Acidic metabolites from Phycomyces blakesleeanus

Barrero, Alejandro F.; Oltra, J. Enrique; Poyatos, Juan A.

doi:10.1016/0031-9422(96)00146-x

Cited by 24 publications

(22 citation statements)

References 18 publications

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“…Searching for new bioactive products from filamentous fungi, chemical analysis and biological screening of metabolites from Gibberella fujikuroi have been the subject of our work over the past few years. [1][2][3] We recently began studying Phycomyces blakesleeanus (Mucoraceae), which is a fungal producer of -carotene (provitamin A), riboflavine (vitamin B 2 ), pyridoxine (vitamin B 6 ), ergosterol (provitamin D 2 ), biotin, and nicotinic acid. 4,5 Therefore, oil from Phycomyces could be an interesting alimentary vitamin complement, if it were proven to be free of mycotoxins.…”

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confidence: 99%

“…These include the new natural sterols (1-3; Chart 1) with a 19-norergostane skeleton and an aromatic B ring. Previous studies of sterols from Phycomyces at the University College of Wales yielded a number of new sterols (4)(5)(6)(7)(8)(9)(10)(11)(12)(13) and certain aspects of fungal ergosterol biosynthesis were resolved. [7][8][9][10][11] However, some sterols present in the fungus were not identified.…”

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confidence: 99%

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Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Oltra

et al. 1998

J. Nat. Prod.

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In the search for novel bioactive products from filamentous fungi, sterols and triterpenoids found in Phycomyces blakesleeanus were analyzed using semipreparative HPLC, GC-MS, and NMR techniques. Structures proposed for the three new compounds identified, phycomysterol A (1), phycomysterol B (2), and neoergosterol (3), were confirmed by chemical synthesis. Phycomysterols possess a new natural 19-norergostane skeleton with an aromatic B ring. Phycomysterol A showed anti-HIV activity.Fungi have been one of the main natural sources of biologically active substances since the discovery of antibiotics. Searching for new bioactive products from filamentous fungi, chemical analysis and biological screening of metabolites from Gibberella fujikuroi have been the subject of our work over the past few years. [1][2][3] We recently began studying Phycomyces blakesleeanus (Mucoraceae), which is a fungal producer of -carotene (provitamin A), riboflavine (vitamin B 2 ), pyridoxine (vitamin B 6 ), ergosterol (provitamin D 2 ), biotin, and nicotinic acid. 4,5 Therefore, oil from Phycomyces could be an interesting alimentary vitamin complement, if it were proven to be free of mycotoxins. We have identified more than forty nontoxic compounds among the acidic metabolites from P. blakesleeanus 6 and are now working on neutral metabolites. In the mycelium of P. blakesleeanus (NRRL1555 wild strain) we have found eleven sterols previously unreported in Phycomyces. These include the new natural sterols (1-3; Chart 1) with a 19-norergostane skeleton and an aromatic B ring. Previous studies of sterols from Phycomyces at the University College of Wales yielded a number of new sterols (4-13) and certain aspects of fungal ergosterol biosynthesis were resolved. 7-11 However, some sterols present in the fungus were not identified. 9 Results and DiscussionSterol and triterpene mixtures isolated from P. blakesleeanus were subjected to semipreparative HPLC. Fractions obtained were studied by NMR spectroscopy and aliquots were treated with N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) to form TMS derivatives for analysis by GC-MS. The sterol ester mixture was saponified, and the nonsaponifiable fraction was analyzed as described above. Results are shown in Table 1. Proportions are only approximate because they were determined from the area of the gas chromatogram peaks, based on total ion current response data. TMS-ethers of sterols were used for GC-MS analysis, instead of free sterols, because the former have better chromatographic properties and afford highly characteristic modes of fragmentation from which structural details may be inferred. 12 In the mass spectrum of 1, as the TMS-ether, the molecular ion was consistent with the TMS derivative of a sterol with the molecular formula C 27 H 40 O, containing four double bonds. The fragment ions [M -TMSOH -C 9 H 17 ] + , [M -TMSOH -C 6 H 11 ] + , and [M -(C 6 H 11 + H)] + indicated a side chain with nine carbon atoms and a double bond. Thus, 1 must possess a nucleus with three double bonds and ...

