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ent-Eudesmane sesquiterpenoids, 8,11-dihydroxy-2,4-cycloeudesmane, 11-hydroxy-2,4-cycloeudesman-8-one and 2,4-cyclo-7(11)-eudesmen-8-one, were isolated from the wood of Platycarya strobilacea, which has been used as an aromatic tree since at least the 18th century. On charring the wood, 2,4-cyclo-7(11)-eudesmen-8-one was detected in the smoke. In the charred wood, the concentrations of ellagitannins, such as galloyl pedunculagin, dramatically decreased, whereas concentrations of pentagalloyl glucose, and other gallotannins were relatively stable. In addition, two other compounds, the 6'-O-m- and p-digalloyl oak lactone precursor and the 3-O-methylellagic acid 4'-O-(4″-O-galloyl)-xylopyranoside, were isolated from the charred wood along with m- and p-digallic acid., identifier:Phytochemistry, 72(8), pp.796-803; 2011

During black tea production, catechins and their galloyl esters are enzymatically oxidized to generate a complex mixture of black tea polyphenols. The role of galloyl ester groups in this process has yet to be determined. Enzymatic oxidation of epicatechin 3-O-gallate (1) yielded two new oxidation products, theaflavate C and bistheaflavate A, along with theaflavate A (2), a known dimer of 1 generated by coupling of the B-ring with the galloyl group. Theaflavate C is a trimer of 1 and possesses two benzotropolone moieties generated by the oxidative coupling of the galloyl groups with the catechol B-rings. Bistheaflavate A was found to be a tetramer produced by intermolecular coupling of two benzotropolone moieties of 2. From the structures of the products, it was deduced that oxidative coupling of galloyl groups resulted in extension of the molecular size of the products in catechin oxidation., identifier:Chemical & Pharmaceutical Bulletin v.55(12) p.1768-1772, 2007

This review will discuss recent progress in the chemistry of secondary polyphenols produced during food processing. The production mechanism of the secondary polyphenols in black tea, whisky, cinnamon, and persimmon fruits will be introduced. In the process of black tea production, tea leaf catechins are enzymatically oxidized to yield a complex mixture of oxidation products, including theaflavins and thearubigins. Despite the importance of the beverage, most of the chemical constituents have not yet been confirmed due to the complexity of the mixture. However, the reaction mechanisms at the initial stages of catechin oxidation are explained by simple quinone-phenol coupling reactions. In vitro model experiments indicated the presence of interesting regio- and stereoselective reactions. Recent results on the reaction mechanisms will be introduced. During the aging of whisky in oak wood barrels, ellagitannins originating from oak wood are oxidized and react with ethanol to give characteristic secondary ellagitannins. The major part of the cinnamon procyanidins is polymerized by copolymerization with cinnamaldehyde. In addition, anthocyanidin structural units are generated in the polymer molecules by oxidation which accounts for the reddish coloration of the cinnamon extract. This reaction is related to the insolubilization of proanthocyanidins in persimmon fruits by condensation with acetaldehyde. In addition to oxidation, the reaction of polyphenols with aldehydes may be important in food processing., identifier:International journal of molecular sciences, 11(1), pp.14-40; 2010

Chromatographic separation of black tea polyphenols is too difficult to supply sufficient quantities of pure compounds for biological experiments. Thus, facile methods to prepare black tea constituents were desired. Treatment of epigallocatechin gallate with copper(II) chloride efficiently afforded an unstable quinone dimer, dehydrotheasinensin A, and subsequent treatment with ascorbic acid stereoselectively yielded theasinensin A. The latter is a dimer with an R-biphenyl bond, one of the major polyphenols found in black tea. The method is simpler and more effective than enzymatic preparation., CHEMICAL & PHARMACEUTICAL BULLETIN, 59(9), pp.1183-1185; 2011

In the course of a chemotaxonomical study of Chinese Castanopsis species, two previously unknown flavan-3-ols, named sclerophynins A and B, were isolated from the leaves of C. sclerophylla, together with five related known compounds. On the basis of spectroscopic analysis, the new compounds were characterized to be (4S,8R,9S)-4-(3,4-dihydroxyphenyl)-8-(3,4,5-trihydroxyphenyl)- 3,4,9,10-tetrahydro-5,9-dihydroxy-2H,8H-benzo[1,2-b:3,4-b']dipyran-2- one and (4S,7S,8R)-4,8-bis(3,4-dihydroxyphenyl)-3,4,6,7-tetrahydro-5-glucopyranosyloxy- 7-hydroxy-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one, respectively., HETEROCYCLES, 83(10), pp.2321-2328; 2011

Two new diketopiperazine derivatives, bacillusamides A (1) and B (2), have been isolated from the EtOAc extract of the sea urchin-derived Bacillus sp. along with the known cyclo(-L-pro-L-val-) (3), cyclo(-L-pro-L-tyr-) (4), cyclo(-L-pro-L-phe-) (5). These structures were elucidated by extensive spectroscopic methods. Furthermore, the absolute configurations of the amino acid residues were determined using Marfey's method. Compound 1 displayed weak antifungal activity against Aspergillus niger., CHEMICAL & PHARMACEUTICAL BULLETIN, 59(1), pp.106-108; 2011

