Elucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B.,Organic Letters

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Elucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B.
Organic Letters ( IF 4.9 ) Pub Date : 2019-05-31 00:00:00 , DOI: 10.1021/acs.orglett.9b01636
Unwoo Kang ₁ , Donald R Caldwell ₂ , Laura K Cartner _{1,

3} , Dongdong Wang ₁ , Chang-Kwon Kim ₁ , Xiangrong Tian _{1,

4} , Heidi R Bokesch _{1,

3} , Curtis J Henrich _{1,

3} , Girma M Woldemichael _{1,

3} , Martin J Schnermann ₂ , Kirk R Gustafson ₁

Affiliation

Spirodactylone (1), a hexacyclic indolizidone alkaloid possessing a novel spiro ring system, was isolated from the marine sponge Dactylia sp. The structure was elucidated by extensive spectroscopic methods including application of the LR-HSQMBC NMR pulse sequence. Oxidative cyclization of denigrin B (2), an aryl-substituted 2-oxo-pyrroline derivative that was also isolated from the sponge extract, provided material identical to spirodactylone (1). This confirmed the assigned structure and provides insight into the probable biogenesis of 1.

中文翻译：

螺指龙（一种来自海绵指藻属的多环生物碱）的阐明，以及来自共代谢物 Denigrin B 的非酶促生成。

Spirodactylone ( 1 ) 是一种六环吲哚齐酮生物碱，具有新型螺环系统，是从海洋海绵Dactylia sp 中分离出来的。通过广泛的光谱方法（包括应用 LR-HSQMBC NMR 脉冲序列）阐明了该结构。脱黑蛋白 B ( 2 ) 是一种芳基取代的 2-氧代吡咯啉衍生物，也从海绵提取物中分离出来，其氧化环化提供了与螺环泰隆 ( 1 ) 相同的材料。这证实了指定的结构并提供了对1可能的生物起源的深入了解。

更新日期：2019-05-31

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