Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

Orsini, Fulvia; Pelizzoni, F.; Bellini, B.; Miglierini, Giuliana

doi:10.1016/s0008-6215(97)00087-6

Cited by 92 publications

(82 citation statements)

References 29 publications

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“…trans-3,5-Dihydroxy-4Ј-methoxystilbene (4Ј-O-methylresveratrol) (compound III) was obtained as previously described (44) by Wittig reaction between the phosphonium salt of the commercially available 4-methoxybenzyl chloride and 3,5-bis-(tert-butyldimethylsilyloxy)benzaldehyde. Butyllithium (2.3 ml, 1.6 M in hexane, 3.6 mmol) was added dropwise to a suspension of (4-methoxybenzyl)triphenylphosphonium chloride (3.6 mmol) in tetrahydrofuran (50 ml) at Ϫ15°C.…”

Section: Resveratrol Derivatives Synthesismentioning

confidence: 99%

Specific Structural Determinants Are Responsible for the Antioxidant Activity and the Cell Cycle Effects of Resveratrol

Stivala¹,

Savio²,

Carafoli³

et al. 2001

Journal of Biological Chemistry

450

346

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Resveratrol (3,4,5-trihydroxy-trans-stilbene) is a natural phytoalexin found in grapes and wine, which shows antioxidant and antiproliferative activities. In this study we have investigated whether these properties are dependent on similar or different structural determinants of the molecule. To this purpose, resveratrol derivatives, in which all or each single hydroxylic function were selectively substituted with methyl groups, were synthesized. Analogues with the stilbenic double bond reduced or with the stereoisomery modified were also investigated. The antioxidant activity of these compounds was evaluated by measuring the inhibition of citronellal thermo-oxidation, or the reduction of 2,2-diphenyl-1-picrylhydrazyl radical. In addition, the protection against lipid peroxidation was determined in rat liver microsomes, and in human primary cell cultures. The antiproliferative activity was evaluated by a clonogenic assay, and by analysis of cell cycle progression and DNA synthesis. The results showed that the hydroxyl group in 4 position is not the sole determinant for antioxidant activity. In contrast, the presence of 4-OH together with stereoisomery in the trans-conformation (4-hydroxystyryl moiety) was absolutely required for inhibition of cell proliferation. Enzymatic assays in vitro demonstrated that inhibition of DNA synthesis was induced by a direct interaction of resveratrol with DNA polymerases ␣ and ␦.

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Section: Resveratrol Derivatives Synthesismentioning

confidence: 99%

Specific Structural Determinants Are Responsible for the Antioxidant Activity and the Cell Cycle Effects of Resveratrol

Stivala¹,

Savio²,

Carafoli³

et al. 2001

Journal of Biological Chemistry

450

346

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“…[127][128][129][130] However, it is isolated from natural sources in trace amounts, 130) so that efficient chemical syntheses of 33h are required. 131,132) The starting materials 4-iodophenol (19j) and 3,5-dihydroxystyrene (34e) 133) were protected by benzoyl group to afford 19k and 34f in 82 and 87% yield respectively. The heterogeneous Heck reaction 12) of aryl iodide 19k and alkene 34f proceeded smoothly in the presence of PdAS-V to furnish the coupling 734 Vol.…”

Section: Efficient Synthesis Of Resveratrol Via the Heck Reaction Bymentioning

confidence: 99%

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Yamada

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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IntroductionDevelopment of immobilized and insoluble metal catalysts is of great interest in recent organic chemistry. [1][2][3][4][5][6][7][8][9] The simple recovery of catalysts by filtration and their reuses resulted in enhancing the economical evaluation of the reaction. At the same time, there is a prospect that the environmental pollution caused by residual metals in the waste fluid will be decreased. Although a great deal of effort has been made to carry out such ideal reactions using immobilized metal catalysts, what seems to be lacking is the efficiency of the catalytic systems. It is obvious that the heterogeneous catalytic systems exhibit generally lower activity than the homogeneous ones. Besides, it is expected that the activity of the catalysts decreases gradually in the recycled systems because the metal species leaches away from their supports. Taking these into consideration, we decided to concentrate on developing insoluble metal catalysts which are highly active and stable. We designed that they were still effective in the use of ppm mol eq, and in the recycled use of many times in any reaction media. To achieve the challenging theme, we have focused on the amphiphilic insoluble catalysts based on a novel concept (Chart 1).Over the past few decades, a considerable numbers of study have been made on solid-phase catalysts which were immobilized with cross-linked polystyrene resins, silica gels or metals. These catalytic systems, however, generally resulted in lower catalytic activity compared with their soluble counterparts, and were often obliged to use hazardous chlorohydrocarbon solvents. [10][11][12][13][14][15] Besides, reuse of these catalysts was often difficult owing to the gradual decline of the catalytic activity. These problems made them less practical.In traditional triphase catalysts, as I have mentioned before, a catalytic species was anchored to a linker that was immobilized to a polymer resin or silica gel (Chart 1, above). In July 2005Chem. Pharm. Bull. 53(7) 723-739 (2005)

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“…6,7) Several attempts have recently been made to synthesize resveratrol glycosides by chemical methods involving tedious protectiondeprotection procedures, and resulted in low yields. 8,9) Plant cell cultures would be useful for the practical preparation of glycosides, due to the high potential of plant glycosyltransferases to diastereoselectively produce glycosides by one-step enzymatic glycosylation.…”

mentioning

confidence: 99%

Glycosylation oftrans-Resveratrol by Plant-Cultured Cells

Imai

Kitagawa

Ishihara

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

Cited by 92 publications

References 29 publications

Specific Structural Determinants Are Responsible for the Antioxidant Activity and the Cell Cycle Effects of Resveratrol

Specific Structural Determinants Are Responsible for the Antioxidant Activity and the Cell Cycle Effects of Resveratrol

Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts

Glycosylation oftrans-Resveratrol by Plant-Cultured Cells

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