Microbial transformation of diterpenes: Hydroxylation of sclareol, manool and derivatives by Mucor plumbeus

Aranda, G.; Kortbi, M. S. El; Lallemand, Jean‐Yves; Neuman, A.; Hammoumi, Abderrahmane; Facon, Isabelle; Azerad, Robert

doi:10.1016/s0040-4020(01)96175-7

Cited by 66 publications

(49 citation statements)

References 27 publications

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“…The location of the hydroxyl group at C-3 was confirmed on the basis of HMBC experiments and this compound was identified as 3b-hydroxysclareolide (4). 17,19,20 Unambiguous and detailed 1 H NMR assignments (in comparison with previous reports 17 ) are shown in Table 2. (Table 2) and the structure was confirmed as 3a,6b-dihydroxysclareolide (16).…”

Section: Resultsmentioning

confidence: 66%

“…Compound 2 was identified as the 3-ketosclareolide by comparison of its spectral data with those reported in the literature. 17,19 The 1 H NMR spectrum of 4 (Table 2) revealed a signal at d H 3.27 (dd, 3 J 11, 5 Hz, 1H,) indicative of an axial proton at C-3 (d C 78.6). The location of the hydroxyl group at C-3 was confirmed on the basis of HMBC experiments and this compound was identified as 3b-hydroxysclareolide (4).…”

Section: Resultsmentioning

confidence: 99%

“…15,16 Regarding the biotransformation of sclareolide (1) it has been previously reported that the incubation of 1 with Mucor plumbeus afforded 3-ketosclareolide (2), 1b-hydroxysclareolide (3) and 3b-hydroxysclareolide (4). 17 The bioconversion of 1 with Cephalosporium aphidicola gave 2, 4 and 3b,6b-dihydroxysclareolide (5). 18 The microbial transformation of 1 by Curvularia lunata yielded 2-4, 1a,3b-hydroxysclareolide (6) and 1b,3b-dihydroxysclareolide (7).…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of sclareolide by filamentous fungi: cytotoxic evaluations of the derivatives

Cano

Ramírez‐Apán

Delgado

2011

J. Braz. Chem. Soc.

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O esclareolido (1) foi incubado com oito diferentes espécies de fungos filamentosos usados convencionalmente para bio-oxidações. O composto 1 metabolizado pelo fungo Aspergilus niger em um meio de cultura A forneceu o 3-cetoesclareolido (2) e 3b-hidroxiesclareolido (4). Quando em um meio de cultura B (mais rico em nutrientes em relação ao meio de cultura A), foram obtidos os compostos 2, 4, e ainda 3a,6b-diidroxiesclareolido (16), 1-cetoesclareolido (17), 3-ceto-15-hidroxiesclareolido (18) e 3b, 15-diidroxiesclareolido (19). Os produtos 16-19 resultantes da biotransformação de 1 são relatados como substâncias inéditas. A fermentação de 1 com Cunninghamella blackesleeana usando o meio de cultura A forneceu os compostos 2 e 4, enquanto que empregando o meio de cultura B, forneceu os compostos 2, 4, 16 e 17. Os compostos 2, 4 e 17 foram obtidos também com Curvularia lunata. A biotransformação de 1 com Beauveria bassiana forneceu o composto 4 com rendimento satisfatório; com Rhizopus oligosporus e com Mucor miehei forneceu os compostos 2 e 4, enquanto que com R. nigricans and Fusarium moliniforme os compostos 2, 4 e 16 foram obtidos. A avaliação dos efeitos citotóxicos do composto 1 e dos produtos obtidos frente as linhagens de células cancerosas humanas selecionadas (U251, PC-3, K562, HCT-15, MCF-7 e SKUL-1) indicaram que o composto 16 (3a,6b-diidroxiesclareolido) apresenta um efeito citotóxico moderado (IC 50 < 100 mM) contra a U251, a PC-3, a HCT-15 e a MCF-7.Sclareolide (1) was incubated with eight different species of filamentous fungi conventionally used for bio-oxidations. Compound 1 was metabolized with Aspergillus niger in medium A to yield 3-ketosclareolide (2) and 3b-hydroxysclareolide (4), while in medium B (containing major number of nutrients with respect to medium A), compounds 2, 4, 3a,6b-dihydroxysclareolide (16), 1-ketosclareolide (17), 3-keto-15-hydroxysclareolide (18) and 3b,15-dihydroxysclareolide (19) were obtained. The biotransformation products 16-19 were found to be new substances. Fermentation of 1 with Cunninghamella blackesleeana using medium A afforded 2 and 4, while using medium B yielded 2, 4, 16 and 17. Compounds 2, 4 and 17 were also obtained with Curvularia lunata. Biotransformation of 1 with Beauveria bassiana yielded 4 in satisfactory yield, with Rhizopus oligosporus and Mucor miehei afforded 2 and 4, while with R. nigricans and Fusarium moliniforme yielded 2, 4 and 16. Cytotoxic evaluation of 1 and the obtained products against selected human cancer cell lines (U251, PC-3, K562, HCT-15, MCF-7 and SKUL-1) indicated that 16 (3a,6b-dihydroxysclareolide) displayed moderate cytotoxic (IC 50 < 100 mM) against U251, PC-3, HCT-15 and MCF-7.

