Benzyl acetate

Metabolic, Enzymatic Activity, and Transcriptomic Analysis Reveals the Mechanism Underlying the Lack of Characteristic Floral Scent in Apricot Mei Varieties.[Pubmed:33193512]

Front Plant Sci. 2020 Oct 22;11:574982.

Apricot mei, a hybrid of Prunus mume and Prunus sibirica, usually has greater cold resistance than P. mume; however, most varieties of Apricot mei lack the characteristic floral scent of P. mume. The volatile and intracellular metabolites, activity levels of key enzymes, and transcriptomes of blooming flowers were comprehensively investigated in five varieties of P. mume. Benzyl acetate and eugenol were determined to be the main components of the P. mume floral scent. However, benzyl benzoate and benzyl alcohol benzoyltransferase activity was detected in only the low-fragrance varieties "Dan Fenghou" and "Yanxing." No benzyl alcohol or benzaldehyde reductase (BAR) activity was detected in the non-fragrant variety "Fenghou." PmBAR1 and PmBAR3 were identified as the key genes responsible for BAR activity. The lack of benzyl alcohol synthesis in the "Fenghou" variety was caused by low activity of PmBAR1-Fen and low expression of PmBAR3. The 60-aa segment at the N-terminus of PmBAR3 was found to play an important role in its enzymatic activity. Correlation tests between floral scent metabolites and the transcriptomes of the five different scented varieties showed that some transcripts associated with hormones, stresses, posttranslational modifications and transporters may also play important regulatory roles in floral scent metabolism in the different varieties.

Chemoselective acid-catalyzed [4 + 2]-cycloaddition reactions of ortho-quinone methides and styrenes/stilbenes/cinnamates.[Pubmed:33179702]

Org Biomol Chem. 2020 Nov 12;18(43):8854-8866.

ortho-Quinone methides (o-QMs) generated from the corresponding Benzyl acetate precursors chemoselectively underwent the formal [4 + 2]-cycloadditions with the olefin of styrene, stilbene, or cinnamate derivatives by using different transition metal salts or Bronsted acids. Such selectivity was obtained when these olefins either separately acted as the dienophiles or were simultaneously present on the same dienophiles. Complete selectivity was also achieved between the stilbene olefin and acetylene to furnish the key chroman intermediate for the subsequent ring-closing metathesis (RCM), affording the corresponding tetracyclic 5H-dihydronaphtho[1,2-c]chromene.

Increased substrate availability reveals the potential of scentless lisianthus flowers in producing fragrant benzenoid-phenylpropanoids.[Pubmed:33161590]

Physiol Plant. 2020 Nov 7.

Lisianthus (Eustoma grandiflorum), a leading plant in the cut flower industry is scentless. Here we show that lisianthus flowers have potential to produce several fragrant benzenoid-phenylpropanoids when substrate availability is not limited. To enable hyperaccumulation of substrates for the production of volatile benzenoid-phenylpropanoids, lisianthus commercial hybrid 'Excalibur Pink' was transformed via floral dipping with a feedback-insensitive E.coli DAHP synthase (AroG*) and Clarkia breweri benzyl alcohol acetyltransferase (BEAT), under constitutive promoters. The T1 progeny of 'Excalibur Pink' plants segregated into four visual phenotypes, with pink or white colored petals and multiple or single petal layers. Interestingly, transformation with AroG* and BEAT caused no significant effect in the pigment composition among phenotypes, but did increase the levels of down-stream fragrant volatile benzenoids. All the transgenic lines exclusively accumulated methyl benzoate, a fragrant benzenoid, either in their petals or leaves. Furthermore, feeding with benzyl alcohol, resulted in the accumulation of two novel benzenoids, Benzyl acetate (the product of BEAT) and benzoate, as well as a dramatic increase in the concentrations of additional benzenoid-phenylpropanoid volatiles. Presumably, the degree of benzaldehyde overproduction after benzyl alcohol feeding in both leaves and flowers revealed their reverse conversion in lisianthus plants. These findings demonstrate the concealed capability of lisianthus plants to produce a wide array of fragrant benzenoid-phenylpropanoids, given high substrate concentrations, which could in turn open opportunities for future scent engineering. This article is protected by copyright. All rights reserved.

