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Importance of Lactones in Food Flavors - Structure, Distribution, Sensory Properties and Biosynthesis
Abstract
Lactones are widely distributed in foods and beverages. Their presence in the aromas of more than 120 foodstuffs (fruit, meat, dairy products, beverages), and their relative importance as flavour impact compounds are reviewed. Their sensory properties, i.e. odour quality, intensity, tenacity and odour threshold, are presented in relation to their structure (4- and 5-olide, molecular weight, length of the side chain, unsaturation) and chirality. The lactone enantiomers are separated either after derivatization (formation of ester diastereoisomers, e.g. Mosher esters) or by direct chiral GC analysis on capillary substituted cyclodextrin columns. Recent data on the relative abundance of R and S enantiomers of lactones present in fruit and dairy products are given. Current knowledge on the biosynthesis and chirality of natural lactones and their link with the lipid metabolism are discussed. Oxo- and the corresponding reduced compounds, i.e. hydroxy fatty acids are likely precursors of lactones. The latter would be subsequently generated from the former through a shortening or, on the contrary, a lengthening of the carbon chain.
... These enzymes hydrolyze esters, such as phenyl acetate, but also have the notable property of hydrolyzing many aliphatic and aromatic lactones (Draganov et al., 2005). Research on the role of salivary PONs in the metabolism of lactones should be conducted in the future, as lactones are an important class of aroma molecules (Dufosse et al., 1994;Maga & Katz, 1976). ...
The oral cavity is an entry path into the body, enabling the intake of nutrients but also leading to the ingestion of harmful substances. Thus, saliva and oral tissues contain enzyme systems that enable the early neutralization of xenobi-otics as soon as they enter the body. Based on recently published oral proteomic data from several research groups, this review identifies and compiles the primary detoxification enzymes (also known as xenobiotic-metabolizing enzymes) present in saliva and the oral epithelium. The functions and the metabolic activity of these enzymes are presented. Then, the activity of these enzymes in saliva, which is an extracellular fluid, is discussed with regard to the salivary parameters. The next part of the review presents research evidencing oral metaboliza-tion of aroma compounds and the putative involved enzymes. The last part discusses the potential role of these enzymatic reactions on the perception of aroma compounds in light of recent pieces of evidence of in vivo oral metabolization of aroma compounds affecting their release in mouth and their perception. Thus, this review highlights different enzymes appearing as relevant to explain aroma metabolism in the oral cavity. It also points out that further works are needed to unravel the effect of the oral enzymatic detoxification system on the perception of food flavor in the context of the consumption of complex food matrices, while considering the impact of food oral processing. Thus, it constitutes a basis to explore these biochemical mechanisms and their impact on flavor perception.
... However, an extremely large variety of perfumes can be accessed with lactones with different structures, ranging from fruity to floral and creamy perfumes [31][32][33]. A list of available lactones with the corresponding perfume can be found in ref. [34]. Therefore, a proper selection of the lactone provides the formulation with the desired perfume. ...
Synthetic polymers are attracting growing attention as additives for laundry and personal care products. In particular, the high volatility of many common fragrances require the development of polymeric particles for their encapsulation and controlled release. Unfortunately, the vast majority of these carriers are made from polymers that are not biodegradable. This poses severe concerns about the accumulation of nano- and microplastics. Hence, such particles are expected to be banned from the market in the coming years. Therefore, biodegradable particles enabling a long-lasting release of the fragrances are urgently needed. In this work, we produced biodegradable nanoparticles (NPs) that are structurally composed of lactones, i.e. well known perfumes that occur naturally and that are already considered safe by regulatory agencies. We polymerized these lactones via ring opening polymerization (ROP) using an ionizable tertiary amine as initiator to produce in a single step amphiphilic oligoesters able to directly self-assemble into NPs once nanoprecipitated in water. In this way, we can produce biodegradable NPs with a perfume loading up to 85 % w/w without the need for additional surfactants. Subsequently we show that the ionizable group is able to confer a positive charge to our nanoparticles and, in turn, a high adsorption capacity on natural fibers (i.e. hairs and cotton fabric). Finally, we demonstrated the nanoparticle resistance to rinsing and their ability to confer a long-lasting fragrance perception to treated hair swatches for at least 3 weeks.
