Bio‐ and chemical syntheses of mangiferin and congeners

Abstract

Mangiferin (2C-β-d-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone) is a xanthone C-glycoside occurring in many plant species. Composed of a glucose unit C1→2 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. © 2016 BioFactors, 42(5):445-458, 2016.

Nrf2/HO-1 mediates the neuroprotective effect of mangiferin on early brain injury after subarachnoid hemorrhage by attenuating mitochondria-related apoptosis and neuroinflammation

“…Mangiferin (MF), usually isolated from a variety of natural plants such as mango trees, Iris unguicularis , Anemarrhena asphodeloides and the family Gentianaceae , was initially identified in the late 1960s as a type of xanthone derivative and C-glucosyl xanthone (2C- -D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone) 8 , 9 . Due to its special structure with C-glycosidic linkage, MF exhibits powerful antioxidant and free radical scavenging properties 10 , 11 .…”

A review of antidiabetic active thiosugar sulfoniums, salacinol and neokotalanol, from plants of the genus Salacia

“…A xanthone C-glycoside mangiferin (41), originally obtained from the stem bark of mango tree (Mangifera indica L.) [83][84][85], was isolated from plants of the genus Salacia as a moderate aldose reductase inhibitor (vide supra) and reported to exert a hypoglycemic effect in KK-A y mice [2,86]. Thereafter, mangiferin (41) has attracted attention as a bio-functional molecule for its antidiabetic [83,84,[87][88][89], antioxidant [83,84,[90][91][92], antibacterial, antiviral [84], antiparasitic [84], antiinflammatory [83,84,[90][91][92][93][94], and anticancer [83,84,95,96] activities.…”

Recent advances in the synthesis of xanthones and azaxanthones

“…Front., 2020, 7, 3027-3066 ities can be achieved like alkoxy, 19,23,24,33,97 which in certain situations can be converted into chlorosulfonyl 24 or amine, 33 ethylenedioxy, 100 and allyl. 39,115,138 Other transformations include the introduction of glycosyl, 55,110,132,135,229,230 ester, 17,62,227 amino, 151 and even prenyl 23,39,40,45,46,49,50,52,53,97,98,[111][112][113][114]117,130,133,221,[231][232][233] moieties, the latter being further used for the synthesis of caged xanthones 39,49,105,138,234 or pyranoxanthones. 40,45,…”