Steroids from Marine Sources

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (31 August 2019) | Viewed by 9643

Special Issue Editor


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Guest Editor
Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS, Muséum National d’Histoire Naturelle, 57, rue Cuvier (C.P. 54), 75005 Paris, France
Interests: chemistry of marine natural substances; molecular diversity within marine sponges and their associated bacteria; cross-talk within microorganisms and their sponge host; role of the microbial community hosted by the sponge
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Special Issue Information

Dear Colleagues,

The discovery during the mid-last century of the first marine steroids with unprecedented structures has opened a large avenue of marine investigations. Thus far, several hundreds of unique steroids have been provided from the marine world, exhibiting a remarkable variety of substitutions and rearrangements. Some of them revealed significant biological activities, including cytotoxic, antimicrobial, antiparasitic, antiviral, anti-inflammatory, and cardiovascular activities.

The most promising unconventional steroid, namely the unusual sulfated aminosterol squalamine, originally isolated from the dogfish Squalus acanthias as a powerful antibiotic, has revealed significant antiangiogenic activity. Squalamine is currently in advanced clinical trials in the treatment of ovarian cancer and also of age-related macular degeneration. Its potential application in Parkinson’s disease has also been suggested. More recently, sterol sulfates appeared as regulatory molecules, able to control the growth of a marine diatom bloom.

While the interest of sterol in ecological studies as biomarkers or for antifouling is pointed out, steroids have been continuously isolated from diverse marine organisms, including sponges, starfishes, gorgonian corals, as well as marine microorganisms. Their structures with unusual side chains are elucidated in detail, their potential biological activities and their mechanisms of action have been intensively investigated.

This Special Issue of Marine Drugs aims to provide recent studies on marine steroids, encompassing novel structures and biosynthetic routes, potential medical applications and ecological roles within the marine organisms and their environments.

Prof. Dr. Marie-Lise Bourguet-Kondracki
Guest Editor

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Keywords

  • Marine steroid
  • Biological activity
  • Medical application
  • Ecological study
  • Environmental application

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Published Papers (2 papers)

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Research

13 pages, 5914 KiB  
Article
Steroids from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475 Induced Apoptosis via Retinoid X Receptor (RXR)-α Pathway
by Chun-Lan Xie, Duo Zhang, Jin-Mei Xia, Chao-Chao Hu, Ting Lin, Yu-Kun Lin, Guang-Hui Wang, Wen-Jing Tian, Zeng-Peng Li, Xiao-Kun Zhang, Xian-Wen Yang and Hai-Feng Chen
Mar. Drugs 2019, 17(3), 178; https://doi.org/10.3390/md17030178 - 19 Mar 2019
Cited by 25 | Viewed by 4905
Abstract
Five new ergostanes, penicisteroids D−H (15), were isolated from the liquid culture of the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, along with 27 known compounds. The structures of the new steroids were established mainly on the basis of extensive [...] Read more.
Five new ergostanes, penicisteroids D−H (15), were isolated from the liquid culture of the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475, along with 27 known compounds. The structures of the new steroids were established mainly on the basis of extensive analysis of 1D and 2D NMR as well as HRESIMS data. Moreover, the absolute configurations of 1 were confirmed unambiguously by the single-crystal X-ray crystallography. Compounds 2 and 47 showed moderate antiproliferative effects selectively against 12 different cancer cell lines with IC50 values of around 5 μM. Compounds 2 and 6, potent RXRα binders with Kd values of 13.8 and 12.9 μM, respectively, could induce apoptosis by a Retinoid X Receptor (RXR)-α-dependent mechanism by regulating RXRα transcriptional expression and promoting the poly-ADP-ribose polymerase (PARP) cleavage. Moreover, they could inhibit proliferation by cell cycle arrest at the G0/G1 phase. Full article
(This article belongs to the Special Issue Steroids from Marine Sources)
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10 pages, 951 KiB  
Article
New 9α-Hydroxy-5α,6α-epoxysterols from the Vietnamese Marine Sponge Ircinia echinata
by Thi Thanh Van Trinh, Bich Ngan Truong, Arlette Longeon, Thi Mai Huong Doan, Alexandre Deville, Van Minh Chau, Van Cuong Pham and Marie-Lise Bourguet-Kondracki
Mar. Drugs 2018, 16(11), 424; https://doi.org/10.3390/md16110424 - 1 Nov 2018
Cited by 6 | Viewed by 3185
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Steroids from Marine Sources)
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