Three Sesquiterpenoid Dimers from Chloranthus japonicus: Absolute Configuration of Chlorahololide A and Related Compounds |
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| Authors: | Xin‐Wei Shi Qiang‐Qiang Lu Gennaro Pescitelli Trpimir Iv?i? Jun‐Hui Zhou Jin‐Ming Gao |
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| Institution: | 1. Xi'an Botanical Garden, Institute of Botany of Shaanxi Province, Xi'an, People's Republic of China;2. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy;3. Division of Organic Chemistry and Biochemistry, Ru?er Bo?kovi? Institute, Zagreb, Croatia;4. Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling, People's Republic of China |
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| Abstract: | 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. |
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| Keywords: | natural products structure elucidation electronic circular dichroism TDDFT calculations exciton chirality method brine shrimp larvae toxicity |
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