Design, synthesis, crystal structure, in vitro cytotoxicity evaluation, density functional theory calculations and docking studies of 2-(benzamido) benzohydrazide derivatives as potent AChE and BChE inhibitors

2-(Benzamido) benzohydrazide derivatives: synthesis from methyl anthranilate and application as potent anti-Alzheimer's agents.

Intermolecular Interactions and In Vitro Performance of Methyl Anthranilate in Commercial Sunscreen Formulations

In order to afford the required level of broad-spectrum photoprotection against UV-B and UV-A radiation, sunscreens must contain a combination of UV filters. It is important that any interactions between UV filters do not adversely affect their photostability nor the overall photostability of the sunscreen formulation. In this work, we explore the feasibility of using methyl anthranilate (MA) as an alternative to the photo-unstable UV-A filter, avobenzone. From the in vitro studies presented here, we conclude that MA does not provide sufficient UV-A protection on its own but that it is more photostable in formulation than avobenzone. In addition, we found that both octocrylene (OCR) and ethylhexyl methoxycinnamate (EHMC), two commonly used UV-B filters, can stabilize MA through quenching of its triplet states, as previously reported, which has a demonstrable effect in formulation. In contrast with previously reported observations for mixtures of EHMC and avobenzone, we found no evidence of [2+2] photocycloadditions taking place between EHMC and MA. This work demonstrates how a clear insight into the photophysics and photochemistry of UV filters, as well as the interactions between them, can inform formulation design to predict sunscreen performance.

Genetic diversity in wild species and cultivars of strawberry for the FanAAMT gene controlling fruit flavor volatiles

Background. An important consumer trait of strawberry fruits is their aroma. Methyl anthranilate makes a considerable contribution to the fruit flavor. The methyl anthranilate content in strawberry fruits is controlled by the FanAAMT (аnthranilic acid methyltransferase) gene. Identification of genetic determinants for this trait facilitates targeted selection of promising forms based on diagnostic DNA markers. The purpose of this study was to study the allelic diversity of the FanAAMT fruit flavor gene in wild strawberry species and strawberry cultivars for identification of promising genotypes.Materials and methods. The objects of this study were wild species of Fragaria L. as well as F. × anaschata Kantor. and F. × ananassa Duch. cultivars of different ecogeographic origin. The FanAAMT gene was identified with the dominant marker FanAAMT.Results and conclusion. In the analyzed collection of strawberry genotypes, the FanAAMT gene was identified in 36.4% of the forms, including the wild species F. vesca L., F. moschata Duch. and F. virginiana subsp. platypetala (Rydb.) Staudt, and cv. ‘Kupchikha’ (F. × anaschata). Among the analyzed F. × ananassa cultivars, the FanAAMT gene was found in 31.6% of the tested forms, specifically in 27.3% of the 22 Russian cultivars, and 37.5% of the analyzed foreign ones. Promising sources of high methyl anthranilate content in fruits were identified: wild spp. F. moschata, F. vesca, and F. virginiana subsp. platypetala; cv. ‘Kupchikha’ (F. × anaschata); Russian garden strawberry cvs. ‘Bylinnaya’, ‘Zenit’, ‘Lastochka’, ‘Neznakomka’, ‘Feyerverk’ and ‘Tsarskoselskaya’; and foreign garden strawberry cvs. ‘Karmen’, ‘Ostara’, ‘Samson’, ‘Symphony’, ‘Troubadour’ and ‘Vima Tarda’, in which the functional allele of the FanAAMT gene was found. In the remaining studied strawberry genotypes the marker FanAAMT was not detected, which presumably indicates that the FanAAMT gene is absent. cells (R9.4.1).

