Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner–Wadsworth–Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%

Effect of Extraction Conditions on the Antioxidant Activity of Olive Wood Extracts

An investigation to optimize the extraction yield and the radical scavenging activity from the agricultural by-product olive tree wood (Olea europaea L., cultivar Picual) using six different extraction protocols was carried out. Four olive wood samples from different geographical origin, and harvesting time have been used for comparison purposes. Among the fifty olive wood extracts obtained in this study, the most active ones were those prepared with ethyl acetate, either through direct extraction or by successive liquid-liquid partitioning procedures, the main components being the secoiridoids oleuropein and ligustroside. An acid hydrolysis pretreatment of olive wood samples before extractions did not improve the results. In the course of this study, two compounds were isolated from the ethanolic extracts of olive wood collected during the olives' harvesting season and identified as (7 R)-7 -ethoxyoleuropein (1) and (7 S)-7 -ethoxyoleuropein (2)

Rapid Analysis of Illegal Cationic Dyes in Foods and Surface Waters Using High Temperature Direct Analysis in Real Time High-Resolution Mass Spectrometry

A high temperature desorption (HTD) direct analysis in real time-high-resolution mass spectrometric (DART-HRMS) method was developed for the rapid analysis of four banned cationic dyes. Rhodamine B is used to dye foods, while malachite green, crystal violet, and methylene blue are added to fishponds as antimicrobials. A simple induced phase separation extraction was used to pretreat samples. The DART-HRMS method employed two temperature steps, i.e., 200 °C for drying, purification, and enrichment of sample solution and 500 °C for thermal desorption and ionization of analytes. The calibration curves of dyes in the range of 50-2000 ng/mL were linear using deuterated malachite green as an internal standard. The LODs vary for all analytes between 0.1 and 30 ppb depending on the matrix and experimental conditions. Through analyses of real samples, two chili powders and one chili oil were found to be contaminated by rhodamine B. The concentrations were comparable with those found by an HPLC-MS/MS method.</p

Field Evaluation of Traditionally Used Plant-Based Insect Repellents and Fumigants Against the Malaria Vector Anopheles darlingi in Riberalta, Bolivian Amazon

Inexpensive insect repellents may be needed to supplement the use of impregnated bed-nets in the Amazon region, where the primary malaria vector, Anopheles darlingi (Root), is exophilic and feeds in the early evening. Three plants that are traditionally used to repel mosquitoes in Riberalta, Bolivian Amazon, were identified by focus group, and then they were tested against An. darlingi as well as Mansonia indubitans (Dyar & Shannon)/Mansonia titillans (Walker). Cymbopogon citratus (Staph), Guatemalan lemongrass, essential oil at 25% was used as a skin repellent, and it provided 74% protection for 2.5 h against predominantly An. darlingi and 95% protection for 2.5 h against Mansonia spp. Attalea princeps (name not verified) husks, burned on charcoal in the traditional way provided 35 and 51% protection against An. darlingi and Mansonia spp., respectively. Kerosene lamps, often used to light rural homes, were used as a heat source to volatilize 100% Mentha arvensis (Malinv ex. Bailey) essential oil, and they reduced biting by 41% inside traditional homes against Mansonia spp., although they were ineffective outdoors against An. darlingi. All three plant-based repellents provided significant protection compared with controls. Plant-based repellents, although less effective than synthetic alternatives, were shown by focus groups to be more culturally acceptable in this setting, in particular para-menthane-3, 8, idol derived from lemon eucalyptus, Corymbia citriodora (Hook). Plant-based repellents have the potential to be produced locally and therefore sold more cheaply than synthetic commercial repellents. Importantly, their low cost may encourage user compliance among indigenous and marginalized populations

The essential oil of patchouli, Pogostemon cablin : A review

The leaves of Pogostemon cablin (Blanco) Benth. (Lamiaceae) are the source of patchouli essential oil, which is - with an annual production of about 1300 tonnes - an important and unique commodity in the fragrance industry. All the literature pertaining to patchouli was critically reviewed with an emphasis on the qualitative and quantitative chemical analysis of the oil but also harvesting, fermentation, drying, distillation, used analytical techniques, sensory aspects including molecules responsible for the odour, adulteration and toxicological aspects, i.e., skin sensitisation, are discussed. In total 72 constituents have been convincingly identified in the oil and another 58 tentatively. The main constituent is the sesquiterpene patchoulol. For this review over 600 papers were consulted and in the supplementary information all patchouli-related references not relevant enough to be cited in the paper itself are listed.</p

Is Low-field NMR a Complementary Tool to GC-MS in Quality Control of Essential Oils? A Case Study : Patchouli Essential Oil *

High-field NMR is an expensive and important quality control technique. In recent years, cheaper and simpler low-field NMR has become available as a new quality control technique. In this study, 60 MHz 1 H-NMR was compared with GC-MS and refractometry for the detection of adulteration of essential oils, taking patchouli essential oil as a test case. Patchouli essential oil is frequently adulterated, even today. In total, 75 genuine patchouli essential oils, 10 commercial patchouli essential oils, 10 other essential oils, 17 adulterants, and 1 patchouli essential oil, spiked at 20% with those adulterants, were measured. Visual inspection of the NMR spectra allowed for easy detection of 14 adulterants, while gurjun and copaiba balsams proved difficult and one adulterant could not be detected. NMR spectra of 10 random essential oils differed not only strongly from patchouli essential oil but also from one another, suggesting that fingerprinting by low-field NMR is not limited to patchouli essential oil. Automated chemometric evaluation of NMR spectra was possible by similarity analysis (Mahalanobis distance) based on the integration from 0.1 – 8.1 ppm in 0.01 ppm increments. Good quality patchouli essential oils were recognised as well as 15 of 17 deliberate adulterations. Visual qualitative inspection by GC-MS allowed for the detection of all volatile adulterants. Nonvolatile adulterants, and all but one volatile adulterant, could be detected by semiquantitation. Different chemometric approaches showed satisfactory results. Similarity analyses were difficult with nonvolatile adulterants. Refractive index measurements could detect only 8 of 17 adulterants. Due to advantages such as simplicity, rapidity, reproducibility, and ability to detect nonvolatile adulterants, 60 MHz 1 H-NMR is complimentary to GC-MS for quality control of essential oils

Microfluidic Chip-Based Induced Phase Separation Extraction as a Fast and Efficient Miniaturized Sample Preparation Method

Induced phase separation extraction (IPSE) is an efficient sample clean-up technique that can replace liquid-liquid extraction (LLE). The purpose of this study was to miniaturize IPSE by carrying it out in a microfluidic chip. An IPSE chip was designed and evaluated for its ability to separate and purify samples on a microscale. The 5 × 2 cm chip was fed with a solution of polar to non-polar model compounds in acetonitrile-water (1:1). In the 100 µm wide and 40 µm deep microchannels, the sample solution was efficiently separated into two immiscible phases by adding a hydrophobic solvent as inducer. Analytes present in the sample solution each migrated to their own favorable phase upon phase separation. After optimization, extraction and fractionation were easily and efficiently achieved. The behavior of analytes with a pH-dependent partitioning could be influenced by adjusting the pH of the sample solution. Scutellaria baicalensis extract, used in Traditional Chinese Medicine (TCM), was successfully separated in aglycones and glycosides. In this microscale system, the sample and solvent consumption is reduced to microliters, while the time needed for the sample pretreatment is less than one minute. Additionally, the extraction efficiency can reach up to 98.8%, and emulsion formation is avoided.</p