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Keywords = glycosidically bound-form volatile compound

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25 pages, 3143 KB  
Review
From Biosynthesis to Regulation: Recent Advances in the Study of Fruit-Bound Aroma Compounds
by Qiaoping Qin, Rongshang Wang, Jinglin Zhang, Chunfang Wang, Hui He, Lili Wang, Chunxi Li, Yongjin Qiao and Hongru Liu
Horticulturae 2025, 11(10), 1185; https://doi.org/10.3390/horticulturae11101185 - 2 Oct 2025
Cited by 5 | Viewed by 3835
Abstract
Aroma volatiles constitute the primary molecular basis of fruit flavor quality, governing sensory attributes and marketability. Based on their chemical states, aroma compounds are categorized into bound and free forms. Bound aroma compounds predominantly exist as non-volatile glycosides, which can be hydrolyzed enzymatically [...] Read more.
Aroma volatiles constitute the primary molecular basis of fruit flavor quality, governing sensory attributes and marketability. Based on their chemical states, aroma compounds are categorized into bound and free forms. Bound aroma compounds predominantly exist as non-volatile glycosides, which can be hydrolyzed enzymatically or through acid treatment to release volatile free aroma compounds, thereby enhancing fruit fragrance. Although the dynamic interconversion between free and bound aroma compounds is pivotal for fruit flavor development, the governing mechanisms, including the principal controlling factors, regulatory networks, and external influences, are still under investigation. This review primarily synthesizes recent advances regarding the structural diversity, analysis, biosynthesis, and regulation of bound aroma compounds. Additionally, it examines how key regulatory networks and environmental factors modulate the synthesis and transformation of these compounds. The integrated overview provides new insights for future regulation of aroma metabolism in fruits. Full article
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17 pages, 5267 KB  
Article
Spatial and Temporal Disparity Analyses of Glycosylated Benzaldehyde and Identification and Expression Pattern Analyses of Uridine Diphosphate Glycosyltransferase Genes in Prunus mume
by Haotian Jia, Xiaoyun Geng, Lina Fan, Xin Li, Jiao Wang and Ruijie Hao
Plants 2024, 13(5), 703; https://doi.org/10.3390/plants13050703 - 1 Mar 2024
Cited by 2 | Viewed by 2246
Abstract
The species Prunus mume consists of uniquely aromatic woody perennials with large amounts of free aromatic substances in the flower cells. Uridine diphosphate glycosyltransferase (UGT) modifies these free aromatic substances into water-soluble glycoside-bound volatiles (GBVs) which play an important role in regulating the [...] Read more.
The species Prunus mume consists of uniquely aromatic woody perennials with large amounts of free aromatic substances in the flower cells. Uridine diphosphate glycosyltransferase (UGT) modifies these free aromatic substances into water-soluble glycoside-bound volatiles (GBVs) which play an important role in regulating the use of volatiles by plants for information exchange, defense, and stress tolerance. To investigate the changes in the glycosidic state of aromatic substances during the flowering period of P. mume and discern the location and expression of glycoside synthesis genes, we extracted and enzymatically hydrolyzed GBVs of P. mume and then utilized gas chromatography–mass spectrometry (GC–MS) to characterize and analyze the types and contents of GBV glycosides. Further, we identified and classified the members of the UGT gene family of P. mume using the bioinformatic method and analyzed the correlation between the expression of the UGT family genes in P. mume and the changes in glycosidic content. The results showed that the benzenoids were the main aromatic substance that was glycosylated during flowering in P. mume and that glycosidic benzaldehyde was the most prevalent compound in different flower parts and at different flowering stages. The titer of glycoside benzaldehyde gradually increased