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Section: Resultsmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biotransformation of sclareolide by filamentous fungi: cytotoxic evaluations of the derivatives

Cano

Ramírez‐Apán

Delgado

2011

J. Braz. Chem. Soc.

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“…3 (2006) 57 (18) group, as in 4, while the splitting pattern of the signal at d(H) 3.55 indicated hydroxylation either at C(2) or C(11). The decoupled 13 C-NMR (DEPT) spectrum of 5 ( Table 2) (Fig. 2, a).…”

Section: Compound 4 Showed the [M à H]mentioning

confidence: 99%

“…Metabolites 2 (C 20 H 36 O 3 ) and 3 (C 20 H 36 O 3 ) were identified as (3b)-3-hydroxy-and (18a)-18-hydroxysclareol, respectively. These compounds had been obtained before from the transformation of 1 by the fungus Mucor plumbeus [13]. Their structures were identified spectroscopically and by comparison with literature data.…”

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confidence: 99%

Structure Elucidation and Antibacterial Activity of New Fungal Metabolites of Sclareol

Choudhary

Siddiqui

Hussain

et al. 2006

C&B

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The transformation of the antibacterial diterpene sclareol (1) by two different fungal strains was investigated (Scheme). In the presence of Rhizopus stolonifer, (3beta)-3-hydroxysclareol (2), 18-hydroxysclareol (3), (6alpha)-6,18-dihydroxysclareol (4), and (11S)-11,18-dihydroxysclareol (5) were formed. Fermentation of 1 with Fusarium lini afforded (1beta)-1-hydroxysclareol (6) and (12S)-12-hydroxysclareol (7). Compounds 4-7 were identified as new compounds, and some of them were active against Bacillus subtilis (Table 3).

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Oxygenation of CH and CC Bonds

Flitsch¹,

Grogan²,

Ashcroft³

2002

Enzyme Catalysis in Organic Synthesis

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Reactions catalyzed by oxygenase enzymes (mono or dioxygenases) are interesting for applications in organic synthesis. There are numerous examples of such reactions in biological systems, yet there are few chemical reagents or catalysts that can compete with biocatalysts. Examples of monoxygenases catalyzed biotransformations are shown in Figure 16.1-1. These include heteroatom oxygenation, aromatic hydroxylation, Bayer-Villiger oxidation, double-bond epoxidation and hydroxylation of nonactivated hydrocarbon atoms. The latter can occur with regio-, stereo-,

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Microbial transformation of diterpenes: Hydroxylation of sclareol, manool and derivatives by Mucor plumbeus

Cited by 66 publications

References 27 publications

Biotransformation of sclareolide by filamentous fungi: cytotoxic evaluations of the derivatives

Biotransformation of sclareolide by filamentous fungi: cytotoxic evaluations of the derivatives

Structure Elucidation and Antibacterial Activity of New Fungal Metabolites of Sclareol

Oxygenation of CH and CC Bonds

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