Novel Flavonoids from the Leaves of Actinidia valvata Dunn: Structural Elucidation and Antioxidant Activity

Abstract

Two novel flavonoids, kaempferol 3-O-α-L-rhamnopyranosyl (1–3) (2,4-di-O-acetyl-α-L-rhamnopyranosyl) (1–6) β-D-galactopyranoside (1) and kaempferol 3-O-α-L-rhamnopyranosyl (1–3) (4-O-acetyl-α-L-rhamnopyranosyl) (1–6) β-D-galactopyranoside (2), along with three known ones, kaempferol-3-O-β-D-galactopyranoside (3), kaempferol (4), and 7-hydroxychromone (5), have been isolated from the leaves of Actinidia valvata Dunn, and their structures were elucidated based on spectroscopic methods. Compounds 1 – 3 exhibited dose-dependent activity in scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals, superoxide anion radicals, and hydroxyl radicals, and inhibited lipid peroxidation of mouse liver homogenate in vitro.

Key words

Actinidia valvata - Actinidiaceae - flavonoid glycosides

References

• 1 Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita .Flora of China (Volume 49, Tomus 2). Beijing; Science Press 1984: 205
• 2 Webby R F, Wilson R D, Ferguson A R. Leaf flavonoids of Actinidia.  Biochem Syst Ecol. 1994;  22 277-286
• 3 Xin H L, Wu Y C, Xu Y F, Zhang Y N, Ling C Q. A comparison between the root and stalk of Actinidia valvata.  Acad J Sec Mil Med Univ. 2008;  29 298-302
• 4 Zhang Y N, Liu L, Ling C Q. Inhibition effect of active fraction from Actinidia valvata on growth of transplanted mouse tumor cells and preliminary study of its mechanism.  Chin J Chin Mater Med. 2006;  31 918-920
• 5 Lv Y, Yang X B, Zhao Y, Ruan Y, Yang Y, Wang Z Z. Separation and quantification of component monosaccharides of the tea polysaccharides from Gynostemma pentaphyllum by HPLC with indirect UV detection.  Food Chem. 2009;  112 742-746
• 6 Lakenbrink C, Lam T M, Engelhardt U H, Wray V. New flavonol triglycosides from tea (Camellia sinensis).  Nat Prod Lett. 2000;  14 233-238
• 7 Kashiwada Y, Nonaka G I, Nishioka I. Studies on rhubarb (Rhei rhizoma). VI. Isolation and characterization of stilbenes.  Chem Pharm Bull. 1984;  32 3501-3517
• 8 Ouyang A M, Zhou J N. Flavonoid glycosides from the leaves of Davidio involucrate.  Guangxi Flora. 2003;  23 568-570
• 9 Nenandis N, Wang L F, Tsimidou M Z, Zhang H Y. Radical scavenging potential of phenolic compounds encountered in O. europaea products as indicated by calculation of bond dissociation enthalpy and ionization potential values.  J Agric Food Chem. 2005;  26 295-299
• 10 Burda S, Oleszek W. Antioxidant and antiradical activities of flavonoids.  J Agric Food Chem. 2001;  49 2774-2779
• 11 Natella F, Nardini M, Di Felice M, Saccini C. Benzoic and cinnamic acid derivatives as antioxidants: structure–activity relation.  J Agric Food Chem. 1999;  47 1453-1459
• 12 Cho J, Lee H K. Wogonin inhibits excitotoxic and oxidative neuronal damage in primary cultured rat cortical cells.  Eur J Pharmacol. 2004;  485 105-110
• 13 Valentova K, Cvak L, Muck A, Ulrichova J, Simanek V. Antioxidant activity of extracts from the leaves of Smallanthus sonchifolius.  Eur J Nutr. 2003;  42 61-66
• 14 Smirnoff N, Cumbes Q J. Hydroxyl radical scavenging activity of compatible solutes.  Phytochemistry. 1989;  28 1057-1060
• 15 Sun X W, Sun Q, Jin M, Piao C M, Li L H. Effect of Sorbaria sorbifolia extract on anti-oxidative activities in rats with precancerosis induced by diethylnitrosamine.  Chin J Integr Med. 2003;  1 47-50

1 Co-first author