Open AccessElucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B
Author(s) -
Unwoo Kang,
Donald R. Caldwell,
Laura K. Cartner,
Dongdong Wang,
ChangKwon Kim,
Xiangrong Tian,
Heidi R. Bokesch,
Curtis J. Henrich,
Girma M. Woldemichael,
Martin J. Schnermann,
Kirk R. Gustafson
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b01636
Subject(s) - chemistry , sponge , alkaloid , biogenesis , stereochemistry , metabolite , derivative (finance) , two dimensional nuclear magnetic resonance spectroscopy , ring (chemistry) , organic chemistry , biochemistry , botany , biology , financial economics , economics , gene
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.