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confidence: 99%

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Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Oltra

et al. 1998

J. Nat. Prod.

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“…As shown in Table 1, ergosterol (9), as well as the sterols 7, 8, 11 and 12 (which also have the ⌬ 5,7 -conjugated diene nucleus) were not detected in mutant H23 and in its progeny, the H37 and H38 strains. This fact indicates that in these mutants the enzyme episterol C-5 dehydrogenase (Scheme 1, step f) is inhibited or absent.…”

Section: Discussionmentioning

confidence: 94%

“…However, some uncertainty still exists regarding the exact sequence of steps from fecosterol to ergosterol in these fungi. Phycomyces (Mucoraceae) is a filamentous fungus producer of ␤-carotene and other beneficial metabolites, whilst mycotoxins never have been found in this organism [8,9]. Different mutants of Phycomyces have proven to be very useful tools in the dissection of various metabolic pathways, especially in the case of carotene biosynthesis [10].…”

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confidence: 99%

Sterols in erg mutants of Phycomyces: metabolic pathways and physiological effects

Barrero¹,

Oltra²,

Robinson³

et al. 2002

Steroids

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Phycomyces is a fungal producer of ␤-carotene and other beneficial metabolites. Several erg mutants of Phycomyces, originally selected to study the effects of membrane alteration on physiological responses, have now been used to gain information about sterol biosynthesis in filamentous fungi. One mutant, H23, and its progeny were found to be blocked at episterol C-5 dehydrogenase and did not produce ergosterol or any other sterol with a conjugated ⌬ 5,7 diene system. This mutant showed abnormal phototropism, which was correlated with the altered sterol composition. Another mutant, H25, seems to be a regulatory mutant. All analyzed mutants synthesized ergosta-7,22,24(28)-trien-3␤-ol, demonstrating for the first time that the sterol C-22 dehydrogenase of Phycomyces is capable of recognizing sterols with a 24(28) unsaturated side chain. New evidence regarding the biogenesis of neoergosterol and phycomysterols, the potential sparking function of cholesterol, as well as the regulation of sterol biosynthesis in this fungus is also reported. Given these results, a pathway for sterol biosynthesis in Phycomyces is proposed.

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“…Citons à titre d'exemple, Phycomyces blakesleeanus (BARRERO et al, 1996), Streptomyces rimosus (CATLIN et al,1968), Ophiostoma crassivaginata (AYER et TRIFONOV, 1995) et Ceratocystis clavigera, C. ips, C. huntii (AYER et al,1986) L'acide myristique, composé naturel présent dans les produits laitiers et les graisses animales et végétales. Il est utilisé en cosmétique et en industrie pharmaceutique (MERCK, 1996).…”

Section: Parmi Les Métabolites Identifiés Nous Citonsunclassified

Contribution à l’étude de la composition chimique des substances secrétées par Pythium diclinum en milieu liquide

Androusse

Aissami

Checti

et al. 2010

rseau

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Pythium diclinum isolé pour la première fois des eaux marocaines, possède l’aptitude de produire plusieurs métabolites volatils qui ont des propriétés très diverses. Commençons par le 4-hydroxybenzaldéhyde qui est impliqué dans la pathogenèse de plusieurs autres microorganismes et le tridécane qui est un polluant. D’autres composés détectés sont des odoriférants tels le cyclotétradécane, l’éthyl-2-hexanol et le benzaldéhyde, ce qui suggère une éventuelle contribution des Oomycètes aux problèmes d’odeurs et de goût dans les eaux potables. Cette étude a montré également que les Pythium sont des agents pathogènes pour plusieurs cultures par la production des enzymes et des toxines.Elles peuvent également produire des composés bénéfiques, notamment l’acide myristique et le phényléthanol utilisés particulièrement en cosmétique, dans les industries pharmaceutique et agro-alimentaire.Pythium diclinum, isolated for the first time from Moroccan waters, produces several volatile metabolites with very diverse properties including, for example, 4-hydroxybenzaldehyde which is involved in the pathogenesis of several other micro-organisms, and tridecane which is a pollutant. Other detected compounds include the odoriferous molecules such as cyclotetradecane, 2 ethylhexanol and benzaldehyde, the presence of which suggests a possible contribution of Oomycetes to odour and taste problems in drinking waters. This study also showed that Pythium species are pathogens for several crops, owing to their production of enzymes and toxins. They are also able to produce beneficial compounds, such as myristic acid and phenylethanol, which are used particularly in the cosmetic, pharmaceutical and agro-alimentary industries

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Acidic metabolites from Phycomyces blakesleeanus

Cited by 24 publications

References 18 publications

Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Sterols in erg mutants of Phycomyces: metabolic pathways and physiological effects

Contribution à l’étude de la composition chimique des substances secrétées par Pythium diclinum en milieu liquide

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