Eating five servings of fruits and vegetables per day! This is what is highly recommended and heavily advertised nowadays to the general public to stay fit and healthy! Drinking green tea on a regular basis, eating chocolate from time to time, as well as savoring a couple of glasses of red wine per day have been claimed to increase life expectancy even further! Why? The answer is in fact still under scientific scrutiny, but a particular class of compounds naturally occurring in fruits and vegetables is considered to be crucial for the expression of such human health benefits: the polyphenols! What are these plant products really? What are their physicochemical properties? How do they express their biological activity? Are they really valuable for disease prevention? Can they be used to develop new pharmaceutical drugs? What recent progress has been made toward their preparation by organic synthesis? This Review gives answers from a chemical perspective, summarizes the state of the art, and highlights the most significant advances in the field of polyphenol research.

Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis

Plant phenolics: recent advances on their biosynthesis, genetics, and ecophysiology.

A ferromagnetically coupled mn(19) aggregate with a record S=83/2 ground spin state.

This work was supported by the Foundation for Science and Technology (FCT), Portugal (projects PTDC/QUI-QUI/113687/2009 and PEst-C/QUI/UI0081/2013). A.G. (SFRH/BD/43531/2008) and M.J.M. (SFRH/BD/61262/2009) thank FCT for grants.

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Chromone: A Valid Scaffold in Medicinal Chemistry

pH directly regulates epidermal permeability barrier homeostasis, and stratum corneum integrity/cohesion.

We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 angstroms in CH2Cl2 and a catalytic amount of BF3 x Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4'-O-glycosylation, promoted with a combination of BF3 x Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1.

Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan.

The chirality of the sugar moiety is responsible for the chiral molecular recognition on formation of a metalloanthocyanin from Salvia patens. This mechanism was revealed by using the synthetic apigenin 7,4'-diglucosides derived from D- or L-glucose. The supermolecule consists of six malonylawobanin molecules (blue) coordinated to two Mg2+ ions (red) with an M-helical arrangement of six 7,4'-diglucoside molecules (yellow) intercalated.

Chiral Molecular Recognition on Formation of a Metalloanthocyanin: A Supramolecular Metal Complex Pigment from Blue Flowers of Salvia patens.

Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

Recent Progress in the Synthesis of Flavonoids: From Monomers to Supra-Complex Molecules

Synthesis of procyanidins by stepwise-and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl -4-dehydro-5,7,3',4' -tetra-O -benzyl-(+)-catechin and (-)-epicatechin as a key building monomer

Kin-ichi Oyama

Papers

Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan.

Chiral Molecular Recognition on Formation of a Metalloanthocyanin: A Supramolecular Metal Complex Pigment from Blue Flowers of Salvia patens.

Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

Recent Progress in the Synthesis of Flavonoids: From Monomers to Supra-Complex Molecules

Synthesis of procyanidins by stepwise-and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl -4-dehydro-5,7,3',4' -tetra-O -benzyl-(+)-catechin and (-)-epicatechin as a key building monomer