Glycosidically Bound Volatiles Research Articles

Comprehensive comparison of aroma profiles and chiral free and glycosidically bound volatiles in Fujian and Yunnan white teas

The Fujian and Yunnan provinces in China are the most representative origins of white tea. However, the key differences in the chemical constituents of the two white teas have rarely been revealed. In this study, a comprehensive comparison of the aroma profiles, chiral volatiles, and glycosidically bound volatiles (GBVs) in Fujian and Yunnan white teas was performed, and 174 volatiles and 28 enantiomers, including 22 volatiles and six GBVs, were identified. Linalool, linalyl-β-primeveroside (LinPrim), and α-terpineol presented the opposite dominant configurations in Fujian and Yunnan white teas, and the chiral GBVs were firstly quantified with significant differences in the contents of R-LinPrim and β-d-glucopyranosides of (2R, 5R)-linalool oxide A and (2R, 5S)-linalool oxide B. Moreover, discrimination functions for Fujian and Yunnan white teas were created using nine key variables with excellent reliability and efficiency. These results provide a new method for objectively distinguishing authentic white teas according to geographical origin.

Re-rolling treatment in the fermentation process improves the taste and liquor color qualities of black tea

Fermentation is a vital process occurred under the premise of rolling affecting black tea quality. Theoretically, re-rolling during fermentation will remodel the biochemical conditions of tea leaves, and thus influence black tea quality. Herein, we studied the effect of re-rolling on black tea taste and liquor color. Sensory evaluation showed that re-rolling significantly weakened the astringency taste and improved the redness and luminance of liquor. With re-rolling, the color attributes of a* and L* and the contents of theaflavins and thearubigins were significantly improved. Metabolomics analysis showed that the contents of 110 non-volatile compounds were significantly different among black teas with different rolling treatments. In summary, re-rolling accelerated the oxidation of polyphenols into pigments, the hydrolysis of proteins into amino acids, and the metabolism of alkaloids, organic acids, glycosidically-bound volatiles, and lipids during the fermentation period. Our study provided a novel and simple way to improve black tea quality.

Release of glycosidically-bound volatiles in orange juice under natural conditions.

Glycosidically-bound volatiles (GBV) can be released by exogenous acid and enzymatic hydrolysis. However, the liberation of GBV in natural juice is not reported. It was found that part of the GBV in orange juice (OJ) under natural conditions can be released and the types of volatiles were considerably fewer than the ones under exogenous acid, or enzymatic hydrolysis. Seven types of aroma substances were released under endogenous enzyme, among which ethyl 3-hydroxyhexanoate and eugenol are characteristic aroma substances of OJ. Six kinds of aroma substances can be released under natural acidic conditions, none are characteristic aroma substances of OJ. Ten kinds of substances were released under endogenous enzymes in combination with the acidic condition, among which benzyl alcohol, ethyl 3-hydroxyhexanoate, citral, and eugenol are characteristic aroma substances of OJ. The results indicated that GBV may play an important role in resisting the decrease of free aroma in OJ during storage.

Comprehensive in situ and ex situ β-glucosidase-assisted assessment reveals Indian mangoes as reservoirs of glycosidic aroma precursors

Mango, a valued commercial fruit in India is popular mostly because of its attractive flavour. Glycosidically bound volatiles (GBV), an underrepresented warehouse of aroma, remain completely unexplored in Indian mangoes. In this study, GBV were profiled in pulps and peels of 10 Indian mango cultivars, leading to detection of 66 GBV which were dominated by monoterpenoids and phenolics. Peels were quantitatively and qualitatively richer in GBV than pulps. Hierarchical clustering and principal component analysis indicated higher contribution of peel GBV to the distinctness of cultivars. Linalool, geraniol, and eugenol were the significant contributors based on the odour units. Direct β-glucosidase treatment to the juice resulted in the release of lesser number of volatiles than those released from the purified GBV extracts. Apart from providing a comprehensive catalogue of GBV in mangoes, our data suggests the need of critical assessment of the usefulness of β-glucosidases in aroma improvement of fruit juices.

Chemical constituents of green teas processed from albino tea cultivars with white and yellow shoots

Green tea processed from albino tea varieties often has umami taste and fresh aroma. This study identified green teas made from two types of albino tea cultivar, one having the white shoots (called Naibai, NB) and the other having the yellow shoots (called Huangjinya, HJY). Taste compounds analyses showed that galloylated catechins were highly concentrated in HJY green teas, whereas non-galloylated catechins and amino acids were more abundant in NB green teas. CsTA (involved in the catabolism of galloylated catechins) showed high expression in HJY tea shoots, resulting in gallic acid as a precursor for β-glucogallin biosynthesis being abundant in HJY. CsPDX2.1 (responsible for theanine hydrolyzation) had a lower expression level in NB than HJY shoots. Fatty acid–derived volatiles (FADVs), glycosidically bound volatiles (GBVs) and carotenoid–derived volatiles (CDVs) were highly concentrated in HJY green teas, whereas amino acids–derived volatiles were highly concentrated in NB green teas.

