BIOTRANSFORMATION OF (-)-CIS-MYRTANOL AND (-TRANS-MYRTANOL BY PLANT-PATHOGENIC FUNGUS, GLOMERELLA-CINGULATA())

The biotransformation of the diastereoisomers, (-)-cis-myrtanol and ()-trans-myrtanol, by Glomerella cingulata has been investigated. (-)-c is-Myrtanol was initially converted to (3S)-3-hydroxy-cis-myrtanol, (4 R)-4-hydroxy-cis-myrtanol, 5-hydroxy-cis-myrtanol and [1R, 4R, SS]-thu jane-7, 10-diol having the cyclopropane ring. (4R)-4-Hydroxy-cis-myrta nol was further converted to 4-oxo-cis-myrtanol. By comparison (+)-tra ns-myrtanol was converted to 3-oxo-trans-myrtanol, 9-hydroxy-trans-myr tanol, 4-oxo-trans-myrtanic acid and 5-hydroxy-trans-myrtanic acid. Th e structures of the metabolic products were determined by spectral met hods. (C) 1997 Elsevier Science Ltd. All rights reserved.