated from the ethanol extract of stems ofCryptocaryachingii. Compounds 7–9 showed significant anti-inflammatory activities at 20 ?M.
Highlights
? The phytochemical constituents ofCryptocaryachingiihave been investigated. ? Six flavonoids and 9 known compounds have been isolated. ? An acetic acid/lactone moiety in the majority of the compounds can be a possible taxonomic marker. ? The anti-inflammatory effects of the compounds have been evaluated. ? Three compounds show activity against TNF and LPS induced proinflammatory responses.
Publication year: 2012 Source: Phytochemistry, Available online 24 January 2012 Sawangjitt Wittayalai, Supaporn Sathalalai, Sakornrat Thorroad, Prateep Worawittayanon, Somsak Ruchirawat, ... Lycopodium serratene triterpenoids, along with an abietane-type diterpene were isolated from methanol extract of club mossLycopodium phlegmariaL. The structures of these hitherto unknown lycopodium terpenoids were elucidated on the basis of spectroscopic analysis. Pentacyclic triterpenoids, 21?-hydroxy-serrat-14-en-3?-ol (1) and 21?-hydroxy-serrat-14-en-3?-yl acetate (2) were isolated together with four serratene triterpeneoids established as 21?,29-dihydroxyserrat-14-en-3?-yl dihydrocaffeate (lycophlegmariol A,5), 21?,24,29-trihydroxyserrat-14-en-3?-yl dihydrocaffeate (lycophlegmariol B,6), 21?,24-dihydroxyserrat-14-en-3?-yl 4-hydroxycinnamate (lycophlegmariol C,7), and 14?,21?,29-trihydroxyserratan-3?-yl dihydrocaffeate (lycophlegmariol D,8) as well as a known lycophlegmarin (9). An abietane-type diterpene, 8,11,13-abietatriene-3?,12-dihydroxy-7-one (margocilin,10), was isolated for the first time from aLycopodiumplant. Lycophlegmariol B (6), D (8) and compound1showed inhibitory effects against MOLT-3 acute lymphoblastic leukemia (T-lymphoblast) with IC50of 14.7, 3.0 and 2.9 ?M, respectively.
Graphical abstract
Investigation of the MeOH extract ofLycopodium phlegmariaL. led to isolation of four (along with three known) lycopodium serratene triterpenes with anticancer activity.
Highlights
? Lycopodium serratene triterpenes, lycophlegmariols A–D, were isolated fromLycopodium phlegmariaL. ? This is the first report of an abietane diterpene, margocilin, isolated from Lycopodiaceae. ? The isolates showed anticancer activity, lymphoblastic leukemia (T-lymphoblast).
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Yuttana Sudjaroen, William E. Hull, Gerhard Erben, Gerd Würtele, Supranee Changbumrung, ... Longan (Dimocarpus longanLour, syn.Euphoria longanLam.) represents an important fruit in Northern Thailand and has significant economic impact. The fruit is either consumed fresh or as commercially prepared dried and canned products. The canning industry in Thailand produces considerable quantities of waste products, in particular Longan seeds. Because these seeds may be an exploitable source of natural phenolic antioxidants, it was of interest to identify, purify and quantitate the major potential antioxidant phenolics contained therein. The polyphenolic fraction from ground Longan seeds was obtained by extraction with methanol after delipidation with hexane. The hexane extract contained predominantly long-chain fatty acids with major contributions from palmitic (35%) and oleic (28%) acids. The polyphenolic fraction (80.90 g/kg dry weight) was dominated by ellagic acid (25.84 g/kg) and the known ellagitannins corilagin (13.31 g/kg), chebulagic acid (13.06 g/kg), ellagic acid 4-O-?-l-arabinofuranoside (9.93 g/kg), isomallotinic acid (8.56 g/kg) and geraniin (5.79 g/kg). Structure elucidation was performed with mass spectrometry and complete assignment ofH andC NMR signals. The methanol extracts exhibited strong antioxidant capacities with an IC50of 154 ?g/ml for reactive oxygen species attack on salicylic acid and 78 ?g/ml for inhibition of xanthine oxidase in the hypoxanthine/xanthine oxidase assay. The extracts were less effective in the 2-deoxyguanosine assay (IC50 = 2.46 mg/ml), indicating that gallates along with ellagic acid and its congeners exert their potential antioxidant effects predominantly by precipitation of proteins such as xanthine oxidase. This was confirmed for the pure compounds gallic acid, methyl gallate, ellagic acid and corilagin.
Graphical abstract
The major polyphenolic antioxidant components of Longan seeds are identified as corilagin, chebulagic acid, isomallotinic acid and geraniin.
