9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

Zhang, Jun; Liu, Lingli; Zhong, Balian; Liao, Xiaojian; Xu, Shi‐Hai

doi:10.1016/j.steroids.2015.03.004

Cited by 18 publications

(10 citation statements)

References 28 publications

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“…The first group of compounds showed C9-C11 bond cleavage in tetracyclic nucleus, while the latter one had higher oxygenation levels due to the presence of an endoperoxide bond. Those characteristic features are often found in marine invertebrates, particularly soft corals [33,34,38,39]. The 5α,8α-endoperoxides 44-51 are oxidized sterols which can be formed during photooxidation reaction by addition of an oxygen molecule to a conjugated 5,7-diene system in the precursor molecule which contains the steroidal core [40][41][42][43].…”

Section: Steroidsmentioning

confidence: 99%

“…The gorgonian coral, Subergorgia suberosa, collected from the South China Sea, was used to extract several secosterols bearing a hydroxyl group at C11, including 38 and 43. Zhang et al reported IC 50 values of 28.1 and 23.3 µM against HeLa cells for 38 and 43, respectively, and hypothesized that the presence of a free -OH group at C11 does not contribute to the observed cytotoxic effects of the tested compounds [38]. That is also consistent with the conclusion reported by Kongkathip et al who have synthesized and evaluated the cytotoxicity of 9,11-secosterol derivatives against KB, HeLa, and MCF-7 cells, as well as non-transformed Vero cells.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

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Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

et al. 2019

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Gorgonian corals, which belong to the genus Eunicella, are known as natural sources of diverse compounds with unique structural characteristics and interesting bioactivities both in vitro and in vivo. This review is focused primarily on the secondary metabolites isolated from various Eunicella species. The chemical structures of 64 compounds were divided into three main groups and comprehensively presented: a) terpenoids, b) sterols, and c) alkaloids and nucleosides. The observed biological activities of depicted metabolites with an impact on cytotoxic, anti-inflammatory, and antimicrobial activities were reviewed. The most promising biological activities of certain metabolites point to potential candidates for further development in pharmaceutical, cosmetic, and other industries, and are highlighted. Total synthesis or the synthetic approaches towards the desired skeletons or natural products are also summarized.

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Section: Steroidsmentioning

confidence: 99%

Section: Cytotoxic Activitymentioning

confidence: 99%

Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

et al. 2019

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“…The previous studies have been reported that several novel sequiterpenes [1][2][3][4][5][6], pregnane derivatives [7,8], secosteroids [9][10][11], and alkaloids [12] were isolated from Subergorgia suberosa. Some of these natural products exhibited a variety of biological activities such as cytotoxicity [2,4,5,13,14], antibacterial [15], antifungal [15], antifouling [16,17], and anti-flu virus effects [8].…”

Section: Introductionmentioning

confidence: 99%

Two Novel Sesquiterpenes and A New Pregnane Derivative from the South China Sea Gorgonian Subergorgia suberosa

Chen¹,

Xing²,

Yang³

et al. 2019

Rec.Nat.Prod.

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Two novel sequiterpenes isosuberosenol A (1), suberosain A (2), and a new pregnane derivative 4hydroxymethyl-5β-pregnan-3, 20-dione (3) have been isolated from the South China Sea gorgonian Subergorgia suberosa. Their structure and relative stereochemistry were established based on the detailed spectroscopic analysis, including HR-ESI-MS, 1D-and 2D NMR spectra. The skeleton of isosuberosenol A (1) have been previously undescribed. The discovery of isosuberosenol A (1) provides some strong support for the plausible biogenetic pathway of quadrone type sesquiterpenes.

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“…As part of our continuous effort to identify structurally and biologically interesting natural products from marine resources [ 12 , 13 , 14 ], the fungus Gliomastix sp. ZSDS1-F7-2 from the marine sponge Phakellia fusca Thiele, which was collected from the South China Sea in March 2012, has been investigated with the discovery of a series of unusual macrolides gliomasolides A—E with cytotoxic effect against the growth of HeLa cell line [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Four New C9 Metabolites from the Sponge-Associated Fungus Gliomastix sp. ZSDS1-F7-2

et al. 2018

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Four new structurally related metabolites, one γ-lactone named gliomasolide F (1), one δ-lactone named gliomasolide G (2), and two medium-chain fatty acids named gliomacids A–B (3–4), each containing nine carbons in total, were identified from the sponge-associated fungus Gliomastix sp. ZSDS1-F7-2. The planar chemical structures of these novel C9 metabolites were elucidated by nuclear magnetic resonance (NMR) spectroscopic methods, in connection with the analysis of high-resolution mass spectrometry (HRMS) and infrared (IR) data. The absolute configuration of 1, was determined by comparisons of experimental circular dichroism (CD) and optical rotation (OR) value with corresponding ones computed by quantum chemistry. The relative configuration of 2 was determined by the Nuclear Overhauser effect spectroscopy (NOESY) spectrum, while its absolute configuration was tentatively determined in view of the biogenetic and biosynthetic relationships between 1 and 2. Compounds 3–4, originally as an inseparable mixture, were successfully isolated after chemical modifications. The stereo-chemistries of compounds 3–4 were assumed by comparison of 13C NMR with those of the similar moiety reported in literature, in addition to the biogenetic and biosynthetic relationships with 1. The plausible biosynthetic relationships among these four C9 metabolites were supposed. Biologically, compounds 1–4 showed no cytotoxic effect against HeLa cell line at concentrations up to 25 μg/mL, while 1 exhibited moderate antifouling activity against the settlement of Balanus amphitrite larvae with IC50 being 12.8 μg/mL and LC50 > 25 μg/mL. The co-occurrence of macrolides gliomasolides A—E and four C9 metabolites in the same fermentation culture made us assume that these C9 metabolites might be biosynthetic building blocks toward the construction of more complex macrolides such as gliomasolides A—E or other unidentified polyketides.

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9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

Cited by 18 publications

References 28 publications

Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

Two Novel Sesquiterpenes and A New Pregnane Derivative from the South China Sea Gorgonian Subergorgia suberosa

Four New C9 Metabolites from the Sponge-Associated Fungus Gliomastix sp. ZSDS1-F7-2

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