- A bidesmosidic oleanolic acid saponin from Panax pseudo-ginseng.
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A novel triterpenoid saponin, pseudo-ginsenoside-RI3, isolated from the rhizomes of Panax pseudo-ginseng subsp. himalaicus var. angustifolius has been characterized as 3-O-beta-D-glucopyranosyl(1----2)-beta-D-glucuronopyranosyl (1----6)-beta-D-glucopyranosyl 28-O-beta-D-xylopyranosyl-olean-12-en-28-oic acid ester by physicochemical methods.
- Shukla,Thakur,Pachaly
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- GENICULATIN, A TRITERPENOID SAPONIN FROM EUPHORBIA GENICULATA
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A new triterpenoid saponin, geniculatin, has been isolated from the ethanolic extract of Euphorbia geniculata (Euphorbiaceae).The saponin has been identified as 3β-4)-D-xylopyranosyl-(1->4)-D-β-glucoronopyranosyl-(1->3)>-oxyolean-12-en-28-oic acid. - Key Word Index: Euphorbia geniculata; Euphorbiaceae; geniculatin; 3β-4)-D-xylopyranosyl-(1->4)-D-β-glucopyranosyl-(1->3)-oxyolean-12-en-28-oic-acid.
- Tripathi, R. D.,Tiwari, K. P.
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- Triterpenes from Cigarrilla mexicana
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-From the aerial parts of Cigarrilla mexicana 3β, 23-dihydroxy-urs-12-en-28-oic acid, a new natural product, has been isolated together with the.
- Mata, Rachel,Rios, Lizeth,del Rayo Camacho, Ma,Reguero, Ma Teresa,Lorence, David
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- Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis
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Four new oleanane-type triterpenoidal glycosides, named gleditsiosides A-D (1-4), were isolated from the anomalous fruits of Gleditsia sinensis. Using modern NMR techniques, including DQF-COSY, HETCOR, HOHAHA, HMBC, and ROESY experiments and MS analysis as well as chemical methods, their structures were determined as 3-O-β-D-xylopyranosyl-(1→2)-α-L- arabinopyranosyl-(1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D- xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)- [(6S,2E)-6-hydroxy-2,6-dimethyl-2,7-octadienoyl-(1→6)]-β-D-glucopyranosyl ester (1); 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-β-D- glucopyranosyl oleanolic acid 28-O-β-D-xylopyranosyl-(1→3)-β-D- xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[(2E)-2-hydroxylmethyl-6- hydroxy-6-methyl-2,7-octadienoyl-(1→6)]-β-D-glucopyranosyl ester (2); 3-O- β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl echinocystic acid 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)- [β-D-galactopyranosyl-(1→2)]-αL-rhamnopyranosyl-(1→2)-[(2E)-2- hydroxylmethyl-6-hydroxy-6-methyl-2,7-octadienoyl-(1→6)]-β-D- glucopyranosyl ester (3); and 3-O-β-D-xylopyranosyl-(1→2)-α-L- arabinopyranosyl-(1→6)-β-D-glucopyranosyl echinocystic acid 28-O-β-D- xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-galactopyranosyl- (1→2)]-α-rhamnopyranosyl-(1→2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2,7- octadienoyl-(1→6)]-β-D-glucopyranosyl ester (4).
- Zhang, Zhizhen,Koike, Kazuo,Jia, Zhonghua,Nikaido, Tamotsu,Guo, Dean,Zheng, Junhua
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- Oleanolic acid from antifilarial triterpene saponins of Dipterocarpus zeylanicus induces oxidative stress and apoptosis in filarial parasite Setaria digitata in?vitro
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Absence of a drug that kills adult filarial parasites remains the major challenge in eliminating human lymphatic filariasis (LF); the second leading cause of long-term and permanent disability. Thus, the discovery of novel antifilarial natural products with potent adulticidal activity is an urgent need. In the present study, methanol extracts of leaves, bark and winged seeds of Dipterocarpus zeylanicus (Dipterocarpaceae) were investigated for macro and microfilaricidal activity. Two antifilarial triterpene saponins were isolated from winged seed extracts by bioactivity guided chromatographic separation and identified using Nuclear Magnetic Resonance and mass spectroscopic analysis as oleanolic acid 3-O-β-D- glucopyranoside (1) (IC50?= 20.54 μM for adult worms, 19.71 μM for microfilariae ) and oleanolic acid 3-O-α-L-arabinopyranoside (2) (IC50?= 29.02 μM for adult worms, 25.99 μM for microfilariae). Acid hydrolysis of both compounds yielded oleanolic acid (3) which was non or least toxic to human peripheral blood mono nuclear cells (Selectivity index?= >10) while retaining similar macrofilaricidal (IC50?= 38.4 μM) and microfilaricidal (IC50?= 35.6 μM) activities. In adult female worms treated with 50 and 100 μM doses of oleanolic acid, condensation of nuclear DNA, apoptotic body formation and tissue damage was observed by using Hoechst 33342 staining, TUNEL assay and Hematoxylin and Eosin staining respectively. A dose dependent increase in caspase 3/CED3 activity and decrease in total protein content were also observed in these parasites. A dose dependant DNA fragmentation was observed in adult parasites and microfilariae. Decreased levels of reduced glutathione (GSH) and elevated levels of glutathione S transferase (GST), superoxide dismutase (SOD) and reactive oxygen species (ROS) were also observed in parasites treated with oleanolic acid indicating an oxidative stress mediated apoptotic event. Compound 3/oleanolic acid was thus identified as a potent and safe antifilarial compound in?vitro.
