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Dimeric Cadinane Sesquiterpenoid Derivatives from Artemisia annua

Author:
Qin, Da-Peng, Pan, Da-Bo, Xiao, Wei, Li, Hai-Bo, Yang, Biao, Yao, Xiao-Jun, Dai, Yi, Yu, Yang, Yao, Xin-Sheng
Source:
Organic letters 2018 v.20 no.2 pp. 453-456
ISSN:
1523-7052
Subject:
Artemisia annua, X-ray diffraction, cell lines, chemical reactions, chemical structure, circular dichroism spectroscopy, inhibitory concentration 50, macrophages, mice, nitric oxide, nuclear magnetic resonance spectroscopy, sesquiterpenoids
Abstract:
Arteannoide A (1), an unusual cadinane dimer featuring a rare fused 6,8-dioxabicyclo[3.2.l]octan-7-one ring system, arteannoides B and C (2 and 3), two novel heterodimers incorporating a rearranged cadinene sesquiterpenoid and a phenylpropanoid, together with two new rearranged cadinene sesquiterpenoids 4 and 5, were isolated from Artemisia annua L. Their structures were determined by a combination of NMR spectroscopy, electronic circular dichroism calculations, and X-ray diffraction analyses. Compounds 2 and 3 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 mouse macrophage cell lines with IC₅₀ values of 4.5 and 2.9 μM, respectively.
Agid:
6083398