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Phytochemistry Letters - Verlag: Elsevier
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Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Hari Prasad Devkota, Masato Watanabe, Takashi Watanabe, Shoji Yahara Two new ?-hydroxy ketone type diarylpentanoids, diplomorphanone A, 2(S)-hydroxy-1-(4-hydroxyphenyl)-5-phenyl-1-pentanone (1) and diplomorphanone B, 2(R)-hydroxy-1,5-diphenyl-1-pentanone (2) were isolated from aerial parts of Diplomorpha canescens (Meisn.) C.A. Meyer and roots of Diplomorpha ganpi (Sieb. et Zucc.) Nakai, respectively. Nine known compounds including diarylpentanoids (3–6), phenylpropanoid derivatives (7–9), (+)-afzelechin (10) and apiosylskimmin (11) were also isolated for the first time from D. ganpi. Structures of these compounds were elucidated on the basis of spectroscopic data.
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Two new diarylpentanoids, diplomorphanone A (1) and diplomorphanone B (2) were isolated from aerial parts of Diplomorpha canescens and roots of Diplomorpha ganpi, respectively.? Diplomorphanone A (1) was isolated from Diplomorpha canescens. ? Diplomorphanone B (2) was isolated from Diplomorpha ganpi. ? Nine known compounds (3–11) were also isolated from D. ganpi.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Yong-Jiang Xu, Kenn Foubert, Liene Dhooghe, Filip Lemière, Kanyanga Cimanga, Kahunu Mesia, Sandra Apers, Luc Pieters The total 80% EtOH extract of stem bark of Nauclea pobeguinii (Rubiaceae), which is active against uncomplicated falciparum malaria as shown in previous clinical studies, was analysed by means of UPLC–MS and HPLC-SPE-NMR. Apart from the main constituent, strictosamide, a series of minor constituents was identified, including two new iridoid-indole alkaloids, i.e. naucleidinic acid and 19-O-methyl-3,14-dihydroangustoline, together with 8 known iridoid-indole alkaloids, i.e. naucleidinal, magniflorine, naucleofficine D, two diastereoisomers of 3,14-dihydroangustoline, strictosidine, desoxycordifoline, 3?,5?-tetrahydrodeoxycordifoline lactam, and a phenol glycoside 3,4,5-trimethoxyphenol ?-d-apiofuranosyl-(1-6)-?-d-glucopyranoside (kelampayoside A).
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The total 80% EtOH extract of stem bark of Nauclea pobeguinii (Rubiaceae), was analysed by means of UPLC–MS and HPLC-SPE-NMR. Apart from the main constituent, strictosamide, a series of minor constituents was identified, including two new iridoid-indole alkaloids, i.e. naucleidinic acid and 19-O-methyl-3,14-dihydroangustoline.? Characterisation of the total stem bark extract of Nauclea pobeguinii by UPLC–MS and HPLC-SPE-NMR. ? Two new iridoid-indole alkaloids: naucleidinic acid and 19-O-methyl-3,14-dihydroangustoline. ? Identification of strictosamide, 8 known iridoid-indole alkaloids, and a phenol glycoside.
Publication year: 2012 Source:Phytochemistry Letters Zhao-Min Lin, Li-Ning Wang, Dong-Xiao Guo, Xiao-Ning Wang, Yong-Qing Liu, Jin-Chuan Zhou, Hong-Xiang Lou A new dihydroisocoumarin derivative, R-(?)-heteroscyphide (1), together with three known terpenoid derivatives (2–4), were isolated from the liverwort Heteroscyphus coalitus. Their structures were elucidated by spectroscopic methods and the biogenetic pathway of compound 1 was proposed. Cytotoxic test revealed that they exhibited moderate inhibitory activity to three human tumor cell lines.
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A new dihydroisocoumarin derivative, R-(?)-heteroscyphide (1), together with three known terpenoid derivatives, were isolated from the liverwort Heteroscyphus coalitus. The biogenetic pathway of compound 1 was proposed. Their cytotoxic activity has been evaluated.? The first report of a new dihydroisocoumarin with a long chain from liverworts. ? The first report of retinane-type diterpenoid from bryophytes. ? The biogenetic pathway of the new compound was proposed. ? The compounds exhibited moderate cytotoxicity to three human tumor cell lines.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Klaudia Michalska, Wanda Kisiel From aerial parts of Lactuca aculeata one new and ten known sesquiterpene lactone aglycones and glycosides were isolated, including four lactucin-type guaianolides, six costus lactone-type guaianolides and one melampolide-type germacranolide. The structure of the new compound was determined as 11?-hydroxycrepidiaside B by high resolution mass spectrometry and 1D- and 2D-NMR spectroscopy.
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? Aerial parts of Lactuca aculeata afforded a total of 11 sesquiterpene lactones. ? Of these, 11?-hydroxycrepidiaside B (1) appeared to be a new natural product. ? Its structure was established on the basis of 1D and 2D NMR spectroscopy, and high resolution mass spectrometry.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Jicheng Shu, Jianqun Liu, Youquan Zhong, Jinghang Pan, Lifang Liu, Rui Zhang Two new pterosin sesquiterpenes named as 2R,3R-13-hydroxy-pterosin L 3-O-?-d-glucopyranoside (1) and 2R,3S-acetylpterosin C (2), along with a known one, 2S,3S-acetylpterosin C (3), were isolated from the whole plant of Pteris multifida and the 1D and 2D NMR data of 3 were reported for the first time in this paper. Their structures were elucidated on the basis of mass and spectral evidence. Compounds 1–3 showed cytotoxicity against HL 60 cells (human leukemia) with the IC50 values of 14.6, 48.3 and 35.7?M, respectively.
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Two new pterosin sesquiterpenes named as 2R,3R-13-hydroxy-pterosin L 3-O-?-d-glucopyranoside (1) and 2R,3S-acetylpterosin C (2), along with a known one, 2S,3S-acetylpterosin C (3), were isolated from the whole plant of Pteris multifida and the 1D and 2D NMR data of 3 were reported for the first time in this paper. Their in vitro cytotoxicity against HL 60 cancer cell line was evaluated.? Two new pterosins along with a known one were isolated from Pteris multifida. ? Their structures were elucidated on the basis of mass and spectral evidence. ? These pterosins showed cytotoxicity against HL 60 cells.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Mohamed L. Ashour, Mahmoud Z. El-Readi, Ahmed Tahrani, Safaa Y. Eid, Michael Wink A detailed phytochemical study of the aerial parts of Bupleurum marginatum Wall. ex DC revealed a novel aryltetraline lactone lignan identified as 9-(benzo[d][1,3]dioxol-5-yl)-6,7,8-trimethoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one (marginatoxin) along with nine known compounds and characterization of five other compounds either by GLC/MS or LC/MS techniques. Chemical structures of the isolated compounds were unambiguously elucidated by both 1D, 2D NMR and mass spectrometry techniques.The in vitro cytotoxic activity of both methanol and dichloromethane extracts as well as the isolated compounds was assessed in two human cancer cell lines HepG2 and HeLa using the MTT assay. The new aryltetraline lactone lignan exhibited a potent cytotoxic activity with IC50 values of 12.14 and 16.90?M after 24h treatment for HepG2 and HeLa cells, respectively.
