Steroids with Aromatic A-Rings from the Hainan Soft Coral Dendronephthya studeri Ridley

Abstract

Eight new marine steroids, characterized by either the presence of an aromatic ring or a cross-conjugated dienone system in ring A, were isolated from the Hainan soft coral Dendronephthya studeri Ridley. Their structures were elucidated on the basis of detailed spectroscopic analysis and by comparison of their NMR data with those reported in the literature.

Origin of an ancient hormone/receptor couple revealed by resurrection of an ancestral estrogen

“…4A). Steroids with an aromatic A-ring and a lateral side chain have been identified in a tropical sponge ( 11 ), and the very molecule we propose as a proxy for this ancestral chordate steroid, 19-norcholesta-1,3,5(10)-trien-3-ol, was recently isolated from a soft coral ( 12 ). The synthesis of these molecules by nonbilaterian animals is probably related to defensive functions rather than to endocrine signaling ( 27 ).…”

“…For the sake of simplicity, we tested the ligand-binding ability of an aromatized steroid with a side chain and with no hydroxylation. We define “paraestrols” as steroids comprising a cholesterol side chain and an aromatized A-ring to avoid confusion with other natural products bearing additional modifications on the side chain, such as ethyl or methyl groups on carbon 24 ( 11 , 12 ). We further refer to 19-norcholesta-1,3,5(10)-trien-3-ol as paraestrol A, being the first member of this class to be synthesized de novo and experimentally characterized.…”

Recent Updates on Corals from Nephtheidae

“…The identified sterols showed weak anti-inflammatory activities in a human neutrophil model with IC 50 values exceeding 10 μM. [14] In another work, investigation of the diethyl ether extract of the soft coral Dendronephthya studeri RIDLEY, collected at a depth of 20 m from the coast of Xiaodong Sea, Hainan Province, China, has led to the characterization of ten steroidal molecules (8,9,19, 20, 24 -26 and 34) with a characteristic aromatic ring or a cross-conjugated dienone system in ring A. Unfortunately, they were all inactive at concentrations up to 20 μg/mL against several tumor cell lines, including BEL-7402, murine lymphocytic leukemia P388, human promyelocytic leukemia HL-60 and human lung adenocarcinoma A549.…”

Functional Gene-Guided Discovery of Type II Polyketides from Culturable Actinomycetes Associated with Soft Coral Scleronephthya sp

“…prostaglandins, diterpenes, alkaloids and steroids) [1] and display a variety of biological activities ( e.g. antitumor, anti-inflammatory and antibacterial activities) [2], [3], [4], [5]. Actinomycetes are widely distributed in marine habitats including the sea surface, water column, marine snow, sediments and marine organisms [6], [7], [8], [9], [10], [11], [12].…”

“…However, to date, related reports on coral-associated actinomycetes are still scarce and mainly limited to stony corals [23], [24], [25]. Novel compounds with biological activity have been extracted from soft corals [2], [3], [4], [5], so, it is significant to investigate the soft coral-associated actinomycetes regarding their diversity as well as their potential in secondary metabolite biosynthesis.…”