Highlights
? This is a comprehensive report of phenolic compounds present in Longan seeds. ? Phenolic compounds were identified by HPLC–ESI-MS, nano-ESI-MS–MS and NMR (600 MHz). ? Complete and unequivocal NMR data is presented for the purified major components. ? The extracts and purified phenolic compounds displayed strong antioxidant activity.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Jie-Qing Liu, Cui-Fang Wang, Yan Li, Jian-Chao Chen, Lin Zhou, ... Twelve limonoids, toonayunnanins A–L (1–12) and eleven known compounds (13–23) were isolated from the leaves ofToona ciliatavar.yunnanensis, and their structures were elucidated by means of extensive spectroscopic analyses, particularly 1D and 2D NMR techniques. The inhibitory effects of all the isolated compounds were evaluated on human tumor cell lines, such as HL-60, SMMC-7721, A-549, MCF-7 and SW480. Cedrelone (13) and dysobinin (18) showed significant cytotoxicity, and toonayunnanin B (2) and epoxyazadiradione (14), were found to be slightly cytotoxic against the above cell lines. Furthermore, this study provides valuable information for the chemotaxonomy ofT. ciliatavarieties.
Graphical abstract
Limonoids, toonayunnanins A–L and eleven known compounds (13–23) were isolated from leaves ofToona ciliatavar.yunnanensis, and the cytotoxicity of all isolated compounds were evaluated. Cedrelone and dysobinin were cytotoxic, whereas toonayunnin B are epoxyazadiradione were slightly cytotoxic against the cell lines studied.
Highlights
? Twenty-three triterpenoids were identified, among them, twelve were previously unknown. ? Among the isolates, four compounds showed cytotoxic activities. ? A possible biogenetic pathway was discussed.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Jun-Li Yang, Yan-Ping Shi Cycloartane-type triterpenoids (1–3), seven sesquiterpenoids (7–13), and five previously reported secondary metabolites, including three cycloartane-type triterpenoids (4–6) and two sesquiterpenoids (14and15), were isolated from the resinous exudates ofCommiphora opobalsamum. Their structures were elucidated by extensive spectroscopic analysis, including UV, IR, NMR, and MS, and comparison with literature data. The structures of1,3, and7were confirmed by single-crystal X-ray diffraction analysis. The absolute configuration of1was interpreted by the incorporation of CHCl3(crystallization solvent) in the crystal and that of10was determined by the CD exciton chirality method. Compound12represents the first example of a 12-norcadinane-type sesquiterpenoid. Furthermore, compounds1,3,7, and10–14were evaluated for cytotoxicity against HeLa and HepG2 cell lines.
Graphical abstract
Ten triterpenoids and sesquiterpenoids were isolated fromCommiphora opobalsamum. Structures of1,3, and7were confirmed by single-crystal X-ray diffraction analysis, and the absolute configurations of1and10were also determined.
Highlights
? Ten new triterpenoids and sesquiterpenoids were isolated and identified. ? Three of their structures were confirmed by X-ray diffraction analysis. ? The absolute configurations of two were also determined. ? The cytotoxicity of selected isolates was evaluated.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Jie-Qing Liu, Cui-Fang Wang, Yan Li, Jian-Chao Chen, Lin Zhou, ... Twelve limonoids, toonayunnanins A–L (1–12) and eleven known compounds (13–23) were isolated from the leaves ofToona ciliatavar.yunnanensis, and their structures were elucidated by means of extensive spectroscopic analyses, particularly 1D and 2D NMR techniques. The inhibitory effects of all the isolated compounds were evaluated on human tumor cell lines, such as HL-60, SMMC-7721, A-549, MCF-7 and SW480. Cedrelone (13) and dysobinin (18) showed significant cytotoxicity, and toonayunnanin B (2) and epoxyazadiradione (14), were found to be slightly cytotoxic against the above cell lines. Furthermore, this study provides valuable information for the chemotaxonomy ofT. ciliatavarieties.
Graphical abstract
Limonoids, toonayunnanins A–L and eleven known compounds (13–23) were isolated from leaves ofToona ciliatavar.yunnanensis, and the cytotoxicity of all isolated compounds were evaluated. Cedrelone and dysobinin were cytotoxic, whereas toonayunnin B are epoxyazadiradione were slightly cytotoxic against the cell lines studied.
