Biotransformation of (−)- cis-myrtanol and (+)- trans-myrtanol by plant pathogenic fungus, Glomerella cingulata

• Published in: Phytochemistry (Oxford) Vol. 45; no. 5; pp. 935 - 943
• Main Authors: Miyazawa, Mitsuo, Suzuki, Yasuhiro, Kameoka, Hiromu
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.07.1997; Elsevier
• Subjects: (+)- trans-myrtanol; (3 S)-3-hydroxy- cis-myrtanol; (4 R)-4-hydroxy- cis-myrtanol; (−)- cis-myrtanol; 3-oxo- trans-myrtanol; 4-oxo- cis-myrtanol; 4-oxo- trans-myrtanic acid; 5-hydroxy- cis-myrtanol; 5-hydroxy- trans-myrtanic acid; 9-hydroxy- trans-myrtanol; [1 R, 4 R, 5 S]-thujane-7, 10-diol; Biochemistry & Molecular Biology; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; biotransformation; Fundamental and applied biological sciences. Psychology; Glomerella cingulata; Life Sciences & Biomedicine; Methods. Procedures. Technologies; plant pathogenic fungus; Plant Sciences; Science & Technology; 4-oxo- cis-myrtanol; 9-hydroxy- trans-myrtanol; 4-oxo- trans-myrtanic acid; Glomerella cingulata; plant pathogenic fungus; [1 R, 4 R, 5 S]-thujane-7, 10-diol; (3 S)-3-hydroxy- cis-myrtanol; biotransformation; 5-hydroxy- cis-myrtanol; (+)- trans-myrtanol; (4 R)-4-hydroxy- cis-myrtanol; 5-hydroxy- trans-myrtanic acid; (−)- cis-myrtanol; 3-oxo- trans-myrtanol; 5-hydroxy-trans-myrtanic acid; 3-oxo-trans-myrtanol; 4-oxo-cis-myrtanol; 9-hydroxy-trans-myrtanol; (4R)-4-hydroxy-cis-myrtanol; 5-hydroxy-cis-myrtanol; H-1; 4-oxo-trans-myrtanic acid; [1R, 4R, 5S]-thujane-7, 10-diol; (3S)-3-hydroxy-cis-myrtanol; (+)-trans-myrtanol; (-)-cis-myrtanol; C-13 NMR; Fungi; Terpenoid; Molecular structure; Metabolite; Biotransformation; Ascomycetes; Diastereomer; Thallophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(97)00037-X

The biotransformation of the diastereoisomers, (−)- cis-myrtanol and (+)- trans-myrtanol, by Glomerella cingulata has been investigated. (−)- cis-Myrtanol was initially converted to (3 S)-3-hydroxy- cis-myrtanol, (4 R)-4-hydroxy- cis-myrtanol, 5-hydroxy- cis-myrtanol and [1 R, 4 R, 5 S]-thujane-7, 10-diol having the cyclopropane ring. (4 R)-4-Hydroxy- cis-myrtanol was further converted to 4-oxo- cis-myrtanol. By comparison (+)- trans-myrtanol was converted to 3-oxo- trans-myrtanol, 9-hydroxy- trans-myrtanol, 4-oxo- trans-myrtanic acid and 5-hydroxy- trans-myrtanic acid. The structures of the metabolic products were determined by spectral methods. © 1997 Elsevier Science Ltd. All rights reserved