- Senathilake,Karunanayake,Samarakoon,Tennekoon,de Silva,Adhikari
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- Saponins as novel TNF-α inhibitors: Isolation of saponins and a nor-pseudoguaianolide from Parthenium hysterophorus
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Two novel saponins and a 13-nor-pseudoguaianolide designated as hysterolactone were isolated from Parthenium hysterophorus. The two saponins were found to be potent inhibitors of TNF-α. Their mode of inhibition was studied through molecular modeling. The
- Shah, Bhahwal Ali,Chib, Renu,Gupta, Pankaj,Sethi, Vijay Kumar,Koul, Surrinder,Andotra, Samar Singh,Nargotra, Amit,Sharma, Sujata,Pandey, Anjali,Bani, Sarang,Purnima, Basant,Taneja, Subhash Chandra
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- A new oleanolic acid derivative from Securinega tinctoria
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The triterpenoid constituents of the chloroform extract of previously defatted material of the stems of Sucurinega tinctoria were examined and, besides β-sitosterol β-D-glucopyranoside, a new oleanolic acid derivative was isolated and identified as 3β-(p-hydroxy-trans-cinnamoyloxy)olean-12-en-28-oic acid.
- Carvalho,Seita
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- Antileishmanial activity of natural diterpenes from Cistus sp. and semisynthetic derivatives thereof
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Eleven cis-clerodane diterpenes, seven labdane type diterpenes and one triterpene isolated from Cistus monspeliensis and the resin "Ladano" of Cistus creticus subsp. creticus were evaluated against Leishmania donovani promastigotes, the causative agent for visceral leishmaniasis. In addition, eleven semisynthetic manoyl oxide, seventeen labdane type derivatives and a triterpene were also evaluated for their antileishmanial activity. 18-Acetoxy-cis-clerod-3-en-15-ol, 15,18-diacetoxy-cis-clerod-3-ene and 13-(E)-8a-hydroxylabd-13-en-15-ol 2-chloroethylcarbamate exhibited the most potent and selective leishmanicidal activity with IC50 values of 3.3 μg/ml, 3.4 μg/ml and 3.5 μg/ml, respectively.
- Fokialakis, Nikolas,Kalpoutzakis, Eleftherios,Tekwani, Babu Lal,Skaltsounis, Alexios Leandros,Duke, Stephen Oscar
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- TRITERPENE GLYCOSIDES OF THE LEAVES OF Digitalis ciliata
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Two new terpene glycosides have been isolated from the leaves of the foxglove Digitalis ciliata Trautv.: β-D-glycopyranosyl oleanolate 3-O-4)-α-L-rhamnopyranoside> and oleanolic acid 3-O-4)-α-L-rhamnopyranoside>.
- Kemertelidze, E. P.,Gvazava, L. N.,Alaniya, M. D.,Kikoladze, V. S.
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- Biosynthesis of Triterpenes, Ursolic Acid and Oleanolic Acid, from Acetate in Tissue Cultures of Rabdosia japonica Hara
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1,2-Hydride shifts in the biosynthesis of ursolic acid (2) and oleanolic acid (6), 20-H from C-19, 19-H from C-18, and 18-H from C-13 in (2) and 19-H from C-18 and 18-H from C-13 in (6), were verified in cultured cells of Rabdosia japonica Hara fed with acetate.
- Seo, Shujiro,Uomori, Atsuko,Yoshimura, Yohko,Takeda, Ken'ichi,Sankawa, Ushio,et al.
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- Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens
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The bisdesmoside oleanolic acid saponin, 3-O-(methyl-β-D-glucuronopyranosiduronoate)-28-O-β-D-glucopyranosyl -oleanoate, along with nine known compounds (two diterpenic acids, one chromene, three triterpenes, one steroidal glycoside, and two monodesmoside oleanolic acid saponins), were obtained from Viguiera decurrens roots. The chemical structure of the bisdesmoside oleanolic saponin was determined by chemical and NMR spectral evidence. A mixture of monodesmoside saponins displayed cytotoxic activity against P388 and COLON cell lines (ED50 = 2.3 and 3.6 μg/ml, respectively). Two of the known compounds showed insecticidal activity against the Mexican bean beetle larvae (Epilachna varivestis).
- Marquina,Maldonado,Garduno-Ramirez,Aranda,Villarreal,Navarro,Bye,Delgado,Alvarez
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- Araliasaponins I-XI, triterpene saponins from the roots of Aralia decaisneana
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Seven new oleanane-type and four new ursane-type triterpene saponins, named araliasaponins I-XI were isolated from the roots of Aralia decaisneana, together with four known triterpene saponins. On the basis of the chemical and spectroscopic evidence, the structures of these new saponins were elucidated as follows: 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-β-D-galactopyranosyl oleanolic acid, 3-O-β-D-glucopyranosyl(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-β-D-galactopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-β-D-galactopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl(1 → 6)-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl ursolic acid 28-O-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 2)]-α-L-arabinopyranosyl ursolic acid, 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl ursolic acid 28- O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester and 3-O-β-D-glucopyranosyl-(1 → 3)-(β-D-xylopyranosyl-(1 → 2)]-β-D-glucopyranosyl ursolic acid 28-O-β-D-glucopyranosyl ester. Copyright
- Miyase, Toshio,Shiokawa, Ken-Ichi,Zhang, Dong Ming,Ueno, Akira
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- Triterpenoidal saponins acylated with two monoterpenic acids from Gleditsia sinensis
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The isolation and characterization of three new oleanane-type triterpenoidal saponins, called gleditsiosides E - G, along with two known ones, from the anomalous fruits of Gleditsia sinensis LAM. are described. Their structural details were unambiguously determined by using a combination of modern NMR techniques, including distortionless enhancement by polarization transfer (DEPT), double-quantum filtered 1H-1H correlated spectroscopy (DQF-COSY), homonuclear hartmann-hahn (HOHAHA), 1H-13C heteronuclear correlation (HETCOR), heteronuclear multiple-bond connectivity (HMBC) and rotating-frame overhauser enhancement spectroscopy (ROESY) experiments as well as some chemical methods. The five bisdesmosidie triterpenoidal saponins consisting of the same sugar sequence were all acylated with two different or identical monoterpenic acids to the C-2 and C- 3 positions of rhamnose moiety.
