Abstract
Myricetin (MY) was firstly synthesized from dihydromyricetin (DMY), and its antioxidant activity was analyzed. FTIR, NMR, and TG measurements confirmed that the DMY turned to MY. Scanning electron microscope observation showed that the 2,3-single bond offered great flexibility on the stage of crystallization to form imperfect crystalline regions; hence, DMY tends to form larger columnar crystals than MY. It has been found that the antioxidative efficiency of DMY was superior to MY, based on the measurement of radical scavenging activity by DPPH and the oxidation induction time of PP-antioxidant samples. The 2,3-double bond in MY structure, known as one of the characteristic determinants, was not an important requirement for antioxidant capacity or even negative correlation observed. Such a deduction was further supported by UV–Vis absorption spectra change when the pH was raised to pH 9. It was concluded that the ortho-trihydroxyl group in the B ring provides an antioxidant defense, and the 2,3-single band of C ring provides the structural stability.
Similar content being viewed by others
References
Towatari K, Yoshida K, Mori N, Shimizu K, Kondo R, Sakai K. Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells. Planta Med. 2002;68:995–8.
Zhang YS, Ning ZX, Yang SZ, Wu H. Antioxidation properties and mechanism of action of dihydromyricetin from Ampelopsis grossedentata. Yao Xue Xue Bao. 2003;38:241–4.
Matsumoto T, Tahara S. Ampelopsin, a major antifungal constituent from Salix sachalinensis, and its methyl ethers. Nippon Nogeik Kaishi. 2001;75:659–67.
Hayashi T, Tahara S, Ohaushi T. Genetically-controlled leaf traits in two chemotypes of Salix sachalinensis Fr. Schm (Salicaceae). Biochem Syst Ecol. 2005;33:27–38.
Guo QQ, Yan J, Zeng JH, He XZ, Li DG. Synthesis of dihydromyricetin–manganese (II) complex and interaction with DNA. J Mol Struct. 2012;1027:64–9.
Aherne SA, O’Brien NM. Dietary flavonols: chemistry, food content, and metabolism. Nutrition. 2002;18:75–81.
Yao Y, Vieira A. Protective activities of vaccinium antioxidants with potential relevance to mitochonrial dysfunction and neurotoxicity. Neurotoxicology. 2007;28:93–100.
Spencer JP, Vauzour D, Rendeiro C. Flavonoids and cognition: the molecular mechanisms underlying their behavioural effects. Arch Biochem Biophys. 2009;492:1–9.
Lei YF, Chen JL, Zhang WT, Fu W, Wu GH, Wei H, Wang Q, Ruan JL. In vivo investigation on the potential of galangin, kaempferol and myricetin for protection of d-galactose-induced cognitive impairment. Food Chem. 2012;135:2702–7.
Xin ML, Ma YJ, Xu K, Chen MC. Dihydromyricetin: an effective non-hindered phenol antioxidant for linear low-density polyethylene stabilization. J Them Anal Calorim. 2013;. doi:10.1007/s10973-013-3169-1.
Piras AM, Dessy A, Dinucci D, Chiellini F. 2-Methoxy aniline grafted poly(maleic anhydride-alt-butyl vinyl ether) hemiester: a new biocompatible polymeric free radical scavenger. Macromolecules. 2011;44:848–56.
Yu X, Liu R, Yang F, Ji D, Li X, Chen J, Huang H, Yi P. Study on the interaction between dihydromyricetin and bovine serum albumin by spectroscopic techniques. J Mol Struct. 2011;985:407–12.
Jurd L, Horowitz RM. Spectral studies on flavonols—the structure of azalein. J Org Chem. 1957;22:1618–22.
Mabry TJ, Markham KR, Thomas MB. The systematic identification of flavonoid. New York: Springer; 1970.
Bi SY, Song DQ, Tian Y, Zhou X, Liu ZY, Zhang HQ. Molecular spectroscopic study on the interaction of tetracyclines with serum albumins. Spectrochim Acta A. 2005;61:629–36.
Guo Q, Zhao B, Shen S, Hou J, Hu J, Xin W. ESR study on the structure–antioxidant activity relationship of tea catechins and their epimers. Biochim Biophys Acta. 1999;1427:13–23.
Nanjo F, Goto K, Seto R, Suzuki M, Sakai M, Hara Y. Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical. Free Radic Biol Med. 1996;21:895–902.
Xin ML, Ma YJ, Xu K, Chen MC. Structure–activity relationship for dihydromyricetin as a new natural antioxidant in polymer. J Appl Polym Sci. 2013;128:1436–42.
Bigger SW, Delatycki O. New approach to the measurement of polymer photooxidation. J Polym Sci Polym Chem. 1987;25:3311–23.
Gao X, Hu G, Qian Z, Ding Y, Zhang S, Wang D, Yang M. Immobilization of antioxidant on nanosilica and the antioxidative behavior in low density polyethylene. Polymer. 2007;48:7309–15.
Acknowledgements
This study was financially supported from National Natural Science Foundation of China, NSFC, (51073174) and the Science and Technology Plan of Guangzhou Municipal Bureau of Science, Information and Technology.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Xin, M., Ma, Y., Lin, W. et al. Study on the structure–activity of dihydromyricetin and its new production. J Therm Anal Calorim 116, 241–248 (2014). https://doi.org/10.1007/s10973-013-3538-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10973-013-3538-9