Aaptodines A-D，来自海绵的萘啶-呋咱并恶唑喹啉杂合生物碱。

Aaptodines A-D, Naphthyridine-Furooxazoloquinoline Hybrid Alkaloids from the Sponge .

作者信息

Wang Pianpian, Huang Jian, Kurtán Tibor, Mándi Attila, Jia Hongli, Cheng Wei, Lin Wenhan

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University, Beijing 100191, P. R. China.

Department of Organic Chemistry, University of Debrecen, P.O. Box 400, 4002 Debrecen, Hungary.

出版信息

Org Lett. 2020 Nov 6;22(21):8215-8218. doi: 10.1021/acs.orglett.0c02645. Epub 2020 Oct 28.

DOI:10.1021/acs.orglett.0c02645

PMID:33112152

Abstract

LC-MS-oriented fractionation of the sponge resulted in the isolation of four heptacyclic alkaloids, aaptodines A-D (-), which contain 9,10-dihydrofuro[2,3-][1,3]oxazolo[5,4-]quinolone and 7,8-dihydrocyclopenta[][1,6]naphthyridine subunits with a carbon atom. The structures were determined on the basis of NMR spectroscopic and single-crystal X-ray diffraction data analysis aided by electronic circular dichroism calculations and Mosher's method. A biosynthetic pathway for the formation of aaptodines A-D is postulated. Aaptodine D exhibits potent inhibition against osteoclast formation.

摘要

以液相色谱-质谱联用为导向对海绵进行分级分离，得到了四种七环生物碱，即aaptodines A-D（-），它们含有9,10-二氢呋喃并[2,3-][1,3]恶唑并[5,4-]喹啉酮和7,8-二氢环戊并[][1,6]萘啶亚基以及一个碳原子。通过电子圆二色性计算和莫舍尔方法辅助的核磁共振光谱和单晶X射线衍射数据分析确定了其结构。推测了aaptodines A-D形成的生物合成途径。Aaptodine D对破骨细胞形成具有强效抑制作用。