期刊
BIOORGANIC CHEMISTRY
卷 127, 期 -, 页码 -出版社
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2022.105970
关键词
Ligusticum chuanxiong; Phthalide dimers; Enantiomers; Absolute configurations; Anti-inflammatory activity
资金
- National Natural Science Foundation of China [82022072, U19A2010, 81891012]
- Fok Ying Tung Education Foundation [171037]
- Ten Thousand Talents Plan of Sichuan Province [168]
- Open Research Fund of Chengdu University of Traditional Chinese Medicine and Key Laboratory of Systematic Research of Distinctive Chinese Medicine Resources in Southwest China [2020XSGG015, 2020BSH013]
Six pairs of enantiomeric phthalide dimers were isolated from Ligusticum chuanxiong rhizomes, with structures and absolute configurations elucidated through various analyses. These compounds showed inhibitory effects against lipopolysaccharide-induced nitric oxide production, with compound (+)-5 exhibiting the strongest activity.
Six pairs of enantiomeric phthalide dimers (1-6) were isolated from the rhizomes of Ligusticum chuanxiong. Their structures and absolute configurations were elucidated by NMR spectroscopy, X-ray diffraction analyses, and electronic circular dichroism calculations. Compounds (+)-1 and (-)-1 are new phthalide dimers, featuring two classes of monomeric units (a phthalide and an unusual 2,3-seco-phthalide) with an uncommon linkage (3,6/8,3'a). Compounds (+)-2 and (-)-3 are also novel phthalide dimers that had not been reported previously. Although (-)-2 and (+)-3 have been successfully isolated in previous studies, their absolute configurations were not unambiguously determined. As for compound 4, it was reported as a racemate in one study, and one of its enantiomers was identified in a subsequent study. Herein, all enantiomeric phthalide dimers were successfully separated, and their absolute configurations were determined. The inhibitory effects of all isolates against lipopolysaccharide-induced nitric oxide production were tested using RAW264.7 cells. The results show that compounds (+)-2, (-)-2, (+)-3, (-)-3, (+)-4, (-)-4, (+)-5, (+)-6, and (-)-6 have inhibitory activities, with compound (+)-5 being the most active (IC50 value of 4.3 +/- 1.3 mu M).
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