... There was an approximately 2.5-fold decrease in 3-hydroxybutan-2-one, which is formed from galactose and glucose due to citrate metabolism (Snoep et al., 1992) and contributes to a buttery aroma (Cornu et al., 2009). δ-Octalactone is generated from UFA by the action of lipoxygenases or hydratases (Dufosse et al., 1994) and may contribute to peach, apricot, and coconut odors in cheese (Bendall, 2001). In this study, the phenol family, which is responsible for putrid flavor (Badings et al., 1968), was also reduced by CLA addition. ...
A shortage in crude protein (CP) and supplementation of conjugated linoleic acids (CLA) in the diets of dairy cows could improve the dairy industry's ecological footprint and the nutritional value of milk, but it is not known what effect such a strategy might have on the aroma profiles of dairy products. The aim of this work was to study the effects of reducing the dietary CP content (from 150 to 123 g/kg of dry matter), with or without a supply of rumen-protected CLA (7.9 g/d C18:2 cis-9,trans-11 and 7.7 g/d C18:2 trans-10,cis-12), on the volatile organic compound (VOC) profile of cheeses ripened for 3 mo. Twenty mid-lactation Holstein-Friesian cows were reared in 4 pens (5 to a pen), and fed 4 different experimental diets over 4 periods of 3 wk each, following a 4 × 4 Latin square design. Twice in each period, 10-L milk samples were taken from each group and used to produce 32 cheeses, which we then analyzed for VOC by solid-phase microextraction and gas chromatography-mass spectrometry. We detected 48 VOC belonging to 10 chemical classes (11 alcohols, 8 ketones, 8 esters, 7 acids, 4 aldehydes, 4 sulfurs, 2 lactones, 2 phenolic, 1 monoterpene, 1 hydrocarbon); these were expressed as concentrations in cheese (quantitative data) or as proportions of total VOC (qualitative data). The results of mixed model analysis showed that the majority of VOC families and individual VOC in ripened cheese were affected by the dietary treatments: CP shortage depressed the concentrations of volatile aldehydes and increased the proportions of some esters and limonene, whereas CLA increased the concentration of total VOC, particularly several acids and esters, and decreased the proportions of ketones and phenolic compounds. The interaction between dietary CP and CLA affected the proportions of alcohols and acids. We performed a factor analysis to extract 5 latent explanatory variables from the individual VOC, which represented 79% of total VOC variance for the quantitative data and 78% for the qualitative data. Addition of CLA decreased the first qualitative factor (the "base aroma" of cheese, explaining 44% of total variance), whereas CP reduction increased the second quantitative factor ("ethyl esters," 15% of total variance) and the third qualitative factor ("butan-," 9% of total variance). In summary, the VOC profile of ripened cheese was heavily influenced by CP content and CLA supplementation in the diets of dairy cows, but the effect on sensorial properties of cheese is also worth considering.
... Ainsi, pour obtenir ces lactones de manière biosourcée, la voie préférentielle de production consiste à isoler les micro-organismes responsables de leurs biosynthèses et optimiser les conditions de cultures. C'est le cas pour la bioconversion de la γ-décalactone à partir de l'huile de ricin via des levures ou des champignons filamenteux [2], de la β-méthyl-γ-octalactone (whisky lactone) à partir de fûts de chêne via des levures [6,7] ou de la β-méthyl-γ-nonalactone (cognac lactone) à partir d'acides gras via la levure de boulanger. On retrouve aussi la bioconversion de la γ-dodéc-6(Z)-enolactone ((6Z)-dairy lactone) qui sera développée dans ce chapitre. ...
Les composés aromatiques sont des molécules omniprésentes responsables
des goûts et des senteurs qui nous entourent. Dès lors, leur production représente un
enjeu majeur pour les industries agroalimentaires, cosmétiques, pharmaceutiques ou de
produits d’hygiène et d’entretien. Deux voies principales d'accès à ces composés existent
: la voie biotechnologique et la voie de synthèse. A travers l'exemple de la dairy lactone,
où les différentes méthodes de production développées sont décrites (dont une méthode
biosourcée à partir de sciure de bois), il est possible d'évaluer les avantages et
inconvénients de chacun de ces modes de production.
... Compounds with the lactone structure on the one hand occur as antifeedants [3][4][5][6][7], on the other play pheromones role in the world of insects [8]. Lactones are described in the literature as important flavor compounds [9][10][11][12]. They exist as naturally occurring odorants in all major food groups and in many different beverages. ...
