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Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains.

ABSTRACT: Biotransformation of natural products by filamentous fungi is a powerful and effective approach to achieve derivatives with valuable new chemical and biological properties. Although diterpenoid substrates usually exhibit good susceptibility towards fungi enzymes, there have been no studies concerning the microbiological transformation of halimane-type diterpenoids up to now. In this work, we investigated the capability of Fusarium oxysporum (a fungus isolated from the rhizosphere of Senna spectabilis) and Myrothecium verrucaria (an endophyte) to transform halimane (1) and labdane (2) acids isolated from Hymenaea stigonocarpa (Fabaceae). Feeding experiments resulted in the production of six derivatives, including hydroxy, oxo, formyl and carboxy analogues. Incubation of 1 with F. oxysporum afforded 2-oxo-derivative (3), while bioconversion with M. verrucaria provided 18,19-dihydroxy (4), 18-formyl (5) and 18-carboxy (6) bioproducts. Transformation of substrate 2 mediated by F. oxysporum produced a 7?-hydroxy (7) derivative, while M. verrucaria yielded 7?- (7) and 3?-hydroxy (8) metabolites. Unlike F. oxysporum, which showed a preference to transform ring B, M. verrucaria exhibited the ability to hydroxylate both rings A and B from substrate 2. Additionally, compounds 1-8 were evaluated for inhibitory activity against Hr-AChE and Hu-BChE enzymes through ICER-IT-MS/MS assay.

SUBMITTER: Monteiro AF

PROVIDER: S-EPMC5717651 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains.

Monteiro Afif F AF Seidl Cláudia C Severino Vanessa G P VGP Cardoso Carmen Lúcia CL Castro-Gamboa Ian I

Royal Society open science 20171108 11

Biotransformation of natural products by filamentous fungi is a powerful and effective approach to achieve derivatives with valuable new chemical and biological properties. Although diterpenoid substrates usually exhibit good susceptibility towards fungi enzymes, there have been no studies concerning the microbiological transformation of halimane-type diterpenoids up to now. In this work, we investigated the capability of <i>Fusarium oxysporum</i> (a fungus isolated from the rhizosphere of <i>Se ...[more]

PMID: 29291077

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Project description:BACKGROUND:Steroid compounds with a 6,19-oxirane bridge possess interesting biological activities including anticonvulsant and analgesic properties, bacteriostatic activity against Gram-positive bacteria and selective anti-glucocorticoid action, while lacking mineralocorticoid and progestagen activity. RESULTS:The study aimed to obtain new derivatives of 3?-acetyloxy-5?-chloro-6,19-oxidoandrostan-17-one by microbial transformation. Twelve filamentous fungal strains were used as catalysts, including entomopathogenic strains with specific activity in the transformation of steroid compounds. All selected strains were characterised by high biotransformation capacity for steroid compounds. However, high substrate conversions were obtained in the cultures of 8 strains: Beauveria bassiana KCh BBT, Beauveria caledonica KCh J3.4, Penicillium commune KCh W7, Penicillium chrysogenum KCh S4, Mucor hiemalis KCh W2, Fusarium acuminatum KCh S1, Trichoderma atroviride KCh TRW and Isaria farinosa KCh KW1.1. Based on gas chromatography (GC) and nuclear magnetic resonance (NMR) analyses, it was found that almost all strains hydrolysed the ester bond of the acetyl group. The strain M. hiemalis KCh W2 reduced the carbonyl group additionally. From the P. commune KCh W7 and P. chrysogenum KCh S4 strain cultures a product of D-ring Baeyer-Villiger oxidation was isolated, whereas from the culture of B. bassiana KCh BBT a product of hydroxylation at the 11? position and oxidation of the D ring was obtained. Three 11?-hydroxy derivatives were obtained in the culture of I. farinosa KCh KW1.1: 3?,11?-dihydroxy-5?-chloro-6,19-oxidoandrostan-17-one, 3?,11?,19-trihydroxy-5?-chloro-6,19-oxidoandrostan-17-one and 3?,11?-dihydroxy-5?-chloro-6,19-oxidoandrostan-17,19-dione. They are a result of consecutive reactions of hydrolysis of the acetyl group at C-3, 11?- hydroxylation, then hydroxylation at C-19 and its further oxidation to lactone. CONCLUSIONS:As a result of the biotransformations, seven steroid derivatives, not previously described in the literature, were obtained: 3?-hydroxy-5?-chloro-6,19-oxidoandrostan-17-one, 3?,17?-dihydroxy-5?-chloro-6,19-oxidoandrostane, 3?-hydroxy-5?-chloro-17?-oxa-D-homo-6,19-oxidoandrostan-17-one, 3?,11?-dihydroxy-5?-chloro-17?-oxa-D-homo-6,19-oxidoandrostan-17-one and the three above-mentioned 11?-hydroxy derivatives. This study will allow a better understanding and characterisation of the catalytic abilities of individual microorganisms, which is crucial for more accurate planning of experiments and achieving more predictable results.

Dataset Information

Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains.

Publications

Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains.

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