Highlights
? Twenty-three triterpenoids were identified, among them, twelve were previously unknown. ? Among the isolates, four compounds showed cytotoxic activities. ? A possible biogenetic pathway was discussed.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Yuttana Sudjaroen, William E. Hull, Gerhard Erben, Gerd Würtele, Supranee Changbumrung, ... Longan (Dimocarpus longanLour, syn.Euphoria longanLam.) represents an important fruit in Northern Thailand and has significant economic impact. The fruit is either consumed fresh or as commercially prepared dried and canned products. The canning industry in Thailand produces considerable quantities of waste products, in particular Longan seeds. Because these seeds may be an exploitable source of natural phenolic antioxidants, it was of interest to identify, purify and quantitate the major potential antioxidant phenolics contained therein. The polyphenolic fraction from ground Longan seeds was obtained by extraction with methanol after delipidation with hexane. The hexane extract contained predominantly long-chain fatty acids with major contributions from palmitic (35%) and oleic (28%) acids. The polyphenolic fraction (80.90 g/kg dry weight) was dominated by ellagic acid (25.84 g/kg) and the known ellagitannins corilagin (13.31 g/kg), chebulagic acid (13.06 g/kg), ellagic acid 4-O-?-l-arabinofuranoside (9.93 g/kg), isomallotinic acid (8.56 g/kg) and geraniin (5.79 g/kg). Structure elucidation was performed with mass spectrometry and complete assignment ofH andC NMR signals. The methanol extracts exhibited strong antioxidant capacities with an IC50of 154 ?g/ml for reactive oxygen species attack on salicylic acid and 78 ?g/ml for inhibition of xanthine oxidase in the hypoxanthine/xanthine oxidase assay. The extracts were less effective in the 2-deoxyguanosine assay (IC50 = 2.46 mg/ml), indicating that gallates along with ellagic acid and its congeners exert their potential antioxidant effects predominantly by precipitation of proteins such as xanthine oxidase. This was confirmed for the pure compounds gallic acid, methyl gallate, ellagic acid and corilagin.
Graphical abstract
The major polyphenolic antioxidant components of Longan seeds are identified as corilagin, chebulagic acid, isomallotinic acid and geraniin.
Highlights
? This is a comprehensive report of phenolic compounds present in Longan seeds. ? Phenolic compounds were identified by HPLC–ESI-MS, nano-ESI-MS–MS and NMR (600 MHz). ? Complete and unequivocal NMR data is presented for the purified major components. ? The extracts and purified phenolic compounds displayed strong antioxidant activity.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Peng Wu, Miao-Xian Su, Ying Wang, Guo-Cai Wang, Wen-Cai Ye, ... Pseudoguaianolide sesquiterpene lactones minimolides A (1), B (2), C (3) and D (4) and two guaianolide sesquiterpene lactones minimolides E (5) and F (6), along with seven known ones (7–13), were isolated from the supercritical fluid extract ofCentipeda minima. The structures of these compounds were elucidated by extensive spectroscopic methods (IR, UV, HRESIMS, 1D-NMR and 2D-NMR), and the complete structure and stereochemistry of1was further confirmed by X-ray diffraction analysis. Compounds1,5–8,11and13displayed inhibitory activity against human nasopharyngeal cancer cells (CNE) with IC50values ranging from 1.1 to 20.3 ?M. Compound13containing both?-methylene-?-lactone and?,?-unsaturated cyclopentenone moieties exhibited even stronger inhibitory activity than that of cisplatin (positive control) through cell cycle arrest at G2/M phase. Isolation of six sesquiterpene lactones fromCentipeda minimahighlighted the potential of supercritical fluid extraction for enrichment of minor constituents for phytochemical study.
Graphical abstract
Sesquiterpene lactones (1–6) with significant inhibitory activity against human nasopharyngeal cancer cells were isolated from the supercritical fluid extract ofCentipeda minima.
Highlights
? Supercritical fluid extraction was used to enrich low polar constituents. ? Six sesquiterpene lactones (1–6) along with seven known ones were isolated. ? Some compounds showed inhibitory activity against human nasopharyngeal cancer cells. ? Structure-relationships are discussed.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Rui Feng, Zhi Kai Guo, Chun Min Yan, Er Guang Li, Ren Xiang Tan, ... Six flavonoids named cryptogiones A–F, and nine known compounds were isolated from an ethanol extract of stems ofCryptocaryachingii. The structures of the compounds were elucidated by interpretation of comprehensive spectroscopic data and X-ray analysis. A majority of these flavonoids contained an acetic acid/lactone moiety, a possible taxonomic marker. Anti-inflammatory effects of the compounds were evaluated using in vitro assays. At 20 ?M concentration, three compounds significantly inhibited TNF?-induced NF-?B activation and LPS-induced IL-1? expression.
Graphical abstract
Six new flavonoids, cryptoginone A–F, together with nine known compounds were isolated from the ethanol extract of stems ofCryptocaryachingii. Compounds 7–9 showed significant anti-inflammatory activities at 20 ?M.
Highlights
? The phytochemical constituents ofCryptocaryachingiihave been investigated. ? Six flavonoids and 9 known compounds have been isolated. ? An acetic acid/lactone moiety in the majority of the compounds can be a possible taxonomic marker. ? The anti-inflammatory effects of the compounds have been evaluated. ? Three compounds show activity against TNF and LPS induced proinflammatory responses.
