Purification and Characterization of Flavonoids from the Leaves of Zanthoxylum bungeanum and Correlation between Their Structure and Antioxidant Activity

Abstract

Nine flavonoids were isolated and characterized from the leaves of Zanthoxylum bungeanum. Their structures were elucidated by spectroscopic techniques as quercetin (1), afzelin (2), quercitrin (3), trifolin (4), quercetin-3-O-β-D-glucoside (5), isorhamnetin 3-O-α-L-rhamnoside (6), hyperoside (7), vitexin (8) and rutin (9). All compounds were isolated from the leaves of Z. bungeanum for the first time. Five compounds (2, 4, 5, 6 and 8) were found for the first time in the genus Zanthoxylum. To learn the mechanisms underlying its health benefits, in vitro (DPPH, ABTS, FRAP and lipid peroxidation inhibition assays) and in vivo (protective effect on Escherichia coli under peroxide stress) antioxidant activities of the nine flavonoids were measured. Quercetin and quercetin glycosides (compounds 1, 3, 5, 7, 9) showed the highest antioxidant activity. Structure-activity relationships indicated that the -OH in 4′ position on the B ring and the -OH in 7 position on the A ring possessed high antioxidant activity; B ring and/or A ring with adjacent -OH groups could greatly increase their antioxidant ability. Also, due to the different structures of various flavonoids, they will certainly exhibit different antioxidant capacity when the reactions occur in solution or in oil-in-water emulsion. These findings suggest that Z. bungeanum leaves may have health benefits when consumed. It could become a useful supplement for pharmaceutical products and functional food ingredients in both nutraceutical and food industries as a potential source of natural antioxidants.

Hypoglycemic effects of Zanthoxylum alkylamides by enhancing glucose metabolism and ameliorating pancreatic dysfunction in streptozotocin-induced diabetic rats

“…[5][6][7] Unsaturated alkylamides, such as α-, β-, γ-, and δ-sanshool, and their analogues have been identified as the tingling taste-producing substances of Zanthoxylum species. et Zucc is an aromatic plant belonging to the genus Zanthoxylum of the family Rutaceae; this plant is mainly distributed in Sichuan, Chongqing, Hebei, Hunan, and Jilin in China, as well as in some Southeast Asian countries.…”

In vitro anthelmintic activity of Zanthoxylum simulans essential oil against Haemonchus contortus

“…China is home to 45 species and 13 varieties of this genus (Zhang et al, 2014). The fruits of some species such as Z. armatum and Z. bungeanum, with the most popular name being "huajiao" (flower pepper), is a traditional spice with strong spiciness and astringent taste.…”

A Modified and Improved Assay Based on Microbial Test System (MTS) to Evaluate Antioxidant Activity

“…25922) (Microbial Culture Collection Center of Guangdong Institute of Microbiology, China); Rutin, quercetin, kaempferol-3-O-α-L-rhamnoside, hyperoside, quercitrin (Isolated and purified from our laboratory, Zhang et al 2014); Banana, apple, kiwi fruit and tomato were bought from market; Dimethyl sulfoxide (DMSO) (Tianjin Bodi Chemical Factroy Co., Ltd. PR China); Sodium chloride, Hydrogen peroxide 30 % (Guangdong Guanghua Chemical Factory Co., Ltd. PR China); Yeast extract, Tryptone (OXOID Ltd., Basingstoke, Hampshire, England); 1,1-Dipheny-2-picrylhydrazyl (DPPH), 2,4,6-Tripyridyl-s-triazine (TPTZ), 2,2´-azino-bis(3-ethyl-benzothiazoline -6-sulphonic acid) di-ammonium salt (ABTS) (Sigma-Aldrich Co., St. Louis, USA).…”