Journal
RSC ADVANCES
Volume 6, Issue 66, Pages 61037-61046Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ra10023f
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Funding
- National Natural Science Foundation of China [81473321]
- National Key Technology R & D Program of China [2011BAI07B08]
- Beijing Municipal Natural Science Foundation [7152086]
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Five new phthalide derivatives, chuanxiongnolides L1-L5 (1-5), together with three known phthalide dimers (6-8), were isolated from the rhizomes of Ligusticum chuanxiong Hort.. Compound 1 represents a novel type of phthalide derivative, biogenetically derived from coniferyl alcohol and ligustilide. Compound 2 is the first example of an E-ring expanded phthalide dimer with a 5/6/6/6/6 fused-ring system, which is different from the 5/6/6/6/5 fused-ring system in normal phthalide dimers. Their structures were established using spectroscopic data, and the absolute configurations were determined by a circular dichroism (CD) exciton chirality method. To confirm the absolute configuration of compound 1, electronic circular dichroism (ECD) calculations were also conducted. Compounds 1, 2, 6, and 7 exhibited inhibitory effects against lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophage cells with half maximal inhibitory concentration (IC50) values ranging from 3.0 to 12.6 mu M. Furthermore, plausible biosynthetic routes for 1 and 2 were also proposed.
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