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The phytochemical study of the aerial parts of Bupleurum marginatum revealed a novel aryltetraline lactone lignan (9) along with 14 known compounds. Their structures have been determined by 1D- and 2D-NMR and MS analyses. The isolated lignans possessed cytotoxic activity against HepG2 and HeLa cells.? A detailed phytochemical study of the aerial parts extract led to isolation and characterization of 15 compounds. ? A new aryltetraline lactone lignan was identified as marginatoxin. ? The cytotoxic activity of the isolated compounds in both HepG2 and HeLa cancer cell lines are reported.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Xiao-Qi Zhang, Fang-Fang Xu, Lei Wang, Mei-Yan Huang, Zhong Liu, Dong-Mei Zhang, Guo-Cai Wang, Yao-Lan Li, Wen-Cai Ye Two pairs of new diastereomeric flavonolignans, hovenins A–D (1–4), were isolated from the seeds of Hovenia acerba. Their structures were established on the basis of spectroscopic methods and circular dichroism experiments. All compounds significantly inhibited NO and IL-6 generation in lipopolysaccharide (LPS)-stimulated macrophages (RAW264.7 cells) in a dose-dependent manner.
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? Four flavonolignans from the seeds of Hovenia acerba have been isolated. ? They are two pairs of new diastereoisomers. ? The anti-inflammatory activity of the isolated compounds was studied. ? All compounds significantly inhibited NO and IL-6 production in a dose-dependent manner.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Ting Zhang, Ting Gong, Yan Yang, Ruo-Yun Chen, De-Quan Yu Two new eudesmane-type sesquiterpene lactones, 1-one-4-epi-alantolactone (1) and 4?,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide (2), were isolated from the roots of Inula racemosa, together with six known compounds (3–8). The cytotoxic activities against five human cancer cell lines had been tested and compounds 3, 6, 7 and 8 exhibited moderate cytotoxic activities. Compounds 4 and 8 showed potent in vitro activities against the release of ?-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF), with the inhibitory ratios 65.4% (P<0.01) and 80.5% (P<0.001), at concentration of 10?M, respectively.
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Two new eudesmane-type sesquiterpene lactones, 1-one-4-epi-alantolactone (1) and 4?,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide (2), were isolated from the roots of Inula racemosa, together with six known compounds (3–8). The cytotoxic activities against five human cancer cell lines had been tested and compounds 3, 6, 7 and 8 exhibited moderate cytotoxic activities. Compounds 4 and 8 showed potent in vitro activities against the release of ?-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF), with the inhibitory ratios 65.4% (P<0.01) and 80.5% (P<0.001), at concentration of 10?M, respectively.? There are two new eudesmanolides from this plant. ? We evaluated cytotoxic activities of compounds 1–8 against five human cancer cell lines, and compounds 3, 6, 7 and 8 exhibited moderate cytotoxic activities. ? The anti-PAF activities were also tested, and compounds 4 and 8 showed activities with the inhibitory ratios 65.4% (P<0.01) and 80.5% (P<0.001), at concentration of 10?M, respectively.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Tawanun Sripisut, Wong Phakhodee, Thunwadee Ritthiwigrom, Sarot Cheenpracha, Surat Laphookhieo Two new furanocoumarins, lucidafuranocoumarins B (1) and C (2), were isolated from the twigs of Feroniella lucida, together with five known compounds (3–7). The structures of these compounds were identified on the basis of extensive spectroscopic methods. The absolute configurations of lucidafuranocoumarin C at C-2? and C-5? were established as R- and S-configurations, respectively, by applying Mosher's method. Some isolates were also evaluated for their cytotoxicity against KB, MCF-7 and NCI-H187 cell lines.
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? The isolation and identification of furanocoumarins from twigs of Feroniella lucida. ? The absolute configurations of lucidafuranocoumarin C (2) was determined by applied Mosher's method. ? Compounds 3 and 6 were selectively active against NCI-H187 (IC50 24.82?M) and KB (IC50 35.51?M) cells, respectively. ? The relative biogenetic pathway of the side chain of furanocoumarins 1–5.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Dawood Hattas, Riitta Julkunen-Tiitto We compared Quebracho with Sorghum tannin as standards for condensed tannin (CT) quantification in selected African savanna tree species in relation to the acid-butanol assay for CTs. Without exception, the use of Quebracho tannin as standard overestimated CTs, ranging from 0.7 to as much as 8.3 times. Sorghum tannin underestimated CTs by 0.26–0.79 times, except in one species where there was no difference in the CT concentration. Condensed tannins in African savanna trees showed qualitative and quantitative differences in chemical composition which may explain the variable reactivity in the acid-butanol assay. We propose the use of condensed tannins purified from the plant under investigation be used as standard since it will closely represent the CT structure and presumably chemical reactivity in the acid-butanol assay.
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Expressing condensed tannin as Quebracho tannin equivalents overestimated concentration by 0.7–8.3 times, whereas Sorghum underestimated concentration, except in one amongst 5 African savanna species.? Quebracho tannin overestimated condensed tannins by 0.7–8.3 times. ? Sorghum tannin underestimated condensed tannins by 0.3–0.8 times. ? Sorghum tannin was an appropriate external standard for Scutia myrtina. ? Tannin chemical characteristics may explain reactivity in the acid-butanol assay.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Niko S. Radulovi?, Milan S. Deki?, Zorica Z. Stojanovi?-Radi? Plant samples of Hornungia petraea were analyzed for glucosinolate (GLS) autolysis metabolites for the first time. GC–MS analysis of the autolysate and the synthesis of a series (12 compounds) of possible glucosinolate breakdown products revealed/corroborated the presence of glucoaubrietin, glucolimnanthin, glucolepigramin and glucotropaeolin in this species as the most likely “mustard oil” precursors. GLS degradation products identified in the autolysate of H. petraea, benzyl isothiocyanate, 3- and 4-methoxybenzyl isothiocyanate, along with several other structurally related compounds were evaluated for antimicrobial activity in order to possibly pinpoint the role of the latter secondary metabolites in the plant tissues. The assays showed a very high antibacterial activity of the tested isothiocyanates against Sarcina lutea and an antifungal effect against Aspergillus fumigatus and Candida albicans with MIC values in the order of 1?g/ml value.
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? First analysis of Hornungia petraea glucosinolate (GLS) autolysis metabolites. ? The structure and identity of the detected GLS products were confirmed by synthesis. ? Antimicrobial assay suggests that the autolysis products serve as defense metabolites. ? High antibacterial activity of the tested isothiocyanates was shown against Sarcina lutea. ? Isothiocyanates also show an antifungal effect against Aspergillus fumigatus and Candida albicans.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Zhangyu Chen, Jianlin Tan, Guangyu Yang, Mingming Miao, Yongkuan Chen, Tianfei Li Two new isoflavones, 7-hydroxy-6,3?,4?,5?-tetramethoxy-isoflavone (1) and 6-hydroxy-7,3?,4?,5?-tetramethoxy-isoflavone (2), together with seven known isoflavones were isolated from the roots and stems of Nicotiana tabacum. Their structures were determined by means of HRESIMS, extensive 1D and 2D NMR spectroscopic studies and chemical evidences. The anti-tobacco mosaic virus (anti-TMV) activities of the isoflavones were also evaluated. The results reveal that compound 9 shows high anti-TMV activity, compound 2 shows moderate anti-TMV activity, and compounds 1, 3–8 show weak anti-TMV activities.