- Zhang, Zhizhen,Koike, Kazuo,Jia, Zhonghua,Nikaido, Tamotsu,Guo, Dean,Zheng, Junhua
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- Triterpenoid saponins from Albizia boromoensis Aubrv. & Pellegr
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As part of our search of new bioactive saponins from Cameroonian medicinal plants, phytochemical investigation of the roots of Albizia boromoensis led to the isolation of four new oleanane-type saponins, named boromoenosides A-D (1-4). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR (1H, 13C NMR, and DEPT) and 2D NMR (COSY, NOESY, HSQC and HMBC), and by comparison with the literature data. All isolated saponins were assayed for their cytotoxicity against U-87 MG human glioblastoma cell lines and TG1 glioblastoma stem-like cells with no positive activity detected.
- Not, Olivier Placide,Jihu, Dong,Antheaume, Cyril,Guillaume, Dominique,Pegnyemb, Dieudonn Emmanuel,Kilhoffer, Marie Claude,Lobstein, Annelise
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- TWO TRITERPENOID SAPONINS FROM PTEROCEPHALUS BRETSCHNEIDRI
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Two new triterpenoid saponins, named bretschnosides A and B, were isolated from the roots of Pterocephalus bretschneidri.On the basis of chemical degradation and spectroscopic evidence, the structures of bretschnosides A and B were shown to be 3-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->3)-α-L-rhamnopyranosyl(1->2)-β-D-xylopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside 4 and 3-O-α-D-glucopyranosyl(1->3)-β-D-xylopyranosyl(1->3)-α-L-rhamnopyranosyl(1->2)-β-D-xylopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside 6, respectively.Key Word Index: Pterocephalus bretschneidri; Dipsacaceae; roots; triterpenoid saponins; bretschnoside A and B.
- Tian, Jun,Wu, Feng-E,Qiu, Ming-Hua,Nie, Rui-Lin
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- Chemical constituents from Aspidosperma illustre (Apocynaceae)
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A new natural product oleanane-type triterpene, olean-12-ene-11α- methoxy-3β-acetate (10) was isolated from Aspidosperma illustre, together with β-amyrin (3), lupeol (4), β-amyrin acetate (5), lupeol acetate (6), olean-12-ene-28-hydroxy-3β-tetradecanoate (7), olean-12-ene-28- carboxy-3β-hexadecanoate (8), ursolic acid (9) triterpenes, and two monoterpenic indole alkaloids, β-yoimbine (1) and 1,2- dehydroaspidospermidine (2). These compounds were characterized on their spectral data basis, mainly one-(1H,13C, APT) and two-dimensional (1H-1H-COSY,1H- 1H-NOESY, HMQC and HMBC) NMR, and mass spectra, involving also comparison with data from the literature.
- Barbosa, Lara F.,Mathias, Leda,Braz-Filho, Raimundo,Vieira, Ivo J. Curcino
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- Achyranthosides A and B, novel cytotoxic saponins from Achyranthes fauriei root
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Two new saponins, achyranthosides A and B, were isolated from Achyranthes fauriei root, and their structures were elucidated on the basis of chemical and physical evidences. Achyranthoside A methyl ester was found to have significant cytotoxic activity against human colon carcinoma and murine melanoma cells.
- Ida, Yoshiteru,Satoh, Yohko,Katoh, Mariko,Katsumata, Masumi,Nagasao, Miki,Yamaguchi, Kentaro,Kamei, Hideo,Shoji, Junzo
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- Polyacanthoside A, a new oleanane-type triterpenoid saponin with cytotoxic effects from the leaves of Acacia polyacantha (Fabaceae)
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The chemical investigation of the leaves and stem bark of Acacia polyacantha (Fabaceae) led to the isolation of a new oleanane-type triterpenoid saponin named polyacanthoside A 1 together with fifteen known compounds. Their structures were established from spectral, mainly HRESIMS, 1D NMR and 2D NMR and by comparison with literature data. The cytotoxicity of compound 1 and the analogues 8 as well as doxorubicin was determined in a panel of 9 cancer cell lines including sensitive and drug resistant phenotypes. Unlike the analogue 8, compound 1 as well as doxorubicin displayed cytotoxic effects in all the 9 tested cancer cell lines with IC50 values ranged from 8.90 μM (towards CCRF-CEM leukemia cells) to 35.21 μM (towards HepG2 hepatocarcinoma cells) for compound 1 and from 0.02 μM (towards CCRF-CEM leukemia cells) to 66.83 μM (against CEM/ADR5000 leukemia cells) for doxorubicin.
- Fotso, Ghislain,Na-Iya, Jean,Mbaveng, Armelle,Ango Yves, Patrick,Demirtas, Ibrahim,Kuete, Victor,Samuel, Yeboah,Ngameni, Bathelemy,Efferth, Thomas,Ngadjui, Bonaventure
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- Cytotoxic triterpenoid saponins from Thalictrum atriplex
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Two new cycloartane glycosides, cycloatriosides A and B (1–2), and a new oleanolic acid glycoside, thaliatrioside A (3), along with 7 known triterpenoids (4–10) were isolated from Thalictrum atriplex. The structures of the new compounds were established as 3-O-β-D-galactopyranosyl (20S, 24 R)-3β,16β,25,29-tetrahydroxy-20,24-epoxycycloartane-29-O-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl-(1→2)-α-arabinopyranosyl-3β,22ξ,30-trihydroxycycloart-24-en-21-oic acid α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (2) and 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-oleanolic acid 28-O-β-D-glucopyranosyl ester (3) on the basis of extensive NMR and HR-ESI-MS analyses, along with acid hydrolysis. Their cytotoxic activities against human lung cancer cells A549 and human breast cancer cells MDA-MB-231 were evaluated using MTT method. Compound 9 showed cytotoxicity against MDA-MB-231 cell line with the IC50 value of 72.53 ± 1.08 μM.
- Meng, FanCheng,Wei, XiaoDong,Sun, Yan,Zeng, QingHong,Wang, Guowei,Lan, XiaoZhong,Liao, ZhiHua,Chen, Min
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p. 5757 - 5764
(2020/10/20)
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- New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.
