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The known antimicrobially active oxygenated terpenes, carvone, terpinen-4-ol, α-terpineol, carveol and myrtenol were found to cause significant K+ leakage from E. coli cells. In contrast, the relatively inactive oxygenated terpenes, 1,8-cineole and p-menth-6-ene-2,8-diol, did not cause significant K+ leakage. Slight structural differences between active terpenes were found to affect the rate of K+ leakage from E. coli cells. The membrane permeabilizing effect of the active terpenes is considered a significant factor in their antimicrobial activity.

Four pairs of oxygenated terpenes, with closely related chemical structures but considerably different minimum inhibitory concentration values (1) against P. aeruginosa or E. coli, showed differences in rate of cells killed over 2 h. Addition of polymyxin B nonapeptide (PMBN) as an outer membrane permeabilising agent was found to significantly increase the initial rates and overall numbers of cells killed for all compounds. The hydrocarbon limonene and the ester geranyl acetate, normally inactive, were also investigated. Both compounds had little killing effect when added alone to the cells but did show an enhanced killing capacity upon the addition of PBMN.

Consumption of certain phenolics in the diet is considered beneficial to human health. In this study, individual phenolics were measured by diode-array HPLC at monthly intervals in the peel of Granny Smith, Lady Williams, and Crofton apple cultivars stored in air at 0 degrees C for 9 months. The concentrations of total phenolics significantly differed among the cultivars examined, with Lady Williams peel having significantly more phenolics (over 4000 microg x g(-1) peel fresh weight) than Crofton (2668 microg x g(-1) peel fresh weight) and Granny Smith, which had the lowest concentration of total phenolics (1275 microg x g(-1) peel fresh weight). There were also significant differences in individual phenolics among cultivars and during storage. Quercetin glycosides were the only flavonols identified, with quercetin rhamnoglucoside being the most abundant phenolic in the peel. Chlorogenic acid was the major cinnamic acid derivative, with high concentrations, up to 412 microg x g(-1)) peel fresh weight, in Crofton peel. A pre-storage diphenylamine (DPA) treatment had few significant effects on peel phenolic metabolism. Where differences did occur, fruit treated with DPA retained higher concentrations of total peel phenolics during storage than fruit not treated with DPA. Storage of all cultivars for up to 9 months in air at 0 degrees C induced few significant changes in the peel phenolic concentrations. This indicates that phenolic metabolism in apple peel is relatively stable, and the health benefits of phenolics in apple peel should be maintained during long-term storage.

Two germacradienols, 4-β-hydroxygermacra-1(10),5-diene (β-germacrenol) and 6-α-hydroxygermacra-1(10), 4-diene (kunzeaol) were identified in the solvent extracts of members of the family Myrtaceae. Acid solvolysis associated with steam distillation or leaf ageing causes these germacradienols to rearrange to a mixture of (+)-δ-cadinene, α-cadinol, τ-cadinol, α-muurolol, τ-muurolol and associated sesquiterpenoids. Copyright © 2001 John Wiley & Sons, Ltd.

The sesquiterpenoids (+)-δ-cadinene, epicubenol and cubenol in the essential oils of the Myrtaceae are by-products of the acid-solvolysis of the sesquiterpene alcohols cubebol and epicubebol. This solvolysis can occur during leaf ageing or steam distillation. Significant proportions of these compounds can be found in many members of the Myrtaceae, most notably commercial tea tree (Melaleuca alternifolia and M. linariifolia). Copyright © 2000 John Wiley & Sons, Ltd.

The steam distillates of the family Myrtaceae are often found to contain the three isomeric sesquiterpene alcohols, β-, β- and γ-eudesmol. Associated with these alcohols but not steam-distilled with them are two hydrates of eudesmol, cryptomeridiol and 4-epicryptomeridiol, compounds which have not been previously reported in the Myrtaceae. These five alcohols are the major by-products of the hydrolysis of hedycaryol, which can occur during leaf ageing or distillation. The use of H218O during distillation implicated the presence of hedycaryol prior to distillation by trapping the eudesmyl-carbocation formed during the hydrolysis. Copyright © 2000 John Wiley & Sons, Ltd.

The minimum inhibitory concentrations (MIC) of 60 terpenoids against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus and Candida albicans have been determined. Hierarchical cluster analysis was used to group the compounds into five groups according to their activity patterns against the four microorganisms. K-Means cluster analysis was then used to confirm these groupings and to show the differences in the activity patterns of the groups. Ten molecular properties of the terpenoids, either calculated via molecular modelling or determined by direct measurement, were then used as variables in a forward stepwise discriminant analysis to identify which variables discriminated between groups. Low water solubility of Group IV compounds, mainly hydrocarbons and acetates, was found to be associated with their relative inactivity. The remaining groups, all containing oxygenated terpenoids, showed characteristic but distinct activity patterns towards the four test organisms. Hydrogen bonding parameters were found to be associated with antimicrobial activity in all cases. Activity against Gram-negative E. coli and P. aeruginosa was associated with a combination of a hydrogen bonding and size parameters. This was not found to be the case for the Gram-positive S. aureus or the yeast C. albicans. Copyright © 1999 John Wiley & Sons, Ltd.