Publication year: 2012 Source: Phytochemistry, Available online 23 January 2012 Sebastian Schmidt, Guido Jürgenliemk, Helen Skaltsa, Jörg Heilmann Five acylphloroglucinols substituted with monoterpenoids (empetrifelixin A–D and empetrikajaforin), three known monocyclic acylphloroglucinols and one monocyclic acylphloroglucinol were isolated from a petrol ether extract ofHypericum empetrifoliumafter fractionation by flash chromatography on silica gel, RP-18 and subsequent purification by preparative HPLC (RP-18). Their structures were elucidated by 1D, 2D NMR techniques and HREIMS. To determine a possible anti-angiogenic activity, inhibition of cell proliferation was measured using a human microvascular endothelial cell line (HMEC-1). Subconfluent grown HMEC-1 cells were treated with all compounds isolated in sufficient amounts and stained with crystal violet. Highest activity was observed for empetrifelixin A and empetrifelixin D showing a concentration dependent inhibition of cell proliferation with IC50values of 6.5 ± 0.1 and 7.3 ± 0.4 ?M, respectively. Empetrifelixin A also showed activity in a cell migration assay with HMEC-1 cells in low micromolar concentrations.
Graphical abstract
Five acylphloroglucinols substituted with monoterpenoids were isolated from a petrol ether extract ofHypericum empetrifoliumby anH NMR guided approach. Inhibition of cell proliferation was measured using a human microvascular endothelial cell line. Most active compounds showed a concentration dependent inhibition of cell proliferation with IC50values in the lower micromolar range.
Highlights
? We isolated five phloroglucinol derivatives fromHypericum empetrifolium. ? We applied aH NMR guided approach. ? We found a rare monoterpenoid substitution of the phloroglucinols. ? We found significant inhibition of cell proliferation in endothelial cells.
Publication year: 2012 Source: Phytochemistry, Available online 22 January 2012 Jaana Liimatainen, Maarit Karonen, Jari Sinkkonen A procyanidin dimer xyloside, catechin-(4? ? 8)-7-O-?-xylopyranosyl-catechin, was isolated from the inner bark ofBetula pendulaand its structure was determined using 1D and 2D NMR, CD and high-resolution ESIMS. Interestingly, the 7-O-?-xylopyranose unit was found to be present in the lower terminal unit of the dimer. In addition to this procyanidin dimer xyloside, an entire series of oligomeric and polymeric procyanidin xylosides was detected. Their structures were investigated by hydrophilic interaction HPLC–HRESIMS. Procyanidin glycosides are still rarely found in nature.
Graphical abstract
Procyanidin xylosides were isolated from the inner bark ofBetula pendula. Their structures were established by NMR and/or HPLC–HRESIMS.
Highlights
? A mixture of procyanidin xylosides was obtained from the inner bark ofBetula pendula. ? A catechin-(4? ? 8)-7-O-?-xylopyranosyl-catechin was isolated and characterized. ? Procyanidin xylosides were detected from dimers up to heptadecamers.
Publication year: 2012 Source: Phytochemistry, Available online 19 January 2012 Fumi Tatsuzawa, Kanako Ito, Hiroki Muraoka, Toshiharu Namauo, Kazuhisa Kato, ... Triacylated peonidin 3-sophoroside-5-glucosides were isolated from the purple flowers ofMoricandia ramburiiWebb. (Family: Brassicaceae), and determined to be peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (1), peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(cis-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (2) and peonidin 3-O-[2-O-(2-O-(trans-sinapoyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (3), respectively, by chemical and spectroscopic methods. In addition, one known acylated cyanidin glycoside, cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (4), was also identified in the flowers. Peonidin glycosides have not been reported hitherto in floral tissues in to Brassicaceae.
Graphical abstract
Triacylated peonidin 3-sophoroside-5-glucosides were isolated from the purple flowers ofMoricandia ramburiiWebb.1, R1 = trans, R2 = H;2, R1 = cis, R2 = H;3, R1 = trans, R2 = OCH3.
Highlights
? Acylated anthocyanins isolated from the purple flowers ofMoricandia ramburiiWebb. (Brassicaceae). ? Anthocyanins were based on 3-sophoroside-5-glucosides of peonidin and cyanidin, respectively. ? Peonidin glycosides in the flowers of Brassicaceae species were hitherto unknown.
