1alpha,3beta,5beta-trihydroxy-24-methylenecholestan-6-one: a novel steroid from a soft coral Sinularia gibberosa

Steroids
Atallah F AhmedJyh-Horng Sheu

Abstract

A novel steroid, 1alpha,3beta,5beta-trihydroxy-24-methylenecholestan-6-one (gibberoketosterol) (1), along with four known steroids, was isolated from the lipophilic extracts of a Taiwanese soft coral Sinularia gibberosa. The structure of the new metabolite was determined on the basis of extensive spectral analyses and chemical reaction. The relative stereochemistry of gibberoketosterol was established by the NOESY experiments and analysis of the pyridine-induced deshielding effect of the axial hydroxy groups. Gibberoketosterol is the first example of 1alpha,3beta,5beta-trihydroxy-6-oxosteroids isolated from natural sources and was found to exhibit a moderate cytotoxicity against the growth of Hepa59T/VGH cancer cells.

References

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Citations

Feb 5, 2005·Natural Product Reports·John W BluntMichele R Prinsep
Jun 3, 2009·Natural Product Research·V Lakshmi, R Kumar
Jun 12, 2013·Phytochemistry·Yi ZangJin-Feng Hu
Feb 7, 2006·Comparative Biochemistry and Physiology. Part B, Biochemistry & Molecular Biology·Charles H BlomquistS Atkinson
Dec 9, 2010·Magnetic Resonance in Chemistry : MRC·Yun-Fu OuLiu Liao
Nov 16, 2012·Natural Product Reports·Jorge A R SalvadorM Luisa Sá e Melo
Mar 6, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wei-Hsuan YenPing-Jyun Sung
Dec 6, 2020·Marine Drugs·Ekaterina V ErmolenkoValery M Dembitsky
Sep 23, 2006·Journal of Natural Products·Atallah F AhmedJyh-Horng Sheu
May 14, 2009·Chemical Reviews·Nittala S SarmaP S Parameswaran
Aug 30, 2005·Journal of Natural Products·Atallah F AhmedJyh-Horng Sheu
Sep 27, 2005·Journal of Natural Products·Chih-Hua ChaoJyh-Horng Sheu
Jul 26, 2005·Journal of Natural Products·Atallah F AhmedJyh-Horng Sheu
Jan 18, 2008·Journal of Natural Products·Atallah F AhmedJyh-Horng Sheu
Jun 1, 2005·Journal of Natural Products·Guoqiang LiWenhan Lin

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