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To investigate the biosynthesis and stereochemistry of syringylglycerol-8-O-4′-(sinapyl alcohol) ether (SGSE), a syringyl 8-O-4′ neolignan, feeding experiments and enzyme assays using Eucommia ulmoideswere carried out. Diastereoselective formation of erythro-SGSE was found. When [8-14C]sinapyl alcohol was administered to excised shoots of E. ulmoides, 14C was incorporated into free SGSE and SGSE glucosides. In stems, incorporation into (+)-erythro-[14C]SGSE (0.037%) with 9.1% enantiomeric excess (% e.e.) was found; incorporation into the threoisomer was not detectable. Erythro-[14C]SGSE glucosides (0.047%) dominated over threoforms (0.007%) with 74.0% diastereomeric excess (% d.e.); both diastereomers were levorotatory with 32.0% e.e. and 18.3% e.e., respectively. In leaves, higher incorporation into (−)-erythro-[14C]SGSE (0.500%, 15.9% e.e.) than into the threoisomer (0.206%, 7.4% e.e.) was observed (41.6% d.e.). (−)-Erythro-[14C]SGSE glucosides (1.692%, 25.0% e.e.) were produced at higher rates than threoisomers (0.177%, 16.4% e.e.) with 81.0% d.e. In incubations of a mixture of [8-14C]sinapyl and [8-14C]coniferyl alcohols with an insoluble enzyme preparation from stems of E. ulmoides, erythro-SGSE was preferentially produced. The highest % d.e. (82.8) was observed at 60 min with the (+)-erythroisomer (21.4% e.e.) and the (−)-threoform (4.3% e.e.).

Stereochemistry and biosynthesis of guaiacylglycerol-8-O-4′-(sinapyl alcohol) ether (GGSE), an 8-O-4′ neolignan, which consists of coniferyl and sinapyl alcohol moieties, in Eucommia ulmoideswere investigated. Four 8-O-4′ neolignans, GGSE, syringylglycerol-8-O-4′-(coniferyl alcohol) ether (SGCE), guaiacylglycerol-8-O-4′-(coniferyl alcohol) ether (GGCE), and syringylglycerol-8-O-4′-(sinapyl alcohol) ether (SGSE), were synthesized. Their erythroand threodiastereomers were separated through acetonide derivatives, intermediates of the synthesis, and identified by means of nuclear magnetic resonance (NMR) spectroscopy. All of the erythro-acetonide derivatives have larger coupling constants (ca 9 Hz) for the C7-H resonances than those of the threoones (1.5–2 Hz). In the case of the four 8-O-4′ neolignans, the C7-H coupling constants of the threo-isomers are not smaller than those of the erythroones. GGSE isolated previously from this plant was identified as the erythroisomer by comparison of the 13C-NMR data with synthetic erythro-GGSE and threo-GGSE and the other 8-O-4′ neolignans mentioned as above. Administration of a mixture of [8-14C]coniferyl alcohol and [8-14C]sinapyl alcohol to excised shoots of E. ulmoideswas carried out and the incorporation of 14C into erythro-[14C]GGSE was found to be higher than that in threo-[14C]GGSE. The occurrence of diastereoselective formation of erythro-GGSE by cross coupling of coniferyl and sinapyl alcohols is suggested.

The effects of acid extracts of tomato (Lycopersicon esculentumMill.) and carrot (Daucus carotaL.) juice wastes from the food industry on the growth of five species of crops and four weeds were examined. The acid extract of the tomato juice waste promoted the shoot and root growth of tomato, Chinese cabbage, corn, and radish, but not the growth of oat seedlings. The extract did not promote the shoot growth of weeds tested, and it inhibited the root growth of the weeds that included barnyardgrass (Echinochloa oryzicolaOhwi), southern crabgrass (Digitaria ciliarisKoel.) and Japanese barnyard millet (Echinochloa utilisOhwi). The carrot juice waste was also examined as another waste from the food industry. The effect of the acid extract of carrot juice waste showed significant promoting effects on the root growth of Chinese cabbage; however, the effects on other plants were lower than that of tomato juice waste. It also did not inhibit the growth of weeds. These results suggested that the acid extract from tomato juice waste is useful as plant‐growth substances because they have a promoting effect on the shoot and root growth of crops, and an inhibitory effect on the root growth of some weeds.

A major laccase isozyme from Grifola frondosa(Lac 1) was found to be effective for decolorizing of synthetic dyes and degrading of bisphenol A. The oxidative capability of Lac 1 toward synthetic dyes and bisphenol A was enhanced in the presence of the redox mediator, 1-hydroxybenzotriazole. The major product from the degradation of bisphenol A by Lac 1 was determined to be 4-isopropenylphenol.

Jatropha seeds have gained popularity as a biodiesel fuel resource. The process of biodiesel production from the seeds, however, also creates a tremendous amount of defatted residue as a byproduct. In this study, the potential for pharmaceutical usage of extracts from the defatted residue of crushed Jatropha curcusL. seed was examined. Organic and water fractions of both ethyl acetate (EtOAc) and methanol (MeOH) extracts from the seed residue exhibited an inhibitory growth effect on the human cancer cell lines hepatocellular carcinoma (HuH-7) and breast cancer (MCF-7). Later, the effect of isoamericanol A from the MeOH-organic fraction was compared across three human cell lines in search of human cell types suitable for treatment (HuH-7, MCF-7, cervical cancer (HeLa)). Our results indicate that the effect of three-day isoamericanol A treatment differs by cell type. Although effective to some extent, HeLa cell growth was most inhibited at the smallest dosage, whereas MCF-7 growth suffered the greatest inhibition at the highest dosage. Our findings reveal possibility for utilization of the Jatropha seed residue extract as well as its active compound, isoamericanol A, as practical cancer treatments for certain cell types in the future.

Six new acylated cyanidin glycosides, cyanidin 3-O-β-(2′′-E-caffeoylglucopyranosyl)-(1→2)-O-β-galactopyranoside (1), cyanidin 3-O-β-(2′′-E-caffeoylglucopyranosyl)-(1→2)-O-β-(6′′-malonylgalactopyranoside) (2), cyanidin 3-O-β-(2′′-E-caffeoylglucopyranosyl)- (1→2)-O-β-(6″-succinylgalactopyranoside) (3), cyanidin 3-O-β-(2′'-E-caffeoylglucopyranosyl)-(1→2)-O-β-galactopyranoside-3′- O-β-glucuronopyranoside (4), cyanidin 3-O-β-(2′′-E-caffeoylglucopyranosyl)-(1→2)-O-β-(6′'-malonylgalactopyranoside)-3′-O-β-glucuronopyranoside (5), and cyanidin 3-O-β-(2′'-E-feruloylglucopyranosyl)-(1→2)-O-β-(6′'-malonylgalactoside)-3′-O-β-glucuronopyranoside (6), were isolated from the red flowers of two Clematiscultivars, ‘Niobe'and ‘Madame Julia Correvon'. The chemical structures of the isolated anthocyanins were determined by UV, LC-MS, HPLC, TLC, characterization of hydrolysates, and 1H and 13C NMR spectroscopy, including H-H COSY, C-H COSY, HMBC, HMQC and NOESY. The last three anthocyanins were widely distributed in 37 red flower Clematiscultivars. On the other hand, the first three compounds were found only in two cultivars. Five known flavonol glycosides, kaempferol 3-O-glucoside, kaempferol 3-O-rutinoside, quercetin 3-O-galactoside, quercetin 3-O-glucoside and quercetin 3-O-rutinoside, were isolated from the flowers of ‘Madame Julia Correvon'.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.