New metabolites of Fusarium moniliforme sheld

Sbrebryakov, E.P.; Simolin, A. V.; Kucherov, V. F.; Rosynov, B.V.

doi:10.1016/s0040-4020(01)98730-7

Cited by 41 publications

(18 citation statements)

References 22 publications

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“…Moreover, no corresponding ∆ 5,7 -sterols were encountered. In agreement with the findings of others (6,21) it is felt that the 5α,8α-epidioxy sterols could also be native metabolites. This was confirmed by Serebryakov et al (21) who isolated these steroids from fungi in the absence of oxygen.…”

Section: Discussionsupporting

confidence: 91%

“…In agreement with the findings of others (6,21) it is felt that the 5α,8α-epidioxy sterols could also be native metabolites. This was confirmed by Serebryakov et al (21) who isolated these steroids from fungi in the absence of oxygen. Several hypotheses were suggested concerning their biological function in marine organisms and notably that they may act as substrates for various enzyme systems.…”

Section: Discussionsupporting

confidence: 91%

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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: Discussionsupporting

confidence: 91%

Section: Discussionsupporting

confidence: 91%

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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“…To these metabolites Serebryakov et al added entkaur-15-ene (31), ent-16ß-hydroxykauranal (32), ent-16ß-hydroxykauranoic acid (33) and, tentatively, ent-kaurenoic acid (34) [114] and Raldugin and Pentegova ent-kaurenal (35) [115]. The cyclic ether 36 can be considered an artifact produced by acid attack of ent-7 ,11 -dihydroxykaurene (37) [116].…”

Section: Diterpenesmentioning

confidence: 99%

“…They include ent-7 -hydroxykaurenolide (38), ent-7 , 18-dihydroxykaurenolide (39), ent-7 ,16 ,18-trihydroxykaurenolide (40) [45,113], ent-7 ,13 -dihydroxy-kaurenolide (41) [114], ent-3 ,7 -dihydroxykaurenolide (42) [117], ent-7 ,11 -dihydroxykaurenolide (43), ent-1 ,7 -dihydroxy-kaurenolide (44) and ent-18-acetoxy-7 -hydroxykaurenolide (45), together with a nor-kaurenolide: ent-7 ,11 -dihydroxy-nor-kaurenolide (46) [118]. Finally, Yamane and cols.…”

Section: Diterpenesmentioning

confidence: 99%

“…In 1970 Serebryakov et al described the isolation of three C28 ergostane sterols containing oxygenated functionalization in the B-ring (63-65) [114]. More recently, Nes et al [139] described the isolation of four ergostatrienes (66)(67)(68)(69) together with brassicasterol, 24--methylcholesterol and ergosterol, and demonstrated the biogenetic sequence from 66 to 68.…”

Section: Steroidsmentioning

confidence: 99%

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Gibberellins and Other Metabolites of Fusarium fujikuroi and Related Fungi

Ávalos¹,

Cerdá‐Olmedo²,

Reyes³

et al. 2007

COC

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The rich metabolism of the fungal strains, now classified as Fusarium fujikuroi and related species covers the production of many secondary products, including different terpenoids and polyketides. Research has concentrated on the gibberellins, growth-promoting plant hormones with multiple applications in agriculture and brewing. The long list of secondary metabolites includes pigments such as carotenoids and bikaverins, mycotoxins such as fusarins and fumonisins and a diversity of other compounds, many of them still being unidentified. This review describes the chemical structures of the secondary metabolites identified in these fungi, with special attention to the terpenoids and particularly to the gibberellins, and summarizes knowledge on the biosynthesis of gibberellins, its regulation and its relation to those of other metabolites.

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Diterpenoids

Connolly¹,

Hill²

1991

Dictionary of Terpenoids

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New metabolites of Fusarium moniliforme sheld

Cited by 41 publications

References 22 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

Gibberellins and Other Metabolites of Fusarium fujikuroi and Related Fungi

Diterpenoids

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