128 Perspecf'ives in Microbiology 



Progesterone (XI) R = H, Ri= H 4-Androstene-3, 17-dione (XIX) 



lYff-Kydroxyprogesterone (XXI) R = H 



R = H, Ri= OH 6/S-Hydroxy-4-androstene-3, 17- 



Reichstein's Compound S (XIII) dione (XX) R=OH 



R=OH, Ri=OH 

 Desoxycorticosterone (XTV) 



R=OH, Ri=H 



Cleavage of the Side Chain and Oxygenation of the 

 Nucleus. With progesterone (XI) Gliocladium catenu- 

 latum also produces 6p-hydroxy-4-androstene-3, 17-dione 

 (XX) (28). 



Cleavage of the Side Chain and Fission of Ring D. With 

 compounds XI, XIII, XIV, and XXI the side chain is re- 

 moved by certain fungi of the Asperigillus and Penicillium 

 groups (28). In these cases ring D is transformed into a 

 lactone to give testololactone (XXII). 



Compounds XI, XIII, XVI and IX ^ j'^N'^^r''^''''^ 



XXII 

 TestXjloL-.ctone 



DEHYDROGENATION OF RING A AND CLEAVAGE OF CARBON 

 TO CARBON SIDE CHAIN 



Streptomyces lavendulae, as shown by Fried et al. (6), 

 and certain Fusarium species, as reported by Vischer and 

 Wettstein (35), are capable of degrading the side chain and 

 dehydrogenating ring A in compounds like progesterone 

 (XI), desoxycorticosterone (XIV), and other steroids to pro- 

 duce l,4-androstadiene-3, 17-dione (XXIII). (This com- 

 pound can then be easily transformed to estrone [XXIV], 

 an estrogenic hormone, by pyrolysis [Inhoffen reaction].) 



