The Butenolide Signaling Molecules SRB1 and SRB2 Induce Lankacidin and Lankamycin Production in Streptomyces rochei
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Butenolide signaling molecules, SRB1 and SRB2, that induce lankacidin and lankamycin production in Streptomyces rochei
Novel signaling molecule(s) that induce lankacidin and lankamycin production in Streptomyces rochei were extracted from the culture filtrate and purified by Sephadex LH20 and silica gel chromatography with the help of bioassay. Chiral HPLC and ESI-MS analyses indicated the presence of two active components, SRB1 and SRB2, and their molecular formulae were established to be C15H24O5 and C16H26O5, respectively. Based on extensive NMR analysis, SRB1 and SRB2 were determined to be 2-(1’-hydroxyl-6’-oxo-8’-methylnonyl)-3-methyl-4-hydroxybut-2-en-1,4-olide and 2-(1’-hydroxyl-6’-oxo-8’-methyldecyl)-3-methyl-4-hydroxybut-2-en-1,4-olide, respectively. These structures were finally confirmed by chemical synthesis and the absolute configuration of C-1’ was determined to be R. The synthetic 1’R-isomers induced production of lankacidin and lankamycin at around 40 nM concentration. Thus, SRB1 and SRB2 are distinct from the well-known 2,3-disubstituted γ-butyrolactone molecules such as A-factor, virginia butanolide, and SCB1 and belong to the γ-butenolide family following avenolide which has been recently isolated from Streptomyces avermitilis.
アクセプト後にタイトル・アブストラクト等変更あり、著者最終稿は変更前のタイトル"Butenolide signaling molecules, SRB1 and SRB2, that induce lankacidin and lankamycin production in Streptomyces rochei"
This work was supported by a Grants‐in‐Aid for Scientific Research on Innovative Areas from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and a Noda Institute for Scientific Research Grant.
Supporting information for this article is available on the WWW underhttp://dx.doi.org/10.1002/cbic.201200149.
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This is the peer reviewed version of the following article: CHEMBIOCHEM. 2012, July 9;13(10):1447-1457, which has been published in final form at https://doi.org/10.1002/cbic.201200149. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Graduate School of Advanced Sciences of Matter