RRC ID 79298
Author Fu L, Zhang S, Li N, Wang J, Zhao M, Sakai J, Hasegawa T, Mitsui T, Kataoka T, Oka S, Kiuchi M, Hirose K, Ando M.
Title Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
Journal J Nat Prod
Abstract New ursane-type triterpene 1, oleanane-type triterpene 2, and dammarane-type triterpene 15 were isolated from the leaves of Nerium oleander together with 12 known triterpenes, 3beta-hydroxy-12-ursen-28-oic acid (ursolic acid, 3), 3beta,27-dihydroxy-12-ursen-28-oic acid (4), 3beta,13beta-dihydroxyurs-11-en-28-oic acid (5), 3beta-hydroxyurs-12-en-28-aldehyde (6), 28-norurs-12-en-3beta-ol (7), urs-12-en-3beta-ol (8), urs-12-ene-3beta,28-diol (9), 3beta-hydroxy-12-oleanen-28-oic acid (oleanolic acid, 10), 3beta,27-dihydroxy-12-oleanen-28-oic acid (11), 3beta-hydroxy-20(29)-lupen-28-oic acid (betulinic acid, 12), 20(29)-lupene-3beta,28-diol (betulin, 13), and (20S,24R)-epoxydammarane-3beta,25-diol (14). On the basis of their spectroscopic data, the structures of the new compounds 1, 2, and 15 were established as 3beta,20alpha-dihydroxyurs-21-en-28-oic acid, 3beta,12alpha-dihydroxyoleanan-28,13beta-olide, and (20S,24S)-epoxydammarane-3beta,25-diol, respectively. The anti-inflammatory activity of the seven isolated compounds and methyl esters of ursolic acid and oleanoic acid in vitro was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). The anticancer activity of the 14 isolated compounds, including 1, 2, 15, and methyl esters of ursolic acid and oleanolic acid in vitro was examined on the basis of the cell growth inhibitory activities toward three kinds of human cell lines.
Volume 68(2)
Pages 198-206
Published 2005-2-1
DOI 10.1021/np040072u
PMID 15730243
MeSH Anti-Inflammatory Agents, Non-Steroidal / chemistry Anti-Inflammatory Agents, Non-Steroidal / isolation & purification* Anti-Inflammatory Agents, Non-Steroidal / pharmacology Drug Screening Assays, Antitumor Humans Intercellular Adhesion Molecule-1 / drug effects Japan Models, Biological Molecular Structure Nerium / chemistry* Oleanolic Acid / analogs & derivatives* Oleanolic Acid / chemistry Oleanolic Acid / isolation & purification* Oleanolic Acid / pharmacology Plant Leaves / chemistry Plants, Medicinal / chemistry* Triterpenes / chemistry Triterpenes / isolation & purification* Triterpenes / pharmacology Tumor Cells, Cultured
IF 3.782
Resource
Human and Animal Cells VA-13(RCB0251) WI-38 Hep G2