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Five new triterpenoid saponin glycosides, trichocucumerisides A-E (1-5), together with eleven known compounds (6-16) were isolated from Trichosanthes cucumerina fruit fibers. The structures of the new compounds were elucidated by detailed analysis of NMR and mass spectroscopic data as well as chemical reactions. The anti-inflammatory study against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells shows that compounds 7 and 9 exhibited stronger NO inhibitory activity, with IC50 values of 3.0 and 2.7 μM, respectively, with comparison to positive references Celecoxib and aminoguanidine (IC50 values 75.7 and 75.0 μM, respectively). Compounds 7 and 9 also possessed a greater selectivity index (SI) of approximately 3-4-fold activity than that of the positive references.
- Chulrik, Wanatsanan,Chunglok, Warangkana,Li, Jian-Xin,Suebsakwong, Parichat,Suksamrarn, Apichart,Yao, Zhu-Jun
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p. 10461 - 10470
(2020/03/27)
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- Albidosides H and I, two new triterpene saponins from the barks of Acacia albida Del. (Mimosaceae)
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Two new triterpene saponins, albidosides H (1) and I (2), along with the three known saponins were isolated from the barks of Acacia albida. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry. Albidosid
- Tchoukoua, Abdou,Kuiate Tabopda, Turibio,Konga Simo, Ingrid,Uesugi, Shota,Ohno, Misa,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu
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p. 924 - 932
(2018/02/15)
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- Phenotype-specific apoptosis induced by three new triterpenoid saponins from Albizia glaberrima (Schumach. & Thonn.) Benth
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As part of our search of new bioactive saponins from Cameroonian medicinal plants, phytochemical investigation of the roots of Albizia glaberrima led to the isolation of three new oleanane-type saponins, named glaberrimosides A-C (1-3). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR (1 H, 13C NMR, and DEPT) and 2D NMR (COSY, ROESY, HSQC and HMBC) as 3-O-[α-l-arabinopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-28-O-[β-d-glucopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-oleanolic acid (1), 3-O-[α-l-arabinopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-28-O-[β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl]-oleanolic acid (2), and 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-28-O-[β-d-glucopyranosyl-(1 → 6)-[β-d-fucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-oleanolic acid (3). The pro-apoptotic effect of the three saponins was evaluated on three human cell lines (pancreatic carcinoma AsPC-1, hematopoietic monocytic THP-1, and human fibroblast cell line BJ). Saponins 1-3 specifically induced apoptosis of pancreatic carcinoma cell (AsPC-1) in a dose-dependent manner. More interestingly, there were inactive on monocytic (THP-1) and normal human fibroblast (BJ) cell lines.
- Noté, Olivier Placide,Azouaou, Sarah Ali,Simo, Line,Antheaume, Cyril,Guillaume, Dominique,Pegnyemb, Dieudonné Emmanuel,Muller, Christian Dominique,Lobstein, Annelise
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- Biological Activities of Oleanolic Acid Derivatives from Calendula officinalis Seeds
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Phytochemical examination of butanol fraction of Calendula officinalis seeds led to the isolation of two compounds identified as 28-O-β-D-glucopyranosyl-oleanolic acid 3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosiduronic acid (CS1) and oleanolic acid 3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosiduronic acid (CS2). Biological evaluation was carried out for these two compounds such as melanin biosynthesis inhibitory, hyaluronic acid production activities, anti obesity using lipase inhibition and adipocyte differentiation as well as evaluation of the protective effect against hydrogen peroxide induced neurotoxicity in neuro-2A cells. The results showed that, compound CS2 has a melanin biosynthesis stimulatory activity; however, compound CS1 has a potent stimulatory effect for the production of hyaluronic acid on normal human dermal fibroblast from adult (NHDF-Ad). Both compounds did not show any inhibitory effect on both lipase and adipocyte differentiation. Compound CS2 could protect neuro-2A cells and increased cell viability against H2O2. These activities (melanin biosynthesis stimulatory and protective effect against H2O2 of CS2 and hyaluronic acid productive activities of these triterpene derivatives) have been reported for the first time.
- Zaki, Ahmed,Ashour, Ahmed,Mira, Amira,Kishikawa, Asuka,Nakagawa, Toshinori,Zhu, Qinchang,Shimizu, Kuniyoshi
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p. 835 - 841
(2016/05/19)
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- Triterpenoid saponins from Albizia boromoensis Aubrév. & Pellegr
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As part of our search of new bioactive saponins from Cameroonian medicinal plants, phytochemical investigation of the roots of Albizia boromoensis led to the isolation of four new oleanane-type saponins, named boromoenosides A-D (1-4). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR (1H, 13C NMR, and DEPT) and 2D NMR (COSY, NOESY, HSQC and HMBC), and by comparison with the literature data. All isolated saponins were assayed for their cytotoxicity against U-87 MG human glioblastoma cell lines and TG1 glioblastoma stem-like cells with no positive activity detected.
- Noté, Olivier Placide,Jihu, Dong,Antheaume, Cyril,Guillaume, Dominique,Pegnyemb, Dieudonné Emmanuel,Kilhoffer, Marie Claude,Lobstein, Annelise
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- The chemical and biological potential of C ring modified triterpenoids
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A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780).
- Siewert, Bianka,Wiemann, Jana,K?witsch, Alexander,Csuk, René
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- Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents
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A broad set of potential bioactive conjugate compounds has been semi-synthesized through solution- and solid-phase organic procedures, coupling two natural pentacyclic triterpene acids, oleanolic (OA) and maslinic acids (MA), at the hydroxyl groups of the A-ring of the triterpene skeleton, with 10 different acyl groups. These acyl OA and MA derivatives have been tested for their anti-proliferative (against the b16f10 murine melanoma cancer cells) and antiviral (as inhibitors of the HIV-1-protease) effects. Several derivatives have shown high levels of early and total apoptosis (up to 90%). Most of the compounds that exhibited anti-proliferative effects also generated ROS, probably involving the activation of an intrinsic apoptotic route. The only four compounds that did not cause the release of ROS could be related to the participation of a probable extrinsic activation of the apoptosis mechanism. A great number of these acyl OA and MA derivatives have proved to be potent inhibitors of the HIV-1-protease, the most active inhibitors having IC 50 values between 0.31 and 15.6 μM, these values being between 4 and 186 times lower than their non-acylated precursors. The potent activities exhibited in the apoptosis-activation processes and in the inhibition of the HIV-1-protease by some OA and MA acylated derivatives imply that these compounds could be used as new, safe, and effective anticancer and/or antiviral drugs.