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? Two new isoflavones, 7-hydroxy-6,3?,4?,5?-tetramethoxy-isoflavone (1) and 6-hydroxy-7,3?,4?,5?-tetramethoxy-isoflavone (2), together with seven known isoflavones (3–9) were isolated from the roots and stems of Nicotiana tabacum. ? The results reveal that compound 9 shows high anti-TMV activity, compound 2 shows moderate anti-TMV activity, and compounds 1, 2–7 show weak anti-TMV activities.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Soledad del Corral, Silvia L. Cuffini, Simone G. Cardoso, Adailton J. Bortoluzzid, Sara M. Palacios From the EtOH extract of the medicinal native plant, Baccharis salicifolia, two novel halimane-type diterpenoids, salicifolic acid (1) and 5-hydroxy-6-hydro-salicifolic acid (2) together with the known compounds sakuranetin (3), apigenin (4) and scopoletin (5) were bioguided isolated against Panicum miliaceum (monocotyledonous). The structures of 1 and 2 were established by extensive spectroscopic analyses. The effective concentration for 50% inhibition of germination (ECg50) and the root (ECr50) and shoot (ECs50) elongations was determined for 1–5 against P. miliaceum and Raphanus sativus (dicotyledonous). Compound 2 was the most active in the inhibition of germination of P. miliaceum (ECg50=1mM), followed by 1, 5 and 3, although 1 was the most effective in regulating the growth of P. miliaceum seedlings, with a ECr50 and ECs50 values of 1.8 and 6.6mM, respectively. Compounds 1 and 3 were the only samples capable of inhibiting the germination of R. sativus, while seedling development was affected by 1, 2, and 3 with different effectiveness.
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? Bio-guided isolation of an extract of Baccharis salicifolia yielded phytotoxic compounds. ? Two new halimanes together with 2 known flavonoids and a coumarin were isolated. ? Germination of Panicum milliaceum and Raphanus sativus were inhibited by halimanes.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Henrik Toft Simonsen Four novel geminally dialkylated, non-aromatic acetophenone derivatives 1–4 were isolated from Melicope coodeana. The compounds, related to hop bitter acids, were named Coodeanones A–C, where Coodeanone B was found in both E and Z configuration of the 6??–7?? double bond. Antibacterial, antifungal and antimalarial activities of the acetophenone derivaties were investigated, and Coodeanone C (4) was found to have activity toward Plasmodium falciparum (malaria) (IC50=42.8?M).
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Coodeanone A (1), E-B (2), Z-B (3), C (4) isolated from Melicope coodeana.? Novel non-aromatic acetophenones, not isolated from Rutaceae and Melicope before. ? Determination of stereochemistry of the core acetophenone structure. ? Discussion on positions of prenyl and geranyl groups in the three molecules.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Ly D. Ha, Poul Erik Hansen, Fritz Duus, Hung D. Pham, Lien-Hoa D. Nguyen A new chromanone acid, calodryobalanoic acid, along with six known compounds, apetalic acid, isoblancoic acid, lupeol, 1-hydroxy-2-methoxyxanthone, 1,7-dihydroxy-3-methoxyxanthone, and 5,7,4?-trihydroxyflavanone, was isolated from the bark of Calophyllum dryobalanoides collected in Vietnam. The structure of the new compound was elucidated using mainly 1-D and 2-D NMR techniques (1H and 13C NMR, HSQC, HMBC, COSY, and NOESY) and IR spectroscopy. The stereochemistry was determined on the basis of NMR results and DFT calculations.
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Calodryobalanoic acid, together with six known compounds, was isolated from Calophyllum dryobalanoides. Its structure and stereochemistry were discussed based on NMR spectroscopy and DFT calculations.? Calodryobalanoic acid was isolated from the bark of Calophyllum dryobalanoides. ? Structural solution was supported using DFT calculations, IR and NMR data. ? DFT calculations showed that calodryobalanoic acid had two almost perpendicular parts. ? Interesting intramolecular hydrogen bonds are found.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Hugues Fouotsa, Alain Meli Lannang, Celine Djama Mbazoa, Saima Rasheed, Bishnu P. Marasini, Zulfiqar Ali, Krishna Prasad Devkota, Augustin Ephrem Kengfack, Farzana Shaheen, Muhammad Iqbal Choudhary, Norbert Sewald One new xanthone, caroxanthone (1) together with six known xanthones, 4-prenyl-2-(3,7-dimethyl-2,6-octadienyl)-1,3,5,8-tetrahydroxyxanthone (2), smeathxanthone A (3), gartanin (4), euxanthone (5), 8-hydroxycudraxanthone G (6) and morusignin I (7) were isolated from the stem bark of Garcinia nobilis. The structures were determined by 1D- and 2D-NMR techniques. All these compounds were tested for anti-glycation, ?-glucosidase and ?-chymotrypsin activities. Some of them exhibited strong to moderate ?-glucosidase activities, while none of them inhibited ?-chymotrypsin. Compounds 6 and 7 were found to be modest ?-glucosidase inhibitors with IC50 values of 76?M and 84?M, respectively.
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One new xanthone, caroxanthone (1) together with six known xanthones were isolated from Garcinia nobilis. All these compounds were tested for anti-glycation, ?-glucosidase and ?-chymotrypsin activities. Some of them exhibited strong to moderate ?-glucosidase activities, while none of them inhibited ?-chymotrypsin.? One new xanthone have been isolated from the stem back of Garcinia nobilis. ? Six other known xanthones have been isolated. ? All these compounds were tested for anti-glycation, ?-glucosidase and ?-chymotrypsin activities.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Laura Faiella, Abeer Temraz, Tiziana Siciliano, Nunziatina De Tommasi, Alessandra Braca Three new terpenoids, 2?,16-dihydroxy-4?-carboxy-O-?-d-glucopyranosyl-19-nor-totarol (1), nagilactone K (2), and 15-hydroxy phaseic acid (3), together with nine known compounds, were isolated from the leaves of Podocarpus gracilior. Their structures were determined by means of 1D and 2D NMR spectroscopy as well as by mass spectrometry analysis.