during the bud stage and reached the highest level at the big bud stage (999.6 μg·g−1). Significantly, titers of glycoside benzaldehyde significantly decreased and stabilized after flowering while the level of free benzaldehyde, in contrast, significantly increased and then reached a plateau after the flowering process was completed. A total of 155 UGT family genes were identified in the P. mume genome, which were divided into 13 subfamilies (A–E, G–N); according to the classification of Arabidopsis thaliana UGT gene subfamilies, the L subfamily contains 17 genes. The transcriptome analysis showed that PmUGTL9 and PmUGTL13 were highly expressed in the bud stage and were strongly correlated with the content of the glycosidic form of benzaldehyde at all stages of flowering. This study provides a theoretical basis to elucidate the function of UGT family genes in P. mume during flower development, to explore the mechanism of the storage and transportation of aromatic compounds in flower tissues, and to exploit industrial applications of aromatic products from P. mume. Full article
(This article belongs to the Section Plant Molecular Biology)
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27 pages, 3814 KB  
Article
Volatile Profiles of Vidal Grapes in the Shangri-La High-Altitude Region during On-Vine Non-Destructive Dehydration
by Qing-Fang Xu, Liang Fan, Kai-Xiang Lu, Dong-Mei Zhao, Ming-Xia Zhang and Jian Cai
Horticulturae 2022, 8(11), 1029; https://doi.org/10.3390/horticulturae8111029 - 3 Nov 2022
Cited by 2 | Viewed by 3029
Abstract
Both free and glycosidically bound forms of volatile compounds in Vidal grapes from the Shangri-La high-altitude region during the on-vine non-destructive dehydration process were investigated by headspace solid-phase micro-extraction (HS-SPME) combined with gas chromatography–mass spectrometry (GC-MS), following which the data were processed by [...] Read more.
Both free and glycosidically bound forms of volatile compounds in Vidal grapes from the Shangri-La high-altitude region during the on-vine non-destructive dehydration process were investigated by headspace solid-phase micro-extraction (HS-SPME) combined with gas chromatography–mass spectrometry (GC-MS), following which the data were processed by multivariate statistical analysis. Fatty-acid-derived volatiles (FADs), amino-acid-derived volatiles (AADs), and isoprene-derived volatiles (IPDs), which occurred mainly in bound forms, were the three major volatiles in dehydrated Vidal grapes. Water-loss concentration, biosynthesis, and biodegradation all occurred during dehydration, eventually modifying some volatiles significantly, especially some powerful odorants such as hexanal, trans-2-hexenal, 2-phenethyl acetate, β-myrcene, linalool, geraniol, cis-rose oxide, and β-damascenone. 1-Octen-3-ol was relatively stable during the non-destructive on-vine dehydration process and its content in grape juice was mainly determined by the concentration effect. 2,4-Di-tert-butylphenol, 2-phenethyl acetate, 2-methyl-1-propanol, and hexanol were screened as some of the most important metabolic markers to discriminate grapes at different dehydration degrees. Our study also highlights the fundamental importance of the expression of volatile content in the metabolomic study of grape berries. Full article
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13 pages, 1045 KB  
Article
Free and Glycosidically Bound Volatile Compounds in Okinawan Pineapple (Ananas comosus)
by Yonathan Asikin, Kazuki Shimoda, Makoto Takeuchi, Ryota Maekawa, Yusuke Kamiyoshihara, Kensaku Takara and Koji Wada
Appl. Sci. 2022, 12(19), 9522; https://doi.org/10.3390/app12199522 - 22 Sep 2022
Cited by 11 | Viewed by 3830
Abstract
Fruit plants produce various volatile compounds that emit distinct aroma characteristics and contribute to their flavor qualities. However, some of these substances, especially hydroxyl-group molecules, are in non-volatile glycosylated forms. This study aimed to determine free and glycosidically bound volatile compounds in three [...] Read more.
