Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
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.
Fu
Liwei
L
Graduate School of Science and Technology, Department of Chemistry and Chemical Engineering, Niigata University, 2-8050 Ikarashi, Niigata 950-2181, Japan.
Zhang
Shujun
S
Li
Na
N
Wang
Jinlan
J
Zhao
Ming
M
Sakai
Junichi
J
Hasegawa
Toshiaki
T
Mitsui
Tomokazu
T
Kataoka
Takao
T
Oka
Seiko
S
Kiuchi
Miwa
M
Hirose
Katutoshi
K
Ando
Masayoshi
M
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D018799:Intercellular Adhesion Molecule-1 / Q000187:drug effects; D007564:Japan; D008954:Models, Biological; D015394:Molecular Structure; D030007:Nerium / Q000737:chemistry*; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
C498239:(20S,24S)-epoxydammarane-3beta,25-diol; D000894:Anti-Inflammatory Agents, Non-Steroidal; D014315:Triterpenes; C498237:oleanderic acid; C498238:oleanderolide; D018799:Intercellular Adhesion Molecule-1; D009828:Oleanolic Acid