Olfactory and behavioral responses to acetate esters in red imported fire ant, Solenopsis invicta.[Pubmed:33089649]

Pest Manag Sci. 2020 Oct 21.

BACKGROUND: The red imported fire ant, Solenopsis invicta Buren, is one of the most successful invasive ants in the world. Previous studies indicated that Benzyl acetate and prenyl acetate elicited significant electroantennography (EAG) response in S. invicta and exhibited as attractants at certain concentrations. In addition, the easy commercial availability, low cost, and low mammalian toxicity make acetate esters ideal candidates to screen for potential use in S. invicta control. RESULTS: We examined the EAG and behavioral responses to 26 acetate esters in all castes of S. invicta. Our results demonstrated a large diversity of EAG tuning and behavioral responses to acetate esters in S. invicta. For linear alkyl acetate esters, EAG response was clearly affected by the carbon chain length of the alkyl group. Linear alkyl acetates with five to seven carbon chain length of the alkyl group elicited significant EAG response in S. invicta, whereas those with shorter (C1 to C4) or longer (C8 to C12) carbon chain lengths did not. Different substitutions also exhibited large variety of EAG and behavioral responses in S. invicta. CONCLUSION: Our works explored the olfactory and behavioral response of S. invicta to structurally different acetate esters, and identified two potential fire ant attractants, pentyl acetate and tran-2-hexenyl acetate, and two potential repellents, hexyl acetate and cis-3-hexenyl acetate. These compounds may be useful in developing new products for fire ant management.

Discrimination and Identification of Aroma Profiles and Characterized Odorants in Citrus Blend Black Tea with Different Citrus Species.[Pubmed:32937894]

Molecules. 2020 Sep 14;25(18). pii: molecules25184208.

Citrus blend black teas are popular worldwide, due to its unique flavor and remarkable health benefits. However, the aroma characteristics, aroma profiles and key odorants of it remain to be distinguished and cognized. In this study, the aroma profiles of 12 representative samples with three different cultivars including citrus (Citrus reticulata), bergamot (Citrus bergamia), and lemon (Citrus limon) were determined by a novel approach combined head space-solid phase microextraction (HS-SPME) with comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGC-TOFMS). A total of 348 volatile compounds, among which comprised esters (60), alkenes (55), aldehydes (45), ketones (45), alcohols (37), aromatic hydrocarbons (20), and some others were ultimately identified. The further partial least squares discrimination analysis (PLS-DA) certified obvious differences existed among the three groups with a screening result of 30 significant differential key volatile compounds. A total of 61 aroma-active compounds that mostly presented green, fresh, fruity, and sweet odors were determined in three groups with gas chromatography-olfactometry/mass spectrometry (GC-O/MS) assisted analysis. Heptanal, limonene, linalool, and trans-beta-ionone were considered the fundamental odorants associated with the flavors of these teas. Comprehensive analysis showed that limonene, ethyl octanoate, copaene, ethyl butyrate (citrus), Benzyl acetate, nerol (bergamot) and furfural (lemon) were determined as the characterized odorants for each type.

Characterization of Volatile Organic Compounds Emitted from Endophytic Burkholderia cenocepacia ETR-B22 by SPME-GC-MS and Their Inhibitory Activity against Various Plant Fungal Pathogens.[Pubmed:32824884]

Molecules. 2020 Aug 19;25(17). pii: molecules25173765.

The use of antagonistic microorganisms and their volatile organic compounds (VOCs) to control plant fungal pathogens is an eco-friendly and promising substitute for chemical fungicides. In this work, endophytic bacterium ETR-B22, isolated from the root of Sophora tonkinensis Gagnep., was found to exhibit strong antagonistic activity against 12 fungal pathogens found in agriculture. Strain ETR-B22 was identified as Burkholderia cenocepacia based on 16S rRNA and recA sequences. We evaluated the antifungal activity of VOCs emitted by ETR-B22. The VOCs from strain ETR-B22 also showed broad-spectrum antifungal activity against 12 fungal pathogens. The composition of the volatile profiles was analyzed based on headspace solid phase microextraction (HS-SPME) gas chromatography coupled to mass spectrometry (GC-MS). Different extraction strategies for the SPME process significantly affected the extraction efficiency of the VOCs. Thirty-two different VOCs were identified. Among the VOC of ETR-B22, dimethyl trisulfide, indole, methyl anthranilate, methyl salicylate, methyl benzoate, benzyl propionate, Benzyl acetate, 3,5-di-tert-butylphenol, allyl benzyl ether and nonanoic acid showed broad-spectrum antifungal activity, and are key inhibitory compounds produced by strain ETR-B22 against various fungal pathogens. Our results suggest that the endophytic strain ETR-B22 and its VOCs have high potential for use as biological controls of plant fungal pathogens.

