Microbial hydroxylation of sclareol by mucor plumbeus

Aranda, G.; Lallemand, Jean‐Yves; Hammoumi, Abderrahmane; Azerad, Robert

doi:10.1016/s0040-4039(00)74329-2

Cited by 34 publications

(10 citation statements)

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“…The fungus M. plumbeus has been used previously for biotransformations, for example, with sesquiterpenes possessing the cedrane 3 and aromadendrane 4 skeletons and with diterpenes of the labdane type. [5][6][7] In the latter case, the main compounds isolated were hydroxylated at ring A.…”

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confidence: 92%

“…In previous work we studied incubation of the same compounds with Gibberella fujikuroi , a fungus that, despite possessing high substrate specificity, produces an enantiomeric derivative of manoyl oxide. The fungus M. plumbeus has been used previously for biotransformations, for example, with sesquiterpenes possessing the cedrane and aromadendrane skeletons and with diterpenes of the labdane type. − In the latter case, the main compounds isolated were hydroxylated at ring A.…”

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confidence: 99%

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Microbiological Transformation of Manoyl Oxide Derivatives by Mucor plumbeus

et al. 1998

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Biotransformations of jhanol (18-hydroxymanoyl oxide) (2), jhanidiol (1beta,18-dihydroxymanoyl oxide) (3), and 1-oxo-jhanol (1-oxo-18-hydroxymanoyl oxide) (4) by the fungus Mucor plumbeus have been studied. In the incubation of 2 there exists a preference for hydroxylation at C-2(alpha) (8) and C-6(beta) (9-11) and, to a lesser degree, at C-1(alpha) (7), C-11(alpha) (6), and C-11(beta) (5 and 10). In the second substrate (3), the presence of a 1beta-hydroxyl group inhibits 6beta- or 11-hydroxylation. Epoxidation of the vinyl group constitutes the main reaction, with the positions 2alpha (14) and 3beta (15) being hydroxylated. In the incubation of 4, there was a preference for 6beta-hydroxylation (21) or epoxidation of the vinyl group (22). Other hydroxylations observed were at the 2alpha (19), 2beta (20), 3alpha (23), 3beta (24), and 11beta (18) positions.

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confidence: 92%

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Microbiological Transformation of Manoyl Oxide Derivatives by Mucor plumbeus

et al. 1998

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“…3), found in clary sage (Salvia sclarea Linn., Labiatae) and a valuable starting material for the hemisynthesis of forskolin, was added to the growing culture of the fungus Mucor plumbeus ATCC 4740 and a mixture of triols was obtained. One of the derivatives, labd-14-en-3β,8α,13β-triol was obtained in high yield [81]. Abraham reported microbial transformations of sclareol by different microorganisms leading to formation of 2α-, 3β-, and 18-hydroxysclareol, while Cunninghamella elegans was shown to form 19-hydroxysclareol additionally [82].…”

Section: Substrate Additionmentioning

confidence: 99%

Microbial Transformations of Plant Secondary Metabolites

Mutafova¹,

Fernandes²,

Mutafov³

et al. 2016

Bioprocessing of Plant in Vitro Systems

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The aim of this chapter is to present the authors' view on the place and role of microbial transformation reactions as a perspective means of processing of plantderived biologically active compounds into metabolites with new and/or increased activity and availability and decreased toxicity. Some microbial transformations providing information regarding metabolism in humans and mammals of plant-derived secondary metabolites applied as drugs and/or food additives are also considered.

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“…Given the supply shortage and price inflation of ambergris, a number of substitutes have been developed. Ambroxide is the most appreciated substitute of ambergris and is obtained from the semi-synthesis of sclareol 5, 6, 7. Sclareol can be transformed to ambroxide through redox and cyclization, during which sclareol glycol and sclareolide are important intermediates (Fig.…”

Section: Introductionmentioning

confidence: 99%

Comparative proteomic analyses of Hyphozyma roseonigra ATCC 20624 in response to sclareol

Wang

Zhang

Yao

et al. 2018

Brazilian Journal of Microbiology

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Sclareol is an important intermediate for ambroxide synthesis industries. Hyphozyma roseonigra ATCC 20624 was the only reported strain capable of degrading sclareol to the main product of sclareol glycol, which is the precursor of ambroxide. To date, knowledge is lacking about the effects of sclareol on cells and the proteins involved in sclareol metabolism. Comparative proteomic analyses were conducted on the strain H. roseonigra ATCC 20624 by using sclareol or glucose as the sole carbon source. A total of 79 up-regulated protein spots with a >2.0-fold difference in abundance on 2-D gels under sclareol stress conditions were collected for further identification. Seventy spots were successfully identified and finally integrated into 30 proteins. The up-regulated proteins under sclareol stress are involved in carbon metabolism; and nitrogen metabolism; and replication, transcription, and translation processes. Eighteen up-regulated spots were identified as aldehyde dehydrogenases, which indicating that aldehyde dehydrogenases might play an important role in sclareol metabolism. Overall, this study may lay the fundamentals for further cell engineering to improve sclareol glycol production.

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Microbial hydroxylation of sclareol by mucor plumbeus

Cited by 34 publications

References 10 publications

Microbiological Transformation of Manoyl Oxide Derivatives by Mucor plumbeus

Microbiological Transformation of Manoyl Oxide Derivatives by Mucor plumbeus

Microbial Transformations of Plant Secondary Metabolites

Comparative proteomic analyses of Hyphozyma roseonigra ATCC 20624 in response to sclareol

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