Multi-omics and enzyme activity analysis of flavour substances formation: Major metabolic pathways alteration during Congou black tea processing

To comprehensively analyse flavour substance formation in Congou black tea, dynamic changes in non-volatile and volatile compositions and enzymatic activity were analysed. In total, 107 non-volatile and 222 volatile compositions were identified via ultra-high performance liquid chromatography coupled with quadrupole-exactive mass spectrometry (UHPLC-Q-Exactive/MS) and stir bar sorptive extraction-gas chromatography-mass spectrometry (SBSE-GC–MS), and eight metabolic pathways were explored during tea processing. Significant variations in metabolites were observed during processing (P < 0.05), especially in the fermentation stage, including high accumulation of taste and colour substances due to decreased flavonoid synthase activity and elevated oxidase activity. Correlation analysis clarified that the mutual transformation between non-volatile and volatile substances occurs in certain types of processing, including amino acids, amino acid-derived volatiles (AADVs), glycosidically bound volatiles (GBVs), and volatile terpenoids (VTs). Our study provides a detailed overview of the dynamic changes of in flavour substrates and key enzyme activities during Congou black tea processing.

Effect of red light on the composition of metabolites in tea leaves during the withering process using untargeted metabolomics.

Red light withering significantly improves the sensory flavor qualities of tea, although changes in metabolites during this process have not been systematically studied until now. The present study comprehensively analyzes metabolites in withered tea leaves at 2-h intervals up to 12 h under red light (630 nm) and dark conditions using ultra performance liquid chromatography-high resolution mass spectrometry (untargeted metabolomics). Ninety-four non-volatile compounds are identified and relatively quantified, including amino acids, catechins, dimeric catechins, flavonol glycosides, glycosidically-bound volatiles, phenolic acids and nucleosides. The results show that amino acids, catechins and dimeric catechins are most affected by red light treatment. Ten free amino acids, theaflavins and theasinensin A increase after red light irradiation, whereas epigallocatechin gallate and catechin fall. The present study provides a comprehensive and systematic profile of the dynamic effects of red light on withering tea and a rationale for its use in tea processing quality control. © 2021 Society of Chemical Industry.

Elucidation of Endogenous Aroma Compounds in Tamarillo (Solanum betaceum) Using a Molecular Sensory Approach.

Glycosidically bound volatiles (GBVs) are flavorless compounds in fruits and may undergo hydrolysis during fruit maturation, storage, and processing, releasing free aglycones that are odor active. However, the contribution of glycosidic aglycones to the sensory attributes of fruits remains unclear. Herein, the key odor-active aglycones in tamarillo fruits were elucidated through the molecular sensory approach. We extracted GBVs from three cultivars of tamarillo fruits using solid-phase extraction and subsequently prepared aglycone isolates by enzymatic hydrolysis of GBVs. Gas chromatography-mass spectrometry-olfactometry (GC-MS-O) coupled with odor activity value (OAV) calculation, comparative aroma extract dilution analysis (cAEDA), and omission tests were used to identify key aromatic aglycones. A total of 42 odorants were determined by GC-MS-O analysis. Among them, trans-2,cis-6-nonadienal, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF), linalool, 4-vinylguaiacol, geraniol, and α-terpineol showed high OAVs. The cultivar Amber had more aglycones with flavor dilution (FD) factors >16 than the Mulligan cultivar (27 vs 21, respectively), and the Laird's Large fruit showed the highest FD of 1024 for glycosidic DMHF. Omission tests indicated 14 aglycones as essential odorants related to GBVs in tamarillo fruits. Moreover, the enzymatic liberation of aglycones affected the sensory attributes of the tamarillo juice, resulting in an intensified odor profile with noticeable fruity and sweet notes. This study gives insights into the role of endogenous aroma during tamarillo-flavor perception, which lays the groundwork for developing tamarillo-based products with improved sensory properties.