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Three terpenoids, 2?,16-dihydroxy-4?-carboxy-O-?-d-glucopyranosyl-19-nor-totarol, nagilactone K, and 15-hydroxy phaseic acid were isolated from the leaves of Podocarpus gracilior. Structures were elucidated by 1D and 2D NMR spectroscopy as well as by mass spectrometry analysis.? Nor- and bis-norditerpenes are interesting cytotoxic metabolites of Podocarpus genus. ? They are considered chemotaxonomic markers for the genus. ? The phytochemical study of P. gracilior leaves was performed. ? Three new terpenoids, including two diterpenes, were identified.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Makio Shibano, Ayaka Misaka, Kayoko Sugiyama, Masahiko Taniguchi, Kimiye Baba Two new steroid glycosides, stauntosaponins A (1) and B (2), were isolated from Cynanchum stauntonii (Decne.) Schltr.ex Levl. (Asclepiadaceae) together with five known compounds, anhydrohirundigenin monothevetoside, glaucogenin C mono-d-thevetoside, hirundoside A, cynatratoside A, and glaucogenin C. Stauntosaponins A and B were formulated as 3-O-?-d-oleandropyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (1) and 3-O-?-d-thevetopyranosyl-14, 16: 15, 20: 18, 20-triepoxy-14, 15-secopregn-4, 6, 8(14)-triene (2). Compounds 1 and 2 showed moderate inhibitory activities against Na+/K+-ATPase with IC50 values of 21 and 29?M, respectively, whereas ouabain as a positive control displayed an IC50 value of 3.5?M.
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? This study reports on isolation of two new steroid glycosides (1 and 2) from the roots extract of Cynanchum stauntonii (Decne.) Schltr.ex Levl. ? Their structures were elucidated on the basis of 1D- and 2D-NMR, mass, IR and UV spectroscopic analyses. ? Na+/K+-ATPase inhibitory activity was tested for 1 and 2, and they showed moderate activity.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Huanxin Zhao, Tiantian Nie, Huanjie Guo, Jun Li, Hong Bai Two new neolignan glycosides, named pittogoside A (1) and pittogoside B (2) were isolated from the roots of Pittosporum glabratum Lindl. Their structures, including the absolute stereochemistry, were determined on the basis of spectroscopic analysis and chemical evidence, with combination of circular dichroism.
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? Isolation and structure elucidation of two new neolignan glycosides. ? Neolignan glycosides were first isolated from the genus Pittosporum. ? Compounds isolated from P. glabratum were evaluated for antioxidant activities.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Ke Zan, Xiao-Qing Chen, Xing-Yun Chai, Qing Wu, Qiang Fu, Si-Xiang Zhou, Peng-Fei Tu Two new eudesmane sesquiterpenoids artanoate (1) and eudesmanomolide (2) were isolated from the aerial parts of Artemisia anomala S. Moore. Their structures were elucidated as methyl (4R, 5S, 6S, 7S, 10R)-1-oxo-4, 6-dihydroxy-eudesma-2, 11 (13)-dien-12-oate (1) and (1R, 5R, 6R, 10R)-3, 13-diacetoxy-1-hydroxy-3, 7(11)-diene-12, 6-olide (2) on the basis of extensive spectroscopic analyses. Compound 1 showed cytotoxicity against HCT-8 cell lines with IC50 value of 9.13?M, and compound 2 exhibited inhibitory activities against HCT-8 and A549 cell lines with IC50 values of 3.76 and 5.49?M, respectively.
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? Two new eudesmane sesquiterpenoids, namely artanoate (1) and eudesmanomolide (2) were isolated from the aerial parts of Artemisia anomala S. Moore. ? Artanoate (1) showed cytotoxicity against HCT-8 cell lines with an IC50 value of 9.13?M. ? Eudesmanomolide (2) exhibited inhibitory activities against HCT-8 and A549 cell lines with IC50 values of 3.76 and 5.49?M, respectively.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Fatih Karabey, Ikhlas A. Khan, Erdal Bedir Three new cycloartane-type triterpene glycosides were isolated from the roots of Astragalus schottianus Boiss. Their structures were established as 20(R),25-epoxy-3-O-?-d-xylopyranosyl-24-O-?-d-glucopyranosyl-3?,6?,16?,24?-tetrahydroxycycloartane (1), 20(R),25-epoxy-3-O-[?-d-glucopyranosyl(1?2)]-?-d-xylopyranosyl-24-O-?-d-glucopyranosyl-3?,6?,16?,24?-tetrahydroxycycloartane (2), 3-O-?-d-xylopyranosyl-3?,6?,16?,20(S),24(S),25-hexahydroxycycloartane (3) by the extensive use of 1D and 2D-NMR techniques and mass spectrometry.
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? A phytochemical study was performed on Astragalus schottianus. ? Three new cycloartane-type triterpene glycosides were isolated. ? Hydroxyl group at C-20 position was reported for the second time in Astragalus cycloartanes.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Marvin J. Núñez, Alejandro E. Ardiles, Morena L. Martínez, David Torres-Romero, Ignacio A. Jiménez, Isabel L. Bazzocchi Three new triterpenoids, including two rare D:B-friedobaccharanes (leonatriol, 1 and leonatriolone, 2) and a 2,3-seco-2,24-epoxy-3,24-olide-D:A-friedooleanane (cassinolide, 3) were isolated from the root bark of Cassine xylocarpa and Celastrus vulcanicola, collected in El Salvador. Their stereostructures were elucidated on the basis of spectroscopic analyses, mainly 1D and 2D NMR techniques, spectrometric analyses, and comparison with data reported in the literature. The absolute configuration of 1 and 2 were determined by the application of the Riguera ester procedure and biogenetic considerations. The possible biogenetic pathway for cassinolide (3) is also discussed.
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? Unusual D:B-friedobaccharanes and friedelane-type triterpenes from Celastraceae species. ? Chemotaxonomic relevance of D:B-friedobaccharanes in Celastraceae species. ? Determination of absolute configuration by application of the Riguera ester procedure. ? Plausible biogenetic pathway for 2,3-seco-2,24-epoxy-3,24-olide-D:A-friedooleanane triterpenes.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Tetsuro Ito, Hiromi Ito, Masayoshi Oyama, Toshiyuki Tanaka, Jin Murata, Dedy Darnaedi, Munekazu Iinuma Our investigations of the chemical constituents in the leaves of Upuna borneensis Sym. (Dipterocarpaceae) resulted in the isolation of two novel diastereomeric acetophenone derivatives, upuborneols A (1) and B (2), along with four known derivatives (3–6). Their structures were determined by spectroscopic analysis including two-dimensional NMR and the speculation of biogenesis. Compounds 1 and 2 had a C6 unit derived from sugar unit and are the first known representatives of natural acetophenone derivatives bearing a spiroketal moiety.
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? The isolated products were the first instance of naturally occurring spiroketal-hexosefuranosides of acetophenone. ? The leaves of Upuna borneensis contain acetophenone C-glycosides. ? Co-occurrence of biogenetically related phloroacetophenone C-glycosides was exhibited.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Rados?aw Gni?ka, Antoni Szumny, Agata Bia?o?ska, Czes?aw Wawrze?czyk The effectivePart 38. See ref. Dams et al., 2012. method of isolation, separation and purification of (?)-?- and (+)-?-thujone (1a and 1b) from Thuja occidentalis was elaborated. Chemical (m-CPBA) and microbial Baeyer–Villiger oxidation of (?)-?- and (+)-?-thujone was carried out. Four new bicyclic ?-lactones (2a, 2b, 3a and 3b) with condensed cyclopropane ring were obtained.
