Bio- and chemical syntheses of mangiferin and congeners

被引:28
作者
Ehianeta, Teddy Stephen [1 ]
Laval, Stephane [1 ]
Yu, Biao [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
mangiferin; C-glycoside; xanthone; biosynthesis; chemical synthesis; ANEMARRHENA-ASPHODELOIDES BUNGE; NATURALLY-OCCURRING XANTHONES; TETRAOXYGENATED XANTHONES; ANTIOXIDANT ACTIVITY; MEDICINAL PROPERTIES; CANSCORA-DECUSSATA; COLORING MATTER; INDICA LINN; BIOSYNTHESIS; DERIVATIVES;
D O I
10.1002/biof.1279
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Mangiferin (2C-b-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone) is a xanthone C-glycoside occurring in many plant species. Composed of a glucose unit C1fi2 linked to a 1,3,6,7-tetrahydroxyxanthone aglycone, mangiferin exhibits a wide range of biological activities, which recently renewed its interest as a potential pharmacophore. Mangiferin is mainly isolated after extraction procedures from natural sources alongside with its isoforms isomangiferin, homomangiferin, and neomangiferin. However, enzymatic and chemical approaches have been developed to access these phytochemicals, which address the challenging construction of the C-glycosidic linkage. In addition, both approaches have been exploited to modify the aglycone and the sugar moiety in order to afford analogues with specific and improved pharmacological activities. Herein, we provide a comprehensive review on the biosynthesis and chemical synthesis of mangiferin and its congeners. (C) 2016 BioFactors.
引用
收藏
页码:445 / 458
页数:14
相关论文
共 71 条
[1]  
ARITOMI M, 1970, CHEM PHARM BULL, V18, P2327
[2]  
ARITOMI M, 1968, CHEM PHARM BULL, V16, P760
[3]   OXIDATIVE COUPLING .7. BIOGENETIC TYPE SYNTHESIS OF NATURALLY OCCURRING XANTHONES [J].
ATKINSON, JE ;
LEWIS, JR .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (02) :281-&
[4]   Characterization and quantitation of polyphenolic compounds in bark, kernel, leaves, and peel of mango (Mangifera indica L.) [J].
Barreto, Jacqueline C. ;
Trevisan, Maria T. S. ;
Hull, William E. ;
Erben, Gerhard ;
de Brito, Edy S. ;
Pfundstein, Beate ;
Wuertele, Gerd ;
Spiegelhalder, Bertold ;
Owen, Robert W. .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (14) :5599-5610
[5]   Medicinal Properties of Mangiferin, Structural Features, Derivative Synthesis, Pharmacokinetics and Biological Activities [J].
Benard, Outhiriaradjou ;
Chi, Yuling .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2015, 15 (07) :582-594
[6]   CONSTITUTION OF MANGIFERIN [J].
BHATIA, VK ;
RAMANATHAN, JD ;
SESHADRI, TR .
TETRAHEDRON, 1967, 23 (03) :1363-+
[7]  
BHATIA VK, 1968, TETRAHEDRON LETT, P1741
[8]   XANTHONES IN HIGHER PLANTS - BIOGENETIC PROPOSALS AND A CHEMOTAXONOMIC SURVEY [J].
CARPENTER, I ;
LOCKSLEY, HD ;
SCHEINMANN, F .
PHYTOCHEMISTRY, 1969, 8 (10) :2013-+
[9]   STUDIES ON CHEMICAL CONSTITUENTS OF CENTIANACEAE .1. XANTHONES OF CANSCORA-DECUSSATA SCHULT [J].
CHAUDHURI, RK .
PHYTOCHEMISTRY, 1971, 10 (10) :2425-+
[10]   Probing the Catalytic Promiscuity of a Regio- and Stereospecific C-Glycosyltransferase from Mangifera indica [J].
Chen, Dawei ;
Chen, Ridao ;
Wang, Ruishan ;
Li, Jianhua ;
Xie, Kebo ;
Bian, Chuancai ;
Sun, Lili ;
Zhang, Xiaolin ;
Liu, Jimei ;
Yang, Lin ;
Ye, Fei ;
Yu, Xiaoming ;
Dai, Jungui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (43) :12678-12682