白藜芦醇合成方法综述
|
摘要
白藜芦醇是一种植物源非黄酮类多酚化合物,具有预防心脏病、抑制血小板凝聚、调控脂质和脂蛋白代谢、抗氧化及抗癌等生理活性,在化妆品、保健品、医药等方面有广阔的应用前景,但目前该类化合物主要通过植物提取得到,资源的缺少限制了对该类化合物的研究,综述了白藜芦醇的7种化学、生物合成方法。化学合成法,步骤复杂存在污染问题;生物合成法环境污染小,资源破坏少,具有较大的应用价值。
The resveratrol is a plant-derived non-flavonoid polyphenol compound which has many physiological activities, such as preventing heart disease, inhibiting blood platelet aggregation, regulating lipid and lipoprotein metabolism, anti-oxidation and anti-cancer; it has extensive appli-cations in the fields of cosmetics, health care products, medicine, etc. However at present the compounds are mainly extracted from plants. The lack of resources has limited the study on this kind of compounds. Seven kinds of chemical and biological synthesis methods for resveratrol are reviewed. The chemical method is complicated and has serious pollution problem; the biosynthesis has less pollution to the environment and smaller destruction to resources, which has greater application value.
The resveratrol is a plant-derived non-flavonoid polyphenol compound which has many physiological activities, such as preventing heart disease, inhibiting blood platelet aggregation, regulating lipid and lipoprotein metabolism, anti-oxidation and anti-cancer; it has extensive appli-cations in the fields of cosmetics, health care products, medicine, etc. However at present the compounds are mainly extracted from plants. The lack of resources has limited the study on this kind of compounds. Seven kinds of chemical and biological synthesis methods for resveratrol are reviewed. The chemical method is complicated and has serious pollution problem; the biosynthesis has less pollution to the environment and smaller destruction to resources, which has greater application value.
引文
[1]ROMEO R, PIER G B, VINCENT R, et al. Synthesis and biological evaluation of 2-(3’, 4’, 5’-trimethoxybenzoyl)-3-amino5-aryl thiophenes as a new class of tubulin inhibitors[J]. J Med Chem, 2006, 49:6425~6428.
[2]GOSSLAU A, CHEN M, HO CI T.A methoxy derivative of resveratrol analogue selectively induced activation of the mitochondrial apoptotic pathway in transformed fibroblasts[J]. Bri J Cancer,2005, 92:513~521.
[3]徐洪耀,吴蕾,胡蕾.二苯乙烯衍生物的制备及结构-光学性能关系的研究[J].光谱学与光谱分析, 2008, 28(10):2356~2359.
[4]YIN S C, XU H Y, SU X Y, et al. Optical-limiting and nonlinear optical polyacetylenes:Synthesis of azobenzene-containing poly(1-alkyne)s with different spacer and tail lengths[J]. J Polym Sci:Part A, Polym Chem, 2006, 44(7):2346~2357.
[5]WANG S T, YANG Y L, ZHU H J, et al. Synthesis and Spectral Characterization of Rare-Earth-Ortho-Amino Phenylbenzoate-2,2’-Bipyridine Complexes[J]. Spectrosc Spect Ana, 2006, 26(5):933~935.
[6]GUY S, YACINE P, JEAN M. A re-investigation of resveratrol synthesis by Perkins reaction[J]. Tetrahedron, 2003, 59(18):3315~3321
[7]MORO A V, CARDOSO F S P, CORREIA C R D. Heck arylation of styrenes with arenediazonium salts:short, efficient and stereoselective synthesis of resveratrol, DMU-212, and analogues[J].Tetrahedron Lett, 2008, 49:5668~5671.
[8]潘华君,帅晓艳,王传金.白藜芦醇的全合成[J].合成化学,2008, 16(2):170~172.
[9]李先宽,李赫宇,李帅,等.白藜芦醇研究进展[J].中草药, 2016,47(14):2568~2578.
[10]郭勇,崔堂兵,谢秀祯.植物细胞培养技术与应用[M].北京:化学工业出版社, 2004:1.
[11]JOSE C, GANAPATHY S, JOHN H, et al. Induced biosynthesis of resveratrol and the Prenylated stilbenoids arachidin-1 and arachidin-3 in hairy root cultures of Peanut:Effects of culture medium and growth stage[J]. Plant Physiol Biochem, 2010, 48(5):310~318.
[12]曹庸,陈雪,唐永红.虎杖愈伤组织的诱导及高产白藜芦醇材料的筛选[J].生命科学研究, 2006, 10(3):270~275.
[13]尉亚辉.大规模葡萄细胞培养生产白藜芦醇[D].西安:西北大学, 2003.
[14]李洁,熊兴耀,曾建国,等.白藜芦醇的研究进展[J].中国现代中药, 2013, 15(2):100~108.
[15]韩晶晶,刘炜,毕玉平.白藜芦醇的研究进展[J].生物工程学报, 2008, 24(11):1851~1859.
[16]LIU S J, HU Y L, WANG X L, et al. High content of resveratrol in lettuce transformed with a stilbene synthase gene of Parthenocissus henryana[J]. J Agric Food Chem, 2006, 54(21):8082~8025.
[17]SCHWEKENDIEK A, SPRING O, HEYERICK A, et al. Constitutive expression of a grapevine stilbene synthase gene in transgenic hop yields resveratrol and its derivatives in substantial quantities[J]. J Agric Food Chem, 2007, 55(17):7002~7009.
[18]BECKER J V W, ARMSTRONG G O, MERWE M J, et al. Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol[J]. FEMS Yeast Research, 2003, 4(1):79~85.
[19]SYDOR T, SCHAFFER S, BOLES E. Considerable increase in resveratrol production by recombinant industrial yeast strains with use of rich medium[J]. Applied and Environmental Microbiology, 2010, 10(76):3361~3363.
[20]KEVIN T WATTS, PYUNG C LEE, CLAUDIA SCHMIDT-DANNERT. Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli[J]. BNC Biol, 2006,6(22):1~12.
[21]KATSUYAMA Y, FUNA N, MIYAHISA I, et al. Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli[J]. Chem Biol, 2007, 14(6):613~621.
[2]GOSSLAU A, CHEN M, HO CI T.A methoxy derivative of resveratrol analogue selectively induced activation of the mitochondrial apoptotic pathway in transformed fibroblasts[J]. Bri J Cancer,2005, 92:513~521.
[3]徐洪耀,吴蕾,胡蕾.二苯乙烯衍生物的制备及结构-光学性能关系的研究[J].光谱学与光谱分析, 2008, 28(10):2356~2359.
[4]YIN S C, XU H Y, SU X Y, et al. Optical-limiting and nonlinear optical polyacetylenes:Synthesis of azobenzene-containing poly(1-alkyne)s with different spacer and tail lengths[J]. J Polym Sci:Part A, Polym Chem, 2006, 44(7):2346~2357.
[5]WANG S T, YANG Y L, ZHU H J, et al. Synthesis and Spectral Characterization of Rare-Earth-Ortho-Amino Phenylbenzoate-2,2’-Bipyridine Complexes[J]. Spectrosc Spect Ana, 2006, 26(5):933~935.
[6]GUY S, YACINE P, JEAN M. A re-investigation of resveratrol synthesis by Perkins reaction[J]. Tetrahedron, 2003, 59(18):3315~3321
[7]MORO A V, CARDOSO F S P, CORREIA C R D. Heck arylation of styrenes with arenediazonium salts:short, efficient and stereoselective synthesis of resveratrol, DMU-212, and analogues[J].Tetrahedron Lett, 2008, 49:5668~5671.
[8]潘华君,帅晓艳,王传金.白藜芦醇的全合成[J].合成化学,2008, 16(2):170~172.
[9]李先宽,李赫宇,李帅,等.白藜芦醇研究进展[J].中草药, 2016,47(14):2568~2578.
[10]郭勇,崔堂兵,谢秀祯.植物细胞培养技术与应用[M].北京:化学工业出版社, 2004:1.
[11]JOSE C, GANAPATHY S, JOHN H, et al. Induced biosynthesis of resveratrol and the Prenylated stilbenoids arachidin-1 and arachidin-3 in hairy root cultures of Peanut:Effects of culture medium and growth stage[J]. Plant Physiol Biochem, 2010, 48(5):310~318.
[12]曹庸,陈雪,唐永红.虎杖愈伤组织的诱导及高产白藜芦醇材料的筛选[J].生命科学研究, 2006, 10(3):270~275.
[13]尉亚辉.大规模葡萄细胞培养生产白藜芦醇[D].西安:西北大学, 2003.
[14]李洁,熊兴耀,曾建国,等.白藜芦醇的研究进展[J].中国现代中药, 2013, 15(2):100~108.
[15]韩晶晶,刘炜,毕玉平.白藜芦醇的研究进展[J].生物工程学报, 2008, 24(11):1851~1859.
[16]LIU S J, HU Y L, WANG X L, et al. High content of resveratrol in lettuce transformed with a stilbene synthase gene of Parthenocissus henryana[J]. J Agric Food Chem, 2006, 54(21):8082~8025.
[17]SCHWEKENDIEK A, SPRING O, HEYERICK A, et al. Constitutive expression of a grapevine stilbene synthase gene in transgenic hop yields resveratrol and its derivatives in substantial quantities[J]. J Agric Food Chem, 2007, 55(17):7002~7009.
[18]BECKER J V W, ARMSTRONG G O, MERWE M J, et al. Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol[J]. FEMS Yeast Research, 2003, 4(1):79~85.
[19]SYDOR T, SCHAFFER S, BOLES E. Considerable increase in resveratrol production by recombinant industrial yeast strains with use of rich medium[J]. Applied and Environmental Microbiology, 2010, 10(76):3361~3363.
[20]KEVIN T WATTS, PYUNG C LEE, CLAUDIA SCHMIDT-DANNERT. Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli[J]. BNC Biol, 2006,6(22):1~12.
[21]KATSUYAMA Y, FUNA N, MIYAHISA I, et al. Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli[J]. Chem Biol, 2007, 14(6):613~621.