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Neolignans with a Rare 2-Oxaspiro[4.5]deca-6,9-dien-8-one Motif from the Stem Bark of Cinnamomum subavenium

Author:
Lai, Yongji, Liu, Tingting, Sa, Rongjian, Wei, Xialan, Xue, Yongbo, Wu, Zhaodi, Luo, Zengwei, Xiang, Ming, Zhang, Yonghui, Yao, Guangmin
Source:
Journal of natural products 2015 v.78 no.7 pp. 1740-1744
ISSN:
1520-6025
Subject:
Cinnamomum, X-ray diffraction, bark, enantiomers, high performance liquid chromatography, inhibitory concentration 50, lignans, lipopolysaccharides, macrophages, mice, nitric oxide, nuclear magnetic resonance spectroscopy, spectral analysis
Abstract:
Two pairs of racemic spirodienone neolignans with a rare 2-oxaspiro[4.5]deca-6,9-dien-8-one motif, named (±)-subaveniumins A (1) and B (2), were isolated from the bark of Cinnamomum subavenium. The chiral separation of the (+)-1, (−)-1, (+)-2, and (−)-2 enantiomers was accomplished via high-performance liquid chromatography on a chiral column. Their structures were elucidated using single-crystal X-ray diffraction and spectroscopic analyses (UV, IR, HRESIMS, and 1D and 2D NMR). The absolute configurations of the enantiomers were determined by comparing the experimental and calculated electronic circular dichroic spectra. The (+)-1, (−)-1, (+)-2, and (−)-2 enantiomers exhibited moderate inhibitory effects against NO production in RAW264.7 mouse macrophages induced by lipopolysaccharide, with IC₅₀ values of 17.9, 5.6, 15.1, and 4.3 μM, respectively.
Agid:
5498277