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The four new bicyclic ?-lactones with condensed cyclopropane ring were obtained from ?- and ?-thujone. Both isomers of thujone were isolated from white cedar leaves oil (Thuja occidentalis).? The monoterpenoid ketones: ?- and ?-thujone were isolated from Thuja occidentalis essential oil. ? Chemical and microbial oxidation of ?- and ?-thujone afforded four new ?-lactones with condensed cyclopropane ring. ? The crystal structures of three new lactones are reported.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Yukio Hitotsuyanagi, Jun-ichi Kusano, Ik-Hwi Kim, Tomoyo Hasuda, Haruhiko Fukaya, Koichi Takeya O-Seco-RA-XXIV, a new cyclic peptide, cyclo-(d-alanyl-l-glutaminyl-N,O-dimethyl-l-tyrosyl-l-alanyl-N-methyl-l-tyrosyl-N-methyl-l-tyrosyl), was isolated from the roots of Rubia cordifolia L. along with RA-XXIV. Its structure and relative stereochemistry were determined by interpretation of the spectroscopic data and X-ray crystallography, and its absolute stereochemistry by the Marfey's amino acid analysis of its acid hydrolysate. Isolation of the two peptides from the same plant source may indicate that O-seco-RA-XXIV is a possible precursor of RA-XXIV and that the formation of the diphenyl ether linkage in the cycloisodityrosine moiety is to be formed after the formation of the cyclohexapeptide chain in this series of peptides.
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? This work deals with important new antitumor peptides. ? A significant clue for the biosynthetic route of RAs and bouvardins is provided. ? The structure was unambiguously established by X-ray crystallography. ? The coordinates from the crystallography will be useful for the subsequent SAR study.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Jun Luo, Yi Li, Jun-Song Wang, Juan Lu, Ling-Yi Kong Three new C-15-isobutyryl 16-norphragmalin-type limonoids, chukvelutins D–F (1–3), were isolated from the stem bark of Chukrasia tabularis var. velutina. Their structures were established on the basis of detailed spectroscopic analysis. Compound 1 possessed a ketonic isobutyryl C-15 substitution previously unreported in phragmalin-type limonoids. Compounds 2 and 3 showed moderate anti-inflammatory activity with IC50 values at 10.01 and 28.54?M.
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Three new C-15-isobutyryl 16-norphragmain-type limonoids, chukvelutins D–F (1–3), were isolated from the stem bark of Chukrasia tabularis var. velutina, and 2 and 3 were evaluated for their anti-inflammatory activity.? Three new C-15-isobutyryl 16-norphragmalin limonoids were isolated. ? Compound 1 was distinguished by a unique ketonic isobutyryl substitution at C-15. ? Compounds 2 and 3 showed anti-inflammatory activity.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Na Liu, Li Zhang, Song Wang, Xiao-Ning Wang, Shu-Qi Wang, Hong-Xiang Lou Phytochemical investigation of the Et2O extract of liverwort Apomarsupella revolute led to isolation and identification of five new eudesmane-type sesquiterpenoids, 6?-hydroxy-9?-acetoxy-eudesma-4,11-dien (1), 6?-hydroxy-9?-acetoxy-eudesma-4,11-dien-3-one (2), 5?,6?-dihydroxy-9?-acetoxy-eudesma-4(15),11-dien (3) 4?-hydroxy-9?-acetoxy-11,12,13-trinor-5-eudesmen-7-one (4) and 4?-methox-9?-acetoxy-11,12,13-trinor-5-eudesmen-7-one (5), two of which were trinorsesquiterpenoids. Their structures were established unequivocally on the basis of spectroscopic data analysis. All compounds were preliminary bioscreened for their cytotoxicities and antifungal activities.
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Three sesquiterpenoids and two trinorsesquiterpenoids were isolated from the Et2O extract of liverwort Apomarsupella revolute. Their structures were elucidated on the basis of NMR and MS data. Their cytotoxic and antifungal activities were also evaluated.? Five new acetylated eudesmane-type sesquiterpenoids were isolated from Apomarsupella revolute. ? Their structures were elucidated using extensive spectroscopic analysis. ? The cytotoxic and antifungal activities of the compounds were evaluated. ? The sesquiterpenoids from A. revolute will play a role as chemical indicators for chemosystematics.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Ratchanaporn Chokchaisiri, Phongsak Innok, Apichart Suksamrarn Four new flavonoid glycosides, curcucomosides A–D (1–4), three known flavonoid glycosides, 5–7, and four known diarylheptanoids, 8–11, were isolated from the ethanol extract of the aerial parts of Curcuma comosa. The structures of the new compounds were established as rhamnazin 3-O-?-l-arabinopyranoside (1), rhamnocitrin 3-O-?-l-arabinopyranoside (2), rhamnazin 3-O-?-l-rhamnopyranosyl-(1?2)-O-?-l-arabinopyranoside (3), and rhamnocitrin 3-O-?-l-rhamnopyranosyl-(1?2)-O-?-l-arabinopyranoside (4) by spectroscopic analysis and chemical reactions whereas those of the known compounds were identified by spectral comparison with those of the reported values.
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Four new and three known flavonoid glycosides, and four diarylheptanoids were isolated.? Four new flavonoid glycosides were isolated from the aerial parts of Curcuma comosa. ? The flavonoid aglycone moieties are rhamnazin and rhamnocitrin. ? The glycoside parts are arabinopyranoside and rhamnopyranosyl arabinopyranoside.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Pratiwi Pudjiastuti, Stephen G. Pyne, Sugiyanto, Wilford Lie A novel croomine derivative, tuberospironine A (3-epi-tuberospironine) was isolated from the root extracts of Stemona tuberosa Lour. found growing on Seram Island, Moluccas Province, Indonesia. The structure of this novel alkaloid, with unprecedented configuration at C-3 for a croomine derivative, was determined from interpretation of its NMR spectroscopic data.
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? A new Stemona alkaloid is reported from Stemona tuberosa Lour. ? Structure elucidation made using spectroscopic analysis. ? NOESY experiments indicated an unprecedented configuration at C-3 for a croomine derivative.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Mudasir A. Tantry, Javid A. Dar, Mohammad A. Khuroo, Abdul S. Shawl Chemical investigation of chloroform–ethyl acetate extract from the roots of Paeonia emodi yielded four hitherto unknown noroleanane triterpenoids (1–4) together with four known compounds (5–8). Their structures were established by analysis of spectroscopic data. Compounds 1–8 were evaluated for cytotoxic activities against human cancer cell lines A549, HL-60, HCT116 and ZR-75-30. Compounds 1, 2, 3, 6 and 7 showed modest cytotoxicity against HL-60, HCT116 and ZR-75-30.