The profile of dynamic changes in yellow tea quality and chemical composition during yellowing process

Yellowing is the key process used to produce the unique yellow tea, but the effect of the yellowing process on tea quality and chemical composition remains unclear. Here, electronic eye and tongue and metabolomics were applied to investigate dynamic changes in tea leaves during the yellowing process for the first time. During the first 18 h of yellowing, the colour of tea leaves was observed becoming yellowish. Compounds related to umami and sweetness (amino acids, catechins, sucrose, phenolic acids, etc.) are at high levels. However, after 24 h of yellowing, the colour of tea becomes darker, with richness of tea infusion decreasing significantly. The levels of most catechins, amino acids, phenolic acids, and glycosidically bound volatiles (GBVs) decreased significantly, whereas betaine, piperidine, theasinensin B, and lysophosphatidylcholines (LPCs) increased significantly. Meanwhile, according to partial least-squares (PLS) analysis, most amino acids and sucrose were positively correlated with umami and sweetness; most catechins and phenolic acids had positively correlated with bitterness and astringency; phaeophorbides were positively correlated with red value (+a*) of tea leaves’ colour. This work provides a comprehensive, novel knowledge on the quality and chemical changes of yellow tea during the yellowing process.

Using power ultrasound to release glycosidically bound volatiles from orange juice: A new method

Acid hydrolysis and enzymatic hydrolysis are the main methods for releasing glycosidically bound volatiles (GBV). However, acid hydrolysis yields a strong pungent odor, and enzymatic hydrolysis is time consuming. In the present study, a new method, ultrasound hydrolysis, is reported to release GBV. This method is simple, environmentally friendly, fast and effective. Large differences were observed in the released aglycones and glycosyls between ultrasound and enzymatic hydrolysis of GBV. More types of aglycones were released under ultrasound than enzymatic hydrolysis. Alcohols and esters were the main aglycones under enzymatic hydrolysis, and terpenoids, esters and aldehydes were the main aglycones under ultrasound hydrolysis. The glycosyls released under ultrasound hydrolysis were mannose, glucose and sucrose, and those released under enzymatic hydrolysis were galactose and sucrose. The present study gives a new insight into a hydrolytic method for GBV by using ultrasound hydrolysis and can provide a reference method for fruit juice aromatization.

Withering degree affects flavor and biological activity of black tea: A non-targeted metabolomics approach

This study focused on non-targeted metabolomics analysis of the relationship of the chemical composition, quality traits, bioactivity of black tea (Camellia sinensis L.) with five withering degrees (WD65, WD60, WD55, WD50, and WD45, corresponding to 65, 60, 55, 50, and 45% water content in withered leaves, respectively) and their effects on sensory quality traits. WD60 was shown as the optimal withering degree (WD) with the highest total quality score (89.7), followed by WD55 (88.7). With increasing WD, the content of most volatile components increased significantly, but with no significant difference between some substances below WD55. The total amount of free amino acids increased with increasing WD, in contrast to a decrease in the total amount of catechins, flavonoids/flavonoid glycosides, theaflavins and glycosidically bound volatiles (GBVs). Black tea with a WD between WD65 and WD60 was shown to have higher antioxidant activity and stronger inhibitory effect on α-amylase and α-glucosidase activity or intestinal glucose uptake. The overall data indicate that WD60 treatment not only benefits the formation of sensory quality traits, but also shows better bioactivity.

Variation patterns in the content of glycosides during green tea manufacturing by a modification-specific metabolomics approach: Enzymatic reaction promoting an increase in the glycosidically bound volatiles at the pan firing stage

The glycosides are presumed to influence the quality of green tea but the molecular mechanism behind remains unclear. To elucidate the contribution of glycosides to the flavor formation of green tea, changes of both glycosidically bound non-volatiles (GBNVs) and glycosidically bound volatiles (GBVs) during the manufacturing of green tea were investigated using a modification-specific metabolomics method. A total of 64 glycosides (47 GBNVs and 17 GBVs) were identified and their contents mainly changed during the pan firing and drying stages of green tea manufacturing. Notably, the contents of GBVs significantly increased by 1.12–4.46-fold during pan firing. Correlation analysis showed that the GBVs contents were negatively related to the contents of volatiles and glucose. Model experiments revealed that enzymatic synthesis contributed to the increase in the content of GBVs during the pan firing. This comprehensive study on the glycosides changes revealed the molecular bases for GBVs increments during the pan firing.

Aroma formation and dynamic changes during white tea processing

The formation of and dynamic changes in aroma during white tea processing have not previously been systematically investigated. In this study, advanced comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry was employed to investigate the mechanism of white tea aroma formation. A total of 172 volatiles were identified and mainly comprising endogenous volatiles, which displayed diverse change trends during the withering period. In this process, free aroma precursor amino acids and glycosidically bound volatiles (GBVs) were found to contribute to the formation of white tea aroma, with the differential expression of aroma-related key genes accounting for various accumulation of endogenous volatiles and GBVs. In addition, the drying was also shown to play an important role in the formation of white tea aroma. Our study provides the first characterization of white tea aroma formation and establishes a theoretical basis for quality control during white tea processing operations.