- Parra, Andres,Martin-Fonseca, Samuel,Rivas, Francisco,Reyes-Zurita, Fernando J.,Medina-O'Donnell, Marta,Martinez, Antonio,Garcia-Granados, Andres,Lupia?ez, Jose A.,Albericio, Fernando
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p. 278 - 301
(2014/02/14)
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- Triterpene glycosides from the stems and leaves of Lonicera japonica
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Five new triterpene glycosides, namely lonicerosides F-J (1-5), together with five known ones, were isolated from the stems and leaves of Lonicera japonica. Based on extensive spectroscopic analysis, including twodimensional (2D)-NMR experiments, and the
- Kuroda, Minpei,Shizume, Takaaki,Mimaki, Yoshihiro
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- Two antiproliferative triterpene saponins from Nematostylis anthophylla from the highlands of central madagascar
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Investigation of the endemic Madagascan plant Nematostylis anthophylla (Rubiaceae) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the known triterpene saponin randianin (1), and the two new bioactive trit
- Dai, Yumin,Harinantenaina, Liva,Brodie, Peggy J.,Birkinshaw, Chris,Randrianaivo, Richard,Applequist, Wendy,Ratsimbason, Michel,Rasamison, Vincent E.,Shen, Yongchun,Tendyke, Karen,Kingston, David G. I.
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p. 233 - 240
(2013/04/10)
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- Triterpene saponins from clematis mandshurica and their antiproliferative activity
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Six new triterpene saponins, clematomandshurica saponins F-K (1-6), together with a known compound (7), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis. Compounds 5-7 exhibited antiproliferative effects against PC-3 human prostate cancer cells with GI50 values of 1.29, 1.50, and 0.71 M, respectively.
- Gong, Yi-Xia,Hua, Hui-Ming,Xu, Yong-Nan,Liu, Jian-Yu,Yu, Zong-Gui,Ma, Jing,Zhang, Hui,Jing, Yong-Kui
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p. 987 - 994
(2013/08/23)
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- Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis
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Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC 50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.
- Wang, Xiao-Yang,Gao, Hui,Zhang, Wei,Li, Yuan,Cheng, Guang,Sun, Xiao-Li,Tang, Hai-Feng
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p. 5714 - 5720
(2013/10/01)
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- PHARMACEUTICAL COMPOSITION FOR TREATING CARDIOVASCULAR DISORDER AND USE THEREOF
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The present invention provides a pharmaceutical composition for treating cardiovascular disorders comprising 3-1 portion echinocystic acid and 1 portion oleanolic acid as the active components. The present invention also provides a gleditsiae extract comprising echinocystic acid and oleanolic acid of 90.0%-99.9% total weight, wherein the weight ratio of echinocystic acid and oleanolic acid is 3:1-1:3. The preparation method and use of the extract are also provided in the present invention. The pharmaceutical composition in the present invention degrades hepatotoxicity by controlling the ratio of echinocystic acid and oleanolic acid in the composition.
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- Cytotoxic triterpene saponins from the stem bark of Kalopanax pictus
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Three new compounds, 3β,6β,23-trihydroxyolean-12-en-28-oic acid 3-O-α-l-arabinopyranoside (1), kalopanaxsaponin L (2), and kalopanaxsaponin M (13), as well as eleven known compounds (3-12 and 14), were isolated from the stem bark of Kalopanax pictus. Their structures were determined on the basis of extentive spectroscopic analyses and acid hydrolysis. The cytotoxicity of the compounds was evaluated in three human carcinoma cell lines, including HL-60, HCT-116, and MCF-7. Compounds 1, 5-8, 10, and 11 exhibited significantly cytotoxic activity toward HL-60 cells, with IC 50 values ranging from 0.1 to 6.9 μM. Compounds 4-7 and 14 showed significant cytotoxicity against HCT-116 cells, with IC50 values ranging from 0.4 to 9.2 μM. Remarkably, the cytotoxic activities of compounds 5-7 against HCT-116 cells were greater than that of the anticancer chemotherapy drug, mitoxantrone (IC50 = 3.7 μM). Compounds 1, 3, 5, and 14 were cytotoxic toward MCF-7 cells with IC50 values in a range of 7.4-14.5 μM.
- Quang, Tran Hong,Ngan, Nguyen Thi Thanh,Minh, Chau Van,Kiem, Phan Van,Boo, Hye-Jin,Hyun, Jin-Won,Kang, Hee-Kyoung,Kim, Young Ho
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experimental part
p. 177 - 182
(2012/05/05)
-
- Triterpenoid saponins from Anemone raddeana
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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
- Li, Fu,Sun, Cui-Rong,Chen, Bin,Ding, Li-Sheng,Wang, Ming-Kui
-
experimental part
p. 258 - 261
(2012/07/03)
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- A new bidesmoside saponin from the bark of guaiacum officinale
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A new bidesmosidic triterpene saponin, guaianin P was isolated from the stem bark of Guaiacum officinale. Its structure was established as oleanolic acid 3-O-{α-L-rhamnopyranosyl- (1→3)-α-L-rhamnopyranosyl- (1→2)-[β-D-glucopyranosyl-(1→3)]-α-L-arabinopyranoside} -28-O- β-D-glucopyranosyl ester by spectroscopic and chemical analyses.
