Radical scavenging activity and cytotoxicity of active quinic acid derivatives from Scorzonera divaricata roots

• Published in: Food chemistry 2013-06, Vol.138 (2-3), p.2057-2063
• Main Authors: Yang, Yong-Jin, Liu, Xu, Wu, Hong-Ru, He, Xiao-Feng, Bi, Yu-Rong, Zhu, Ying, Liu, Zhen-Ling
• Format: Article
• Language: English
• Subjects: Antioxidants - chemistry; Antioxidants - toxicity; Biological and medical sciences; Cell Line; Cytotoxicity; Food industries; Free Radical Scavengers - chemistry; Free Radical Scavengers - toxicity; Fundamental and applied biological sciences. Psychology; Humans; Plant Extracts - chemistry; Plant Extracts - toxicity; Plant Roots - chemistry; Quinic Acid - chemistry; Quinic Acid - toxicity; Quinic acid derivatives; Radical scavenging capacity; Scorzonera - chemistry; Scorzonera divaricata
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2012.10.122

► Seven quinic acid derivatives are isolated in genus Scorzonera for the first time. ► Five new compounds were identified as dihydrocaffeoylquinic acid. ► Three compounds possess strong antioxidative activity. ► Quinic acid derivatives can be used as the chemosystematic marker of Scorzonera divaricata. Five new quinic acid derivatives and two known 3-O-feruloylquinic acids were isolated from the roots of Scorzonera divaricata Turcz. The new compounds were elucidated as (–)–1,4-di-O-feruloyl-3-O-dihydrocaffeoylquinic acid, (–)–1-O-feruloyl-4-O- dihydrocaffeoylquinic acid, (–)–3,5-di-O-feruloylquinic acid, (–)–1-O-feruloyl-3-O-dihydro- caffeoylquinic acid, and (–)–1-O-feruloyl-5-O-dihydrocaffeoylquinic acid based on extensive spectroscopic studies, including one- and two-dimensional NMR, HRESIMS, UV, and IR results. Five compounds were assessed for antioxidant activity by ABTS and DPPH radical-scavenging assays and for their cytotoxicity against HL-60 and Hep-G2 cell lines by the MTT assay. Three quinic acid derivatives exhibited strong antioxidant activity, with IC50 values of 3.95, 5.87, and 7.45μg/mL against ABTS+ and 11.7, 13.6, and 50.1μg/mL against DPPH. (–)–1,4-Di-O-feruloyl-3-O-dihydrocaffeoylquinic acid also exhibited moderate activity against Hep-G2 cell lines with an IC50 value of 14.6μg/mL.