Novel compounds of octahydroheptaprenyl mycolic acyl ester and monocyclic C35-terpene, heptaprenylcycline B, from non-pathogenic mycobacterium species.
A search for C(35)-terpenes from non-saponified extracts of 12 non-pathogenic Mycobacterium species was carried out. Octahydroheptaprenyl mycolic acyl esters were isolated from M. chlorophenolicum cells which were also found from M. thermoresistibile, M. vanbaalenii, M. aichiense, M. smegmatis, and M. parafortuitum. This is the first report on a polyprenol esterified by a mycolate. A novel monocyclic C(35)-terpene possessing a ketone, named heptaprenylcycline B, was isolated, which was detected from M. chlorophenolicum and M. vanbaalenii. The biosynthetic pathway to heptaprenylcycline B was investigated with ancymidol which acts as an inhibitor of a P450 monooxygenase. This experiment suggested that the P450 monooxygenase may be responsible for the production of heptaprenylcycline B.
Sato
Tsutomu
T
Department of Applied Biological Chemistry, Faculty of Agriculture, and Graduate School of Science and Technology, Niigata University, Japan. satot@agr.niigata-u.ac.jp
Takagi
Ryosuke
R
Orito
Yuriko
Y
Ono
Eri
E
Hoshino
Tsutomu
T
D055162:Biocatalysis; D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004952:Esters / Q000737:chemistry* / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009161:Mycobacterium / Q000737:chemistry* / Q000378:metabolism; D009171:Mycolic Acids / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism
D065607:Cytochrome P-450 Enzyme Inhibitors; D004791:Enzyme Inhibitors; D004952:Esters; D009171:Mycolic Acids; D013729:Terpenes; C548353:heptaprenylcycline B; D003577:Cytochrome P-450 Enzyme System