Three Sesquiterpenoid Dimers from Chloranthus japonicus: Absolute Configuration of Chlorahololide A and Related Compounds

A novel sesquiterpenoid dimer, named multistalide C (1), together with two known congeners, shizukaols C (2) and D (3), was isolated from the whole plant of Chloranthus japonicus Sieb. The structures of compounds 1, 2, 3 were elucidated by extensive HR-ESI-MS, 1D, and 2D NMR spectroscopic analysis. Compounds 1, 2, 3 exhibited significant toxic effects on brine shrimp larvae (Artemia salina). The absolute configuration of 1 was established by CD/TDDFT calculations. The related compound chlorahololide A was also reinvestigated. The previous assignment of the absolute configuration of chlorahololide A and several related sesquiterpenoid dimers, based on an incorrect application of the exciton chirality method, is criticized. Chirality 28:158-163, 2015.