The enantiomerically enriched γ- and δ-decalactones (4a and 4b) were prepared from corresponding racemic primary-secondary 1,4- and 1,5-diols (1a and 1b), as products of enzymatic oxidation catalyzed by different alcohol dehydrogenases. The results of biotransformations indicated that the oxidation processes catalyzed by alcohol dehydrogenase (HLADH), both isolated from horse liver and recombinant in Escherichia coli, were characterized by the highest degree of conversion with moderate enantioselectivity of the reaction. Useful, environmentally friendly extraction procedure of decalactones (4a and 4b) based on hydrodistillation using a Deryng apparatus was developed. Both racemic lactones (4a and 4b), as well as their enantiomerically enriched isomers, were tested for feeding deterrent activity against Myzus persicae. The effect of these compounds on probing, feeding and settling behavior of M. persicae was studied in vivo. The deterrent activity of decalactones (4a and 4b) against aphids depended on the size of the lactone ring and the enantiomeric purity of the compounds. δ-Decalactone (4b) appeared inactive against M. persicae while γ-decalactone (4a) restrained aphid probing at ingestional phase. Only (-)-(S)-γ-decalactone (4a) had strong and durable (i.e. lasting for at least 24 hours) limiting effect, expressed at phloem level.
... This lactone is considered to be a potent dairy flavor compound in butter and buttermilk (McGorrin, 2001) and is generally used in combination with free fatty acids (FFA) and methyl ketones to produce creamy fatty notes in commercial flavorants. Lactones contribute to cheese flavor giving fruity and sweet creamy fermented notes (Dufosse et al., 1994). Parlimnet et al. (1966) concluded that the precursors for lactones were triglycerides that contain a hydroxyl acid moiety. ...
... The significant correlation found between butyl acetate with flavor and degree of liking is in accordance with previous studies where esters are considered to be main contributors to fruity and floral notes in peaches and nectarines (Sumitani et al., 1994). Lactones have been previously reported as being major contributors to mature fruit aroma in peach ( Eduardo et al., 2010), and particularly-hexalactone has been described to contribute with hot, sweet and grassy notes to the overall aroma ( Dufosse et al., 1994). Agreeing with the results found in this study,-hexalactone (L3) was identified also as the most abundant and stable lactone in a previous study with different nectarine cultivars (Cano-Salazar et al., 2013). ...
Six cling-stone melting nectarine cultivars (‘Big Top’, ‘Luciana’, ‘Honey Royale’, ‘Nectareine’, ‘Big Nectared’ and ‘Nectalady’) were cut and dipped into an aqueous solution of 2% ascorbic acid, 1% citric acid and 1% calcium chloride before being stored in amorphous polyethylene terephthalate trays. Their suitability to be processed as fresh-cut product was then investigated on the basis of their initial quality, browning potential and sensory attributes as well as the changes in these parameters after processing. At harvest, two maturity stages were selected for each cultivar based on their index of absorbance difference. Nonetheless, no significant effect of maturity stage at harvest was observed for most of the physico-chemical and/or sensory parameters during storage. On the contrary, differences among cultivars were emphasized when comparing ethanol and acetaldehyde production, polyphenol oxidase (PPO) activity, volatiles production, sensory profile, and consumer acceptance. ‘Honey Royale’ and ‘Nectalady’ wedges showed higher volatiles production, whereas ‘Big Nectared’ and ‘Luciana’ had a slightly lower browning index (BI). In the sensory evaluation, ‘Nectareine’ had the highest acceptability scores, whereas ‘Big Nectared’ had the lowest. The significant correlations between volatiles, sensory attributes and degree of liking observed in this study underline the importance of aroma in fresh-cut products.
... d-Octalactone, d-decalactone, and d-dodecalactone were found to be present in small amounts in the volatile fraction of Vastedda. Lactones contribute to cheese flavor giving fruity and sweet creamy fermented notes (Dufosse, Latrasse, & Spinnler, 1994) and are present in higher amounts in cheese obtained from pasteurized milk. The terpenes and hydrocarbons identified are probably because of the sheep feeding (Dumont & Adda, 1979). ...
