Sterol composition and biosynthesis in the Black Sea sponge Dysidea fragilis

Elenkov, Ivaylo; Milkova, Tsenka; Andreev, Stoitse; Попов, Симеон

doi:10.1016/0305-0491(94)90183-x

Cited by 12 publications

(8 citation statements)

References 7 publications

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“…For example, the cooccurence of epidioxy sterols and ∆ 4,7 -3,6-diketones in the marine sponge Raphidostila incisa has led to the proposal that epidioxy sterols may be biosynthetic precursors for the latter group of compounds (5). 5α,8α-Epidioxy sterols could also be biogenetic precursors of polyhydroxylated sterols in Dysidea species (10). The isolation of polyketide peroxides from a number of marine sponges of the genus Plakortis suggests the possible occurrence of peroxydase enzymes in these organisms (22).…”

Section: Discussionmentioning

confidence: 98%

“…In the present paper, we report the isolation and the structure elucidation of these 5α,8α-epidioxy sterols which contain a variety of side chains. This group of steroids with oxygenated functionalities in the nucleus, constitutes a longrecognized class of metabolites isolated from marine organisms such as sponges (3)(4)(5)(6)(7)(8)(9)(10), tunicates (6,11,12), sea hares (6,13), gorgonians (14), sea anemones (15), mussels (11,16), and other marine specimens (12,16,17,18). However, this is the first time that they have been isolated from a sponge of the genus Luffariella, and that attention is called to their potential antiviral and antitumor activities.…”

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confidence: 99%

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Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis

Gauvin¹,

Smadja²,

Aknin³

et al. 2000

Can. J. Chem.

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The lipid extract of the marine sponge Luffariella cf. variabilis from Mayotte (Indian Ocean) has proven to be an extraordinarily rich source of a wide variety of unusual steroids belonging to the 5α,8α-epidioxy sterol family. Ten epidioxy sterols have been identified: 5α,8α-epidioxycholesta-6,22-dien-3β-ol, 5α,8α-epidioxycholest-6-en-3β-ol, 5α,8α-epidioxy-24(ξ)-methylcholesta-6,22-dien-3β-ol, 5α,8α-epidioxy-24(S)-methylcholest-6-en-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholesta-6,22-dien-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholest-6-en-3β-ol and its epimer (24R), along with 5α,8α-epidioxy-24(ξ)-methylcholesta-6,9(11),22-trien-3β-ol. Their structures were determined by nuclear magnetic resonance ( 1 H, 13 C) and electron impact mass spectrometry. The mixture of the 10 steroids showed inhibitive activity against the human T-cell leukemia/lymphotropic virus type I (HTLV-I) and also displayed cytotoxic activity against the human breast cancer cell line (MCF 7 WT).Key words: Luffariella cf. variabilis, marine sponge, 5α,8α-epidioxy sterols, antitumor and antiviral activities.Résumé : L'extrait lipidique de l'éponge marine Luffariella cf. variabilis de Mayotte (Océan Indien) s'est révélé être une source extraordinairement riche d'une grande variété de stéroïdes particuliers appartenant à la famille des 5α,8α-épidioxy stérols. Dix épidioxy stérols ont été identifiés: 5α,8α-épidioxycholesta-6,22-dien-3β-ol, 5α,8α-épidioxycholest-6-en-3β-ol, 5α,8α-épidioxy-24(ξ)-methylcholesta-6,22-dien-3β-ol, 5α,8α-épidioxy-24(S)-methylcholest-6-en-3β-ol et son épimère (24R), 5α,8α-épidioxy-24(S)-ethylcholesta-6,22-dien-3β-ol et son épimère (24R), 5α,8α-épidioxy-24(S)-ethylcholest-6-en-3β-ol et son épimère (24R), ainsi que le 5α,8α-épidioxy-24(ξ)-methylcholesta-6,9(11),22-trien-3β-ol. Leurs structures ont été déterminées par résonance magnétique nucléaire ( 1 H, 13 C) et par spectrométrie de masse en impact électronique. Le mélange des 10 stéroïdes a montré une activité inhibitrice sur le virus de la leucémie-lymphome à cellules-T humain de type I (HTLV-I) et possède également une activité cytotoxique sur les cellules cancéreuses humaines du sein (MCF 7 WT).Mots clés : Luffariella cf. variabilis, éponge marine, 5α,8α-épidioxy stérols, activités antitumorale et antivirale. Gauvin et al. 992

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Section: Discussionmentioning

confidence: 98%

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confidence: 99%

Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis

Gauvin¹,

Smadja²,

Aknin³

et al. 2000

Can. J. Chem.

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“…Sterol 3 was the next most active against T. b. brucei .The 5α,8α-epidioxy sterol could be an artefact, a result of oxidation of a ∆ 5,7 -sterol, as has been observed in Dysidea sp. [ 40 ]. However, 5α,8α-epidioxy sterols have previously been isolated from the sponge Luffariella cf.…”

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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“…Concerning first “Δ 5,7 sterols extraction ”, it is very common for Δ 5,7 -sterols to be accompanied by a high proportion of 5α,8α-epidioxy sterols. The conjugated diene system in Δ 5,7 -sterols can easily be photooxidized during storage and/or chromatographic separation [ 20 – 22 ] ( Figure 4 ). To avoid Δ 5,7 -sterols photooxidation, Arreguin-Espinosa et al [ 21 ] proposed two methods for the investigation of marine invertebrates rich in di-unsaturated Δ 5,7 sterols: (1) the fresh marine invertebrate must be dipped in alcohol and transported as soon as possible to the laboratory, where it must be extracted immediately in the dark; or (2) marine invertebrates should be stored in the dark with 0.1% antioxidant such as BHA (Butylated HydroxyAnisole).…”

Section: Resultsmentioning

confidence: 99%

Sterols from the Madagascar Sponge Fascaplysinopsis sp.

et al. 2010

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The sponge Fascaplysinopsis sp. (order Dictyoceratida, Family Thorectidae) from the west coast of Madagascar (Indian Ocean) is a particularly rich source of bioactive nitrogenous macrolides. The previous studies on this organism led to the suggestion that the latter should originate from associated microsymbionts. In order to evaluate the influence of microsymbionts on lipid content, 10 samples of Fascaplysinopsis sp. were investigated for their sterol composition. Contrary to the secondary metabolites, the sterol patterns established were qualitatively and quantitatively stable: 14 sterols with different unsaturated nuclei, Δ5, Δ7 and Δ5,7, were identified; the last ones being the main sterols of the investigated sponges. The chemotaxonomic significance of these results for the order Dictyoceratida is also discussed in the context of the literature. The conjugated diene system in Δ5,7 sterols is known to be unstable and easily photo-oxidized during storage and/or experiments to produce 5α,8α-epidioxy sterols. However, in this study, no 5α,8α-epidioxysterols (or only trace amounts) were observed. Thus, it was supposed that photo-oxidation was avoided thanks to the natural antioxidants detected in Fascaplysinopsis sp. by both the DPPH and β-caroten bleaching assays.

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Sterol composition and biosynthesis in the Black Sea sponge Dysidea fragilis

Cited by 12 publications

References 7 publications

Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis

Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis

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

Sterols from the Madagascar Sponge Fascaplysinopsis sp.

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