Design and Synthesis of Resveratrol Analogs
Resveratrol (3,5,4′-trihydroxy-trans-stilbene), a naturally occurring hydroxystilbene, is considered as an essential anti-oxidative and possessing chemopreventive properties, and is found in various medical plants. It has been proven that resveratrol is a
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Design and Synthesis of Resveratrol Analogs Yuanmou Chen, Fei Hu, Yinghao Gao, Na Ji, Weizhu Liu and Erbing Hua
Abstract Resveratrol (3,5,40 -trihydroxy-trans-stilbene), a naturally occurring hydroxystilbene, is considered as an essential anti-oxidative and possessing chemopreventive properties, and is found in various medical plants. It has been proven that resveratrol is a Sirt1 activator and kinds of biological activities. In this paper, we designed and synthesized a series of resveratrol derivatives through a five-step synthetic procedure. Total 11 resveratrol derivatives were prepared from two kinds of hydroxybenzoic acid by methylation and reduction followed by bromination and reaction with triethyl phosphate to get methoxylated diethyl benzylphosphonates, then condensation with a series of aromatic aldehydes by Wittig-Horner reaction to offer the desired compounds in overall yield of about 17.2–48.5 %. These synthesized compounds were characterized on the basis of 1H NMR. Keywords Resveratrol analogs reaction
Synthesis
Sirt1 activator
Wittig-Horner
146.1 Introduction Resveratrol (3,5,40 -trihydroxystilbene) was identified as one ingredient of red wine, which could cause the so-called ‘‘French paradox’’ [1]. This compound, which is a naturally occurring phytoalexin produced by a wide range of plants in response to environmental stress or pathogenic attack, was first isolated from the roots of the white hellebore lily Veratrum grandiflorum by O. Loes in 1940 [2]. Since the discovery of its cardioprotective activity in 1992, resveratrol research has steadily accelerated. Y. Chen F. Hu Y. Gao N. Ji W. Liu E. Hua (&) Key Laboratory of Industrial Microbiology of Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, People’s Republic of China e-mail: [email protected]
T.-C. Zhang et al. (eds.), Proceedings of the 2012 International Conference on Applied Biotechnology (ICAB 2012), Lecture Notes in Electrical Engineering 251, DOI: 10.1007/978-3-642-37925-3_146, Ó Springer-Verlag Berlin Heidelberg 2014
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In past years, there have been a large of reports about resveratrol that exerts a variety of biological activities. Among the most significant activities of resveratrol are its cancer chemo-preventive properties [3, 4], antioxidant [5], antibacterial, and anti-inflammatory activities [6–8]. Some of these have been reported to inhibit LDL oxidation in human [9], in addition to its blocking of platelet aggregation [10] and vasorelaxing activities [11]. In yeast assays, resveratrol was also found to significantly mimic calorie restriction by stimulating Sirt2 which is the most homologic homolog of Sirt1 of mammalian and extended lifespan by 70 % [12]. In recent years, a large number of papers have been published on resveratrol, which report a wide range of novel discoveries, such as new extraction methods, new applications [13–15], and resveratrol analogs [16–18]. This intrigued us to prepare its analogs and their
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