- Saba, Nikhat,Khatoon, Rasheeda,Ali, Zulfiqar,Ahmad, Viqar Uddin
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experimental part
p. 448 - 450
(2012/07/14)
-
- Novel biologically active glycosides from the aerial parts of Cephalaria gazipashensis
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Two new triterpene glycosides, 3-O-β -D-glucopyranosyl-(1→4)- β -D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-( 1→3)-a-L-arabinopyranosyl olean-12-ene 28-O-β -D-glucopyranosyl- (1→6)-β -D-glucopyranosyl ester (gazipashoside A, 1) and 3-O-β -D-glucopyranosyl-(1→4)-β -D-xylopyranosyl-(1→3)-α-L- rhamnopyranosyl-( 1→2)-α-L-arabinopyranosyl hederagenin 28-O-β -D-glucopyranosyl-(1→6)-β -D-glucopyranosyl ester (gazipashoside B, 2), were isolated together with 11 known compounds including 7 triterpene, 1 flavonoid, and 3 iridoidal metabolites from the aerial parts of Cephalaria gazipashensis (Dipsacaceae). The structures of all compounds were elucidated by extensive evaluation of the spectroscopic data (1D- and 2D- NMR, HRESI-MS), as well as chemical examinations. The antimicrobial effects of all pure compounds were tested against gram-positive and gram-negative bacteria. The results indicated that the 2 new triterpene glycosides might be acceptable as antimicrobial active agents.
- Sarikahya, Nazli Boeke,Kirmiziguel, Sueheyla
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experimental part
p. 323 - 334
(2012/06/18)
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- Design and synthesis of a dual linker for solid phase synthesis of oleanolic acid derivatives
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A hydrophilic amino-terminated poly(ethylene glycol)-type dual linker for solid phase synthesis of oleanolic acid derivatives using trityl chloride resin was designed and synthesized for the first time. Model reactions in both liquid and solid phase were performed to show the feasibility of its selective cleavage at two different sites. The biological assay results indicated that the long and flexible alkyl ether functionality in the linker is less likely to be critical for the binding event. Following the successful solid-phase synthesis of model compounds, the potential of this dual linker in reaction monitoring and target identification is deemed worthy of further study.
- Wang, Shaorong,Fang, Weishuo
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experimental part
p. 4748 - 4763
(2011/08/22)
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- Cytotoxic and antioxidant triterpene saponins from Butyrospermum parkii (Sapotaceae)
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Three new triterpenoid saponins, elucidated as 3-O-β-d- glucopyranosyloleanolic acid 28-O-β-d-xylopyranosyl-(1→4)-α-l- rhamnopyranosyl-(1→2)-β-d-xylopyranoside (parkioside A, 1), 3-O-[β-d-apifuranosyl-(1→3)-β-d-glucopyranosyl]oleanolic acid 28-O-[β-d-apifuranosyl-(1→3)-β-d-xylopyranosyl-(1→4) -[α-l-rhamnopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2) β-d-xylopyranoside (parkioside B, 2) and 3-O-β-d-glucuronopyranosyl- 16α-hydroxyprotobassic acid 28-O-α-l-rhamnopyranosyl-(1→3)- β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2) -β-d-xylopyranoside (parkioside C, 3), were isolated from the n-BuOH extract of the root bark of Butyrospermum parkii, along with the known 3-O-β-d-glucopyranosyloleanolic acid (androseptoside A). The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. The new compounds were tested for both radical scavenging and cytotoxic activities. Compound 2 showed cytotoxic activity against A375 and T98G cell lines, with IC50 values of 2.74 and 2.93 μM, respectively. Furthermore, it showed an antioxidant activity comparable to that of Trolox or butylated hydroxytoluene (BHT), used as controls, against 2,2-diphenyl-1-picryl hydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), oxygen and nitric oxide radicals.
- Tapondjou, Léon A.,Nyaa, Laurentine B.T.,Tane, Pierre,Ricciutelli, Massimo,Quassinti, Luana,Bramucci, Massimo,Lupidi, Giulio,Ponou, Beaudelaire K.,Barboni, Luciano
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experimental part
p. 2699 - 2704
(2012/01/02)
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- Oleanolic triterpene saponins from the roots of Panax bipinnatifidus
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Ten oleanane-type saponins (1-10), including three new compounds, namely bifinosides A-C (1-3), were isolated from the roots of Panax bipinnatifidus SEEM. Their structures were elucidated on the basis of chemical and spectroscopic methods.
- Tung, Nguyen Huu,Quang, Tran Hong,Ngan, Nguyen Thi Thanh,Minh, Chau Van,Anh, Bui Kim,Long, Pham Quoc,Cuong, Nguyen Manh,Kim, Young Ho
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experimental part
p. 1417 - 1420
(2012/02/03)
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- Halimodendrin I, a new acylated triterpene glycoside from Halimodendron halodendron (Fabaceae)
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Halimodendrin I, a new acylated triterpene glycoside (1), was isolated and chemically characterized as 3β-O-palmitoyl-28-[3′-palmitoyl-β-d- glucopyranosyl]-olean-12-en-28-oic acid from the aerial part of Halimodendron halodendron (Fabaceae) by IR, 1D and 2D NMR, HR-ESI-MS and LR-ESI-MS experiments. In addition, seven known compounds were isolated and identified as: palmitic acid, glycerol-2-linoleneate, glycerol-1,3-dilinoleneate, ferulic acid, 3-O-methylquercetin, β-sitosterol, and β-sitosterol-3-O-β- d-glucopyranoside. Nine fatty acids were identified and quantified in the saponifiable matter of the hexane extract. These fatty acids are: myristic, n-pentadecanoic, palmitoleic, palmitic, linoleic, oleic, stearic, arachidic, and behenic acids. The volatile oil was isolated by hydrodistillation (0.013%, w/w) with unpleasant smell. Twenty-seven components were identified in the oil by GC/MS.
- Kozhamkulova, Zhanar A.,Radwan, Mohamed M.,Zhusupova, Galiya E.,Abilov, Zharilkasin A.,Ross, Samir A.
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experimental part
p. 323 - 327
(2012/05/04)
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- Triterpene saponins from clematis chinensis and their potential anti-inflammatory activity
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Seven new triterpene saponins, clematochinenosides A-G (1-7), together with 17 known saponins (8-24), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1, 3-7, and 20-24 showed inhibitory activities against COX-1 and COX-2 enzymes.
- Fu, Qiang,Zan, Ke,Zhao, Mingbo,Zhou, Sixiang,Shi, Shepo,Jiang, Yong,Tu, Pengfei
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experimental part
p. 1234 - 1239
(2010/11/04)
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- Triterpene glycosides from the aerial parts of Larrea tridentata
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Chemical study of the aerial parts of Larrea tridentata (Zygophyllaceae) resulted in the isolation of 25 triterpene glycosides, 13 of which were previously unknown. Their structures were determined on the basis of comprehensive spectroscopic analyses, including 2D NMR spectroscopy, and hydrolytic cleavage followed by chromatographic and spectroscopic analyses. This is the first systematic phytochemical study of L. tridentata with attention paid to its triterpene glycoside constituents. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells.