Publication year: 2012 Source: Phytochemistry, Available online 18 January 2012 François Luro, Nicolas Venturini, Gilles Costantino, Julien Paolini, Patrick Ollitrault, ... Native to southeast Asia, the citron (Citrus medicaL.) was the first citrus fruit to be introduced to the Mediterranean area, in the third century BC, and remained its only citrus representative until the tenth century. The citron was used for its aroma – stemming from its essential oils in leaves and fruit peels – and as symbols in the Jewish religion. Subsequently, the cultivation of citron was extended significantly, peaking in the nineteenth century, when its fruits were used in cosmetics and confectioneries. The objective of this study was to examine the genetic diversity of the Mediterranean citron with regard to the multiplication and dissemination practices that were related to its uses.We studied the polymorphisms of 27 nuclear and cytoplasmic genetic markers of 24 citron varieties, preserved in the citrus germplasm of INRA-CIRAD, San Giuliano, France. The composition of leaf essential oils was determined to establish varieties and phylogenic relationships between accessions. Other major citrus species were included in the molecular analysis, which demonstrated the existence of 13 genetically linked citrons, differing from other citrus species, based on low heterozygosity and specific alleles; these citrons were considered true-type citrons, confirmed by their convergent chemical profiles. We also detected a polymorphism in the chloroplastic genome in these 13 citrons, which, when combined with allelic diversity of 2.4 alleles per locus, suggests that multiple citrons were introduced to the Mediterranean area in last 2 millennia. We determined the genetic origin and relationships of several varieties, such as Corsican, which could have arisen from the selfing of Poncire Commun.We noted a higher-than-expected polymorphism rate among Mediterranean citron varieties, likely due to crossfecundation. The chemical leaf oil composition of several economical varieties, such as Corsican, is distinct and can increase the quality of specific agriculture products for the cosmetics and candy industries.
Graphical abstract
The genetic and chemical diversity of the Mediterranean citron was examined with regard to the multiplication and dissemination practices that were related to its uses.
Highlights
? Twenty four citron varieties were studied. ? Study of the polymorphisms of 27 nuclear and cytoplasmic genetic markers. ? Composition of leaf essential oils was determined. ? Relationships were established between varieties, genetics and chemistry.
Publication year: 2012 Source: Phytochemistry, Available online 16 January 2012 Milena ?avi?, Milica Grozdanovi?, Aleksandar Baji?, Tatjana Srdi?-Raji?, Pavle R. An?us, ... Actinidin belongs to the papain-like family of cysteine proteases and is a major kiwifruit allergen. In this study, the effect of actinidin on cellular morphology and adhesion of T84 intestinal cells was investigated. Both rounding and detachment of T84 cells were observed upon actinidin treatment. The morphological changes and cell desquamation was protease-dependent, as well as time- and concentration-dependent. Changes of intercellular adhesion and adhesion of epithelial cells to collagen upon actinidin treatment could be responsible for the cell rounding and give rise to discontinuous breaches in the epithelial monolayer observed in this study. Actinidin’s action on cell morphology, adhesion and monolayer integrity were not due to compromised viability of T84 epithelial cells, as confirmed by MTT assay and flow cytometric analysis of the cell cycle. Damage to the epithelial monolayer of the intestine induced by actinidin should be further evaluated as an important factor in the development of kiwifruit allergy and other intestinal disorders.
Graphical abstract
Kiwifruit allergen actinidin induces protease-dependent morphology changes of T84 intestinal cells, leading to cell rounding and desquamation of the epithelial monolayer, without affecting cell viability.
Highlights
? Actinidin is a cysteine protease from kiwifruit with allergenic properties. ? We investigated if actinidin induces changes in morphology and adhesion of T84 cells. ? Actinidin led to cell rounding and desquamation of the T84 epithelial monolayer. ? The observed effects were protease-, time- and concentration-dependant. ? Viability of T84 epithelial cells was not compromised upon actinidin treatment.
Publication year: 2012 Source: Phytochemistry, Available online 14 January 2012 Ademir E. do Vale, Jorge M. David, Edlene O. dos Santos, Juceni P. David, Lidercia C.R.C. e Silva, ... This work reports isolation of an unusual lignan with a bicyclic [2.2.2] octene skeleton, named rufescenolide (1), from stems ofCordia rufescens, along with ?-sitosterol, stigmasterol, syringaldehyde, 3-?-O-d-glucopyranosyl-sitosterol, methyl caffeate, 4-methoxy-protocatechuic acid and methyl rosmarinate. Structural characterizations employed IR spectroscopic, ESIHRMS and mono and dimensional NMR spectroscopy.
Graphical abstract
Rufescenolide, was isolated from stems ofCordia rufescens, and is a lignan with an unusual bicyclic [2.2.2] skeleton.
Highlights
? Cordia rufescens(Syn:Cordia piauhiensis) already afforded arylnaphthalene lignans. ? Bicyclic [2.2.2] octane lignan was isolated from leaves ofC. rufescens. ? The isolated lignan possesses a new skeleton.