Genetic Analysis of Methyl Anthranilate, Mesifurane, Linalool, and Other Flavor Compounds in Cultivated Strawberry (Fragaria × ananassa)

The cultivated strawberry (Fragaria × ananassa) is an economically important fruit crop that is intensively bred for improved sensory qualities. The diversity of fruit flavors and aromas in strawberry results mainly from the interactions of sugars, acids, and volatile organic compounds (VOCs) that are derived from diverse biochemical pathways influenced by the expression of many genes. This study integrates multiomic analyses to identify QTL and candidate genes for multiple aroma compounds in a complex strawberry breeding population. Novel fruit volatile QTL was discovered for methyl anthranilate, methyl 2-hexenoate, methyl 2-methylbutyrate, mesifurane, and a shared QTL on Chr 3 was found for nine monoterpene and sesquiterpene compounds, including linalool, 3-carene, β-phellandrene, α-limonene, linalool oxide, nerolidol, α-caryophellene, α-farnesene, and β-farnesene. Fruit transcriptomes from a subset of 64 individuals were used to support candidate gene identification. For methyl esters including the grape-like methyl anthranilate, a novel ANTHANILIC ACID METHYL TRANSFERASE–like gene was identified. Two mesifurane QTL correspond with the known biosynthesis gene O-METHYL TRANSFERASE 1 and a novel FURANEOL GLUCOSYLTRANSFERASE. The shared terpene QTL contains multiple fruit-expressed terpenoid pathway-related genes including NEROLIDOL SYNTHASE 1 (FanNES1). The abundance of linalool and other monoterpenes is partially governed by a co-segregating expression-QTL (eQTL) for FanNES1 transcript variation, and there is additional evidence for quantitative effects from other terpenoid-pathway genes in this narrow genomic region. These QTLs present new opportunities in breeding for improved flavor in commercial strawberry.

Engineering of Saccharomyces cerevisiae for anthranilate and methyl anthranilate production

Background Anthranilate is a platform chemical used by the industry in the synthesis of a broad range of high-value products, such as dyes, perfumes and pharmaceutical compounds. Currently anthranilate is produced via chemical synthesis from non-renewable resources. Biological synthesis would allow the use of renewable carbon sources and avoid accumulation of toxic by-products. Microorganisms produce anthranilate as an intermediate in the tryptophan biosynthetic pathway. Several prokaryotic microorganisms have been engineered to overproduce anthranilate but attempts to engineer eukaryotic microorganisms for anthranilate production are scarce. Results We subjected Saccharomyces cerevisiae, a widely used eukaryotic production host organism, to metabolic engineering for anthranilate production. A single gene knockout was sufficient to trigger anthranilate accumulation both in minimal and SCD media and the titer could be further improved by subsequent genomic alterations. The effects of the modifications on anthranilate production depended heavily on the growth medium used. By growing an engineered strain in SCD medium an anthranilate titer of 567.9 mg l−1 was obtained, which is the highest reported with an eukaryotic microorganism. Furthermore, the anthranilate biosynthetic pathway was extended by expression of anthranilic acid methyltransferase 1 from Medicago truncatula. When cultivated in YPD medium, this pathway extension enabled production of the grape flavor compound methyl anthranilate in S. cerevisiae at 414 mg l−1. Conclusions In this study we have engineered metabolism of S. cerevisiae for improved anthranilate production. The resulting strains may serve as a basis for development of efficient production host organisms for anthranilate-derived compounds. In order to demonstrate suitability of the engineered S. cerevisiae strains for production of such compounds, we successfully extended the anthranilate biosynthesis pathway to synthesis of methyl anthranilate.

The Effect of Methyl Anthranilate-Based Repellent on Chemical Composition and Selected Physiological Parameters of Sweet Cherry (Prunus avium L.)

Maturing sweet cherry fruits are exposed to damage caused by birds. In order to repel birds from orchards, it is increasingly common to use repellents based on plant extracts and compounds that undergo complete biodegradation. One such compound is methyl anthranilate (2-aminobenzoic acid methyl ester), which has an irritating effect on birds’ senses of taste and smell. The objective of this study was to assess the effect of methyl anthranilate-based repellent (commercial name: Goose Chase/Fruit Shield) on the chemical composition and selected physiological parameters of sweet cherry cv. ‘Burlat’. The repellent containing methyl anthranilate (26.4%) was applied in the form of a foliar spray seven days prior to fruit harvest at a 1% concentration (500 dm3∙ha−1 of working liquid). In the study, methyl anthranilate-based repellent was found to have no influence on the chemical composition of fruits and leaves or the selected physiological parameters of sweet cherry cv. ‘Burlat’. Moreover, the use of methyl anthranilate did not affect the cracking susceptibility of sweet cherry fruits. This compound may constitute an interesting alternative to support sweet cherry orchard protection against birds and in organic cultures.