- Jitsuno, Maki,Mimaki, Yoshihiro
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experimental part
p. 2157 - 2167
(2011/07/08)
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- Separation and identification of anew saponin from the flowers of Guaiacum officinale L.
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A triterpenoid saponin, guaianin O (1), oleanolic acid 3-O-{α-L- rhamnopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 3)]-α-L-arabinopyranoside}-28-O-[β-D-glucopyranosyl]-ester, was isolated from the n-butanol extract of flowers of Guaiacum officinale L. The structural elucidation of 1 was accomplished by extensive studies of both one and two dimensional 1H, 13C-NMR spectra, the FAB mass spectrum, and alkaline and acid hydrolyses.
- Saba, Nikhat,Ahmad, Viqar Uddin,Ali, Zulfiqar,Khan, Khalid Mohammed
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experimental part
p. 1877 - 1882
(2011/02/26)
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- Triterpenoid glycosides from Stauntonia chinensis
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A new bidesmoside triterpenoid saponin, named stauntoside C1 (1), along with three known saponins (2-4) was isolated from Stauntonia chinensis DC. (Lardizabalaceae). Their structures were established by means of spectral and chemical methods as 3-O-β-D-xylopyranosyl-(1→2)-O-β-D- xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2) -α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl- (1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1), scabiosaponin E (2), sieboldianoside B (3), and kizutasaponin K12 (4).
- Wang, Dong,Tian, Jin,Zhou, Guo-Ping,Yang, Yi-Sheng,Su, Ya-Lun,Ji, Teng-Fei
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experimental part
p. 150 - 156
(2010/08/20)
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- Saponins and polyphenols from Fadogia ancylantha (Makoni tea)
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Three new saponins (1-3) and a known saponin, together with four known polyphenols compounds, have been isolated from the fermented and dried leaves of Fadogia ancylantha (Makoni tea). The structures of compounds 1-3 were established by analysis of their spectroscopic data. Both an ethanol-water extract of F. ancylantha and its phenolic constituents showed significant free-radical-scavenging and antimicrobial activities. No cytotoxicity, as evaluated by analysis of hypodiploid nuclei in HUVEC cells using propidium iodide staining, was observed for either the plant crude extract or its constituents.
- Mencherini, Teresa,Picerno, Patrizia,Del Gaudio, Pasquale,Festa, Michela,Capasso, Anna,Aquino, Rita
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experimental part
p. 247 - 251
(2010/06/14)
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- Triterpene glycosides from the whole plant of Anemone hupehensis var. japonica and their cytotoxic activity
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Three new triterpene glycosides (1-3), together with eight known triterpene glycosides (4-11), were isolated from the whole plant of Anemone hupehensis var. japonica (Ranunculaceae). The structures of the new compounds were determined on the basis of spec
- Yokosuka, Akihito,Sano, Tomoe,Hashimoto, Ken,Sakagami, Hiroshi,Mimaki, Yoshihiro
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experimental part
p. 1425 - 1430
(2010/06/20)
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- New triterpenic saponins from the aerial parts of Medicago arabica (L.) Huds
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The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago species. They have been identified as glycosides of oleanolic acid, 2β,3β-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-α-L- arabinopyranosyl(1→2)-β-D-glucuronopyranosyl]-30-O-β-D- glucopyranosyl 2β,3β,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl] -30-O-[β-D-glucopyranosyl]3β,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-|β-D-glucuronopyranosyl]-30-O-[α-L-arabinopyranosyl(1→2) -β-D-glucopyranosyl] 2β,3β,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[β-D-glucuronopyranosyl]-30-O-[α-L- arabinopyranosyl(1→2)-β-D-glucopyranosyl] 3β,30-dihydroxyolean- 12-en-28-oic acid (4) and 3-O-[β-D-glucuronopyranosyl]-30-O-[β-D- glucopyranosyl] 2β,3β,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.
- Tava, Aldo,Mella, Mariella,Avato, Pinarosa,Biazzi, Elisa,Pecetti, Luciano,Bialy, Zbigniew,Jurzysta, Marian
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experimental part
p. 2826 - 2835
(2010/06/11)
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- Brazilian natural medicines. III1 structures of triterpene oligoglycosides and lipase inhibitors from mate, leaves of ilex paraguariensis
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The methanolic extract from the leaves of Ilex paraguariensis (Aquifoliaceae) was found to show an inhibitory activity on porcine pancreatic lipase. From the methanolic extract, three new triterpene oligoglycosides, mateglycosides A, B, and C, were isolat
- Sugimoto, Sachiko,Nakamura, Seikou,Yamamoto, Sachiyo,Yamashita, Chihiro,Oda, Yoshimi,Matsuda, Hisashi,Yoshikawa, Masayuki
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experimental part
p. 257 - 261
(2009/11/30)
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- New triterpene glycosides of Clematis montana and their cytotoxic activities
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Two new triterpene glycosides designated as montanosides 1 and 2 were isolated from methanolic extract of Clematis montana. Their structures have been elucidated as 3-O-β-D-glucopyranosyl-oleanolic acid-28-O-β-D- glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)] -β-D-xylopyranoside and 3-O-β-D-glucopyranosyl-oleanolic acid-28-O-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3) -α-L-rhamnopyranosyl-(1→2)]-β-D-xylopyranoside, respectively by NMR and MS data. Cytotoxic activity of the compounds were evaluated against various squamous carcinoma cells (HSC-2) and human gingival fibroblast cells (HGF). Both of the compounds showed potent cytotoxic activity against the test cells.
- Jangwan,Dobhal, Maneesha
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experimental part
p. 313 - 316
(2009/06/25)
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- Dimethylaluminum methyltellurate, a new reagent for the cleavage of hindered methyl esters under exceptionally mild conditions by a novel mechanism
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An efficient and effective new reagent (Me2AlTeMe)2 has been developed for the conversion of methyl esters to the corresponding carboxylic acids in toluene solution at 23°C.
