Biosynthesis of Resorcylic Acid Lactone Lasiodiplodin in Lasiodiplodia theobromae

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概要

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• The biosynthesis of lasiodiplodin (1) and its (5S)-5-hydroxylated derivative (2) were investigated by the administration of 13C-labeled acetates to Lasiodiplodia theobromae. The labeling patterns of biosynthetically 13C-labeled 1 and 2 were determined by 13C-NMR and INADEQUATE spectra, demonstrating the octaketide origins of 1 and 2. Taking into account the biosynthetic study of resorcylic acid lactones, the involvement of highly reduced acyl intermediates in the biosynthesis of lasiodiplodins was presumed; thus, we synthesized 2H-labeled hypothetical acyl intermediates of 1, 9-hydroxydecanoic acid (4) and its N-acetylcysteamine thioester (SNAC, 5). When L. theobromae was incubated with 5 mM of a 2H-labeled intermediate, the 2H-label from the intermediate was incorporated at the expected position of 1. These incorporation studies revealed that 1 was produced via a pathway which closely resembles that of resorcylic acid lactone biosynthesis.

• 社団法人 日本農芸化学会の論文
• 2009-05-23

著者

• 森 春英

  北海道大学大学院農学研究院応用生命科学部門

• Nabeta Kensuke

  Hokkaido Univ. Sapporo Jpn

• Matsui Hirokazu

  Dept. Biosci. Chem. Fac. Agric. Hokkaido Univ.

• Matsui Hirokazu

  Hokkaido Univ. Sapporo Jpn

• Matsuura Hideyuki

  Laboratory Of Bioorganic Chemistry Division Of Applied Life Science Graduate School Of Agriculture H

• Matsuura Hideyuki

  Division Of Applied Bioscience Graduate School Of Agriculture Hokkaido University

• Matsuura Hideyuki

  Graduate School Of Agriculture Hokkaido University

• Matsuura Hideyuki

  Hokkaido Univ. Sapporo

• Takahashi Kosaku

  Div. Of Applied Bioscience Res. Fac. Of Agriculture Hokkaido Univ. Kita-9 Nishi-9 Kita-ku Sapporo 06

• Takahashi Kosaku

  Division Of Applied Bioscience Graduate School Of Agriculture Hokkaido University

• Nabeta Kensuke

  Division Of Applied Bioscience Research Faculty Of Agriculture Hokkaido University

• KASHIMA Takasumi

  Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University

• Matsui Hirokazu

  Division Of Applied Bioscience Research Faculty Of Agriculture Hokkaido University

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