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? The chemistry of Paeonia emodi was investigated, with 8 compounds including 4 new ones, were isolated and identified. ? New compounds are noroleanane triterpenoids (1–4). ? Compounds 1–8 were evaluated for cytotoxic activities against human cancer cell lines A549, HL-60, HCT116 and ZR-75-30.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Buket Bozkurt Sarikaya, Gulen Irem Kaya, Mustafa Ali Onur, Francesc Viladomat, Carles Codina, Jaume Bastida, Nehir Unver Somer Two new Amaryllidaceae alkaloid N-oxides, incartine N-oxide (1) and lycorine N-oxide (2) together with one ?-carboline alkaloid, 1-acetyl-?-carboline (3) and six known alkaloids namely, incartine (4), N-trans feruloyltyramine (5), lycorine (6), O-methylnorbelladine (7), vittatine (8) and 11-hydroxyvittatine (9) were isolated from Galanthus rizehensis Stern (Amaryllidaceae). The structures of the alkaloids were elucidated by spectroscopic analyses (UV, IR, MS, 1D and 2D NMR). Acetylcholinesterase inhibitory activity potentials of the compounds were also determined.
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? Two new alkaloid N-oxides (1, 2) were isolated from Galanthus rizehensis (Amaryllidaceae). ? 1-Acetyl-?-carboline (3) was reported for the first time from an Amaryllidaceae species. ? Galanthus rizehensis is an interesting source of alkaloids with diverse structures.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Tawanun Sripisut, Thunwadee Ritthiwigrom, Trinop Promgool, Kulsiri Yossathera, Suwanna Deachathai, Wong Phakhodee, Sarot Cheenpracha, Surat Laphookhieo A new hydroperoxyquinolone alkaloid, glycopentaphyllone (1), along with nine compounds (2–10), was isolated from the fruits of Glycosmis pentaphylla. Their structures were elucidated on the basis of spectroscopic methods. The absolute configuration of glycopentaphyllone at C-2? was established as S-configuration by applying Mosher's method. In addition, the completed assignments of 13C NMR as well as 2D NMR spectral data of compound 5 were reported herein for the first time. Also, all isolates were evaluated for antibacterial activity against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphylococcus aureus TISTR 1466, and Methicillin-resistant S. aureus SK1.
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? The first isolation of hydroperoxyquinolone from Glycosmis pentaphylla ? The first completed assignment of 13C NMR spectral data and confirmation the structure 5 by 2D NMR spectral data. ? The absolute configuration of glycopentaphyllone was established.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Teigo Asai, Yui Hirayama, Yoshinori Fujimoto A new sesquiterpene glycoside, (?)-epi-?-bisabolol 6-deoxy-?-d-gulopyranodide (1), has been isolated from the glandular trichome exudate of Brillantaisia owariensis (Acanthaceae). The structure of compound 1 was determined by spectroscopic analysis as well as acidic hydrolysis of 1 leading to (?)-epi-?-bisabolol (2) and 6-deoxy-d-gulose (3). This is the first study to analyze secondary metabolites from glandular trichome exudates of plants belonging to the Acanthaceae family. 6-Deoxygulopyranoside is the first example of an epi-?-bisabolol glycoside of plant origin.
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The structure was elucidated by spectroscopic analysis and acidic hydrolysis leading to (?)-epi-?-bisabolol and 6-deoxy-d-gulose.? Chemical investigation of the glandular trichome exudate from Brillantaisia owariensis was conducted. ? The structure determination of (?)-epi-?-bisabolol 6-deoxy-?-d-gulopyranoside was reported. ? This is the first report of the isolation of epi-?-bisabolol glycosides from plants.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Fu Li, Cui-Rong Sun, Bin Chen, Li-Sheng Ding, Ming-Kui Wang Three new triterpenoid saponins, named raddeanoside R20 (1), raddeanoside R21 (2) and raddeanoside R22 (3), were isolated from the water soluble part of Anemone raddeana. The chemical structures of these new compounds were elucidated by chemical and spectroscopic methods.
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Three new triterpenoid saponins were isolated from the roots of Anemone raddeana. The chemical structures of these compounds were determined based on chemical methods and various spectroscopic data.? Three new triterpenoid saponins were isolated from the roots of Anemone raddeana. ? All the compounds contain at least 8 sugar residues. ? Their structures were deduced from chemical methods and spectroscopic analysis.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Rodney Lacret, Rosa M. Varela, José M.G. Molinillo, Clara Nogueiras, Francisco A. Macías A phytochemical study on the most bioactive extract from Tectona grandis led to the isolation of two new norlignans, tectonoelin A and tectonoelin B, together with ten known compounds. The structures of the compounds were determined by a combination of 1D and 2D NMR techniques. This is the first time that this type of compound (C8–C8? linkage norlignans) has been isolated from a dicotyledon. The general bioactivities of the isolated compounds have been studied using etiolated wheat coleoptiles. The activities showed that the isolated lignans and norlignans should be part of the defence mechanisms of this plant.
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The bioactive extract from Tectona grandis has yielded two new norlignans – tectonoelin A and tectonoelin B – together with ten known compounds. The compounds were tested in the etiolated coleoptile bioassay and this showed that the lignans and norlignans should be part of the defence mechanisms of this plant.? Teak wood is an excellent source of natural bioactive compounds. ? The structure elucidation of new norlignans, tectonoelin A and B, is reported. ? This is the first isolation of C8–C8? linkage norlignans from a dicot. ? The bioactivities of the isolated compounds have been studied. ? The isolated lignans and norlignans should be part of the defence mechanisms.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Qing-Fa Tang, Wen-Cai Ye, Jing-Han Liu, Chun-Hua Yang Three new hetisine-type diterpenoid alkaloids, Guan-fu base V (GFV, 1), Guan-fu base W (GFW, 2) and Guan-fu base X (GFX, 3) were isolated from the roots of Aconitum coreanum (Lèvl.) Rapaics. Their structures were established by direct interpretation of their spectral data, mainly high resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D and 2D NMR (1H–1H COSY, ROESY, HSQC and HMBC). GFX is the third N-oxygenated hetisine-type diterpenoid alkaloid isolated from A. coreanum.
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The structures of new compounds 1–2 isolated from Aconitum coreanum.? A phytochemical study was performed on Aconitum coreanum. ? Three new hetisine-type diterpenoid alkaloids were isolated. ? GFX is the third N-oxygenated hetisine-type alkaloid isolated from A. coreanum.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Ahlam Elwekeel, Ahlam Elfishway, Sameh AbouZid Root cultures of Silybum marianum (L.) Gaertn. (Asteraceae) were established from in vitro germinated sterile plantlets. The cultures grew in hormone-free Murashige and Skoog medium. The flavonolignan content in the cultured roots was determined by HPLC using 30% acetonitrile in acidified water (0.5% phosphoric acid). The major flavonolignans produced by the cultured roots were silychristin (74.2?gg?1 fresh weight (FW)) and silydianin (8.1?gg?1 FW). The flavonolignan precursor taxifolin was also detected in the cultured roots (40.8?gg?1 FW). Addition of methyl jasmonate to 7-days-old root cultures for 48h increased the content of the produced flavonolignans and taxifolin to approximately 300% of the control cultures. Methyl jasmonate also enhanced about sixfold the accumulation of a compound identified as 3,3?,5,5?,7-pentahydroxyflavanone.