- Reddy, B.V. Subba,Reddy, Leleti Rajender,Corey
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p. 4589 - 4593
(2007/10/03)
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- Novel biotransformation of pentacyclic triterpenoid acids by Nocardia sp. NRRL 5646
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Six pentacyclic triterpene acids, ursolic acid, oleanolic acid, betulinic acid, 23-hydroxybetulinic acid, glycyrrhetinic acid, and senegenin, were metabolized by the microbe Nocardia sp. NRRL 5646 to selectively furnish their corresponding 28-methyl esters. Notably, ursolic acid (1) was converted to oleanolic acid methyl ester (4) via two intermediates, oleanolic acid (2), and ursolic acid methyl ester (3), which are formed by participation of 'retro-biosynthetic' methyl migration from C-19 to C-20. Senegenin (11) was selectively converted to a nortriterpene methyl ester, senegenic acid methyl ester (12), via an unprecedented C-C bond cleavage. The stereochemical assignments of compounds 11 and 12 were made unambiguously for the first time using 2D NMR spectroscopy.
- Zhang, Jian,Cheng, Zhi-Hong,Yu, Bo-Yang,Cordell, Geoffrey A.,Qiu, Samuel X.
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p. 2337 - 2340
(2007/10/03)
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- New cytotoxic oleanane saponins from the infructescences of Polyscias amplifolia from the Madagascar rainforest
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Bioassay-guided fractionation of an ethanolic extract of the infructescences of Polyscias amplifolia resulted in the isolation of two new oleanolic acid saponins, polyfoliolides A (1) and B (2), in addition to the two known saponins 3-O-β-D-galactopyrano-syloleanolic acid (3) and 3-O-β-D-galactopyranosyl-(1→4)-β-D-galactopyranosyloleanolic acid (4). The structures of the two new compounds were established as 3-O-β-D-galactopyranosyl-(1→4)-β-D-xylopyranosyloleanolic acid (1) and 3-O-β-D-galactopyranosyl-(1→4)-α-L-arabinopyranosyloleanolic acid (2) on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against A2780 human ovarian cancer cell line, with IC50 values in the range 6.7 to 10.8 μg/mL.
- Chaturvedula, V. S. Prakash,Schilling, Jennifer K.,Miller, James S.,Andriantsiferana, Rabodo,Rasamison, Vincent E.,Kingston, David G. I.
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p. 440 - 444
(2007/10/03)
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- Two pentacyclic triterpenes from the stem of Calotropis procera
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Two saponins have been isolated from the stem of Calotropis procera and their structures stablished as 3-O-{α-L-rhamnopyranosyl(1→2)-β -D-xylopyranosyl(1γ2)-βB-D-glucopyranosyl-(1→6) -β-D-glucopyranosyl(1→3)-β-D-glucopyranoside}-3β -hydroxyolean-12-ene-oic acid 1 and 3β-hydroxy olean-12-ene-28-oic acid-28-O-β-D-glucopyranoside 2 on the basis of chemical and spectral evidences.
- Gupta, Aditi,Singh, Rachana,Purwar, Chhavi,Chauhan, Deepa,Singh
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p. 2030 - 2033
(2007/10/03)
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- Triterpenoid saponins from Schefflera arboricola
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Nine triterpenoid saponins were isolated from the leaves and stems of Schefflera arboricola. The saponins were characterised, on the basis of chemical and spectral evidence, as 3-O-[α-L-rhamnopyranosyl-(1→4)-β-D-glucuronopyranosyl] oleanolic acid, 3-O-[α-
- Melek,Miyase, Toshio,Abdel Khalik,El-Gindi
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p. 401 - 407
(2007/10/03)
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- Triterpenoid glycosides of Fatsia japonica. II. Isolation and structure of glycosides from the leaves
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The previously known triterpenoid 3-O-α-L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ethers of the 3-O-α-L-arabinopyranoside of hederagenin, and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical methods and 13C NMR spectroscopy.
- Grishkovets,Sobolev,Shashkov,Chirva
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p. 501 - 505
(2007/10/03)
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- New triterpenoid saponins from the stem of Calotropis procera
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From the stem of Calotropis procera, olean-12-en-28 oic acid-3-?-α-L-rhamnopyranosyl (1→2) β-D-glucopyranosyl (1→2) β-D-galactopyranoside 1 and 3-?-{-β- D-glucopyranosyl (1→2)-β- D-glucopyranosyl (1→6)-β- D-glucopyranosyl (1→3)-α-L-arabinopyranoside} olean-12-en-28-?-β- D-glucopyranosyl 2 have been isolated. Their structures have been elucidated on the basis of spectral data and by chemical methods.
- Gupta,Siddique,Singh
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p. 941 - 945
(2007/10/03)
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- Medicinal foodstuffs. XIII.1 saponin constituents with adjuvant activity from hyacinth bean, the seeds of Dolichos lablab L. (2) : Structures of lablabosides D, E, and F
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Following the characterization of lablabosides A, B, and C, new oleanane-type triterpene bisdesmosides, lablabosides D, E, and F, were isolated from the glycosidic fraction with adjuvant activity obtained from the seeds of Dolichos lablab L. (Leguminosae). Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows : 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[6-O-(3-hydroxy-3-methylglutaroyl)-β-D-glucopyranosyl] 24-epi-hederagenin (lablaboside D), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] 24-epi-hederagenin (lablaboside E), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] oleanolic acid (lablaboside F).
- Komatsu, Hajime,Murakami, Toshiyuki,Matsuda, Hisashi,Yoshikawa, Masayuki
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p. 703 - 710
(2007/10/03)
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- A Novel Cleavage of Allyl Protection
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A novel, efficient, and mild cleavage of allyl protection is developed employing perfluoroalkylation and subsequent elimination.
- Yu, Biao,Li, Bing,Zhang, Jianbo,Hui, Yongzheng
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p. 4871 - 4874
(2007/10/03)
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