Nocardia restrictus

Soladulcidine (solasodanol) (196) Nocardia restrictus Solasoda-1,4-diene-3-one (198) — 188... 

Nocardia restrictus is capable of oxidizing the conessine derivative 5a-conanin-3/i-ol (220) to both the A4-3-ketone 222 and the A1,4-3-ketone 221, the latter being the major product of the incubation (189). Preliminary screening experiments have demonstrated that Trichothecium rosevan transforms conessine (223), solanocapsine (224), jervine (225), and pseudojervine (226) (42). Transformation of the latter is claimed to produce 20-30% jervine by glycoside hydrolysis, along with an unidentified product that may be further biotransformation product of jervine. Jervine is also metabolized by Polystictus versicolor and Piricularia oryzae, but no products have been identified (42). 

The bases (9) and (10) have been found to be dehydrogenated in ring a by the micro-organism Nocardia restrictus to give (11). A similar dienone was obtained from (12) but only in low yield. No further degradation of any of the dienones was observed. Instead of dienone derivatives, (13) yielded the simple N-acetyl derivative. 

In apparently unrelated investigations, which were to assume importance later on, Dodson and Muir (D-171) showed that 19-hydroxy-4-androstene-3,17-dione was converted into estrone readily and in good yield by Pseudomonas sp. Sih and Rahim (S-894) showed that this was also true for Nocardia restrictus. Sih recognized that... 

For this purpose he chose 19-hydroxy-4-cholesten-3-one, which might yield 19-hydroxy-4-androstene-3,17-dione as the sought-after intermediate of degradation. When he incubated the former with Nocardia restrictus, estrone was indeed formed in 8% yield. A culture (CSD-10), Isolated from soil usii cholesterol as the sole... 

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