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Silychristin and silydianin were the main flavonolignans found in Silybum marianum root culture. Production of 3,3?,5,5?,7-pentahydroxyflavanone was enhanced by methyl jasmonate. The latter compound was isolated and identified from grown plant root.? Root culture of Silybum marianum was established. ? Elicitation of flavonolignans and pentahydroxyflavanone in the cultured roots was affected by methyl jasmonate. ? Pentahydroxyflavanone was isolated from grown plant roots and its structure was identified by spectroscopic means.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Ming-Jen Cheng, Ming-Der Wu, Yung-Shun Su, Gwo-Fang Yuan, Yen-Lin Chen, Ih-Sheng Chen Phytochemical analysis of the n-BuOH-soluble fraction of the 95% EtOH extract of the red yeast rice fermented with the yellow mutant of the fungus Monascus kaoliang BCRC 31506 led to the isolation of one new azaphilone metabolite, designated as monascuskaolin (1), along with 9 known compounds (2–10). Monascuskaolin (1) contains an isochroman-6-one azaphilone skeleton connected with one ?-lactone ring, one propan-2-yl acetate moiety, and one decanoyl side chain. Their structures were elucidated by detailed spectroscopic analyses, including HRESIMS and 1D and 2D NMR data (COSY, HSQC, HMBC, and NOESY). The relative configuration of 1 was confirmed by NOESY experiment. Other known compounds were identified by comparison of their spectral data with the literature data of authentic samples. Inhibitory effects of some isolates on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages were evaluated. Compounds 1–4 showed inhibition on NO production in LPS-stimulated RAW 264.7 macrophages in vitro, showing MIC values of 7.62, 18.78, 26.72, and 32.80?g/mL, respectively.
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Investigation of the 95% ethanolic extract of red yeast rice fermented with the yellow mutant of the fungus Monascus kaoliang BCRC 31506 led to the isolation of one new azaphilone derivative, namely monascuskaolin (1), together with 9 known compounds (2–10). The inhibitory effects of some isolates on the production of nitric oxide (NO) induced by lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages were evaluated.? Ten compounds were isolated from the fungus Monascus kaoliang. ? Compound 1 was an isochroman-6-one azaphilone derivative. ? Compounds 1–4 showed inhibition on NO production.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Cristiane Justino do Nascimento, Ivana Maria Povoa Violante, Walmir Silva Garcez, Arnildo Pott, Fernanda Rodrigues Garcez Bioassay-guided fractionation of the ethanol extract from the branches of Erythroxylum suberosum, which was toxic to brine shrimp larvae, afforded five diterpenes bearing abietane and ent-kaurane-type skeletons from an active fraction. From these, four were new, 7-oxo-16-hydroxy-abiet-15(17)-en-19-al, 16-hydroxyabiet-15(17)-en-7-one, 7?,16-dihydroxy-abiet-15(17)-en-19-al and ent-12?-hydroxy-kaur-16-en-19-al, while methyl ent-7?,15?-dihydroxy-kaur-16-en-19-oate is reported for the first time as a natural product. This is also the first reported occurrence of abietane-type diterpenes in the genus Erythroxylum. The flavonoid ombuin-3-rutinoside was isolated from an inactive fraction, while rutin (quercetin-3-rutinoside) was obtained from the non-toxic ethanol extract of the leaves. The structures of the new and known compounds were established by analyses of 1D- and 2D-NMR and mass spectrometry data.
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? Brine shrimp toxicity guided investigation of extracts of the branches of Erythroxylum suberosum. ? Three new abietanes and one ent-kaurane were isolated from the bioactive fractions. ? Another bioactive ent-kaurane was first isolated from a natural source. ? Abietane-type diterpenes are first reported in the genus Erythroxylum. ? Two known inactive flavonoid glycosides were obtained from the leaves and branches.
Publication year: 2012 Source:Phytochemistry Letters Valerie Tedjon Sielinou, Juliette Catherine Vardamides, Augustin Ephrem Nkengfack, Hartmut Laatsch The structures of two new compounds from the root bark of Turraeanthus mannii (Meliaceae) were determined as (3R,4R,3?R,4?R)-6,6?-dimethoxy-3,4,3?,4?-tetrahydro-2H,2?H-[3,3?]bichromenyl-4,4?-diol (1) and 15-acetoxy-labda-8(17),12E,14Z-trien-16-al (2) by means of spectroscopic analysis. Five further known compounds including one coumarin derivative, one chromenone, two labdane diterpenes and one pregnane steroid have been isolated from the same source. In antifungal and cytotoxic assays, 15-acetoxy-labda-8(17),12E,14Z-trien-16-al (2) was highly active against Mucor miehei and Artemia salina, respectively.
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The structures of two new compounds from the root bark of Turraeanthus mannii (Meliaceae) were determined as (3R,4R,3?R,4?R)-6,6?-dimethoxy-3,4,3?,4?-tetrahydro-2H,2?H-[3,3?]bichromenyl-4,4?-diol (1) and 15-acetoxy-labda-8(17),12E,14Z-trien-16-al (2) by means of spectroscopic analysis. 15-Acetoxy-labda-8(17),12E,14Z-trien-16-al (2) was found to exhibit antifungal and cytotoxic activities against Mucor miehei and Artemia salina, respectively.? Two new compounds have been isolated from the root bark of Turraeanthus mannii (Meliaceae). ? (3R,4R,3?R,4?R)-6,6?-Dimethoxy-3,4,3?,4?-tetrahydro-2H,2?H-[3,3?]bichromenyl-4,4?-diol and 15-acetoxy-labda-8(17),12E,14Z-trien-16-al. ? 15-Acetoxy-labda-8(17),12E,14Z-trien-16-al exhibited antifungal and cytotoxic activities against Mucor miehei and Artemia salina, respectively.
Publication year: 2012 Source:Phytochemistry Letters Denise O. Guimarães, Norberto P. Lopes, Mônica T. Pupo Two new guignardones and one tricycloalternarene derivatives, named guignardone D, E (2–3) and tricycloalternare F (4), and the known guignardone A (1) were isolated from Guignardia mangiferae, an endophytic fungus from the leaves of Viguiera arenaria (Asteraceae), after fermentation in Czapek medium. Structures were established on the basis of their spectroscopic data, including 1H NMR, 13C NMR, HMQC, HMBC and HRESI-MS.
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? The endophytic fungus Guignardia mangiferae found in association with Viguiera arenaria (Asteraceae) were investigated. ? Guignardones and tricycloalternarene derivatives were isolated. ? Three new compounds and one known were identified based on spectroscopic data.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Tetsuro Ito, Hidetatsu Endo, Masayoshi Oyama, Munekazu Iinuma Three stereoisomeric stilbene trimers bearing an (E)-2,3,5,6-tetraphenyl-4-styryl-2,3,5,6-tetrahydrobenzo[1,2-b:5,4-b?]difuran skeleton, (+)- and (?)-(E)-cyperusphenol A (1, 2) and (E)-mesocyperusphenol A (3), were isolated from a cyperus rhizome. Moreover, the geometrical isomers (4–6) were identified as the artifacts of their (E)-forms (1–3). The isolated products are the first instance of the co-occurrence of racemates (1, 2: new compounds) and a meso isomer (3), which resembles the C2 symmetrical structure of an oligostilbenoid. These structures were characterized by NMR and CD spectroscopy. This is the first report that shows the occurrence of a racemate of a stilbenoid in the same plant material and the achievement of the optical separation of stilbene oligomers.
