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Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius.
Phytochemistry. 2005 May; 66(10):1168-73.P

Abstract

Two new cycloartane-type glycosides oleifoliosides A (1) and B (2) were isolated from the lower stem parts of Astragalus oleifolius. Their structures were identified as 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-xylopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane and 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Three known cycloartane glycosides cyclocanthoside E (3), astragaloside II (4) and astragaloside IV (5) were also isolated and characterized. All five compounds were evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Except for the compound 5, all compounds showed notable growth inhibitory activity against Leishmania donovani with IC50 values ranging from 13.2 to 21.3 microg/ml. Only weak activity against Trypanosoma brucei rhodesiense was observed with the known compounds astragaloside II (4, IC50 66.6 microg/ml) and cyclocanthoside E (3, IC50 85.2 microg/ml), while all compounds were inactive against Trypanosoma cruzi and Plasmodium falciparum. None of the compounds were toxic to mammalian cells (IC50's > 90 microg/ml). This is the first report of leishmanicidal and trypanocidal activity of cycloartane-type triterpene glycosides.

Authors+Show Affiliations

Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey. meltemozipek@yahoo.comNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15922377

Citation

Ozipek, Meltem, et al. "Leishmanicidal Cycloartane-type Triterpene Glycosides From Astragalus Oleifolius." Phytochemistry, vol. 66, no. 10, 2005, pp. 1168-73.
Ozipek M, Dönmez AA, Caliş I, et al. Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius. Phytochemistry. 2005;66(10):1168-73.
Ozipek, M., Dönmez, A. A., Caliş, I., Brun, R., Rüedi, P., & Tasdemir, D. (2005). Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius. Phytochemistry, 66(10), 1168-73.
Ozipek M, et al. Leishmanicidal Cycloartane-type Triterpene Glycosides From Astragalus Oleifolius. Phytochemistry. 2005;66(10):1168-73. PubMed PMID: 15922377.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius. AU - Ozipek,Meltem, AU - Dönmez,Ali A, AU - Caliş,Ihsan, AU - Brun,Reto, AU - Rüedi,Peter, AU - Tasdemir,Deniz, PY - 2005/01/31/received PY - 2005/04/08/revised PY - 2005/04/08/accepted PY - 2005/6/1/pubmed PY - 2005/8/20/medline PY - 2005/6/1/entrez SP - 1168 EP - 73 JF - Phytochemistry JO - Phytochemistry VL - 66 IS - 10 N2 - Two new cycloartane-type glycosides oleifoliosides A (1) and B (2) were isolated from the lower stem parts of Astragalus oleifolius. Their structures were identified as 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-xylopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane and 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Three known cycloartane glycosides cyclocanthoside E (3), astragaloside II (4) and astragaloside IV (5) were also isolated and characterized. All five compounds were evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Except for the compound 5, all compounds showed notable growth inhibitory activity against Leishmania donovani with IC50 values ranging from 13.2 to 21.3 microg/ml. Only weak activity against Trypanosoma brucei rhodesiense was observed with the known compounds astragaloside II (4, IC50 66.6 microg/ml) and cyclocanthoside E (3, IC50 85.2 microg/ml), while all compounds were inactive against Trypanosoma cruzi and Plasmodium falciparum. None of the compounds were toxic to mammalian cells (IC50's > 90 microg/ml). This is the first report of leishmanicidal and trypanocidal activity of cycloartane-type triterpene glycosides. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/15922377/Leishmanicidal_cycloartane_type_triterpene_glycosides_from_Astragalus_oleifolius_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(05)00174-3 DB - PRIME DP - Unbound Medicine ER -