Identification of a flavonoid C-glycoside as potent antioxidant

Lingrong Wen; Yupeng Zhao; Yueming Jiang; Limei Yu; Xiaofang Zeng; Jiali Yang; Miaomiao Tian; Huiling Liu; Bao Yang

doi:10.1016/j.freeradbiomed.2017.05.027

Identification of a flavonoid C-glycoside as potent antioxidant

Free Radic Biol Med. 2017 Sep:110:92-101. doi: 10.1016/j.freeradbiomed.2017.05.027. Epub 2017 Jun 3.

Authors

Lingrong Wen¹, Yupeng Zhao², Yueming Jiang¹, Limei Yu³, Xiaofang Zeng³, Jiali Yang¹, Miaomiao Tian¹, Huiling Liu¹, Bao Yang⁴

Affiliations

¹ Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China.
² Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China; College of Light Industry and Food Sciences, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China.
³ College of Light Industry and Food Sciences, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China.
⁴ Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China. Electronic address: [email protected].

PMID: 28587909
DOI: 10.1016/j.freeradbiomed.2017.05.027

Abstract

Flavonoids have been documented to have good antioxidant activities in vitro. However, reports on the cellular antioxidant activities of flavonoid C-glycosides are very limited. In this work, an apigenin C-glycoside was purified from Artocarpus heterophyllus by column chromatography and was identified to be 2″-O-β-D-xylosylvitexin by nuclear magnetic resonance spectroscopy. The cellular antioxidant activity and anticancer activity of 2″-O-β-D-xylosylvitexin were evaluated for the first time. The quantitative structure-activity relationship was analysed by molecular modeling. Apigenin presented an unexpected cellular antioxidation behaviour. It had an antioxidant activity at low concentration and a prooxidant activity at high concentration, whereas 2″-O-β-D-xylosylvitexin showed a dose-dependent cellular antioxidant activity. It indicated that C-glycosidation improved the cellular antioxidation performance of apigenin and eliminated the prooxidant effect. The ortho-dihydroxyl at C-3'/C-4' and C-3 hydroxyl in the flavonoid skeleton play important roles in the antioxidation behaviour. The cell proliferation assay revealed a low cytotoxicity of 2″-O-β-D-xylosylvitexin.

Keywords: 2″-O-β-D-xylosylvitexin; Artocarpus heterophyllus; Cellular antioxidant activity; Cytotoxicity; NMR.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology
Antioxidants / chemistry
Antioxidants / isolation & purification*
Antioxidants / pharmacology
Apigenin / chemistry
Apigenin / isolation & purification
Apigenin / pharmacology
Artocarpus / chemistry*
Biphenyl Compounds / antagonists & inhibitors
Biphenyl Compounds / chemistry
Cell Proliferation / drug effects
Cell Survival / drug effects
Chromans / pharmacology
Dose-Response Relationship, Drug
Flavonoids / chemistry
Flavonoids / isolation & purification*
Flavonoids / pharmacology
Glycosides / chemistry
Glycosides / isolation & purification
Glycosides / pharmacology
Hep G2 Cells
Humans
Hydroxyl Radical / antagonists & inhibitors
Hydroxyl Radical / chemistry
MCF-7 Cells
Monosaccharides / chemistry
Monosaccharides / isolation & purification*
Monosaccharides / pharmacology
Picrates / antagonists & inhibitors
Picrates / chemistry
Plant Extracts / chemistry
Plant Leaves / chemistry
Quercetin / chemistry
Quercetin / isolation & purification
Quercetin / pharmacology

Substances

Antineoplastic Agents, Phytogenic
Antioxidants
Biphenyl Compounds
C-glycoside
Chromans
Flavonoids
Glycosides
Monosaccharides
Picrates
Plant Extracts
vitexin-2-O-xyloside
Hydroxyl Radical
Apigenin
Quercetin
1,1-diphenyl-2-picrylhydrazyl
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid