title: Chemo-enzymatic synthesis of vinyl and l-ascorbyl phenolates and their inhibitory effects on advanced glycation end products.
abstract: This study successfully established the feasibility of a two-step chemo-enzymatic synthesis of l-ascorbyl phenolates. Intermediate vinyl phenolates were first chemically produced and then underwent trans-esterification with l-ascorbic acid in the presence of Novozyme 435® (Candida Antarctica lipase B) as a catalyst. Twenty vinyl phenolates and 11 ascorbyl phenolates were subjected to in vitro bioassays to investigate their inhibitory activity against advanced glycation end products (AGEs). Among them, vinyl 4-hydroxycinnamate (17VP), vinyl 4-hydroxy-3-methoxycinnamate (18VP), vinyl 4-hydroxy-3,5-dimethoxycinnamate (20VP), ascorbyl 4-hydroxy-3-methoxycinnamate (18AP) and ascorbyl 3,4-dimethoxycinnamate (19AP) showed 2-10 times stronger inhibitory activities than positive control (aminoguanidine and its precursors). These results indicated that chemo-enzymatically synthesized compounds have AGE inhibitory effect and thus are effective in either preventing or retarding glycation protein formation.
authors: Department of Food Science and Nutrition, Hallym University, Chuncheon, Gangwon-do, Republic of Korea; Institute of Korean Nutrition, Hallym University, Chuncheon, Gangwon-do, Republic of Korea.
authors: Seung Hwan
authors: SH
authors: Hwang
authors: Department of Food Science and Nutrition, Hallym University, Chuncheon, Gangwon-do, Republic of Korea; Institute of Korean Nutrition, Hallym University, Chuncheon, Gangwon-do, Republic of Korea.
authors: Zhiqiang
authors: Z
authors: Wang
authors: Department of Food Science and Nutrition, Hallym University, Chuncheon, Gangwon-do, Republic of Korea; Institute of Korean Nutrition, Hallym University, Chuncheon, Gangwon-do, Republic of Korea. Electronic address: limss@hallym.ac.kr.
authors: Soon Sung
authors: SS
authors: Lim
mesh_terms: D000818:Animals; D001205:Ascorbic Acid / Q000737:chemistry; D001681:Biological Assay; D002384:Catalysis; D002417:Cattle; D004800:Enzymes, Immobilized; D004951:Esterification; D005656:Fungal Proteins / Q000737:chemistry*; D017127:Glycation End Products, Advanced / Q000737:chemistry*; D006031:Glycosylation; D006454:Hemoglobins / Q000737:chemistry; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry; D008049:Lipase / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D011143:Polyvinyl Chloride / Q000737:chemistry; D012710:Serum Albumin, Bovine / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D017127:Glycation End Products, Advanced; D006454:Hemoglobins; D007783:Lactones; D010636:Phenols; D012997:Solvents; D012710:Serum Albumin, Bovine; D011143:Polyvinyl Chloride; C093667:Novozyme 435; D008049:Lipase; C431349:lipase B, Candida antarctica; D001205:Ascorbic Acid
keywords: Advanced glycation end products; Chemo-enzymatic synthesis; Novozyme 435®; Phenolic acid; l-ascorbic acid