Fruit plants produce various volatile compounds that emit distinct aroma characteristics and contribute to their flavor qualities. However, some of these substances, especially hydroxyl-group molecules, are in non-volatile glycosylated forms. This study aimed to determine free and glycosidically bound volatile compounds in three Okinawan pineapple cultivars (‘N67-10′, ‘Yugafu’, and ‘Yonekura’). The free volatile components of squashed pineapple juice were analyzed using solid-phase microextraction (SPME)–arrow-gas chromatography–flame ionization detection/mass spectrometry (GC-FID/MS). The glycosides were collected through solid-phase extraction, hydrolyzed by β-glucosidase, and the released volatile compounds were measured. The sugar moieties of the glycosides were confirmed using GC-MS, and their glycoside constituents were analyzed using liquid chromatography (LC)-MS. Okinawan pineapple varied in its content and composition of free volatile components, which were predominantly comprised of esters, followed by alcohols, terpenes, and ketones. Eight hydroxyl-group compounds, including chavicol, eugenol, geraniol, phenylethyl alcohol, benzyl alcohol, 2-ethyl-1-hexanol, 1-hexanol, and 3-methyl-2-butenol, were released from their glycosylated forms via enzymatic hydrolysis, wherein the amounts of most of them were greater in ‘Yonekura’ than in the other cultivars. Moreover, two glycosides, chavicol-O-β-D-glucopyranoside and eugenol-O-β-D-glucopyranoside, were identified in all the cultivars, wherein the aglycones of both glycosides could be potential odor sources of the medicinal-herbal aromas. These results provide important information regarding both volatile-aroma qualities and bounded-aroma resources in Okinawan pineapple for fresh consumption and agroindustrial processing. Full article
(This article belongs to the Special Issue Advances in Food Flavor Analysis II)
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29 pages, 971 KB  
Article
Approach to the Chemotaxonomic Characterization of Traditional Cultivation Grape Varieties through Their Varietal Aroma Profile
by Ángela Díaz-Fernández, Emilia Díaz-Losada and Sandra Cortés-Diéguez
Foods 2022, 11(10), 1427; https://doi.org/10.3390/foods11101427 - 15 May 2022
Cited by 10 | Viewed by 3221
Abstract
In this study, the aroma profile of 12 minority grape varieties of Vitis vinifera L., included in the ‘Caiño group’, was defined along three vintages by solid phase microextraction followed by the gas chromatography–mass spectrometry method (SPME-GC-MS). Principal objectives were to assess the [...] Read more.
In this study, the aroma profile of 12 minority grape varieties of Vitis vinifera L., included in the ‘Caiño group’, was defined along three vintages by solid phase microextraction followed by the gas chromatography–mass spectrometry method (SPME-GC-MS). Principal objectives were to assess the aromatic profile as a useful fingerprint to differentiate them, recover traditionally cultivated grape varieties for the differentiation of an important wine-growing area and discover their chemotaxonomic potential. In each variety, free and bound volatile profile was carried out by grouping varietal compounds into thirteen families. In total, 339 volatile compounds were identified, 230 as free forms and 205 as aromatic precursors. Remarkable quantitative differences were observed between aromatic profiles for terpenes in the free fraction and for C6 compounds, alcohols, sesquiterpenes and phenols in the glycosidic fraction. Principal component analysis based on their aromatic profile highlights a good differentiation between varieties and suggests a certain degree of aromatic chemotaxonomic proximity between previously known parental varieties, ‘Caiño Blanco’ with respect to ‘Caiño Bravo’ and ‘Albariño’. This study shows the preliminary results of a large research project involving a larger number of grape varieties and thus a broader spectrum of genetic relationships between them. Full article
(This article belongs to the Section Food Analytical Methods)
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28 pages, 860 KB  
Article
Two Sides to One Story—Aroma Chemical and Sensory Signature of Lugana and Verdicchio Wines
by Davide Slaghenaufi, Giovanni Luzzini, Jessica Samaniego Solis, Filippo Forte and Maurizio Ugliano
Molecules 2021, 26(8), 2127; https://doi.org/10.3390/molecules26082127 - 7 Apr 2021
Cited by 26 | Viewed by 4747
Abstract
Lugana and Verdicchio are two Italian white wines with a Protected Designation of Origin (PDO) label. These two wine types are produced in different regions using the same grape variety. The aim of this work is to investigate the existence of volatile chemical [...] Read more.
