508-02-1Relevant articles and documents
A bidesmosidic oleanolic acid saponin from Panax pseudo-ginseng.
Shukla,Thakur,Pachaly
, p. 1046 - 1048 (1992)
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.
GENICULATIN, A TRITERPENOID SAPONIN FROM EUPHORBIA GENICULATA
Tripathi, R. D.,Tiwari, K. P.
, p. 2163 - 2166 (1980)
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.
Triterpenes from Cigarrilla mexicana
Mata, Rachel,Rios, Lizeth,del Rayo Camacho, Ma,Reguero, Ma Teresa,Lorence, David
, p. 1887 - 1889 (1988)
-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.
Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis
Zhang, Zhizhen,Koike, Kazuo,Jia, Zhonghua,Nikaido, Tamotsu,Guo, Dean,Zheng, Junhua
, p. 740 - 745 (1999)
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).
Oleanolic acid from antifilarial triterpene saponins of Dipterocarpus zeylanicus induces oxidative stress and apoptosis in filarial parasite Setaria digitata in?vitro
Senathilake,Karunanayake,Samarakoon,Tennekoon,de Silva,Adhikari
, p. 13 - 21 (2017)
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.
Saponins as novel TNF-α inhibitors: Isolation of saponins and a nor-pseudoguaianolide from Parthenium hysterophorus
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
, p. 3230 - 3235 (2009)
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
A new oleanolic acid derivative from Securinega tinctoria
Carvalho,Seita
, p. 369 - 372 (1993)
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.
Antileishmanial activity of natural diterpenes from Cistus sp. and semisynthetic derivatives thereof
Fokialakis, Nikolas,Kalpoutzakis, Eleftherios,Tekwani, Babu Lal,Skaltsounis, Alexios Leandros,Duke, Stephen Oscar
, p. 1775 - 1778 (2006)
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.
TRITERPENE GLYCOSIDES OF THE LEAVES OF Digitalis ciliata
Kemertelidze, E. P.,Gvazava, L. N.,Alaniya, M. D.,Kikoladze, V. S.
, p. 212 - 215 (1991)
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>.
Biosynthesis of Triterpenes, Ursolic Acid and Oleanolic Acid, from Acetate in Tissue Cultures of Rabdosia japonica Hara
Seo, Shujiro,Uomori, Atsuko,Yoshimura, Yohko,Takeda, Ken'ichi,Sankawa, Ushio,et al.
, p. 1141 - 1143 (1986)
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.