Black tea is rich in polyphenols and has been shown to have various health benefits; however, its components have not yet been clarified in detail. Enzymatic oxidation of epigallocatechin-3-O-gallate, the most abundant polyphenol in tea, is thought to contribute significantly to the production of black tea polyphenols. We identified theacitrin C, an unstable black tea pigment, as an enzymatic oxidation product of epigallocatechin-3-O-gallate. Degradation of theacitrin C afforded theacitrinin A and 2,3,5,7- tetrahydroxychroman-3-O-gallate. Furthermore, theacitrinin B, which was isolated from black tea, is deduced to be a degradation product of theacitrin A, the desgalloyl analogue of theacitrin C. The structures of theacitrinins A and B were elucidated based on spectroscopic data. This is the first time that a degradation product of theacitrin has been isolated from black tea. We also examined the influence of esterification of the epigallocatechin C-3 hydroxyl group on the decomposition of bicyclo[3.2.1]octane-type intermediates., Tetrahedron, 67(11), pp.2051-2059; 2011

Chemical constituents of the leaves of rabbiteye blueberry (Vaccinium ashei READE) were investigated in detail. The major phenolic components were caffeoyl quinic acids, flavonol glycosides, flavan-3-ols and proanthocyanidins. Catechins and proanthocyanidins having additional phenylpropanoid units, such as cinchonains, kandelins and mururins, characterised the polyphenols of this plant. Among them, vaccinin A, an isomer of mururin A, was found to be a new compound, and the structure was characterised by spectroscopic methods. The most abundant polyphenols (11.3% of freeze-dried leaves) were oligomeric proanthocyanidins. Thiol degradation with mercaptoethanol indicated that the polymer was constituted of (+)-catechin and (-)-epicatechin as the terminal units and (-)-epicatechin, procyanidin A-2, and cinchonains Ia and Ib as the extension units. Mass spectral analysis suggested the presence of at least dodecamers with A-type linkages and phenylpropanoid moieties., Food Chemistry, 121(4), pp.1073-1079; 2010

A new ellagitannin dimer named euscaphinin was isolated from the leaves of Euscaphis japonica (THUNB.) KANITZ. The structure of this dimer was determined on the basis of spectroscopic and chemical evidence. The resulting structure indicated that it was produced by intermolecular C-O oxidative coupling between the galloyl groups of molecules of 1(beta)-O-galloyl pedunculagin, the major ellagitannin of the leaves. The ellagitannins were not detected in the bark and wood part of the plant. This is the first example of the isolation of ellagitannins from Staphyleaceaeous plants., Chemical & Pharmaceutical Bulletin, 57(4), pp.421-423; 2009

Four new dammarane-type triterpene saponins named floranotoginsenosides A (1), B (2), C (3) and D (4), together with five known triterpene saponins, were isolated from the flowers of Panax notoginseng. Their structures were elucidated on the basis of spectral and chemical evidence., Molecules, 14(6), pp.2087-2094; 2009

Lipase and amylase inhibitory activities of black tea were examined. After solvent partitioning of a black tea extract with the ethyl acetate and n-butanol, the two soluble fractions showed comparable inhibitory activities. Activity in the ethyl acetate fraction was mainly attributable to polyphenols with low-molecular weights, such as theaflavin gallates. On the other hand, the active substance in the n-butanol layer was ascertained to be a polymer-like substance. 1H- and 13C-NMR spectra showed signals arising from the flavan A-ring and galloyl groups, although signals due to flavan B-rings were not detected, suggesting that the polymer-like substances were generated by oxidative condensation of flavan B-rings, a result which was previously deduced from our results of in vitro catechin oxidation experiments. Enzymatic oxidation of epicatechin 3-O-gallate produced a similar polymer-like substance and suggested that condensation between a B-ring and galloyl groups was involved in the polymerization reaction., Chemical & Pharmaceutical Bulletin v.56(3) p.266-272, 2008

Three new ellagitannins named balanophotannins A?C having a 1,1′-(3,3′,4,4′-tetrahydroxy)dibenzofurandicarboxyl group in their molecules and four known lignan glycosides were isolated from the extracts of fresh aboveground and underground parts of a medicinal parasitic plant Balanophora japonica (Balanophoraceae). Their structures were elucidated on the basis of spectral and chemical evidence. Chemotaxonomic significance of the known lignan glycosides in Balanophora japonica was discussed., Chemical & Pharmaceutical Bulletin v.53(3) p.339-341, 2005

Eighteen main compounds, including four norsesquiterpenoids (1?4) and 14 phenolic compounds (5?18) isolated previously from Phyllanthus emblica, together with a main constituent, proanthocyanidin polymers (19) identified at this time from the roots, were estimated for their antiproliferative activities against MK-1 (human gastric adenocarcinoma), HeLa (human uterine carcinoma), and B16F10 (murine melanoma) cells using an MTT method. All of the phenolic compounds including the major components 5?8 from the fruit juice, 8, 9, and 12 from the branches and leaves, and 19 from the roots showed stronger inhibition against B16F10 cell growth than against HeLa and MK-1 cell growth. Norsesquiterpenoid glycosides 3 and 4 from the roots exhibited significant antiproliferative activities, although their aglycon 1 and monoglucoside 2 showed no inhibitory activity against these tumor cells., Biological & Pharmaceutical Bulletin v.27(2) p.251-255, 2004