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瓦科十氢萘碱A和B,从真菌类球壳孢属菌株RK10 - F058中分离出的新型十氢萘代谢产物。

Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058.

作者信息

Nogawa Toshihiko, Kato Naoki, Shimizu Takeshi, Okano Akiko, Futamura Yushi, Takahashi Shunji, Osada Hiroyuki

机构信息

RIKEN Center for Sustainable Resource Science, Chemical Biology Research Group, Wako, Saitama, Japan.

RIKEN Center for Sustainable Resource Science, Natural Product Biosynthesis Research Unit, Saitama, Japan.

出版信息

J Antibiot (Tokyo). 2017 Sep 13. doi: 10.1038/ja.2017.103.

Abstract

Two new decaline metabolites, wakodecalines A and B, were isolated from a fungus, Pyrenochaetopsis sp. RK10-F058, by screening for structurally unique metabolites using LC/MS analysis. Their structures were determined on the basis of NMR and mass spectrometric measurements. The absolute structures were confirmed by a combination of chemical methods including chemical degradation, a modified Mosher's method and Marfey's method, and comparison of the experimental electronic CD (ECD) spectrum with calculated one. Both compounds had a cyclopentanone-fused decaline skeleton and an N-methylated amino acid moiety derived from a serine. They showed moderate antimalarial activity against the Plasmodium falciparum 3D7 strain.The Journal of Antibiotics advance online publication, 13 September 2017; doi:10.1038/ja.2017.103.

摘要

通过液相色谱/质谱分析筛选结构独特的代谢产物,从真菌Pyrenochaetopsis sp. RK10-F058中分离出两种新的十氢化萘代谢产物,即和歌十氢化萘A和B。通过核磁共振和质谱测量确定了它们的结构。通过化学降解、改良的莫舍尔法和马尔菲法等化学方法的组合,以及将实验性电子圆二色光谱(ECD)与计算光谱进行比较,确认了其绝对结构。这两种化合物都具有环戊酮稠合的十氢化萘骨架和源自丝氨酸的N-甲基化氨基酸部分。它们对恶性疟原虫3D7菌株表现出中等的抗疟活性。《抗生素杂志》在线优先发表,2017年9月13日;doi:10.1038/ja.2017.103 。

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