Minor and trace sterols in marine invertebrates

Carlson, Robert M. K.; Попов, Симеон; Massey, Ian J.; Delseth, Claude; Ayanoğlu, Ender; Varkony, Tomas H.; Djerassi, Carl

doi:10.1016/0045-2068(78)90036-6

Cited by 48 publications

(13 citation statements)

References 77 publications

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“…In an early study, the incorporation of [2-14C]acetate and of sodium [14C]carbonate into the tips of the gorgonian Pseudoplexaura porosa was investigated. 182 The major metabolite, crassin acetate (146), was more effectively labelled by acetate, with close to half the label being shown to be located in the acetate ester moiety by acid hydrolytic degradation. Positive evidence for the labelling of the cembrane ring was not obtained.…”

Section: Gorgonians and Other Coelenteratesmentioning

confidence: 99%

Biosynthetic studies on marine natural products

Garson¹

1989

Nat. Prod. Rep.

112

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Section: Gorgonians and Other Coelenteratesmentioning

confidence: 99%

Biosynthetic studies on marine natural products

Garson¹

1989

Nat. Prod. Rep.

112

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“…La presence dans des extraits marins de ces composes, produits d'auto-oxydation reconnus ou plausibles de sterols, est un sujet delicat, particulierement pour l'analyse de composants mineurs ou presents en traces. Une evaluation des origines de ces derives, rencontres en quantitt mineure dans d'autres extraits marins, fera l'objet d'une prochaine communication [9].…”

unclassified

Identification de stérols à chaînes latérales courtes dans l′éponge Damiriana hawaiiana

Delseth

Carlson

Djerassi

et al. 1978

Helvetica Chimica Acta

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Identification of short side chain sterols in the sponge Damiriana hawaiiana SummaryThe steroidal composition of the sponge Damiriana hawaiiana is examined. Twenty-seven components are identified. In addition to the (&-CZ9, A*-mono and diunsaturated sterols, the sponge contains sterols without side-chain: androsta-5,16-dien-3/3-01 (l), androst-5-en-3P-o1(2); sterols with a non-functionalized sidechain consisting of two, three, four, five and six carbon atoms: pregna-5,20-dien-38-01 (5), pregn-5-en-3P-o1(6), 23,24-bisnor-chola-5,20-dien-3,B-ol(7), 23,24-bisnorcho1-5-en-3P-o1(8), 24-nor-chol-5-en-38-01 (lo), chol-5-en-3P-01 (ll), 26,27-bisnorcholest-5-en-3j?-ol(12), and sterols possessing a short oxygenated side-chain such as 3~-hydroxy-androst-5-en-l7-one (3), androst-5-en-38,17j?-diol(4) and 3,B-hydroxy-26,27-bisnor-22-trans-cholesta-5,22-dien-24-one (14). The probable biological or dietary origin rather than artifact production of these hitherto undescribed components from marine sources is supported by their relatively high concentration and their relative proportions, both very different from those expected for autoxidation.

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“…Another endoperoxide-containing natural product well-known for its anti-protozoal activity is artemisinin. Short side chain sterols are uncommon but have previously been isolated from marine invertebrates, including from tunicates, gorgonians and sponges [44,45]. These sterols may be in vivo oxidative products from sterols with unsaturated side chains and not degradation products obtained during laboratory work-up.…”

Section: Resultsmentioning

confidence: 99%

“…These sterols may be in vivo oxidative products from sterols with unsaturated side chains and not degradation products obtained during laboratory work-up. A sterol bearing the same side chain as in 3 has been isolated from the gorgonian Murecia californica and the sponge Damiriana hawaiiana [45]. …”

Section: Resultsmentioning

confidence: 99%

Isolation and Identification of Antitrypanosomal and Antimycobacterial Active Steroids from the Sponge Haliclona simulans

et al. 2014

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The marine sponge Haliclona simulans collected from the Irish Sea yielded two new steroids: 24-vinyl-cholest-9-ene-3β,24-diol and 20-methyl-pregn-6-en-3β-ol,5α,8α-epidioxy, along with the widely distributed 24-methylenecholesterol. One of the steroids possesses an unusually short hydrocarbon side chain. The structures were elucidated using nuclear magnetic resonance spectroscopy and confirmed using electron impact- and high resolution electrospray-mass spectrometry. All three steroids possess antitrypanosomal and anti-mycobacterial activity. All the steroids were found to possess low cytotoxicity against Hs27 which was above their detected antitrypanosomal potent concentrations.

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Minor and trace sterols in marine invertebrates

Cited by 48 publications

References 77 publications

Biosynthetic studies on marine natural products

Biosynthetic studies on marine natural products

Identification de stérols à chaînes latérales courtes dans l′éponge Damiriana hawaiiana

Isolation and Identification of Antitrypanosomal and Antimycobacterial Active Steroids from the Sponge Haliclona simulans

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