7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic Aspergillus ochraceus EN-31

7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3β,11α-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3β-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endo...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2010-11, Vol.73 (11), p.1780-1784
Main Authors: Cui, Chuan-Ming, Li, Xiao-Ming, Meng, Li, Li, Chun-Shun, Huang, Cai-Guo, Wang, Bin-Gui
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Aspergillus ochraceus - chemistry
Biological and medical sciences
Drug Screening Assays, Antitumor
General pharmacology
Humans
Inhibitory Concentration 50
Marine Biology
Medical sciences
Molecular Structure
Norsteroids - chemistry
Norsteroids - isolation & purification
Norsteroids - pharmacology
Nuclear Magnetic Resonance, Biomolecular
Phaeophyceae - microbiology
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Stereoisomerism
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Summary:7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3β,11α-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3β-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endophytic fungus isolated from the marine brown alga Sargassum kjellmanianum. In addition, nine known related steroids were isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration of the new steroids (1−3) was determined by application of the modified Mosher’s method. Compound 1, which represents the first example of a 7-nor-ergosteroid possessing a pentalactone B-ring system in a naturally occurring steroid, displayed cytotoxicity against NCI-H460, SMMC-7721, and SW1990 cell lines with IC50 values of 5.0, 7.0, and 28.0 μg/mL, respectively. Compound 2 also displayed cytotoxicity against the SMMC-7721 cell line with an IC50 value of 28.0 μg/mL.
ISSN:0163-3864
1520-6025
DOI:10.1021/np100386q