Enzymatic synthesis and biological characterization of a novel mangiferin glucoside

Septiana, Iis; Nguyen, Thi Thanh Hanh; Lim, Sangyong; Lee, Seonmin; Park, Byeongsu; Kwak, So-Hyung; Park, Sung-Hee; Kim, Seong Bo; Kim, Doman

doi:10.1016/j.enzmictec.2019.109479

Cited by 13 publications

(8 citation statements)

References 44 publications

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“…For example, Zarena et al used enzyme catalysis to achieve glycosylation of α−mangostin (193) in a supercritical carbon dioxide system [134], and Sohng completed the diversified glycosylation of 193 by a one-pot enzymatic catalysis [135]. In addition, Kim and coworkers modified 1 with glucansucrase to obtain the disglycation product mangiferin-(1→6)-α-D-glucopyranoside (194), thus improving the activity and solubility of mangiferin [24].…”

Section: Synthesis Of Xanthone Glucosides or Derivativesmentioning

confidence: 99%

“…More recently, xanthone glucosides have been explored, and the mutation of these glycosyl groups can change the biological activity of xanthone, which has a wide range of clinical applications [21,22]. However, xanthones usually have poor solubility; herein, many studies are being devoted to the synthesis of glycosylated xanthones to improve their solubility and activity and minimize their toxicity [23,24]. Xanthone glucosides are an important class of xanthones that are extensively dispersed in the plant families Gentianaceae and Polygalaceae.…”

Section: Introductionmentioning

confidence: 99%

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Xanthone Glucosides: Isolation, Bioactivity and Synthesis

Huang

Wang

et al. 2021

Molecules

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Xanthones are secondary metabolites found in plants, fungi, lichens, and bacteria from a variety of families and genera, with the majority found in the Gentianaceae, Polygalaceae, and Clusiaceae. They have a diverse range of bioactivities, including anti-oxidant, anti-bacterial, anti-malarial, anti-tuberculosis, and cytotoxic properties. Xanthone glucosides are a significant branch of xanthones. After glycosylation, xanthones may have improved characteristics (such as solubility and pharmacological activity). Currently, no critical review of xanthone glucosides has been published. A literature survey including reports of naturally occurring xanthone glucosides is included in this review. The isolation, structure, bioactivity, and synthesis of these compounds were all explored in depth.

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Section: Synthesis Of Xanthone Glucosides or Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Xanthone Glucosides: Isolation, Bioactivity and Synthesis

Huang

Wang

et al. 2021

Molecules

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“…Therefore, the oil-water partition coefficient and membrane permeability can be improved effectively. [21] Most studies have focused on improving the solubility of mangiferin by increasing its water solubility, [22] but there are few studies on the liposolubility of mangiferin. It was found that the structure and lipophilicity of mangiferin-esterified derivatives are positively related:…”

Section: Introductionmentioning

confidence: 99%

“…Most studies have focused on improving the solubility of mangiferin by increasing its water solubility, [ 22 ] but there are few studies on the liposolubility of mangiferin. It was found that the structure and lipophilicity of mangiferin‐esterified derivatives are positively related: The larger the ester group, the higher the liposolubility.…”

Section: Introductionmentioning

confidence: 99%

Improving liposolubility and lipid antioxidant activity of mangiferin through esterification by lipase

Yu,

Yang,

Qian

et al. 2024

Euro J Lipid Sci & Tech

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Mangiferin is one of the main bioactive ingredients in leaves of Mangifera indica. But the poor liposolubility and low bioavailability restrict its application. This study aimed to esterify mangiferin with lipase to improve its lipophilicity, and evaluate its antioxidant activity and hypoglycemic properties. Four fatty acids (palmitic acid, lauric acid, stearic acid, oleic acid) were selected for enzymatic esterification with mangiferin by single‐factor experiments. Under the following optimum reaction conditions of tetrahydrofuran (THF):tert‐amyl alcohol (2:1) was used as solvent, water activity was 0.31, TLIM lipase was 45 mg mL–1, The ratio of mangiferin to fatty acid was 1:50, and the substrates were pretreated by ultrasonic for 0.5 h, then reacted at 55°C for 21 h, the resulting conversion rates of mangiferin‐esterified derivatives exceeded 70.0%.Lipophilicity, antioxidant, and PTP1B inhibitory activity of mangiferin‐esterified derivatives were determined. The results demonstrated that compared with mangiferin, the ability to scavenge DPPH radicals decreased by about 9%, but the lipophilicity was increased by 10–30 times, and the lipid antioxidant capacity was also improved significantly. Moreover, the inhibitory activity of protein tyrosine phosphatase 1B (PTP1B) exhibited minimal alteration. This indicates that esterification can not only improve the lipophilicity of mangiferin, but also improve its lipid antioxidant capacity.Practical Applications: In the study, a series of mangiferin‐esterified derivatives were synthesized and their lipophilicity, antioxidant properties, and PTP1B inhibitory activity were determined. The results indicated that, compared with the untreated mangiferin, the mangiferin‐esterified derivatives exhibited superior lipid antioxidant and hypoglycemic activities. Furthermore, the enzymatic esterification method employed in this study offered greater economic and environmental advantages when compared to chemical catalysis. Therefore, the preparation of mangiferin derivatives through enzymatic esterification were deemed feasible with potential application value for enhancing lipid antioxidant capacity in high‐fat foods.

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“…The best-defined ones are related to oxidative stress, inflammation, and regulation of autophagy. Some beneficial effects of gut microbes on tau phosphorylation dynamics are exemplified by Clostridium sporogeneses, which uses tryptophan to produce the strong antioxidant 3-indole propionic acid, and by lactic acid bacteria, which synthesize metabolic factors that significantly improve the activity of SOD and GSH-Px, thus reducing oxidative stress and tau aggregation [ 70 – 72 ]. Savignac et al designed a rat model of peripheral infection by tail vein injection of LPS.…”

Section: Impact Of the Gut Microbiota On Cerebral Amyloid And Tau Proteinsmentioning

confidence: 99%

Gut microbial involvement in Alzheimer's disease pathogenesis

Geng

2021

Aging

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Alzheimer's disease (AD) is a chronic, progressive neurodegenerative disease characterized by memory loss, inability to carry out everyday daily life, and noticeable behavioral changes. The essential neuropathologic criteria for an AD diagnosis are extracellular β-amyloid deposition and intracellular accumulation of hyperphosphorylated tau. However, the exact pathogenic mechanisms underlying AD remain elusive, and current treatment options show only limited success. New research indicates that the gut microbiota contributes to AD development and progression by accelerating neuroinflammation, promoting senile plaque formation, and modifying neurotransmitter production. This review highlights laboratory and clinical evidence for the pathogenic role of gut dysbiosis on AD and provides potential cues for improved AD diagnostic criteria and therapeutic interventions based on the gut microbiota.

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Enzymatic synthesis and biological characterization of a novel mangiferin glucoside

Cited by 13 publications

References 44 publications

Xanthone Glucosides: Isolation, Bioactivity and Synthesis

Xanthone Glucosides: Isolation, Bioactivity and Synthesis

Improving liposolubility and lipid antioxidant activity of mangiferin through esterification by lipase

Gut microbial involvement in Alzheimer's disease pathogenesis

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