DNA-damaging steroidal alkaloids from Eclipta alba from the suriname rainforest1

Bioassay-guided fractionation of the MeOH extract of Eclipta alba using three yeast strains (1138, 1140, and 1353) resulted in the isolation of eight bioactive steroidal alkaloids (1-8), six of which are reported for the first time from nature. The major alkaloid was identified as (20S)(25S)-22,26-i...

Full description

Saved in:
Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1998-10, Vol.61 (10), p.1202-1208
Main Authors: Abdel-Kader, M S, Bahler, B D, Malone, S, Werkhoven, M C, van Troon, F, David, Wisse, J H, Bursuker, I, Neddermann, K M, Mamber, S W, Kingston, D G
Format: Article
Language:English
Subjects:
Alkaloids - isolation & purification
Alkaloids - pharmacology
Asteraceae - chemistry
Candida albicans - drug effects
Cell Line
DNA - drug effects
DNA Damage
India
Magnetic Resonance Spectroscopy
Phytosterols - isolation & purification
Phytosterols - pharmacology
Plants, Medicinal - chemistry
Saccharomyces cerevisiae - drug effects
Suriname
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Bioassay-guided fractionation of the MeOH extract of Eclipta alba using three yeast strains (1138, 1140, and 1353) resulted in the isolation of eight bioactive steroidal alkaloids (1-8), six of which are reported for the first time from nature. The major alkaloid was identified as (20S)(25S)-22,26-imino-cholesta-5,22(N)-dien-3beta-ol (verazine, 3), while the new alkaloids were identified as 20-epi-3-dehydroxy-3-oxo-5,6-dihydro-4,5-dehydroverazine (1), ecliptalbine [(20R)-20-pyridyl-cholesta-5-ene-3beta,23-diol] (4), (20R)-4beta-hydroxyverazine (5), 4beta-hydroxyverazine (6), (20R)-25beta-hydroxyverazine (7), and 25beta-hydroxyverazine (8). Ecliptalbine (4), in which the 22,26-imino ring of verazine was replaced by a 3-hydroxypyridine moiety, had comparable bioactivity to verazine in these assays, while a second alkaloid (8) showed good activity against Candida albicans. All the alkaloids showed weak cytotoxicity against the M-109 cell line.
ISSN:0163-3864