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Issue 28, 2020
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Neophathalides A and B, two pairs of unusual phthalide analog enantiomers from Ligusticum chuanxiong

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Abstract

Two pairs of unusual phthalide analog enantiomers, (+)- and (−)-neophathalides A and B [(+)- and (−)-1 and 2], were isolated from the rhizome of Ligusticum chuanxiong Hort. Notably, neophathalide A presented a novel spiro-[4.5]dec-6-ene skeleton that originated from an aldol condensation process from sedanonic acid. Neophathalide B is an unprecedented 3-substituted phthalide analog that possesses a four-membered lactone ring system. The structures of the compounds were established using UV, IR, HRESIMS, NMR and ECD methods. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 1a, 1b, and 2a exhibited moderate hepatoprotective activity compared with the positive control drug bicyclol at a concentration of 10 μM (p < 0.01).

Graphical abstract: Neophathalides A and B, two pairs of unusual phthalide analog enantiomers from Ligusticum chuanxiong

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Article information


Submitted
17 May 2020
Accepted
23 Jun 2020
First published
06 Jul 2020

Org. Biomol. Chem., 2020,18, 5453-5457
Article type
Paper

Neophathalides A and B, two pairs of unusual phthalide analog enantiomers from Ligusticum chuanxiong

X. Zhang, H. Yan, Z. Feng, Y. Yang, J. Jiang and P. Zhang, Org. Biomol. Chem., 2020, 18, 5453
DOI: 10.1039/D0OB01014F

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