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Mar. Drugs 2018, 16(11), 424;

New 9α-Hydroxy-5α,6α-epoxysterols from the Vietnamese Marine Sponge Ircinia echinata

Advanced Center for Bioorganic Chemistry of the Institute of Marine Biochemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Caugiay 8424, Hanoi, Vietnam
Molécules de Communication et Adaptation des Microorganismes, UMR 7245 CNRS, Muséum National d’Histoire Naturelle, 57 rue Cuvier (CP54), 75005 Paris, France
These authors contributed equally to this paper.
Authors to whom correspondence should be addressed.
Received: 9 October 2018 / Revised: 19 October 2018 / Accepted: 23 October 2018 / Published: 1 November 2018
(This article belongs to the Special Issue Steroids from Marine Sources)
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Chemical investigation of the methanol extract of the Vietnamese marine sponge Ircinia echinata led to the isolation of six new 9α-hydroxy-5α,6α-epoxysterols: 5α,6α-epoxycholesta-7,22(E)-dien-3β,9α-diol (1), 5α,6α-epoxycholesta-7,24(28)-dien-3β,9α-diol (2), (24R)-5α,6α-epoxy-24-ethyl-cholesta-7-en-3β,9α-diol (3), 5α,6α-epoxycholesta-7-en-3β,9α-diol (4), (24S)-5α,6α-epoxyergosta-7,22-dien-3β,9α-diol (5), and (24R)-5α,6α-epoxy-24-methyl-cholesta-7-en-3β,9α-diol (6) along with the known 5α-6α-epoxysterols: 5α,6α-epoxystigmasta-7-en-3β-ol (7), 5α,6α-epoxystigmasta-7,22-dien-3β-ol (8), and 5α,6α-epoxyergosta-7-en-3β-ol (9). Their structures and their configurations were established on the basis of high resolution mass spectra and extensive 1D and 2D NMR spectroscopic data and by comparison with the literature. Their cytotoxic activity, evaluated against three human cancer cell lines, MCF-7, Hep-G2 and LU-1, revealed that only compounds 3 and 4 exhibited significant antiproliferative activity and compound 3 showed a selective inhibition towards the MCF-7 human breast cancer cells. View Full-Text
Keywords: marine sponge; Ircinia echinata; 9α-hydroxy-5α,6α-epoxysterols; cytotoxicity marine sponge; Ircinia echinata; 9α-hydroxy-5α,6α-epoxysterols; cytotoxicity

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Trinh, T.T.V.; Truong, B.N.; Longeon, A.; Doan, T.M.H.; Deville, A.; Chau, V.M.; Pham, V.C.; Bourguet-Kondracki, M.-L. New 9α-Hydroxy-5α,6α-epoxysterols from the Vietnamese Marine Sponge Ircinia echinata. Mar. Drugs 2018, 16, 424.

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