10(B-6) マイコパラサイトLambertella sp.代謝物の構造、生合成、生物活性(口頭発表の部)

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In the course of the studies investigating key substances in the mycoparasitism between Lambertella and Monilinia, we isolated lambertellols A (1) and B (2), novel naphthoquinones carrying a spiro-butenolide in the molecules. The structures of them were elucidated by detailed NMR studies involving NOE experiments. Chemical derivatization into dibenzoate 6 and the following CD spectral measurement as well as conformational search deduced the absolute stereochemistry of 2 as (3R,4S). The absolute stereochemistry of 1 was estimated to be (3R,4S) by mechanistic analysis for the isomerization between 1 and 2. Labeling experiments disclosed their biosynthetic pathways. We achieved to introduce the labeled acetates as much as 40% incorporation rate by reducing the time for the cultivation, which realized to provide 2D-INADEQUATE spectra of both 1 and 2 in good quality employing sub-milligram of the samples. This high incorporation also made us allow isolating labile lambertellol C (12) by taking advantage of characteristic signal pattern of molecular ion peaks due to existence of many isotopomers in LC-MS. Our studies revealed that L. sp. 1346 produces lambertellols very much, while L. corni-maris makes quite small amount of them under simple cultivation conditions in PS and PSA media. Interestingly, addition of the culture broth of Monilinia remarkably accelerated the production of lambertellols. Our biological investigations revealed that both 1 and 2 inhibit hyphal germination of Monilinia fructicola, one of the hosts of L. corni-maris. These studies suggested that lambertellols can be substances responsible to the mycoparasitism and lambertellols play offensively at the stage invading into the host.
天然有機化合物討論会の論文
2004-10-01

10(B-6) マイコパラサイトLambertella sp.代謝物の構造、生合成、生物活性(口頭発表の部)

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