Publication year: 2012 Source: Phytochemistry, Available online 13 January 2012 Mariana P. Silva, Leonardo A. Piazza, Daniela López, Marisa J. López Rivilli, Mauricio D. Turco, ... An aqueous extract fromFlourensia campestris(Asteraceae) dry aerial parts showed strong inhibition on the germination and growth ofLactuca sativa. Based on bio-guided chromatographic fractionation of aq. extracts from dry and fresh leaves and spectroscopic means, (-)-hamanasic acid A (7-carboxy-8-hydroxy-1(2), 12(13)-dien-bisabolene (1)) was isolated as the most inhibitory active principle on germination (ECg50 = 2.9 mM) and on root (ECr50 = 1.5 mM)/shoot (ECs50 = 2.0 mM) growth. As measured by GC, and correlated with a simple designed 2D-TLC, compound1was distributed throughout the plant, with a remarkably high concentration (1.6%) in the leaves and the inflorescences. At least a quarter of the amount of1was found in aqueous extracts suggesting that leaching would be a key route for its release into the environment. By contrast, leaf essential oils (HD) between 0.5 and 1.5 ?l mldid not show herbicidal effects and1was not found in them (TLC) nor among volatiles (HS-SPME). Volatile compositions were assessed by GC-FID and GC–MS and led to the identification of 23 compounds (4 monoterpenes and 19 sesquiterpenes) with a wide seasonal (spring–summer%) variation, represented principally by bicyclo-germacrene (37–6%), spathulenol (4–32%), globulol (20–0%), beta-caryophyllene (15–6%), caryophyllene oxide (1–13%) and bicycloelemene (10–1%), respectively. The high amount of1inF. campestristogether with its feasibility of being extracted with water suggest that (?)-hamanasic acid A is an allelochemical in this species. Species-specific studies must be carried out to evaluate the potential of1as a natural herbicidal compound.
Graphical abstract
Phytotoxic activity of leaf aq. extracts fromFlourensia campestris(Asteraceae) on lettuce led to isolation of (?)-hamanasic acid A. Its high concentration among the organs and in aq. extracts suggests its putative role as an allelochemical. The essential oils (0.5–1.5 ?l ml) did not exhibit phytotoxicity against lettuce.
Highlights
? Phytotoxic effects ofFlourensia campestriswas investigated ? Aq. leaf extracts showed strong inhibition on germination and growth ofL.sativa. ? The principal phytocompound isolated was (?)-hamanasic acid A. ? Leaf essential oils did not display phytotoxicity and volatiles were characterized. ? High stores and release of1strongly suggest its role as allelochemical.
Publication year: 2012 Source: Phytochemistry, Available online 13 January 2012 Nan Huang, Ludmila Rizshsky, Catherine C. Hauck, Basil J. Nikolau, Patricia A. Murphy, ... Our previous studies found that 4 compounds, namely pseudohypericin, amentoflavone, quercetin, and chlorogenic acid, inHypericum perforatumethanol extract synergistically inhibited lipopolysaccharide (LPS)-induced macrophage production of prostaglandin E2 (PGE2). Microarray studies led us to hypothesize that these compounds inhibited PGE2 production by activating suppressor of cytokine signaling 3 (SOCS3). In the current study, siRNA was used to knockdown expression of SOCS3 in RAW 264.7 macrophages and investigated the impact ofH. perforatumextract and the 4 compounds on inflammatory mediators and cytokines. It was found that the SOCS3 knockdown significantly compromised the inhibition of PGE2 and nitric oxide (NO) by the 4 compounds, but not by the extract. The 4 compounds, but not the extract, decreased interleukin-6 (IL-6) and tumor necrosis factor-? (TNF-?), while both lowered interleukine-1?. SOCS3 knockdown further decreased IL-6 and TNF-?. Pseudohypericin was the major contributor to the PGE2 and NO inhibition in cells treated with the 4 compounds, and its activity was lost with the SOCS3 knockdown. Cyclooxygenase-2 (COX-2) and inducible NO synthase protein expression were not altered by the treatments, while COX-2 activity was decreased by the extract and the 4 compounds and increased by SOCS3 knockdown. In summary, it was demonstrated that the 4 compounds inhibited LPS-induced PGE2 and NO through SOCS3 activation. The reduction of PGE2 can be partially attributed to COX-2 enzyme activity, which was significantly elevated with SOCS3 knockdown. At the same time, these results also suggest that constituents inH. perforatumextract were alleviating LPS-induced macrophage response through SOCS3 independent mechanisms.
Graphical abstract
A group of 4 compounds inHypericum perforatumsynergistically inhibited LPS-stimulated PGE2 and NO productions in mouse macrophages. The knockdown of the SOCS3 gene in macrophages significantly compromised such an inhibitory effect. However, the PGE2 and NO inhibition by the whole ethanol extract ofH. perforatumwere not affected by SOCS3 knockdown.
Highlights
?Hypericum perforatumand the 4 compound mixture inhibited inflammatory mediators in macrophages. ? The 4 compounds required SOCS3 activation to inhibit the inflammatory response. ?H. perforatumethanol extract had SOCS3 independent anti-inflammatory activity. ? The 4 compounds inhibited LPS-induced cytokines without activating SOCS3.
