Crassocolides A−F, Cembranoids with a trans-Fused Lactone from the Soft Coral Sarcophyton crassocaule

Six new polyoxygenated cembrane-based diterpenoids possessing a trans-fused α-methylene-γ-lactone, crassocolides A−F (1−6), have been isolated along with the known compound 7 from the ethyl acetate extract of a Taiwanese soft coral, Sarcophyton crassocaule. The structures of 1−6 have been establishe...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-11, Vol.69 (11), p.1554-1559
Main Authors: Huang, Ho-Cheng, Ahmed, Atallah F, Su, Jui-Hsin, Chao, Chih-Hua, Wu, Yang-Chang, Chiang, Michael Y, Sheu, Jyh-Horng
Format: Article
Language:English
Subjects:
anticarcinogenic activity
Biological and medical sciences
cembrane ditepene
cembranoid
chemical structure
corals
crassocolide
cultured cells
cytotoxicity
diterpenoids
General pharmacology
humans
lactones
Medical sciences
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Sarcophyton
Sarcophyton crassocaule
spectral analysis
stereochemistry
X-ray diffraction
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Summary:Six new polyoxygenated cembrane-based diterpenoids possessing a trans-fused α-methylene-γ-lactone, crassocolides A−F (1−6), have been isolated along with the known compound 7 from the ethyl acetate extract of a Taiwanese soft coral, Sarcophyton crassocaule. The structures of 1−6 have been established by detailed spectroscopic analysis, including 2D NMR (1H−H COSY, HMQC, HMBC, and NOESY) spectroscopy, while their absolute configurations were determined using a modified Mosher's method for 1. The structure of 5 was further proven by X-ray diffraction analysis. The full assignment of NMR data of 7 is reported herein for the first time. The cytotoxicity of crassocolides 1−4, 6, and 7 against a limited panel of cancer cells was also determined.
ISSN:0163-3864
1520-6025
DOI:10.1021/np060182w