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? The isolated products were the first instance of the co-occurrence of racemates and a meso isomer, which resembles the C2 symmetrical structure. ? This was the first report that shows the occurrence of a racemate of stilbenoids in the same plant material. ? This was the first achievement of the optical separation of stilbene oligomers. ? Cyperus rhizome contained oligostilbenoids bearing blocking units of resveratrol and piceatannol. ? The determination of the absolute configuration of isolates was based on optical rotations and CD spectral properties.
Publication year: 2012 Source:Phytochemistry Letters Yoshihisa Tanaka, Daiki Honma, Masayoshi Tamura, Akio Yanagida, Ping Zhao, Toshihiko Shoji, Motoyuki Tagashira, Yoichi Shibusawa, Tomomasa Kanda A chromanone glycoside, 5-?-d-glucopyranosyloxy-7-hydroxy-2-isopropylchromanone, and two acylphloroglucinol glycosides, 2-(3-methylbutyryl)phloroglucinol-4,6-di-C-?-d-glucopyranoside and 2-isobutyrylphloroglucinol-1,5-di-O-?-d-glucopyranoside, along with 15 known compounds were isolated from the bracts of hops (Humulus lupulus L.). Their structures were elucidated based on spectroscopic data, including TOFMS and 1D/2D NMR.
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A chromanone glycoside (1) and two acylphloroglucinol glycosides (2 and 3) along with 15 known compounds were isolated from the bracts of hops (Humulus lupulus L.).? The chemical composition of the bracts of hops (Humulus lupulus L.) was investigated. ? New chromanone and acylphloroglucinol glycosides were isolated from the bracts. ? Their structures were elucidated based on TOFMS and 1D/2D NMR. ? 2-Isopropylchromanones are encountered in nature for the first time. ? The acylphloroglucinol C-glycoside and di-O-glycoside have not been reported in hops.
Publication year: 2012 Source:Phytochemistry Letters Simone Quintana de Oliveira, Maria Tereza Rojo de Almeida, Flora Maraslis, Izabella Thaís Silva, Thais Cristine Marques Sincero, Jorge Alejandro Palermo, Gabriela Myriam Cabrera, Miguel Soriano Balparda Caro, Cláudia Maria Oliveira Simões, Eloir Paulo Schenkel Investigation of the crude ethanolic extract obtained from the aerial parts of Dodonaea viscosa led to the isolation of three new ent-labdane diterpenes (1–3). The structures were established on the basis of their ESI–MS, UV, IR and NMR spectral data. The crude extract, fractions and compounds were evaluated for in vitro antiviral activity against Herpes Simplex Virus type 1 (HSV-1). The crude extract showed promising antiherpes activity expressed by a selectivity index of 6.2.
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? Three new ent-labdane diterpenes were isolated from Dodonaea viscosa. ? All of the compounds were fully characterized by 1D and 2D NMR experiments. ? The crude ethanol extracts showed antiherpes activity.
Publication year: 2012 Source:Phytochemistry Letters Desi Harneti, Roekmiati Tjokronegoro, Agus Safari, Unang Supratman, Xe-Min Loong, Mat Ropi Mukhtar, Khalit Mohamad, Khalijah Awang, Hideo Hayashi Two new dammarane triterpenoids, aglinone (1) and aglinin E (20S,24S-epoxy-25-hydroxy-1-en-dammarene) (2) along with three known compounds, 3-epiocotillol (3), aglinin A (4), and eichlerianic acid (5), were isolated from the bark of Aglaia smithii. The chemical structures of the new compound were elucidated on the basis of spectroscopic data interpretation. All the compounds isolated were evaluated for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1, 2, 4 and 5 showed cytotoxicity against P-388 murine leukemia cells with IC50 values of 21, 42, 34, and 11?g/mL, respectively.
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Two new dammarane triterpenoids, aglinone (1) and aglinin E (20S,24S-epoxy-25-hydroxy-1-en-dammarene) (2) along with three known compounds, 3-epiocotillol (3), aglinin A (4), and eichlerianic acid (5), were isolated from the bark of Aglaia smithii. Compounds 1, 2, 4 and 5 showed cytotoxicity against P-388 murine leukemia cells with IC50 values of 21, 42, 34, and 11?g/mL, respectively.? Two new dammarane triterpenoids, namely aglinone (1) and aglinin E (2) were isolated from Aglaia smithii (Meliaceae). ? The novel compounds and three known compounds were identified by extensive spectroscopic techniques. ? Cytotoxic activity was tested for the pure isolates (1–5), and they showed weak-moderate activity against P-388 murine leukemia cell lines, in vitro.
Publication year: 2012 Source:Phytochemistry Letters, Volume 5, Issue 2 Bo Wang, Xiao-Ning Wang, Tao Shen, Shu-Qi Wang, Dong-Xiao Guo, Hong-Xiang Lou Four new rearranged abietane diterpenoid hydroquinones, ajudecumins A–D (1–4), together with two known rearranged abietane diterpenoids, three neo-clerodane diterpenoids, four megastigmane derivatives, two flavonoids as well as a bisabolene sesquiterpenoid were isolated from the aerial parts of Ajuga decumbens. Their structures were established on the basis of extensive spectroscopic analysis and the stereochemistry of 1 was confirmed by single-crystal X-ray diffraction analysis. Among the diterpenoids, compounds 1 and 3 exhibited moderate inhibitory activity on the proliferation of human breast cancer MCF-7 cells.
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? Four rearranged abietane diterpenoids were first found from Ajuga decumbens. ? The structure of new compounds was determined by spectroscopic methods. ? The structure of ajudecumin A was also verified by X-ray diffraction analysis. ? Ajudecumins A and C moderately inhibited the proliferation of MCF-7 cells.
Publication year: 2012 Source:Phytochemistry Letters Marcelo A. Muñoz, Martina Martínez, Pedro Joseph-Nathan Both enantiomers of 3?,6?-dibenzoyloxytropane (1) have been prepared from optical active 6?-hydroxyhyoscyamines establishing their absolute configurations as (?)-(3R,6R) and (+)-(3S,6S)-dibenzoyloxytropane. Independent stereochemical confirmation was obtained by vibrational circular dichroism measurements, since bands characteristic of (3R,6R) and (3S,6S) configurations of tropanediols derivatives were observed. In addition, a chiral HPLC method was developed for determining absolute configurations of tropane-related natural substances at the microgram (?g) level. The complete 1H NMR characterization of the scaffold of 1 is also reported.
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? Absolute configurations of 3?,6?-dibenzoyloxytropane are (?)-(3R,6R) and (+)-(3S,6S). ? VCD bands permit absolute configuration determination without DFT calculations. ? All aliphatic 1H NMR coupling constants of 3?,6?-dibenzoyloxytropane were obtained.
Posted on 27 May 2012 | 1:24 am
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