Lugana and Verdicchio are two Italian white wines with a Protected Designation of Origin (PDO) label. These two wine types are produced in different regions using the same grape variety. The aim of this work is to investigate the existence of volatile chemical markers that could help to elucidate differences between Lugana and Verdicchio wines both at chemical and sensory levels. Thirteen commercial wine samples were analyzed by Gas Chromatography-Mass Spectrometry (GC-MS), and 76 volatile compounds were identified and quantified. Verdicchio and Lugana had been differentiated on the basis of 19 free and glycosidically bound compounds belonging to the chemical classes of terpenes, benzenoids, higher alcohols, C6 alcohols and norisoprenoids. Samples were assessed by means of a sorting task sensory analysis, resulting in two clusters formed. These results suggested the existence of 2 product types with specific sensory spaces that can be related, to a good extend, to Verdicchio and Lugana wines. Cluster 1 was composed of six wines, 4 of which were Lugana, while Cluster 2 was formed of 7 wines, 5 of which were Verdicchio. The first cluster was described as “fruity”, and “fresh/minty”, while the second as “fermentative” and “spicy”. An attempt was made to relate analytical and sensory data, the results showed that damascenone and the sum of 3 of esters the ethyl hexanoate, ethyl octanoate and isoamyl acetate, was characterizing Cluster 1. These results highlighted the primary importance of geographical origin to the volatile composition and perceived aroma of Lugana and Verdicchio wines. Full article
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15 pages, 937 KB  
Review
Drying Treatments Change the Composition of Aromatic Compounds from Fresh to Dried Centennial Seedless Grapes
by Hafiz Umer Javed, Dong Wang, Rani Andaleeb, Muhammad Salman Zahid, Ying Shi, Saeed Akhtar, Wang Shiping and Chang-Qing Duan
Foods 2021, 10(3), 559; https://doi.org/10.3390/foods10030559 - 8 Mar 2021
Cited by 19 | Viewed by 4707
Abstract
Raisin aroma is a vital sensory characteristic that determines consumers’ acceptance. Volatile organic compounds (VOCs) in fresh grapes, air-dried (AD), pre-treated air-dried (PAD), sun-dried (SD), and pre-treated sun-dried (PSD) raisins were analyzed, with 99 and 77 free- and bound-form compounds identified in centennial [...] Read more.
Raisin aroma is a vital sensory characteristic that determines consumers’ acceptance. Volatile organic compounds (VOCs) in fresh grapes, air-dried (AD), pre-treated air-dried (PAD), sun-dried (SD), and pre-treated sun-dried (PSD) raisins were analyzed, with 99 and 77 free- and bound-form compounds identified in centennial seedless grapes, respectively. The hexenal, (E)-2-hexenal, 1-hexanol, ethyl alcohol, and ethyl acetate in free-form while benzyl alcohol, β-damascenone, gerenic acid in bound-form were the leading compounds. Overall, the concentration of aldehydes, alcohols, esters, acids, terpenoids, ketones, benzene, and phenols were abundant in fresh grapes but pyrazine and furan were identified in raisin. Out of 99 VOCs, 30 compounds had an odour active value above 1. The intensity of green, floral, and fruity aromas were quite higher in fresh grapes followed by AD-raisins, PAD-raisins, SD-raisins, and PSD-raisins. The intense roasted aroma was found in SD-raisins due to 2,6-diethylpyrazine and 3-ethyl-2,5-dimethylpyrazine. Among raisins, the concentration of unsaturated fatty acid oxidized and Maillard reaction volatiles were higher in SD-raisins and mainly contributed green, fruity and floral, and roasted aromas, respectively. Full article
(This article belongs to the Special Issue Volatile and Bioactive Compounds in Raw and Processed Food)
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14 pages, 661 KB  
Article
Free and Bound Volatile Aroma Compounds of ´Maraština´ Grapes as Influenced by Dehydration Techniques
by Irena Budić-Leto, Iva Humar, Jasenka Gajdoš Kljusurić, Goran Zdunić and Emil Zlatić
Appl. Sci. 2020, 10(24), 8928; https://doi.org/10.3390/app10248928 - 14 Dec 2020
Cited by 18 | Viewed by 4449
Abstract
Dehydration or drying of grapes is one of the most important steps in the production of Croatian traditional dessert wine Prošek. The natural sun drying of grapes is the traditionally used method in Prošek production. Alternative methods, such as dehydration under controlled conditions, [...] Read more.
