Bioactive pregnanes from Nerium oleander.

Abstract

Three new pregnanes, 21-hydroxypregna-4,6-diene-3,12,20-trione (1), 20R-hydroxypregna-4,6-diene-3,12-dione (2), and 16beta,17beta-epoxy-12beta-hydroxypregna-4,6-diene-3,20-dione (3), were isolated from Nerium oleander, together with two known compounds, 12beta-hydroxypregna-4,6,16-triene-3,20-dione (neridienone A, 4) and 20S,21-dihydroxypregna-4,6-diene-3,12-dione (neridienone B, 5). The structures of compounds 1-3 were established on the basis of their spectroscopic data. The anti-inflammatory activity in vitro of compounds 2-4 was examined on the basis of inhibitory activity against the induction of intercellular adhesion molecule-1 (ICAM-1), and compound 4 was active. The cytotoxic activity of compounds 1-5 was evaluated against four human cell lines, normal human fibroblast cells (WI-38), malignant tumor cells induced from WI-38 (VA-13), human liver tumor cells (HepG2), and human lung carcinoma cells (A-549). Compound 4 showed significant cell growth inhibition of VA-13 and HepG2 cells. The MDR-reversal activity of compounds 1-5 was evaluated on the basis of the amount of calcein accumulated in MDR human ovarian cancer 2780AD cells in the presence of each compound. Compounds 1, 2, and 5 showed significant effects on calcein accumulation.

• Authors: Liming Bai, Liyan Wang, Ming Zhao, Asami Toki, Toshiaki Hasegawa, Hirotsugu Ogura, Takao Kataoka, Katutoshi Hirose, Junichi Sakai, Jiao Bai, Masayoshi Ando
• Journal: Journal of natural products (J Nat Prod) Vol. 70 Issue 1 Pg. 14-8 (Jan 2007) ISSN: 0163-3864 [Print] United States
• PMID: 17253842 (Publication Type: Journal Article)

Chemical References

• 16beta,17beta-epoxy-12beta-hydroxypregna-4,6-diene-3,20-dione
• 20R-hydroxypregna-4,6-diene-3,12-dione
• 21-hydroxypregna-4,6-diene-3,12,20-trione
• Anti-Inflammatory Agents
• Antineoplastic Agents, Phytogenic
• Fluoresceins
• Pregnanes
• Intercellular Adhesion Molecule-1
• fluorexon

Topics

• Anti-Inflammatory Agents (chemistry, isolation & purification, pharmacology)
• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Cells, Cultured
• Drug Screening Assays, Antitumor
• Fluoresceins (metabolism)
• Humans
• Intercellular Adhesion Molecule-1 (drug effects, metabolism)
• Japan
• Molecular Structure
• Nerium (chemistry)
• Plants, Medicinal (chemistry)
• Pregnanes (chemistry, isolation & purification, pharmacology)
• Stereoisomerism