Characteristic Fluctuations in Glycosidically Bound Volatiles during Tea Processing and Identification of Their Unstable Derivatives.

A recently developed method enabled us to simultaneously characterize and quantitate glycosidically bound volatiles (GBVs) at picomole levels using liquid chromatography-mass spectrometry (LC-MS). On the basis of the analytical data it is possible to screen tea varieties most suitable for black tea processing, in which higher concentrations of primeverosides accumulate. The primeverosides decreased at the rolling step in black tea processing, whereas the glucopyranosides did not change much. The total contents of GBVs gradually increased at the withering steps and then remarkably increased after the fixing step at 230 °C, during oolong tea processing. The presence of 6'-O-malonyl ester type β-D-glucopyranosides in the tea samples suggested a contribution to the increment in glucopyranosides during oolong tea processing. The method was also used to analyze GBVs and their derivatives to understand their possible role in the metabolic pathway of tea.

Does Enzymatic Hydrolysis of Glycosidically Bound Volatile Compounds Really Contribute to the Formation of Volatile Compounds During the Oolong Tea Manufacturing Process?

It was generally thought that aroma of oolong tea resulted from hydrolysis of glycosidically bound volatiles (GBVs). In this study, most GBVs showed no reduction during the oolong tea manufacturing process. β-Glycosidases either at protein or gene level were not activated during the manufacturing process. Subcellular localization of β-primeverosidase provided evidence that β-primeverosidase was located in the leaf cell wall. The cell wall remained intact during the enzyme-active manufacturing process. After the leaf cell disruption, GBV content was reduced. These findings reveal that, during the enzyme-active process of oolong tea, nondisruption of the leaf cell walls resulted in impossibility of interaction of GBVs and β-glycosidases. Indole, jasmine lactone, and trans-nerolidol were characteristic volatiles produced from the manufacturing process. Interestingly, the contents of the three volatiles was reduced after the leaf cell disruption, suggesting that mechanical damage with the cell disruption, which is similar to black tea manufacturing, did not induce accumulation of the three volatiles. In addition, 11 volatiles with flavor dilution factor ≥4(4) were identified as relatively potent odorants in the oolong tea. These results suggest that enzymatic hydrolysis of GBVs was not involved in the formation of volatiles of oolong tea, and some characteristic volatiles with potent odorants were produced from the manufacturing process.

Free and bound volatile chemicals in mulberry (Morus atropurpurea Roxb.).

Mulberry (Morus atropurpurea Roxb.) is a popular and desirable fruit that is widely cultivated in China. Despite its popularity, the free volatile chemicals and glycosidically bound volatiles (GBVs) of mulberry have been minimally studied. To this end, we have investigated these compounds in 4 mulberry cultivars via solid phase extraction (SPE) and headspace solid phase microextraction with gas chromatography-mass spectrometry (HS-SPME-GC-MS). A total of 55 free volatile chemicals and 57 GBVs were identified and quantified. In 3 of the cultivars ("YFS," "T10," and "D10"), the GBVs were found in higher amounts than their free counterparts, corresponding to a ratio of 1.2 to 1.8. The characteristic aromas were determined by their odor activity values (OAVs) and by generating an aroma series (AS). A total of 20 volatile compounds had OAVs ≥ 1.0. In particular, ethyl butanoate, hexanal, (Z)-3-hexenal (E)-2-hexenal, (E)-2-nonenal, and eugenol had relatively high OAVs and were considered to be the key aromas contributing to the mulberry flavor. Consequently, mulberry was characterized by a variety of herbaceous scents having a background of sweet, spicy, fruity, and floral notes. The free volatiles exhibited strong herbaceous notes, whereas the GBVs were responsible for the sweet and spicy qualities of the fruit. Based on our results, 2 cultivars ("YFS" and "D10") are proposed to be good candidates suitable for the further development of mulberry-based food products due to their complex and desirable aromas.

Formation of fragrance materials from odourless glycosidically‐bound volatiles by skin microflora (Part 1)

AbstractThe applicability of using odourless glycosidically bound volatiles (GBVs) as fragrance materials was investigated. After incubating skin microflora with various kinds of GBVs, the amounts of fragrance materials generated and the remaining glycosides were analysed by GC and HPLC. Most GBVs, particularly β‐D‐glucosides, were metabolized by various skin microflora to release their aglycones as fragrance materials. It was assumed that this was due to differences in enzymatic activity of the microflora. The results also suggest their considerable usefulness as alternative fragrance materials. Copyright © 2002 John Wiley &amp; Sons, Ltd.