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

• DOI: 10.1021/acs.orglett.9b01636
• Publication Date: 2019-05-31T19:59:45Z
• Authors: Unwoo Kang; Donald R. Caldwell; Laura K. Cartner; Dongdong Wang; Chang-Kwon Kim; Xiangrong Tian; Heidi R. Bokesch; Curtis J. Henrich; Girma M. Woldemic...; Martin J. Schnermann; Kirk R. Gustafson
• Keywords: Sponge; Derivative (finance)

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