beta-ionone and geranylacetone

Carotenoids and apocarotenoids function as pigments and flavor volatiles in plants that enhance consumer appeal and offer health benefits. Tomato (Solanum lycopersicum.) fruit, especially those of wild species, exhibit a high degree of natural variation in carotenoid and apocarotenoid contents. Using positional cloning and an introgression line (IL) of Solanum habrochaites "LA1777', IL8A, we identified carotenoid cleavage dioxygenase 4 (CCD4) as the factor responsible for controlling the dark orange fruit color. CCD4b expression in ripe fruit of IL8A plants was ∼8,000 times greater than that in the wild type, presumably due to 5' cis-regulatory changes. The ShCCD4b-GFP fusion protein localized in the plastid. Phytoene, ζ-carotene, and neurosporene levels increased in ShCCD4b-overexpressing ripe fruit, whereas trans-lycopene, β-carotene, and lutein levels were reduced, suggestive of feedback regulation in the carotenoid pathway by an unknown apocarotenoid. Solid-phase microextraction-gas chromatography-mass spectrometry analysis showed increased levels of geranylacetone and β-ionone in ShCCD4b-overexpressing ripe fruit coupled with a β-cyclocitral deficiency. In carotenoid-accumulating Escherichia coli strains, ShCCD4b cleaved both ζ-carotene and β-carotene at the C9-C10 (C9'-C10') positions to produce geranylacetone and β-ionone, respectively. Exogenous β-cyclocitral decreased carotenoid synthesis in the ripening fruit of tomato and pepper (Capsicum annuum), suggesting feedback inhibition in the pathway. Our findings will be helpful for enhancing the aesthetic and nutritional value of tomato and for understanding the complex regulatory mechanisms of carotenoid and apocarotenoid biogenesis.

Topics: beta Carotene; Carotenoids; Dioxygenases; Fruit; Solanum lycopersicum; zeta Carotene

Carotenoid cleavage dioxygenases (CCDs) drive carotenoid catabolism to produce various apocarotenoids and immediate derivatives with particular developmental, ecological, and agricultural importance. How

Topics: Arabidopsis; beta Carotene; Carotenoids; Dioxygenases; Norisoprenoids; Phosphates; Plant Proteins; Terpenes; Xanthophylls; Zea mays

The aim of this study was to determine the chemical composition of Urtica dioica essential oil, and to evaluate its cytotoxic and genotoxic effects, using cytogenetic tests such as the cytokinesis-block micronucleus assay and chromosomal aberration analysis in human lymphocyte cultures in vitro. GC-MS analysis of U. dioica essential oil identified 43 compounds, representing 95.8% of the oil. GC and GC-MS analysis of the essential oil of U. dioica revealed that carvacrol (38.2%), carvone (9.0%), naphthalene (8.9%), (E)-anethol (4.7%), hexahydrofarnesyl acetone (3.0%), (E)-geranyl acetone (2.9%), (E)-β-ionone (2.8%) and phytol (2.7%) are the main components, comprising 72.2% of the oil. A significant correlation was found between the concentration of essential oil and the following: chromosomal aberrations, micronuclei frequency, apoptotic cells, necrotic cells, and binucleated cells.

Topics: Cyclohexane Monoterpenes; Cymenes; Cytotoxins; Monoterpenes; Mutagens; Norisoprenoids; Oils, Volatile; Terpenes; Urtica dioica

Volatile terpenoid compounds, potentially derived from carotenoids, are important components of flavor and aroma in many fruits, vegetables and ornamentals. Despite their importance, little is known about the enzymes that generate these volatiles. The tomato genome contains two closely related genes potentially encoding carotenoid cleavage dioxygenases, LeCCD1A and LeCCD1B. A quantitative reverse transcriptase-polymerase chain reaction analysis revealed that one of these two genes, LeCCD1B, is highly expressed in ripening fruit (4 days post-breaker), where it constitutes 0.11% of total RNA. Unlike the related neoxanthin cleavage dioxygenases, import assays using pea chloroplasts showed that the LeCCD1 proteins are not plastid-localized. The biochemical functions of the LeCCD1 proteins were determined by bacterial expression and in vitro assays, where it was shown that they symmetrically cleave multiple carotenoid substrates at the 9,10 (9',10') positions to produce a C14 dialdehyde and two C13 cyclohexones that vary depending on the substrate. The potential roles of the LeCCD1 genes in vivo were assessed in transgenic tomato plants constitutively expressing the LeCCD1B gene in reverse orientation. This over-expression of the antisense transcript led to 87-93% reductions in mRNA levels of both LeCCD1A and LeCCD1B in the leaves and fruits of selected lines. Transgenic plants exhibited no obvious morphological alterations. High-performance liquid chromatography analysis showed no significant modification in the carotenoid content of fruit tissue. However, volatile analysis showed a > or =50% decrease in beta-ionone (a beta-carotene-derived C13 cyclohexone) and a > or =60% decrease in geranylacetone (a C13 acyclic product likely derived from a lycopene precursor) in selected lines, implicating the LeCCD1 genes in the formation of these important flavor volatiles in vivo.

Topics: Chloroplasts; Dioxygenases; Escherichia coli; Fruit; Gene Expression; Models, Chemical; Norisoprenoids; Plant Proteins; Plants, Genetically Modified; Reverse Transcriptase Polymerase Chain Reaction; Solanum lycopersicum; Terpenes

Changes in volatile aroma constituents of fresh-cut cantaloupe melon with storage were determined by headspace solid-phase microextraction gas chromatography-mass spectrometry. The compounds isolated from the fruit immediately after cutting were predominantly aliphatic and aromatic esters. Storage of fruit at 4 degrees C caused a considerable decrease in concentration of esters and synthesis of the terpenoid compounds beta-ionone and geranylacetone over a period of 24 h. This change in the volatile profile with storage is consistent with that of a stress-induced defense response in the cut fruit as an adaptation process to tissue exposure and cell disruption. The same effect occurred in fruit stored at 22 degrees C and in those treated with sodium azide and ascorbic acid prior to storage. Fruit treated with ascorbic acid and sodium azide had higher concentrations of beta-ionone and geranylacetone and retained these compounds better with storage time. The reduction of esters appears to be an important early reaction step in the loss of freshness during storage of fresh-cut cantaloupe.

Topics: Ascorbic Acid; Cold Temperature; Cucumis; Esters; Food Handling; Food Preservation; Fruit; Gas Chromatography-Mass Spectrometry; Norisoprenoids; Odorants; Sodium Azide; Terpenes; Volatilization