Polyoxygenated 24,28-epoxyergosterols inhibiting the proliferation of glioma cells from sea anemone Anthopleura midori

Yu, Siran; Ye, Xuewei; Chen, Lu; Lian, Xiao-Yuan; Zhang, Zhizhen

doi:10.1016/j.steroids.2014.06.013

Cited by 25 publications

(24 citation statements)

References 27 publications

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“…The absolute configuration 24S of 2 was assigned by circular dichroism (CD) spectrum with a negative Cotton effect at 286 nm. 17) Consequently, the structure 24(S),28-epoxyergost-5-ene-3β,4α-diol was elucidated for 2.…”

Section: Resultsmentioning

confidence: 99%

Steroid Constituents from the Soft Coral Sinularia nanolobata

et al. 2016

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Section: Resultsmentioning

confidence: 99%

Steroid Constituents from the Soft Coral Sinularia nanolobata

et al. 2016

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“…1) were isolated from a methanol extract of the soft coral S. leptoclados. The known compounds, 7-oxogorgosterol (3), 6) crassumsterol (4), 9) 7β-hydroxygorgosterol (5), 10) sarcophytosterol (6), 11) 3β-hydroxyergosta-5-ene-7-one (7), 12) ergost-5-en-3β,7β-diol (8), 13) ergost-5-en-3β,7α-diol (9), 14,15) ergosta-5,24(28)-diene-3β-ol (10), 16) 3β-hydroxyergost a-5,24(28)-diene-7-one (11), 17,18) ergosta-5,22,24(28)-trien-3β-ol (12), 19) 3β,7β-dihydroxyergosta-5,24(28)-diene (13), 20) 3β,7α-di hydroxyergosta-5,24(28)-diene (14), 20) and 3β,4α-dihydroxyergosta-5,24(28)-diene (15), 7) were identified by detailed analysis of their one and two dimensional (1-and 2D)-NMR and MS data as well as comparison of them with those reported in the literatures. Pos.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Steroids from the Vietnamese Soft Coral Sinularia leptoclados

et al. 2017

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Fifteen steroids, including two new compounds, leptosteroid (1) and 5,6β-epoxygorgosterol (2), were isolated and structurally elucidated from the Vietnamese soft coral Sinularia leptoclados. Their cytotoxic effect against a panel of eight human cancer cell lines was evaluated using sulforhodamine B (SRB) method. Key words Sinularia leptoclados; Alcyoniidae; soft coral; steroid; cytotoxic activityThe phylum Cnidaria includes about 10000 species which are traditionally divided into three classes: Anthozoa, Hydrozoa, and Scyphozoa. The best-known representatives of the class Anthozoa are the gorgonians and soft corals among the subclass Octocorallia and the sea anemones and stony corals among the subclass Hexacorallia. Soft corals attracted considerable attention because of the wide range of their bioactive secondary metabolites. In these marine invertebrates, genus Sinularia (phylum Cnidaria, class Anthozoa, subclass Octocorallia, order Alcyonacea) is one of the most widely distributed soft corals and constitutes a dominant portion of the biomass in the tropical reef environment.1,2) Sinularia soft corals are a rich source of steroids and terpenoids. 2-5)As a part of our ongoing investigations on cytotoxic steroids from Vietnamese Sinularia soft corals, [6][7][8] this paper addressed the isolation, structure elucidation, and cytotoxic evaluation of fifteen steroids, including two new compounds, leptosteroid (1) and 5,6β-epoxygorgosterol (2), from the soft coral S. leptoclados. Results and DiscussionUsing various chromatographic separations, fifteen steroids (Fig. 1) were isolated from a methanol extract of the soft coral S. leptoclados. The known compounds, 7-oxogorgosterol (3), 6) crassumsterol (4), 9) 7β-hydroxygorgosterol (5), 10) sarcophytosterol (6), 11) 3β-hydroxyergosta-5-ene-7-one (7), 12) ergost-5-en-3β,7β-diol (8), 13) ergost-5-en-3β,7α-diol (9), 14,15) ergosta-5,24(28)-diene-3β-ol (10), 16) 3β-hydroxyergost a-5,24(28)-diene-7-one (11), 17,18) ergosta-5,22,24(28)-trien-3β-ol (12), 19) 3β,7β-dihydroxyergosta-5,24(28)-diene (13), 20) 3β,7α-di hydroxyergosta-5,24(28)-diene (14), 20) and 3β,4α-dihydroxyergosta-5,24(28)-diene (15), 7) were identified by detailed analysis of their one and two dimensional (1-and 2D)-NMR and MS data as well as comparison of them with those reported in the literatures.Leptosteroid (1) was isolated as a white powder with molecular formula of C 29 H 48 O 3 , determined by high-resolution electrospray ionization (HR-ESI)-MS at m/z 445.36819 [M+H]

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“…There is therefore a need to discover lead compounds for the development of novel anti-glioma drugs. Natural products are highly significant sources of new drug leads (Newman & Cragg 2012 During the course of our ongoing programme for the discovery of novel anti-glioma agents from natural sources (Xin et al 2012;Ye et al 2014;Yu, Ye, Chen et al 2014;Yu et al 2015;Yu, Ye, Xin et al 2014), the cultured broth of marine actinomycete strain HS7 isolated from the cloacal aperture of sea cucumber Holothuria moebii was found to be active against the proliferation of glioma cells. The strain HS7 was identified by 16S rDNA sequence analysis and its top16S rDNA sequence was 100% sequence match to Pseudonocardia antitumoralis strain SCSIO 01299.…”

Section: Introductionmentioning

confidence: 99%

A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

Anjum

Song

et al. 2015

Natural Product Research

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Five curvularin macrolides (1-5) were isolated from the cultured broth of marine actinomycete Pseudonocardia sp. HS7 that was obtained from the cloacal aperture of sea cucumber Holothuria moebii. The structures of these isolates were characterized as (11S,15R)-11-hydroxycurvularin (1), (11R,15R)-11-hydroxycurvularin (2), curvularin-7-O-α-D-glucopyranoside (3), trans-dehydrocurvularin (4) and curvularin (5) based on their NMR and HRESIMS data as well as chemical degradation. Compound 3 is a new macrolide with a rare α-D-glucopyranose substituent. Compounds 1-4, 5a and 5c (the acyl products of 5), suppressed the proliferation of all six tested cancer cell lines and 4 is the most active compound with IC50 values ranging from 0.59 to 3.39 μM. The 11-hydroxycurvularins 1 and 2 also showed antibacterial activity inhibiting the growth of Escherichia coli.

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Polyoxygenated 24,28-epoxyergosterols inhibiting the proliferation of glioma cells from sea anemone Anthopleura midori

Cited by 25 publications

References 27 publications

Steroid Constituents from the Soft Coral <i>Sinularia nanolobata</i>

Steroid Constituents from the Soft Coral <i>Sinularia nanolobata</i>

Cytotoxic Steroids from the Vietnamese Soft Coral <i>Sinularia leptoclados</i>

A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

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