Oenological Characteristics of Fermented Apple Musts and Volatile Profile of Brandies Obtained from Different Apple Cultivars.[Pubmed:32503312]

Biomolecules. 2020 Jun 3;10(6). pii: biom10060853.

Volatile profile of spirits is the most important factor, because it can contribute to pleasant flavor. The aim of the study was to determine the impact of dessert apple cultivar used for fermentation on the concentration of volatile compounds in apple spirits. SPME-GC-MS (solid-phase microextraction- gas chromatography- mass spectrometry) method enables the detection of 69 substances and GC-FID (gas chromatography - flame ionization detector) 31 compounds. Characteristic volatiles for brandies obtained from Topaz were limonene, myrcene, methyl valerate and 1,1-diethoxy-propane, from Rubin-beta-citronellol and isopropyl acetate, Elise-limonene, myrcene Benzyl acetate and isopropyl acetate, Szampion-beta-citronellol, Idared-1,1-diethoxy-propane and Jonagored-ethyl trans-4-decanoate. Of the ten analyzed apple spirits, those obtained from Topaz, Rubin and Elise cultivars demonstrated the most diverse profile of volatile compounds. Moreover, their oenological parameters that are the most important in the production of alcoholic beverages were the most favorable. On the other hand, the content of sugars was relatively low in Elise must, while it was highest in Topaz must, which later on translated into differences in alcohol content. Brandies obtained from Gloster contained the smallest concentrations of esters and terpenes. Results of the sensory analysis showed that highest rated brandies were obtained from Topaz, Rubin, Elise and Florina.

Colletotrichum gloesporioides inhibition using chitosan-Ruta graveolens L essential oil coatings: Studies in vitro and in situ on Carica papaya fruit.[Pubmed:32402917]

Int J Food Microbiol. 2020 Aug 2;326:108649.

In this study we assessed the efficacy of chitosan (CHI) (2%) emulsion added with Ruta graveolens L. essential oil (REO) at different concentrations (0.5%, 1.0% and 1.5%) to control C. gloesporioides grows both "in situ" and "in vitro" in papaya Maradol (Carica papaya L.). In vitro studies showed a decrease on fungal growth (mycelia diameter) with the increase of REO concentration, while 0.5% of REO induce a reduction of 56.42%, REO at 1.0% and 1.5% induced a reduction of 97%. Microscopic analysis showed irreversible deleterious morphological and ultrastructural alterations as well as changes in conidia morphology, and conidia germination inhibition up to 90%. Among the most abundant REO constituents, 2-Nonanol showed strong antifungal activity followed by 2-Undecanone, Benzyl acetate, 2-Nonanone, 2-Tridecanone and 2-Dodecanone. Studies "in situ" on papaya fruit during 12 days at 20 degrees C, showed a reduction of the C. gloesporioides lesion expansion by 50% using CHI-REO 0.5% emulsions and by 100% with treatments of CHI-REO 1.0 and 1.5%, in addition the emulsions were efficacious to reduce the fruit surface microbiota. On the other hand, physicochemical analysis of the papaya fruits demonstrated that CHI-REO emulsions treatment delayed papaya ripening without affecting the organoleptic characteristics. All these results demonstrated for the first time the application of coatings CHI-REO as a postharvest treatment for the control of anthracnose on papaya fruit.

Effect of the type of wood used for ageing on the volatile composition of Pedro Ximenez sweet wine.[Pubmed:31960973]

J Sci Food Agric. 2020 Apr;100(6):2512-2521.

