Biotransformation of the diperpenoid, isosteviol, by Aspergillus niger, Penicillium chrysogenum and Rhizopus arrhizus

Oliveira, B de

doi:10.1016/s0031-9422(99)00058-8

Cited by 48 publications

(80 citation statements)

References 5 publications

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“…Recently reported diterpene biotransformations by A. niger included the hydroxylation of dehydroabietic acid [20] solidagenone [21] grindelic acid derivatives [22], terpenes from Stemodia maritima [18] and isosteviol [23].…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of Jatrophone by Aspergillus niger ATCC 16404

Pertino

Schmeda‐Hirschmann

Santos

et al. 2007

Zeitschrift Für Naturforschung B

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Biotransformation of the diterpene jatrophone (1) by Aspergillus niger ATCC 16404 afforded the new diterpene 9β -hydroxyisabellione (2). The compounds were characterized by spectroscopic analysis. The cytotoxicity of the compounds as IC 50 values on AGS and lung fibroblasts was 2.4 and 2.8 µ M for compound 1 and 53.1 and 260 µ M for 2, respectively. Microbial transformation of 1 into compound 2 strongly reduced the cytotoxicity and enhanced the selectivity against AGS cells.

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Section: Resultsmentioning

confidence: 99%

Biotransformation of Jatrophone by Aspergillus niger ATCC 16404

Pertino

Schmeda‐Hirschmann

Santos

et al. 2007

Zeitschrift Für Naturforschung B

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“…The NMR spectral data of compound 2 are summarized in the Table 1. Among the several recently reported diterpene biotransformations by A. niger [9,11,12], only in the bioconversion of isoesteviol, in which the 1α,7α-dihydroxy derivative is obtained, was the 1α position hydroxylated [13]. Related compounds with an additional OH function include 3,15-dihydroxy-8(17)-labden-19-oic acid from Juniperus thurifera [14,15], the 6,15-dihydroxyderivative from Viburnum suspensum [16] and 7α-hydroxy-8(17)labdene-15,18-dioic acid from Haplopappus pulchellus [17].…”

Section: Resultsmentioning

confidence: 99%

Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

et al. 2007

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Microbial transformation of imbricatolic acid (1) by Aspergillus niger afforded 1α-hydroxyimbricatolic acid (2), while transformation with Rhizopus nigricans yielded 15-hydroxy-8,17-epoxylabdan-19-oic acid (3). When the diterpene 1 was added to a Cunninghamella echinulata culture, the main products were the microbial metabolites mycophenolic acid (4) and its 3-hydroxy derivative 5. All the structures were elucidated by spectroscopic methods. The cytotoxicity of these compounds towards human lung fibroblasts and AGS cells was assessed. While 4 and 5 showed low cytotoxicity, with IC 50 values > 1000 µM against AGS cells and fibroblasts, 1α-hydroxyimbricatolic acid (2) presented moderate toxicity towards these targets, with IC 50 values of 307 and 631 µM, respectively. The structure of 2 is presented for the first time.

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“…8 Diterpenoids have been subject to this kind of transformation in a number of occasions 9 and our previous results have shown that these diterpenes are prone to hydroxylation by some fungi. 10,11 Therefore this technique can be useful for obtaining new diterpenoid derivatives.…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of steviol derivatives by Aspergillus niger and Fusarium moniliforme

Oliveira

Filho

Leal

2005

J. Braz. Chem. Soc.

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Derivados do esteviol foram submetidos a biotransformações por fungos. O ent-11β,13-diidróxi-15,16-epoxicauran-19-oato de metila foi hidroxilado em C-11 por Aspergillus niger enquanto que o ácido ent-16β-hidróxibaierano-19-óico foi hidroxilado em C-6 e C-7 pelo Fusarium moniliforme. A hidroxilação em posições não ativadas do esqueleto carbônico é discutida tendo em vista as propriedades de importantes diterpenóides descritos na literatura.Steviol derivatives have been submitted to biotransformations by fungi. Methyl ent-11β,13-dihydroxy-15,16-epoxikauran-19-oate was hydroxylated at C-11 by Aspergillus niger, whereas ent-16β-hydroxybeyeran-19-oic acid was hydroxylated at C-6 and C-7 by Fusarium moniliforme. The hydroxylation at non-activated positions at the carbon skeleton is discussed in connection with the properties of important polyhydroxylated diterpenoids described in the literature.

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Biotransformation of the diperpenoid, isosteviol, by Aspergillus niger, Penicillium chrysogenum and Rhizopus arrhizus

Cited by 48 publications

References 5 publications

Biotransformation of Jatrophone by Aspergillus niger ATCC 16404

Biotransformation of Jatrophone by Aspergillus niger ATCC 16404

Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

Biotransformation of steviol derivatives by Aspergillus niger and Fusarium moniliforme

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