The presence of terpinen-4-ol in the steam distillates from Melaleuca argentea, M. dissitiflora and M. linariifolia can be linked to high levels of (+)-sabinene and cis- and trans-sabinene hydrate in the leaf material. Incorporation of 18O into the terpinen-4-ol from steam distillates performed in H2 18O confirms the generation of the terpinen-4-yl carbocation intermediate from (+)-sabinene and cis- and trans-sabinene hydrate. This same mechanism is also operating during leaf aging.

(Z)-β-ocimene has been found to occur in amounts of 85% in foliage of Homoranthus montanus Craven and S. R. Jones and 69–71% in H. flavescens Cunn. ex. Schauer. (E)-β-ocimene also occurred in amounts of 5–9% and 2–5% respectively. The oil yield in both cases was 0.3–0.5% based on fresh leaves.

A hydrodistilled oil obtained from the leaves of Leucas milanjiana Gurke (Lamiaceae) was analysed by capillary GC and GC-MS. The leaf volatile oil contained 30 components, out of which 26 were identified. The predominant components were found to be β-cubebene (38.15%), α-pinene (19.71%), trans-caryophyllene (7.41%) and α-terpinolene (5.34%). The results are qualitatively and quantitatively at variance with data on other Leucas species and may therefore be of some chemotaxonomic significance for the genus. Copyright © 2006 John Wiley & Sons, Ltd.

Changes in the aroma volatiles, free amino acids, sugars, principal acids, and soluble minerals were studied during the development and ripening of the fruit of Cucumis melo L. Reticulatis group cv. Makdimon. Ethyl acetate was the most abundant volatile produced during the final growth stage, but ethanol was the major volatile found in immature fruit. Most of the free amino acids exhibited increases in concentration as the fruit underwent the ripening process. Sucrose, although absent in immature fruit, showed a dramatic increase during ripening to become the major carbohydrate constituent in the ripe fruit. The changes in total soluble solids during ripening showed close correlation with those found for pH, certain amino acids, and the elements sodium and potassium. Sucrose concentration has been shown to be an important fruit quality indicator, so these further correlations suggest that some of these parameters may be significant additional determinants of eating quality. Keywords: Melons; fruit develop...

Steam distillation of young leaves of Melaleuca alternifolia in 18O-labelled water resulted in the 180-labelling of the principal oxygenated p-menthanes, terpinen-4-ol and α-terpineol. The p-methanes; terpinen-4-ol, γ-terpinene, α-terpinene, terpinolene and p-cymene, found in M. alternifolia oil are primarily formed from cis-sabinene hydrate and to a lesser extent from trans-sabinene hydrate and sabinene. The pattern of the p-menthanes and the enantiomeric composition of terpinen-4-ol found in young and old leaves, regardless of the isolation process are similar to those formed during the acid catalyzed transformations of sabinene or sabinene hydrate. The incorporation of 180 into terpinen-4-ol during steam distillation in H2 18O supports the formation of terpinen-4-ol and the other p-menthanes from the terpinen-4-yl cation, generated from the hydration of sabinene and/or sabinene hydrate. This same mechanism appears to operate during leaf aging. Around 60% of the terpinen-4-ol obtained from the ...

The concentrations and enantiomeric purity of the major monoterpene constituents in a number of Melaleuca alternifolia (tea tree) oils have been determined by enantioselective gas chromatography. Consrstent enantiomeric ratios of 65:35 (+:-) for terpinen-4-ol and 76:24 (+:-) for a-terpineol were observed for the range of oils analyzed. Attempts to validate these ratios in the intact oil by 1 H NMR together with chiral lanthanide shift reagents have not yet been successful. 1 H NMR was, however, successful in confirming the enantiomeric purity determined by gas chromatography of standard terpinen4-ol [79:21 (+:-)] and α-terpineol [35:65 (+:-)] samples

A simple, rapid method for the extraction of cotton terpenoid aldehydes from green tissues and seed is described. Samples were treated by ultrasonification with acidified acetonitrile/water followed by centrifugation. The resulting extract was injected directly onto a C18 HPLC column and no sample concentration or further cleanup steps were required. The level of gossypol, the most labile of the target analytes, decreased by only 2% after 12 h of storage at room temperature, thus enabling automated analysis of individual terpenoid aldehydes by HPLC. The method gives excellent reproducibility and enables large numbers of samples to be screened quickly and accurately. Keywords: Terpenoid aldehydes; gossypol stability; cotton; Gossypium; HPLC

Analysis of the volatile constituents of melon by HRGC-MS has led to the identification of a number of compounds not previously reported in other varieties. These compounds include a range of thioether and several diesters derived from butane-2,3-diol and propane-1,2-diol. The properties of the thioethers esters are of considerable sensory importance and hence play a role in determining consumer preference.

Separation, dosage et identification, par chromatographie gazeuse sur colonne capillaire et spectrometrie de masse. Tous les composes identifies sont des mono- ou sesquiterpenes, dont les pinenes, le germacrene D et le bicyclogermacrene. La maturation des fruits n'a pas d'incidence sur leurs teneurs en composes volatils