Biotransformation of acyclic terpenoid (2 E,6 E)-farnesol by plant pathogenic fungus Glomerella cingulata

• Published in: Phytochemistry (Oxford) Vol. 43; no. 1; pp. 105 - 109
• Main Authors: Miyazawa, Mitsuo, Nankai, Hirokazu, Kameoka, Hiromu
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.09.1996; Elsevier
• Subjects: Biochemistry & Molecular Biology; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Fundamental and applied biological sciences. Psychology; Life Sciences & Biomedicine; Methods. Procedures. Technologies; Plant Sciences; Science & Technology; microbial transformation; biotransformation; Glomerella cingulata; (2 E,6 E)-farnesol; isomerization; plant pathogenic fungus; (2E,6E)-farnesol; Terpenoid; Plant pathogen; Hydroxylation; Molecular structure; Isomerization; Metabolic pathway; Fungi; Biotransformation; Microorganism culture; Ascomycetes; Oxidation; Thallophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/0031-9422(96)00249-X

The microbial transformation of (2 E,6 E)-farnesol was investigated using the plant pathogenic fungus, Glomerella cingulata. At the first step, oxidation proceeded at the remote double bond to give (2 E,6 E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol and (2 E,6 E)-3,7,11-trimethyl-2,6-dodecadien-1,10,11-triol. In the second step, (2 E,6 E)-3,7,11-trimethyl-2,6-dodecadien-1,11-diol was hydroxylated at the C-5 position and to give (2 E,6 E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol. In addition, (2 E,6 E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol was isomerized to (2 Z,6 E)-3,7,11-trimethyl-2,6-dodecadien-1,5,11-triol.