Hydroxylation of steroids by Fusarium oxysporum, Exophiala jeanselmei and Ceratocystis paradoxa

A new simple and high-yield synthesis of 5α-dihydrotestosterone (DHT), a potent androgen receptor agonist

“…We reviewed numerous synthetic strategies, including a few enzymatic biotransformation reactions [23–25] and several that involve the catalytic hydrogenation of steroidal Δ 4 -ketone moiety [22, 26–29]. We found that none of these procedures yielded desired pure 5α-hydrogenated product, but instead gave low yields of mixed 5α and 5β hydrogenated products as summarized in Scheme 1A and Table 1: entries 1–4.…”

Microorganisms as Biocatalysts and Enzyme Sources

“…Reduction of the C-17 carbonyl group of steroids by (17βHSDs) different microorganisms. [54, 55, 70-73, 76, 77, 80, 81], testosterone [54,55,[74][75][76]81], cortexolone (126) [78,79], and prednisone (127) (Figure 11a-d) [54,55,82].…”

“…Glycyrrhetinic acid has been shown to possess several pharmacological activities, such as antiulcerative, anti-inflammatory, immunomodulating, antitumor, antiviral, antihepatitis effects, and anticancer. Biotransformation 48 with a fungus C. blakesleeana (AS 3.970) yielded 3-oxo-7β-hydroxyglycyrrhetinic acid (49) and 7β-hydroxyglycyrrhetinic acid (50)[27], while of 48 using Absidia pseudocylindrospora (ATCC 24169), Gliocladium viride (ATCC 10097) and Cunninghamella echinulata (ATCC 8688a) afforded seven derivatives: 51, 52,7β,15α-dihydroxy-18β-glycyrrhetinic acid (53), 15α-hydroxy-18β-glycyrrhetinic acid (54), 1α-hydroxy-18β-glycyrrhetinic acid(55) and 13β-hydroxy-7α,27-oxy-12-dihydro-18β-glycyrrhetinic acid(56), and the epimer of compound 53 on C-17 (Figure 3)[28].Ginsenoside Rb1(61)is the most predominant protopanaxadiol-type ginsenoside in Panax species (ginseng). Several microbial transformations of this substrate (Ginsenoside Rb1) have been accomplished with an ample and varied group of microorganisms, all of these having β-glucosidase activities.…”

Efficient hydroxylation of functionalized steroids by Colletotrichum lini ST-1

“…In this paper, a range of structurally diverse compounds including estranes [estradiol (1), estrone (2)], androstanes [androst-4-en-3,17-dione (3), testosterone (4)], and pregnanes [canrenone (5), 16␣,17␣-epoxyprogesterone (6), progesterone (7)] were incubated with C. lini ST-1. Then the transformed products and sequence of hydroxylations were further determined.…”