BACKGROUND: The present study investigated the volatile composition of a Pedro Ximenez sweet wine that had been aged in barrels made of different types of wood (Spanish oak, French oak, American oak and chestnut) and subjected to different degrees of toasting (medium toasting and intense toasting). The analyses were carried out using stir bar sorptive extraction gas chromatography-mass spectrometry after validation of the matrix in this case. RESULTS: Good values of linearity, precision, limits of detection and limits of quantification were obtained for the 36 compounds studied, six of which were identified for the first time in Pedro Ximenez (propyl acetate, cis-3-hexenyl acetate, Benzyl acetate, guaiacol, trans-whiskeylactone and 4-ethylguaiacol). The volatile composition of the samples varied as the ageing process progressed, and higher volatile concentrations were obtained in samples aged in barrels that had been intensely toasted compared to in those with medium toasting. A multivariate statistical study allowed the samples to be correctly classified according to ageing time, wood toasting and the type of wood used for ageing. CONCLUSION: The organoleptic analysis performed on the Pedro Ximenez sweet wine samples resulted in differences between the wines aged in the different types of wood during the early weeks of ageing, and scarce differences towards the end of the study period. At the end of the process, all of the wines were better valued and wines aged in medium toasted barrels were the best rated by the panel of judges for all four woods under investigation. This fact could indicate the suitability of alternative woods for the ageing of Pedro Ximenez sweet wines. (c) 2020 Society of Chemical Industry.

A Comparative Analysis of Floral Scent Compounds in Intraspecific Cultivars of Prunus mume with Different Corolla Colours.[Pubmed:31905838]

Molecules. 2019 Dec 30;25(1). pii: molecules25010145.

Prunus mume is the only fragrant flowering species of Prunus. According to the previous studies, Benzyl acetate and eugenol dominate its floral scent. However, the diversity of its floral scents remains to be elucidated. In this work, the floral volatiles emitted from eight intraspecific cultivars of P. mume with white, pink and red flowers, were collected and analyzed using headspace solid-phase microextraction combined with gas chromatograms-mass spectrometry (HS-SPME-GC-MS). In total, 31 volatile compounds were identified, in which phenylpropanoids/benzenoids accounted for over 95% of the total emission amounts. Surprisingly, except for Benzyl acetate and eugenol, several novel components, such as benzyl alcohol, cinnamyl acohol, cinnamy acetate, and benzyl benzoate were found in some cultivars. The composition of floral volatiles in cultivars with white flowers was similar, in which Benzyl acetate was dominant, while within pink flowers, there were differences of floral volatile compositions. Principal component analysis (PCA) showed that the emissions of benzyl alcohol, cinnamyl alcohol, Benzyl acetate, eugenol, cinnamyl acetate, and benzyl benzoate could make these intraspecific cultivars distinguishable from each other. Further, hierarchical cluster analysis indicated that cultivars with similar a category and amount of floral compounds were grouped together. Our findings lay a theoretical basis for fragrant plant breeding in P. mume.

Fighting on two fronts: Elevated insect resistance in flooded maize.[Pubmed:31411732]

Plant Cell Environ. 2020 Jan;43(1):223-234.

To grow and thrive plants must be able to adapt to both adverse environmental conditions and attack by a variety of pests. Elucidating the sophisticated mechanisms plants have developed to achieve this has been the focus of many studies. What is less well understood is how plants respond when faced with multiple stressors simultaneously. In this study, we assess the response of Zea mays (maize) to the combinatorial stress of flooding and infestation with the insect pest Spodoptera frugiperda (fall armyworm). This combined stress leads to elevated production of the defence hormone salicylic acid, which does not occur in the individual stresses, and the resultant salicylic acid-dependent increase in S. frugiperda resistance. Remodelling of phenylpropanoid pathways also occurs in response to this combinatorial stress leading to increased production of the anti-insect C-glycosyl flavones (maysins) and the herbivore-induced volatile phenolics, Benzyl acetate, and phenethyl acetate. Furthermore, changes in cellular redox status also occur, as indicated by reductions in peroxidase and polyphenol oxidase activity. These data suggest that metabolite changes important for flooding tolerance and anti-insect defence may act both additively and synergistically to provide extra protection to the plant.

Metabolism of Odorant Molecules in Human Nasal/Oral Cavity Affects the Odorant Perception.[Pubmed:31254383]

Chem Senses. 2019 Sep 7;44(7):465-481.