The analysis of the volatile constituents of “Vastedda della valle del Belìce”, a typical Sicilian pasta filata cheese, was performed using solid phase microextraction and high-resolution gas chromatography/mass spectrometry. The research aimed to verify if the volatile fraction, determinant for cheese flavor, differs among producers and/or production seasons. The samples were provided by four producers from the area of the Protected Designation of Origin (PDO) production, during two different seasons of production. A total of 42 volatile components were identified: the main components were found to be butanoic, hexanoic, octanoic, and decanoic acid. Free fatty acids were quantified using the standard addition method, their concentrations were in the range 1273.7–1918.0 mg/kg. The analysis of variance and a multivariate approach showed that producer and season factors significantly influenced the content of almost all the identified volatile components; the artisanal cheese-making, the utilization of raw milk, and the environmental differences that characterized the various farmers are strong causes of cheeses variability.El análisis de los constituyentes volátiles de ‘Vastedda della valle del Belìce’, un queso de pasta hilada (pasta filata) típica siciliana, fue llevado a cabo usando Microextracción en Fase Sólida y Cromatografía de Gases/Espectrometría de Masa de Alta Resolución. El objetivo de la investigación fue verificar si la fracción volátil, determinante para el sabor del queso, difiere entre productores y/o temporadas de producción. Las muestras fueron proporcionadas por cuatro productores del área de la Denominación de Origen Protegida (DOP) durante dos temporadas de producción diferentes. Se identificaron un total de cuarenta y dos componentes volátiles: los principales componentes encontrados fueron ácido butanoico, hexanoico, octanoico y decanoico. Los ácidos grasos libres fueron cuantificados usando el método de adición estándar, su concentración se encontró en el intervalo de 1273, 7–1918,0 mg/kg. El análisis de varianza y un a aproximación multivariada mostraron que productor y temporada influyeron significativamente en el contenido de casi todos los componentes volátiles identificados; la elaboración artesanal de queso, la utilización de leche cruda y las diferencias ambientales que caracterizaban a los diferentes productores son la causa de la variabilidad de los quesos.
To overcome texture and flavor challenges in fermented plant-based product development, the potential of microorganisms is generating great interest in the food industry. This study examines the effect of Lactobacillus rhamnosus on physicochemical properties of fermented soy, oat, and coconut. L. rhamnosus was combined with different lactic acid bacteria strains and Bifidobacterium. Acidification, titratable acidity, and viability of L. rhamnosus and Bifidobacterium were evaluated. Oscillation and flow tests were performed to characterize rheological properties of fermented samples. Targeted and untargeted volatile organic compounds in fermented samples were assessed, and sensory evaluation with a trained panel was conducted. L. rhamnosus reduced fermentation time in soy, oat, and coconut. L. rhamnosus and Bifidobacterium grew in all fermented raw materials above 107 CFU/g. No significant effect on rheological behavior was observed when L. rhamnosus was present in fermented samples. Acetoin levels increased and acetaldehyde content decreased in the presence of L. rhamnosus in all three bases. Diacetyl levels increased in fermented oat and coconut samples when L. rhamnosus was combined with a starter culture containing Streptococcus thermophilus and with another starter culture containing S. thermophilus, L. bulgaricus and Bifidobacterium. In all fermented oat samples, L. rhamnosus significantly enhanced fermented flavor notes, such as sourness, lemon, and fruity taste, which in turn led to reduced perception of base-related attributes. In fermented coconut samples, gel firmness perception was significantly improved with L. rhamnosus. The findings suggest that L. rhamnosus can improve fermentation time and sensory perception of fermented plant-based products.
Cold temperature is a common method to store peach after harvest. While long-term cold storage leads to the occurrence of chilling injury and loss of volatile organic compounds (VOCs) after transferring peach to shelf life. Nitric oxide (NO) treatment has been proven to alleviate peach chilling injury. However, the effect of NO treatment on peach VOCs during cold storage plus shelf life is still unknown. In this study, 10 μL/L NO was used to fumigate peach before 4 °C cold storage. After cold storage for 21 days, peach were transferred to 20 °C for 3 days to simulate shelf life. Results showed that NO treatment promoted the emission of main VOCs including C6 aldehydes, C6 alcohols, straight-chain esters and lactones after cold storage, supported by the changes of fatty acids and genes expression of PpFADs, PpLOXs, PpHPL, PpADH, PpAATs and PpACXs. Besides, NO also alleviated the occurrence of chilling injury and promoted the recovery of respiration rate and ethylene production during shelf life. In conclusion, treatment with NO effectively prevented the loss of VOCs when transferring peach from cold temperature to shelf life in ‘Xiahui 6’ peach and the possible mechanisms were discussed.
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