Possible Biosynthetic Pathways for all cis-3,6,9,12,15,19,22,25,28-Hentriacontanonaene in Bacteria

Sugihara, Shinji; Hori, Ryuji; Nakanowatari, Hitomi; Takada, Yasuhiro; Yumoto, Isao; Morita, Naoki; Yano, Yutaka; Watanabe, Kazuo; Okuyama, Hidetoshi

Possible Biosynthetic Pathways for all cis-3,6,9,12,15,19,22,25,28-Hentriacontanonaene in Bacteria

Sugihara, Shinji; Hori, Ryuji; Nakanowatari, Hitomi et al.

Lipids, 2010, 45(2), 167-177

Permalink : https://hdl.handle.net/2115/43824

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アクセス権	open access
URI	https://hdl.handle.net/2115/43824
タイトル	Possible Biosynthetic Pathways for all cis-3,6,9,12,15,19,22,25,28-Hentriacontanonaene in Bacteria
著者	Sugihara, Shinji ; Hori, Ryuji ; Nakanowatari, Hitomi ; Takada, Yasuhiro ; Yumoto, Isao ; Morita, Naoki ; Yano, Yutaka ; Watanabe, Kazuo ; Okuyama, Hidetoshi
著者名 Sugihara, Shinji
著者名 Hori, Ryuji
著者名 Nakanowatari, Hitomi
著者名 Takada, Yasuhiro
著者名 Yumoto, Isao
著者名 Morita, Naoki
著者名 Yano, Yutaka
著者名 Watanabe, Kazuo
著者名 Okuyama, Hidetoshi
言語	英語
キーワード	Decarboxylation
	Eicosapentaenoic acid
	Head-to-head condensation
	Hentriacontanonaene
	pfa Genes
	Polyunsaturated fatty acid
	Polyunsaturated hydrocarbon
	Shewanella sp
発行日	2010-02
収録物名	Lipids
巻(号)	45(2)
ページ	167-177
抄録	A very long chain polyunsaturated hydrocarbon, hentriacontanonaene (C31:9), was detected in an eicosapentaenoic acid (EPA)-producing marine bacterium, which was isolated from the mid-latitude seashore of Hokkaido, Japan, and was tentatively identified as mesophilic Shewanella sp. strain osh08 from 16S rRNA gene sequencing. The geometry and position of the double bonds in this compound were determined physicochemically to be all cis at positions 3, 6, 9, 12, 15, 19, 22, 25, and 28. Although C31:9 was detected in all of the seven EPA- or/and docosahexaenoic acid-producing bacteria tested, an EPA-deficient mutant (strain IK-1Δ8) of one of these bacteria had no C31:9. Strain IK-1Δ8 had defects in the pfaD gene, one of the five pfa genes responsible for the biosynthesis of EPA. Although Escherichia coli DH5α does not produce EPA or DHA inherently, cells transformed with the pfa genes responsible for the biosynthesis of EPA and DHA produced EPA and DHA, respectively, but not C31:9. These results suggest that the Pfa protein complex is involved in the biosynthesis of C31:9 and that pfa genes must not be the only genes responsible for the formation of C31:9. In this report, we determined for the first time the molecular structure of the C31:9 and discuss the possible biosynthetic pathways of this compound.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	0024-4201
関連情報	PMID 20037794
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1007/s11745-009-3380-9
関連情報 (isPartOf)	Title Springer