Novel sterols from the finger sponge Haliclonaoculata

Findlay, John A.; Patil, Ashok D.

doi:10.1139/v85-398

Cited by 36 publications

(38 citation statements)

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“…1) after subjecting it on various chromatographic separations. Detailed analysis of the spectroscopic data one and two dimensional (1D-and 2D)-NMR and MS and comparison with literature values led to elucidation of the known compounds as dissesterol (3), 11) 3β-hydroxy-24-methylenecholest-5-en-7-one (4), 12,13) 16α-hydroxysarcosterol (5), 10) and sarcophytosterol (6). 14) Compound 1 was isolated as a colorless powder with the molecular formula C 28 (Fig.…”

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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“…5,24(24Ј)-diene-3b,7b-diol (10), 10,12) cholesta-5,24(24Ј)-diene3b,7a-diol (11), 10,12) b-sitosterol (12), 13) stigmast-5-en-3b-ol-7-one (13), 13) stigmast-5-ene-3b,7b-diol (14), 13) stigmast-5-ene-3b,7a-diol (15), 13) cholest-24(24Ј)-ene-3b,5a,6b-triol (16), 14) stigmastane-3b,5a,6b-triol (17), 15) and desmosterol (18) 16) by comparison of their 1 H-and 13 C-NMR spectroscopic data with those described in the literature.…”

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Compositions of Royal Jelly II. Organic Acid Glycosides and Sterols of the Royal Jelly of Honeybees (Apis mellifera)

et al. 2007

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Royal jelly is a secretion from the hypopharyngeal and mandibular glands of worker bees, and it is the exclusive food of the queen bee for the entire span of both her larval and adult lives. With regard to the constituents of this material, it contains remarkably high amounts of organic acids in the total lipid fraction.1) Many organic acids mainly consisting of 8 to 11 carbon atoms such as 10-hydroxy-2-decenoic 2,3) and 10-hydroxydecanoic acids have been isolated. Among them, a minor component, 9-hydroxy-2-decenoic acid, 4) is known to be a queen honeybee pheromone with swarm-stabilizing activity, 5) and it is also regarded as a precursor of the so-called queen substance, 9-keto-2-decenoic acid, which controls the caste of honeybee colonies.6) Recently, we have isolated mono-or diesters of 10-hydroxy-2-decenoic acid in which the hydroxyl group was esterified by another organic acid residue from the total lipid fraction of the royal jelly of the honeybees (Apis mellifera). 7) In view of these findings, it seems that other unknown compounds including pheromones or their precursors exist in royal jelly. The present study was undertaken to examine the constituents of royal jelly in the hope of discovering the biologically active compounds that control the hierarchy of honeybee colonies. By application of the recycling HPLC technique for the isolation of minor constituents from a complex mixture, two glycosides (1, 2) together with 16 compounds (3-18) were obtained in the pure state. The former two were fatty acid monoglucosides and the latter were sterols mainly composed of 28 or 29 carbons. This paper deals with the isolation and structural elucidation of these compounds. Results and DiscussionThe total lipid fraction obtained from lyophilized royal jelly powder (6.0 kg) was separated repeatedly on silica gel column chromatography with a mixture of CHCl 3 -MeOH to yield crude glycoside and sterol fractions (see Experimental). Both fractions were further separated with HPLC including a recycling mode, and two (1, 2) from the former and 16 (3-18) compounds from the latter were isolated in pure form. Among them, compounds 7-18 were identified as the known sterols 24-methylenecholesterol (7), 8) isofucosterol (8), 9) cholesta-5,24(24Ј)-dien-3b-ol-7-one (9), 10,11) cholesta-5,24(24Ј)-diene-3b,7b-diol (10), 10,12) cholesta-5,24(24Ј)-diene3b,7a-diol (11), 10,12) b-sitosterol (12), 13) stigmast-5-en-3b-ol-7-one (13), 13) stigmast-5-ene-3b,7b-diol (14), 13) stigmast-5-ene-3b,7a-diol (15), 13) cholest-24(24Ј)-ene-3b,5a,6b-triol (16), 14) stigmastane-3b,5a,6b-triol (17), 15) and desmosterol (18) 16) by comparison of their 1 H-and 13 C-NMR spectroscopic data with those described in the literature. Structures of Compounds 1 and 2 Negative-ion FAB-MS of 1 gave an [MϪH]Ϫ ion peak at m/z 347, and HR-FAB-MS revealed the molecular formula of 1 to be C 16 H 28 O 8 . The 1 H-NMR spectrum showed one anomeric proton signal at d 4.87 ppm, in addition to typical signals ascribable to a 10-hydroxy-2-decenoyl group. 7) Based on the couplin...

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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.…”

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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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Novel sterols from the finger sponge Haliclonaoculata

Cited by 36 publications

References 7 publications

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

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

Compositions of Royal Jelly II. Organic Acid Glycosides and Sterols of the Royal Jelly of Honeybees (Apis mellifera)

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

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