Lignan and Phthalide Derivatives from the Rhizome of Ligusticum chuanxiong (Rhizoma chuanxiong) and Evaluation of Their anti-Xanthine Oxidase Activities

Abstract

The previous research results showed that the extracts of ethyl acetate of the rhizome of Ligusticum chuanxiong (Rhizoma chuanxiong) possessed significant antigout effects in model mice. To explore the active ingredients responsible for the effects, phytochemical studies were performed, which led to the isolation of three rare 8′, 9-linked neolignans, ligusticumins A–C (1–3), together with two novel phthalide-phenylpropanoid heterodimers, ligusticumalides A–B (4 and 5). It is noteworthy that 4 possesses an unprecedented 7-styryl phthalide skeleton. The structures and absolute configurations of 1–5 were elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and electron-capture detector (ECD) spectroscopic methods. The bioassay results showed that compounds 1, 2, 3, and 5 presented moderate inhibitory activities against xanthine oxidase (XO) and 4 possessed a significant XO inhibitory effect with an IC50 value of 93.88 μM. This is the first time to investigate the anti-XO active ingredients of R. chuanxiong, which provides valuable information for searching for new antigout agents from natural products.

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“…Ligusticumalide A 18 , from rhizomes of Ligusticum chuanxiong , is an unprecedented 7-styryl phthalide. 13 Citriquinolinone A 19 , a metabolite of deep-sea-derived Aspergillus versicolor 170217, is the first example of a citrinin analogue featuring an isoquinolinone ring system. 14 …”