Genetic Analysis of Methyl Anthranilate, Mesifurane, Linalool and Other Flavor Compounds in Cultivated Strawberry (Fragaria ×ananassa)

ABSTRACTThe cultivated strawberry (Fragaria ×ananassa) is an economically important fruit crop that is intensively bred for improved sensory qualities. The diversity of fruit flavors and aromas in strawberry result mainly from the interactions of sugars, acids, and volatile organic compounds (VOCs) that are derived from diverse biochemical pathways influenced by the expression of many genes. This study integrates multi-omics analyses to identify QTL and candidate genes for multiple aroma compounds in a complex strawberry breeding population. Novel fruit volatile QTL were discovered for methyl anthranilate, methyl 2-hexenoate, methyl 2-methylbutyrate, mesifurane, and a shared QTL on Chr 3 was found for nine monoterpene and sesquiterpene compounds, including linalool, 3-carene, β-phellandrene, α-limonene, linalool oxide, nerolidol, α-caryophellene, α-farnesene, and β-farnesene. Fruit transcriptomes from a subset of sixty-four individuals were used to support candidate gene identification. For methyl esters including the grape-like methyl anthranilate, a novel ANTHANILIC ACID METHYL TRANSFERASE–like gene was identified. Two mesifurane QTL correspond with the known biosynthesis gene O-METHYL TRANSFERASE 1 and a novel FURANEOL GLUCOSYLTRANSFERASE. The shared terpene QTL contains multiple fruit-expressed terpenoid pathway-related genes including NEROLIDOL SYNTHASE 1 (FanNES1). The abundance of linalool and other monoterpenes is partially governed by a co-segregating expression-QTL (eQTL) for FanNES1 transcript variation, and there is additional evidence for quantitative effects from other terpenoid-pathway genes in this narrow genomic region. These QTL present new opportunities in breeding for improved flavor in commercial strawberry.

RESTRAIN HYPERCHOLESTEROLEMIA WITH ORANGE AND MANDARIN VOLATILE AND FOLDED OILS

ABSTRACT The findings of this study proved that orange peels contain more twice oil yield over mandarin peels (0.24% and 0.12%, respectively). Concentrated orange and mandarin peel essential oils were obtained by fractional distillation. The chemical constituents of original orange and mandarin oils (OO and MO) and their fivefold (5FOO and 5FMO) were fractionated and identified by GC/MS and GC. Limonene was the major monoterpene component in orange and mandarin oils, 89.65% and 65.57%, respectively, followed by myrcene (3.95%) and γ-terpinene (23.07%) in orange and mandarin oils, respectively. Octanal (1.47%) and linalool (1.5%) were the abundant oxygenated components in orange and mandarin oils, respectively. The decrement percentages of limonene were 18.58 and19.25% in five fold orange and mandarin oils, respectively. The major oxygenated component in 5FOO was the alcoholic β- Cis-terpeneol (4.27%). The main esters of mandarin oil, methyl N-methyl anthranilate and geranyl acetate were increased to 0.45% and 1.05%, respectively in 5FMO. In general, total oxygenated compounds percentages increased by 6.9 and7.3 times after folding of orange and mandarin oils, respectively. The above mentioned oils, pure limonene and synthetic antioxidant (BHT) were orally administrated for hypercholesterolemic rats for four weeks. No significant differences were recorded among groups of rats administrated with all different tested oils in body weight gain (%) or feed intake (g) (p≤ 0.05). In general, all rat groups administrated with orange and mandarin oils and their concentrates, showed improvement in HDL levels nearly to normal level compared to the negative control. Thus, the decrement of serum cholesterol level among cholesterol-fed groups did not correlate with the amount of limonene consumed by rats and may be related to other minor components associated with limonene and shared in the antioxidant effect. The efficiency of folded oils on hypocholesterolemic rats did not affect by decreasing limonene by deterpenation process.