In this study, we examined the mode of metabolism of food odorant molecules in the human nasal/oral cavity in vitro and in vivo. We selected 4 odorants, 2-furfurylthiol (2-FT), hexanal, Benzyl acetate, and methyl raspberry ketone, which are potentially important for designing food flavors. In vitro metabolic assays of odorants with saliva/nasal mucus analyzed by gas chromatography mass spectrometry revealed that human saliva and nasal mucus exhibit the following 3 enzymatic activities: (i) methylation of 2-FT into furfuryl methylsulfide (FMS); (ii) reduction of hexanal into hexanol; and (iii) hydrolysis of Benzyl acetate into benzyl alcohol. However, (iv) demethylation of methyl raspberry ketone was not observed. Real-time in vivo analysis using proton transfer reaction-mass spectrometry demonstrated that the application of 2-FT and hexanal through 3 different pathways via the nostril or through the mouth generated the metabolites FMS and hexanol within a few seconds. The concentration of FMS and hexanol in the exhaled air was above the perception threshold. A cross-adaptation study based on the activation pattern of human odorant receptors suggested that this metabolism affects odor perception. These results suggest that some odorants in food are metabolized in the human nasal mucus/saliva, and the resulting metabolites are perceived as part of the odor quality of the substrates. Our results help improve the understanding of the mechanism of food odor perception and may enable improved design and development of foods in relation to odor.

The Use of Enteric Capsules for Releasing a Fragrance over an Extended Period of Time.[Pubmed:31061376]

Chem Pharm Bull (Tokyo). 2019;67(5):493-497.

A system for releasing a fragrance, citral (CR) over an extended period of time using three types of enteric capsules is reported. The L- and M-type capsules released CR into media with a pH above 6, while the H-type capsule released CR at a pH above 7. The pH of the releasing medium was controlled by sodium borate (SB), i.e., by adding SB-methylcellulose (MC) prepared in different weight ratios (SB-MC 1 : 2, 1 : 1 and 2 : 1) to tablets and by compressing them at different pressures. The tablet containing a large amount of SB and that was pressed at higher pressures permitted the pH of the releasing medium to be changed from 5 to 9, at 4-5 h after the addition of SB to the tablets, while negligible changes were observed for tablets containing low amounts of SB and which were compressed at lower pressures. Reflecting these pH changes, CR was released after different periods of time when SB-MC tablets and capsules containing CR were simultaneously added to the releasing medium. When enteric capsules containing CR and the pH adjusting tablets were simultaneously added to a Benzyl acetate (BA) solution, BA was released at a constant rate, while CR was released for different periods of time depending on the type of capsule used. The results suggest that fragrances could be released over different time frames by using enteric capsules and pH adjusting agents, for example, the release of fragrances with sedative effects at night time and with stimulating effects in the morning.

Nocturnal floral scent profiles of Myrtaceae fruit crops.[Pubmed:30939396]

Phytochemistry. 2019 Jun;162:193-198.

Communication between plants and nocturnal pollinators in low light conditions is mainly guided by floral scents, which is well documented for plants pollinated by bats, moths, and beetles. Just recently, nocturnal bees have been added to the list of pollinators known to respond to floral scents of their host plants. Little is known about the floral scent chemistry of plants visited and pollinated by nocturnal bees. Among these plants are economically important fruit crops of the family Myrtaceae. We aimed to analyze the nocturnal floral scent profiles of 10 species of Myrtaceae (only diurnal P. cattleianum was sampled after sunrise) and address the following questions: i) What are the main floral scent compounds emitted by the species? ii) Are the floral scent profiles similar to those described for other species pollinated by nocturnal bees? Floral scents were collected by dynamic headspace and analyzed by GC-MS (gas chromatography - mass spectrometry). The total amount of scent trapped ranged from 74 ng/flower/hour for Syzygium malaccense to 7556 ng/flower/hour for Eugenia dysenterica. A total of 46 floral scent compounds were detected in the samples with the most abundant compounds being the aromatics benzaldehyde, benzyl alcohol, 2-phenylethanol, methyl salicylate, 2-phenylethyl acetate, and Benzyl acetate; the aliphatic compound 1-octanol; and the monoterpene linalool. The different species exhibited different relative scent patterns. Overall, the nocturnal scents of the studied species of Myrtaceae are dominated by aromatic compounds, which is in contrast to the scent profiles described for other plants pollinated by nocturnal bees.