Publication year: 2012 Source: Phytochemistry, Available online 11 January 2012 Lin Yang, Lirui Qiao, Dan Xie, Yuhe Yuan, Naihong Chen, ... 2-(2-Phenylethyl) chromones and a 2-(2-phenylethenyl) chromone, were isolated from the ethanolic extract of Chinese eaglewood. Their structures were determined on the basis of extensive analyses of spectroscopic data. Among those, one showed significant neuroprotective activities against both glutamate-induced and corticosterone-induced neurotoxicity in P12 pheochromocytoma and human U251 glioma cells at a concentration of 10 ?M and increased cell viability by 82.2% and 86.9%, respectively.
Highlights
? Eight new compounds were isolated from the ethanolic extract of Chinese eaglewood. ? The structures of these compounds were determined to be 2-phenylethyl or 2-phenylethenyl chromones. ? One compound showed significant neuroprotective activity.
Publication year: 2012 Source: Phytochemistry, Available online 7 January 2012 Yuan Zhou, Xiao Yan Xu, Li Qian Chen, Jian Li Yang, Shao Jian Zheng Aluminum (Al) toxicity is one of the most widespread problems for crop production on acid soils, and nitric oxide (NO) is a key signaling molecule involved in the mediation of various biotic and abiotic stresses in plants. Here we found that exogenous application of the NO donor sodium nitroprusside (SNP) exacerbated the inhibition of Al-induced root growth in rice bean [Vigna umbellata(Thunb.) Ohwi & Ohashi ‘Jiangnan’, Fabaceae]. This was accompanied by an increased accumulation of Al in the root apex. However, Al treatments had no effect on endogenous NO concentrations in root apices. These results indicate that a change in NO concentration is not the cause of Al-induced root growth inhibition and the adverse effect of SNP on Al-induced root growth inhibition should result from increased Al accumulation. Al could significantly induce citrate efflux but SNP had no effects on citrate efflux either in the absence or presence of Al. On the other hand, SNP pretreatment significantly increased Al-induced malondialdehyde accumulation and Evans Blue staining, indicating an intensification of the disruption of plasma membrane integrity. Furthermore, SNP pretreatment also caused greater induction of pectin methylesterase activity by Al, which could be the cause of the increased Al accumulation. Taken together, it is concluded that NO exacerbates Al-induced root growth inhibition by affecting cell wall and plasma membrane properties.
Graphical abstract
Exogenous application of a NO donor, sodium nitroprusside, exacerbated inhibition of Al-induced root growth in rice bean by increasing pectin methylesterase activity and lipid peroxidation.
Highlights
? NO donor (SNP) exacerbated the Al-induced inhibition of root growth in rice bean. ? SNP pretreatment resulted in an increased accumulation of Al in root apex. ? SNP aggravated Al-induced oxidation and increased pectin methylesterase activity.
Publication year: 2012 Source: Phytochemistry, Available online 7 January 2012 Yuan Zhou, Xiao Yan Xu, Li Qian Chen, Jian Li Yang, Shao Jian Zheng Aluminum (Al) toxicity is one of the most widespread problems for crop production on acid soils, and nitric oxide (NO) is a key signaling molecule involved in the mediation of various biotic and abiotic stresses in plants. Here we found that exogenous application of the NO donor sodium nitroprusside (SNP) exacerbated the inhibition of Al-induced root growth in rice bean [Vigna umbellata(Thunb.) Ohwi & Ohashi ‘Jiangnan’, Fabaceae]. This was accompanied by an increased accumulation of Al in the root apex. However, Al treatments had no effect on endogenous NO concentrations in root apices. These results indicate that a change in NO concentration is not the cause of Al-induced root growth inhibition and the adverse effect of SNP on Al-induced root growth inhibition should result from increased Al accumulation. Al could significantly induce citrate efflux but SNP had no effects on citrate efflux either in the absence or presence of Al. On the other hand, SNP pretreatment significantly increased Al-induced malondialdehyde accumulation and Evans Blue staining, indicating an intensification of the disruption of plasma membrane integrity. Furthermore, SNP pretreatment also caused greater induction of pectin methylesterase activity by Al, which could be the cause of the increased Al accumulation. Taken together, it is concluded that NO exacerbates Al-induced root growth inhibition by affecting cell wall and plasma membrane properties.
Graphical abstract
Exogenous application of a NO donor, sodium nitroprusside, exacerbated inhibition of Al-induced root growth in rice bean by increasing pectin methylesterase activity and lipid peroxidation.
Highlights
? NO donor (SNP) exacerbated the Al-induced inhibition of root growth in rice bean. ? SNP pretreatment resulted in an increased accumulation of Al in root apex. ? SNP aggravated Al-induced oxidation and increased pectin methylesterase activity.
