Concise Synthesis of Chafurosides A and B

Furuta, Takumi; Nakayama, Miho; Suzuki, Hirotaka; Tajimi, Hiroko; Inai, Makoto; Nukaya, Haruo; Wakimoto, Toshiyuki; Kan, Toshiyuki

doi:10.1021/ol900689m

Cited by 55 publications

(49 citation statements)

References 30 publications

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“…In this case, aryl C-glycosylation of non-functional C-9 carbonyl groups is necessary because of the lack of electrons [10, 11]. In the presence of sodium methoxide (NaOMe), mangiferin gives 0.1% yield followed by the formation of an O-glycosidic bond through hydrolysis by treatment of the aglycone 1,3,6,7-tetrahydroxyxanthone with R-acetobromoglucose [12, 24].…”

Section: Mangiferin Synthesis and Metabolismmentioning

confidence: 99%

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Mangiferin: a natural miracle bioactive compound against lifestyle related disorders

et al. 2017

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The current review article is an attempt to explain the therapeutic potential of mangiferin, a bioactive compound of the mango, against lifestyle-related disorders. Mangiferin (2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one) can be isolated from higher plants as well as the mango fruit and their byproducts (i.e. peel, seed, and kernel). It possesses several health endorsing properties such as antioxidant, antimicrobial, antidiabetic, antiallergic, anticancer, hypocholesterolemic, and immunomodulatory. It suppresses the activation of peroxisome proliferator activated receptor isoforms by changing the transcription process. Mangiferin protects against different human cancers, including lung, colon, breast, and neuronal cancers, through the suppression of tumor necrosis factor α expression, inducible nitric oxide synthase potential, and proliferation and induction of apoptosis. It also protects against neural and breast cancers by suppressing the expression of matrix metalloproteinase (MMP)-9 and MMP-7 and inhibiting enzymatic activity, metastatic potential, and activation of the β-catenin pathway. It has the capacity to block lipid peroxidation, in order to provide a shielding effect against physiological threats. Additionally, mangiferin enhances the capacity of the monocyte-macrophage system and possesses antibacterial activity against gram-positive and gram-negative bacteria. This review summarizes the literature pertaining to mangiferin and its associated health claims.

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Section: Mangiferin Synthesis and Metabolismmentioning

confidence: 99%

“…Similarly, without the function of the C-9 carbonyl, aryl C-glycosylation is required due to electron deficiency [10, 11]. Mangiferin is synthesized through the hydrolysis of aglycone 1,3,6,7-tetrahydroxy-xanthone with R-acetobromoglucose, followed by a reaction entailing the formation of O-glycosidic bonds [12].…”

Section: Introductionmentioning

confidence: 99%

Mangiferin: a natural miracle bioactive compound against lifestyle related disorders

et al. 2017

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“…7) Kan and co-workers employed a tert-butyldiphenylsilyl group so it could be distinguished from a benzyl group. 10) Although Schmidt and co-workers first used a methyl group for phenol protection, because of the difficulty of deprotection, they later selected a tert-butyldimethylsilyl group.…”

mentioning

confidence: 99%

First Synthesis of Saponarin, 6-C- and 7-O-Di-β-D-glucosylapigenin

2013

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Saponarin, apigenin 6-C-and 7-O-bis-β-d-glucoside, was synthesized in an overall yield of 37% via 11 steps, which included the C-glycosylation of 2,4-O-dibenzylphloroacetophenone, the introduction of a cinnamoyl residue by aldol condensation, the formation of a flavone by regioselective deprotection, and oxidative ring-closure to the final regioselective deprotection and stereoselective O-glycosylation.

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“…3,3′,4′,5′-Tetrahydroxyflavone was synthesized using our recently developed synthetic method for flavones. 18,19) Fisetin and 3,3′,4′,5′-tetrahydroxyflavone were dissolved at 50 mM in 100% dimethyl sulfoxide and stored at −30°C until use. Immediately before use, flavonoids were diluted with 50 mM phosphate buffer (pH 7.4) to give the desired concentrations.…”

Section: Methodsmentioning

confidence: 99%

3,3′,4′,5′-Tetrahydroxyflavone Induces Formation of Large Aggregates of Amyloid β Protein

Ushikubo

Tanimoto

Abe

et al. 2014

Biological & Pharmaceutical Bulletin

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Amyloid β protein (Aβ) self-assembles into insoluble fibrils, and forms the senile plaques associated with Alzheimer's disease. 3,3′,4′,5′-Tetrahydroxyflavone, a synthetic analogue of the natural flavonoid fisetin, has been found to potently inhibit Aβ fibril formation. In the present study, we investigated how inhibition of Aβ fibril formation by this flavonoid affects Aβ conformation and neurotoxicity. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) analysis of Aβ1-42 (20 µM) incubated with or without 3,3′,4′,5′-tetrahydroxyflavone demonstrated that 3,3′,4′,5′-tetrahydroxyflavone (100 µM) rapidly caused formation of atypical Aβ conformers, which appeared as a very broad, smear-like band in the high molecular weight region and were distinguishable from soluble Aβ oligomers or mature Aβ fibrils. Transmission electron microscopy (TEM) revealed that large spherical Aβ aggregates were preferentially formed in the presence of 3,3′,4′,5′-tetrahydroxyflavone. The SDS-resistant, smear-like band on SDS-PAGE and the large spherical aggregates in TEM both disappeared after heat treatment (100°C, 10 min). Furthermore, a neurotoxicity assay with cultured rat hippocampal neurons demonstrated that Aβ incubated with 3,3′,4′,5′-tetrahydroxyflavone was significantly less toxic than Aβ incubated without the flavonoid. These results suggest that the newly synthesized fisetin analogue 3,3′,4′,5′-tetrahydroxyflavone directly produces atypical, large Aβ aggregates and reduces Aβ toxicity.

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Concise Synthesis of Chafurosides A and B

Cited by 55 publications

References 30 publications

Mangiferin: a natural miracle bioactive compound against lifestyle related disorders

Mangiferin: a natural miracle bioactive compound against lifestyle related disorders

First Synthesis of Saponarin, 6-<i>C</i>- and 7-<i>O</i>-Di-<i>β</i>-D-glucosylapigenin

3,3′,4′,5′-Tetrahydroxyflavone Induces Formation of Large Aggregates of Amyloid β Protein

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