Next Article in Journal
Suboptimal Temperature Acclimation Affects Kennedy Pathway Gene Expression, Lipidome and Metabolite Profile of Nannochloropsis salina during PUFA Enriched TAG Synthesis
Previous Article in Journal
Distribution of Saponins in the Sea Cucumber Holothuria lessoni; the Body Wall Versus the Viscera, and Their Biological Activities
Article Menu
Issue 11 (November) cover image

Export Article

Open AccessArticle
Mar. Drugs 2018, 16(11), 424; https://doi.org/10.3390/md16110424

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

1
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
2
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)
Full-Text   |   PDF [951 KB, uploaded 8 November 2018]   |  

Abstract

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
Figures

Graphical abstract

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).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top