Publication year: 2012 Source: Phytochemistry, Available online 5 January 2012 Joseph Msanne, Di Xu, Anji Reddy Konda, J. Armando Casas-Mollano, Tala Awada, ... Microalgae are emerging as suitable feedstocks for renewable biofuel production. Characterizing the metabolic pathways involved in the biosynthesis of energy-rich compounds, such as lipids and carbohydrates, and the environmental factors influencing their accumulation is necessary to realize the full potential of these organisms as energy resources. The model green algaChlamydomonas reinhardtiiaccumulates significant amounts of triacylglycerols (TAGs) under nitrogen starvation or salt stress in medium containing acetate. However, since cultivation of microalgae for biofuel production may need to rely on sunlight as the main source of energy for biomass synthesis, metabolic and gene expression changes occurring inChlamydomonasandCoccomyxasubjected to nitrogen deprivation were examined under strictly photoautotrophic conditions. Interestingly, nutrient depletion triggered a similar pattern of early synthesis of starch followed by substantial TAG accumulation in both of these fairly divergent green microalgae. A marked decrease in chlorophyll and protein contents was also observed, including reduction in ribosomal polypeptides and some key enzymes for CO2assimilation like ribulose-1,5-bisphosphate carboxylase/oxygenase. These results suggest that turnover of nitrogen-rich compounds such as proteins may provide carbon/energy for TAG biosynthesis in the nutrient deprived cells. InChlamydomonas, several genes coding for diacylglycerol:acyl-CoA acyltransferases, catalyzing the acylation of diacylglycerol to TAG, displayed increased transcript abundance under nitrogen depletion but, counterintuitively, genes encoding enzymes forde novofatty acid synthesis, such as 3-ketoacyl-ACP synthase I, were down-regulated. Understanding the interdependence of these anabolic and catabolic processes and their regulation may allow the engineering of algal strains with improved capacity to convert their biomass into useful biofuel precursors.
Graphical abstract
Nitrogen depletion under photoautotrophic conditions induced synthesis of starch followed by triacylglycerol accumulation in green microalgae. The turnover of nitrogen-rich compounds such as proteins may provide substrates/energy for TAG biosynthesis in the nutrient deprived cells.
Highlights
? N deprivation induces starch and triacylglycerol accumulation in green microalgae. ? Chlorophyll and protein contents are considerably reduced. ? Protein turnover may provide carbon intermediates/energy for TAG synthesis. ? N depletion also affects the expression of lipid biosynthesis genes. ? Anabolic and catabolic processes underlie microalgal production of biofuel precursors.
Publication year: 2012 Source: Phytochemistry, Available online 5 January 2012 Li-Ming Yang, Shwu-Fen Chang, Wen-Kuang Lin, Bo-Hon Chou, Li-Hsuan Wang, ... Fourteen oxygenated compounds were isolated from the preparative-scale biotransformation of isostevic acid (ent-beyeran-19-oic acid). Incubation of it withAspergillus nigerBCRC 32720 produced eight metabolites, four withBacillus megateriumATCC 14581, and another four withMortierella isabellinaATCC 38063. In addition to their structural elucidation by NMR spectroscopy and HRMS, structures of four of these were further confirmed by X-ray diffraction studies. Real-time reverse transcription PCR analysis found that 15 of these compounds displayed significant in vitro anti-inflammatory activity in lipopolysaccharide-stimulated RAW 264.7 macrophages by reducing the levels of both TNF-? and COX-2 mRNA relative to control cells stimulated by LPS alone. The activity of one metabolite was similar to that of dexamethasone in inhibiting the expression of TNF-? mRNA, while all test compounds except two of them were more potent than dexamethasone in inhibiting the expression of the COX-2 mRNA.
Graphical abstract
Several oxygenated compounds were isolated from the bioconversion of isostevic acid (2). Real-time reverse transcription PCR analysis found that these compounds displayed significant in vitro anti-inflammatory activity in lipopolysaccharide-stimulated RAW 264.7 macrophages by reducing the levels of both TNF-? and COX-2 mRNA relative to control cells stimulated by LPS alone.
Highlights
? Fourteen oxygenated compounds were obtained from the bioconversion of isostevic acid. ? Structures were elucidated by 2D NMR and HRMS. ? Four compounds were confirmed by X-ray crystallographic analyses. ? Several compounds exhibited anti-inflammatory activity.
Publication year: 2012 Source: Phytochemistry, Available online 5 January 2012 Jun-Hua Liu, Abdul Latif, Mumtaz Ali, Gui-Ping Zhang, Wen-Juan Xiang, ... Nine diterpenoids were isolated from the stems ofEuphorbia neriifoliaLinn. with their structures established by 1D and 2D NMR techniques. Relative stereochemistries were determined by ROESY, and single-crystal X-ray experiments.
Graphical abstract
Diterpenoids1–9were isolated from the stem ofEuphorbia neriifoliaLinn. Their structures were established by 1D and 2D NMR techniques, X-ray single-crystal experiments and comparison with published literature data.
Highlights
? Nine diterpenoids were isolated and characterized by mass and NMR spectroscopic analyses. ? Two of these compounds were characterized further by single-crystal X-ray experiments. ? The discovery of atisane-derived compounds adds to their diversity in nature.
Posted on 7 January 2012 | 2:51 am
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