title: Novel terpenes generated by heterologous expression of bacterial terpene synthase genes in an engineered Streptomyces host.
abstract: Mining of bacterial genome data has revealed numerous presumptive terpene synthases. Heterologous expression of several putative terpene synthase genes in an engineered Streptomyces host has revealed 13 newly discovered terpenes whose GC-MS and NMR data did not match with any known compounds in spectroscopic databases. Each of the genes encoding the corresponding terpene synthases were silent in their parent microorganisms. Heterologous expression and detailed NMR spectroscopic analysis allowed assignment of the structures of 13 new cyclic terpenes. Among these newly identified compounds, two were found to be linear triquinane sesquiterpenes that have never previously been isolated from bacteria or any other source. The remaining 11 new compounds were shown to be diterpene hydrocarbons and alcohol, including hydropyrene (1), hydropyrenol (2), tsukubadiene (11) and odyverdienes A (12) and B (13) each displaying a novel diterpene skeleton that had not previously been reported.
authors.affiliation: Kitasato Institute for Life Sciences, Kitasato University, Kitasato, Sagamihara, Kanagawa, Japan.
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Yamada
authors.affiliation: School of Pharmacy, Kitasato University, Shirokane, Minato-ku, Tokyo, Japan.
authors.forename: Shiho
authors.initials: S
authors.lastname: Arima
authors.affiliation: School of Pharmacy, Kitasato University, Shirokane, Minato-ku, Tokyo, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Nagamitsu
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Johmoto
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, Japan.
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Uekusa
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, Japan.
authors.forename: Tadashi
authors.initials: T
authors.lastname: Eguchi
authors.affiliation: National Institute of Advanced Industrial Science and Technology, Aomi, Koto-ku, Tokyo, Japan.
authors.forename: Kazuo
authors.initials: K
authors.lastname: Shin-ya
authors.affiliation: Department of Chemistry, Box H, Brown University, Providence, RI, USA.
authors.forename: David E
authors.initials: DE
authors.lastname: Cane
authors.affiliation: Kitasato Institute for Life Sciences, Kitasato University, Kitasato, Sagamihara, Kanagawa, Japan.
authors.forename: Haruo
authors.initials: H
authors.lastname: Ikeda
mesh_terms: D000192:Actinomycetales / Q000201:enzymology* / Q000235:genetics / Q000378:metabolism; D019883:Alkyl and Aryl Transferases / Q000235:genetics / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D055598:Chemical Phenomena; D018360:Crystallography, X-Ray; D062126:Databases, Chemical; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D055808:Drug Discovery; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D030781:Organisms, Genetically Modified / Q000235:genetics / Q000378:metabolism*; D011994:Recombinant Proteins / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D013302:Streptomyces / Q000201:enzymology* / Q000235:genetics / Q000378:metabolism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D004224:Diterpenes; D011994:Recombinant Proteins; D012717:Sesquiterpenes; D013729:Terpenes; D019883:Alkyl and Aryl Transferases; C108877:terpene synthase