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Three Sesquiterpenoid Dimers from Chloranthus japonicus : Absolute Configuration of Chlorahololide A and Related Compounds
Author(s) -
Shi XinWei,
Lu QiangQiang,
Pescitelli Gennaro,
Ivšić Trpimir,
Zhou JunHui,
Gao JinMing
Publication year - 2016
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22561
Subject(s) - chemistry , absolute configuration , chirality (physics) , artemia salina , brine shrimp , stereochemistry , dimer , two dimensional nuclear magnetic resonance spectroscopy , organic chemistry , chiral symmetry , medicine , physics , toxicity , quantum mechanics , nambu–jona lasinio model , quark , traditional medicine
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 . © 2015 Wiley Periodicals, Inc.