ChemInform Abstract: Microbial Hydroxylation of Some Steroids by Aspergillus wentii MRC 200316.

Kudret Yildirim

doi:10.1002/chin.201111204

Microbial hydroxylation of some steroids by Aspergillus wentii MRC 200316

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc2010112 ◽

2010 ◽

Vol 75 (12) ◽

pp. 1273-1281 ◽

Cited By ~ 8

Author(s):

Kudret Yildirim

Keyword(s):

Microbial Hydroxylation ◽

Aspergillus Wentii

Biotransformations of epiandrosterone (1), dehydroepiandrosterone (2) and pregnenolone (3) byAspergillus wentiiMRC 200316 for 5 days have been reported. Incubation of epiandrosterone (1) afforded 11α-hydroxy-5α-androstane-3,17-dione (4) and 3β,11α-dihydroxy-5α-androstan-17-one (5). Incubation of dehydroepiandrosterone (2) afforded 3β,7β-di-hydroxyandrost-5-en-17-one (6) and 3β,7α-dihydroxyandrost-5-en-17-one (7). Incubation of pregnenolone (3) afforded only 11α-hydroxypregn-4-ene-3,20-dione (8).

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Microbial hydroxylation of acronycine

Journal of Medicinal Chemistry ◽

10.1021/jm00252a019 ◽

1974 ◽

Vol 17 (6) ◽

pp. 653-654 ◽

Cited By ~ 20

Author(s):

D. R. Brannon ◽

D. R. Horton ◽

Gordon H. Svoboda

Keyword(s):

Microbial Hydroxylation

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Microbial hydroxylation of progesterone withAcremonium strictum

FEMS Microbiology Letters ◽

10.1016/s0378-1097(03)00257-x ◽

2003 ◽

Vol 222 (2) ◽

pp. 183-186 ◽

Cited By ~ 19

Author(s):

Mohammad Ali Faramarzi ◽

Mojtaba Tabatabaei Yazdi ◽

Mohsen Amini ◽

Gholamreza Zarrini ◽

Abbas Shafiee

Keyword(s):

Microbial Hydroxylation

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Tetranorlabdane Diterpenoids from the Deep Sea Sediment-Derived Fungus Aspergillus wentii SD-310

Planta Medica ◽

10.1055/s-0042-102965 ◽

2016 ◽

Vol 82 (09/10) ◽

pp. 877-881 ◽

Cited By ~ 9

Author(s):

Xiao-Dong Li ◽

Xin Li ◽

Xiao-Ming Li ◽

Gang-Ming Xu ◽

Peng Zhang ◽

...

Keyword(s):

Deep Sea ◽

Deep Sea Sediment ◽

Aspergillus Wentii

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The Mechanism of the Microbial Hydroxylation of Steroids. Part 2. Hydroxylation of a Δ4-3-Ketosteroid Analog by Rhizopus arrhizus ATCC 11145

Canadian Journal of Chemistry ◽

10.1139/v75-284 ◽

1975 ◽

Vol 53 (14) ◽

pp. 2041-2044 ◽

Cited By ~ 19

Author(s):

Herbert L. Holland ◽

Barbara J. Auret

Keyword(s):

Transition State ◽

Rhizopus Arrhizus ◽

Microbial Hydroxylation ◽

Microbial C

The Δ4-3-ketosteroid analog (± )-4a-methyl-4,4a,5,6,7,8-hexahydro-2(3H) naphthalenone (1) is hydroxylated at both C-8α and C-8β by Rhizopusarrhizus ATCC 11145. The ratio of C-8α to C-8β hydroxylation is compared with that obtained from the peracid oxidation of 2-ethoxy-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene (4) and a mechanism is proposed for both microbial and chemical hydroxylation in which the stereochemistry of the product is transition state controlled. The significance of this to the mechanism of microbial C-6β hydroxylation of Δ4-3-ketosteroids is discussed.

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Asperolides A–C, Tetranorlabdane Diterpenoids from the Marine Alga-Derived Endophytic Fungus Aspergillus wentii EN-48

Journal of Natural Products ◽

10.1021/np2006742 ◽

2012 ◽

Vol 75 (2) ◽

pp. 148-152 ◽

Cited By ~ 69

Author(s):

Hao-Fen Sun ◽

Xiao-Ming Li ◽

Li Meng ◽

Chuan-Ming Cui ◽

Shu-Shan Gao ◽

...

Keyword(s):

Endophytic Fungus ◽

Marine Alga ◽

Aspergillus Wentii

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Microbial hydroxylation of steroids. 6. Hydroxylation of C-6-substituted androst-4-ene-3,17-diones by Rhizopusarrhizus ATCC 11145

Canadian Journal of Chemistry ◽

10.1139/v79-257 ◽

1979 ◽

Vol 57 (13) ◽

pp. 1585-1587 ◽

Cited By ~ 4

Author(s):

Herbert L. Holland ◽

Peter R. P. Diakow

Keyword(s):

Microbial Hydroxylation ◽

Enol Acetates

The products arising from the incubations of C-6α and C-6β chloro-, fluoro-, and methyl-substituted Δ4-3-keto steroids with the C-6β hydroxylating fungus Rhizopusarrhizus ATCC 11145 have been identified, and their formation rationalised in terms of Δ3,5 enolic intermediates. The incubations of C-6 chloro and methyl Δ3,5 enol acetates with R. arrhizus, and the oxidations by m-chloroperoxybenzoic acid of the corresponding enol ethyl ethers have also been described. The relevance of the results so obtained to the mechanism of C-6β hydroxylation of Δ4-3-keto steroids by R. arrhizus is discussed.

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Microbial hydroxylation of steroids. 11. Hydroxylation of A-nor-, B-homo-Δ1-, and Δ1-testosterone acetates by Rhizopusarrhizus

Canadian Journal of Chemistry ◽

10.1139/v85-191 ◽

1985 ◽

Vol 63 (5) ◽

pp. 1127-1131 ◽

Cited By ~ 13

Author(s):

Herbert L. Holland ◽

P. Chinna Chenchaiah

Keyword(s):

Microbial Hydroxylation

The testosterone derivatives A-nortestosterone acetate and B-homo-Δ1-testosterone acetate have been incubated with Rhizopusarrhizus, a fungus which hydroxylates testosterone at the C-6β and C-11 α positions. These modes of hydroxylation were also observed for the A-nor steroid. The B-homo steroid, however, was oxidized at C-2β and concurrently hydroxylated at C-6β and C-7aβ (but not at C-11) by R. arrhizus. Δ1 steroids of conventional skeleton were hydroxylated at C-11α by R. arrhizus; in addition, Δ1-androstenedione was epoxidized at the 1,2β position. No C-6 hydroxylation of conventional Δ1,4-3-ketosteroids was observed.

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