Novel Compounds of Octahydroheptaprenyl Mycolic Acyl Ester and Monocyclic C35-Terpene, Heptaprenylcycline B, from Non-PathogenicMycobacteriumSpecies | Zendy

Tsutomu Sato | Zendy; Ryosuke Takagi | Zendy; Yuriko Orito | Zendy; Eri Ono | Zendy; Tsutomu Hoshino | Zendy

Open Access

Novel Compounds of Octahydroheptaprenyl Mycolic Acyl Ester and Monocyclic C₃₅-Terpene, Heptaprenylcycline B, from Non-PathogenicMycobacteriumSpecies

Author(s) -

Tsutomu Sato,

Ryosuke Takagi,

Yuriko Orito,

Eri Ono,

Tsutomu Hoshino

Publication year - 2010

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.90669

Subject(s) - terpene , mycobacterium , mycolic acid , chemistry , stereochemistry , microbiology and biotechnology , biology , bacteria , genetics

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.

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