Dehydration or drying of grapes is one of the most important steps in the production of Croatian traditional dessert wine Prošek. The natural sun drying of grapes is the traditionally used method in Prošek production. Alternative methods, such as dehydration under controlled conditions, have been studied as safer and faster methods than the traditional sun drying but without precise knowledge of the effect on volatile compounds. The objective of this work was to study how dehydration of grapes carried out in a greenhouse and an environmentally controlled chamber impacts on the free and glycosidically bound volatile compounds of native grape cv. ‘Maraština’. The 36 volatile compounds were identified and quantified using headspace solid-phase micro extraction coupled with gas chromatography-mass spectrophotometry (HS-SPME-GC/MS). The results showed that the aroma profile of dehydrated grapes was significantly different from that of fresh grapes. Regarding free forms, significant increases in the concentration of 2-methyl-1-propanol, 1-butanol, 2-hexen-1-ol, 1-hexanol, ethyl hexanoate, hexyl acetate, o-cymene, linalool oxide, and terpinen-4-ol and geraniol were found in greenhouse-dried grapes, whereas increases in cis-limonene-epoxide, trans-limonene epoxide, and γ-hexalactone were higher in chamber-dried grapes compared to greenhouse-dried grapes. Glycosidically bound forms of o-cymene, linalool oxide, linalool, and terpinen-4-ol were increased in both types of drying, whereas β-damascenone was increased only in greenhouse-dried grapes. Full article
(This article belongs to the Special Issue Advances in Food Flavor Analysis)
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19 pages, 734 KB  
Review
Applications of Solid-Phase Microextraction and Gas Chromatography/Mass Spectrometry (SPME-GC/MS) in the Study of Grape and Wine Volatile Compounds
by Annarita Panighel and Riccardo Flamini
Molecules 2014, 19(12), 21291-21309; https://doi.org/10.3390/molecules191221291 - 18 Dec 2014
Cited by 87 | Viewed by 19415
Abstract
Volatile compounds are responsible for the wine “bouquet”, which is perceived by sniffing the headspace of a glass, and of the aroma component (palate-aroma) of the overall flavor, which is perceived on drinking. Grape aroma compounds are transferred to the wine and undergo [...] Read more.
Volatile compounds are responsible for the wine “bouquet”, which is perceived by sniffing the headspace of a glass, and of the aroma component (palate-aroma) of the overall flavor, which is perceived on drinking. Grape aroma compounds are transferred to the wine and undergo minimal alteration during fermentation (e.g., monoterpenes and methoxypyrazines); others are precursors of aroma compounds which form in winemaking and during wine aging (e.g., glycosidically-bound volatile compounds and C13-norisoprenoids). Headspace solid phase microextraction (HS-SPME) is a fast and simple technique which was developed for analysis of volatile compounds. This review describes some SPME methods coupled with gas chromatography/mass spectrometry (GC/MS) used to study the grape and wine volatiles. Full article
(This article belongs to the Special Issue Aromas and Volatiles of Fruits)
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