Isolation of Peribysins O, P, and Q from <i>Periconia macrospinosa</i> KT3863 and Configurational Reinvestigation of Peribysin E Diacetate from <i>Periconia byssoides</i> OUPS-N133
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- Kota Inose
- Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan
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- Kazuaki Tanaka
- Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan
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- Takeshi Yamada
- Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka, 569-1094, Japan
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- Hiroyuki Koshino
- RIKEN Center for Sustainable Resource Science, Wako, 351-0198, Japan
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- Masaru Hashimoto
- Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan
書誌事項
- 公開日
- 2019-02-15
- 資源種別
- journal article
- 権利情報
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- https://doi.org/10.15223/policy-029
- https://doi.org/10.15223/policy-037
- https://doi.org/10.15223/policy-045
- DOI
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- 10.1021/acs.jnatprod.8b01001
- 公開者
- American Chemical Society (ACS)
この論文をさがす
説明
Peribysins O (1), P (3), and Q (4) were isolated from Periconia macrospinosa KT3863. The relative configuration of the 6,7-epoxide of 1 was elucidated by performing quantitative NOE experiments. The structure of 2, which is a tautomer of 1 present in CDCl3 solutions in 5% abundance, was also fully characterized by NMR analysis. Their absolute configurations were independently determined by the modified Mosher's method (for 1 and 3), the electronic circular dichroism (ECD) exciton coupling theory after conversion into dibenzoate 9 (for 3), and theoretical ECD calculations (for 1, 3, and 4). The obtained relative structures 1, 3, and 4 were verified by calculating their 13C chemical shifts using density functional theory (DFT). Although the established (4 S)-enantiomer for 1-4 is in accordance with that of other peribysins isolated from the related fungus Periconia byssoides OUPS-N133, Danishefsky's total synthesis of peribysin E (5) led to the subsequent revision of the (2 R,4 S,5 R,6 S,7 S,8 R,10 S)-enantiomer to the (2 S,4 R,5 S,6 R,7 R,8 S,10 R)-enantiomer. This discordance led us to reinvestigate the configuration using time-dependent DFT-based ECD spectral calculations, which supported the original (4 S)-enantiomer.
収録刊行物
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- Journal of Natural Products
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Journal of Natural Products 82 (4), 911-918, 2019-02-15
American Chemical Society (ACS)
