Identification of male-produced aggregation pheromone of the curculionid beetle Acrotomopus atropunctellus.

The sugarcane stem weevil, Acrotomopus atropunctellus (Boheman) (Curculionidae: Molytinae: Cholini) is an important economic pest from the Northwestern region of Argentina. Analyses of the headspace volatiles produced by separated males and females revealed one male-specific compound. Its structural identification is reported here in using gas chromatography coupled with mass spectroscopy analysis and chemical micro-reactions. Besides, two laboratory olfactometry assays allowed us to propose 6-methyl-5-hepten-2-one (sulcatone) as an aggregation pheromone for this insect, being attractive to both conspecific males and females. This compound is reported for the first time as involved in the Curculionidae family communication.

Antiradical activity of gallic acid included in lipid interphases.

Polyphenols are well known as antioxidant agents and by their effects on the hydration layers of lipid interphases. Among them, gallic acid and its derivatives are able to decrease the dipole potential and to act in water as a strong antioxidant. In this work we have studied both effects on lipid interphases in monolayers and bilayers of dimyristoylphosphatidylcholine. The results show that gallic acid (GA) increases the negative surface charges of large unilamellar vesicles (LUVs) and decreases the dipole potential of the lipid interphase. As a result, positively charged radical species such as ABTS(+) are able to penetrate the membrane forming an association with GA. These results allow discussing the antiradical activity (ARA) of GA at the membrane phase which may be taking place in water spaces between the lipids.

Interaction of chlorogenic acid with model lipid membranes and its influence on antiradical activity.

Chlorogenic acid (CGA) is a strong phenolic antioxidant with antibacterial properties composed by a caffeoyl ester of quinic acid. Although a number of benefits has been reported and related to interactions with the red blood cell membranes, details on its membrane action and how composition and membrane state may affect it, is not yet well defined. In this work, the interaction of CGA with lipid monolayers and bilayers composed by 1,2-dimiristoyl-sn-glycero-3-phosphocholine (DMPC); 1,2-di-O-tetradecyl-sn-glycero-3-phosphocholine (14:0 diether PC); 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-di-O-hexadecyl-sn-glycero-3-phosphocholine (16:0 diether PC) were studied at different surface pressures (π). The kinetics of interaction was found to be more rapid in DMPC than in the absence of carbonyl groups. Measurements by FTIR-ATR at different water activities confirm specific interactions of CGA with carbonyl and phosphate groups affecting water level along hydrocarbon region. The antioxidant activity of CGA in the presence of DMPC unilamellar vesicles, evidenced by the absorbance reduction of the radical cation ABTS•+, is significantly different with respect to aqueous solution. The influence of CGA on antiradical activity (ARA) with lipid membranes depending on the hydration state of the lipid interface is discussed.

Cooked garlic and antioxidant activity: Correlation with organosulfur compound composition.

The antioxidant properties and the main beneficial organosulphur compounds of home-cooked garlic samples were studied in order to establish relationships between them. Antioxidant activity was tested by free radical scavenging against 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and 2,2'-azino-bis-(3-ethylbenzo-thiazoline-6-sulfonic acid) diammonium salt (ABTS+), Fe(III) reducing ability (FRAP) and linoleic acid co-oxidation initiated by soybean lipoxygenase in a micelle system. DPPH, ABTS and FRAP assays showed the highest activity for raw garlic samples, while ß-carotene bleaching assay yielded the highest activity for stir-fried garlic. Pure organosulphur compounds tested by DPPH, FRAP and ß-carotene bleaching assays showed that allicin had an antiradical action mechanism, as well as iron reducing capacity; while antioxidant activity was the main mechanism for ajoenes and 2-VD. To our knowledge, this study is the first demonstration that home-cooked garlic retains its antioxidant activity, and, at the same time, elucidates the mechanisms involved in this activity.

Carotenoid composition and vitamin A value of an Argentinian squash (Cucurbita moschata).

The carotenoid composition of butternut squash (Cucurbita moschata) cultivated in the province of Santiago del Estero, Argentina, was determined. The main carotenoids isolated were identified as beta-carotene (beta,beta-carotene), alpha-carotene (beta,epsilon-carotene), and lutein (beta,epsilon-carotene-3,3'-diol) and the minor carotenoids, as phytofluene (7,8,11,12,7',8'-hexahydro-psi,psi-carotene), zeta-carotene (7,8,7',8'-tetrahydro-psi,psi-carotene), neurosporene (7,8-dihydro-psi,psi-carotene), violaxanthin (5,6,5',6'- diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene-3,3'-diol) and neoxanthin (5,6-epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-beta,beta- carotene-3,5,3'-triol). In some samples, 5,6,5',6'-beta-carotene diepoxide, (5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene) and flavoxanthin (5,8-epoxy-5,8-dihydro-beta,epsilon-carotene-3,3'-diol) were detected. The presence of cis-isomers of beta,beta-carotene was also detected by HPLC. The vitamin A value obtained was 432 micrograms RE/100 g fresh sample, which indicates that this vegetable is an important source of provitamin A.

Surface and hysteresis properties of lipid interphases composed by head group substituted phosphatidylethanolamines.

This work analyzes the surface properties of PE-containing membranes modified at the head group region by the addition of methyl and ethyl residues at or near the amine group. These residues alter the lipid-lipid and lipid-water interactions by changes in the hydrogen bonding capability and the charge density of the amine group thus affecting the electrostatic interaction. The results obtained by measuring the dipole potential, the zeta potential, the area per lipid and the compressibility properties allow to conclude that the H-bonding capability prevails in the lipid-lipid interaction. The non polar groups attached to the C2-carbon of the ethanolamine chain introduces a steric hindrance against compression and increases the dipole potential. The analysis of areas suggests that lipids with methylated head groups have a much larger compressibility at expense of the elimination of hydration water, which is congruent with the broader extent of the hysteresis loop.