Recent studies of the volatile compounds in tea

doi:10.1016/J.FOODRES.2013.02.011

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Recent studies of the volatile compounds in tea

Journal Article•DOI•

Recent studies of the volatile compounds in tea

Ziyin Yang¹, Susanne Baldermann², Susanne Baldermann³, Naoharu Watanabe⁴•Institutions (4)

Chinese Academy of Sciences¹, University of Potsdam², Leibniz Association³, Shizuoka University⁴

01 Oct 2013-Food Research International (Elsevier)-Vol. 53, Iss: 2, pp 585-599

TL;DR: The authors summarized the recent investigations into tea volatile compounds: the volatile compounds in tea products, the metabolic pathways of volatile formation in tea plants and the glycosidically-bound volatile compounds, and the techniques used for studying such compounds.

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About: This article is published in Food Research International.The article was published on 2013-10-01. It has received 381 citations till now.

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Journal Article•DOI•

Draft genome sequence of Camellia sinensis var. sinensis provides insights into the evolution of the tea genome and tea quality.

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Chaoling Wei¹, Hua Yang¹, Songbo Wang², Jian Zhao¹, Chun Liu², Liping Gao¹, En-Hua Xia¹, Ying Lu³, Yuling Tai¹, Guangbiao She¹, Jun Sun¹, Haisheng Cao¹, Wei Tong¹, Qiang Gao², Yeyun Li¹, Wei-Wei Deng¹, Xiaolan Jiang¹, Wenzhao Wang¹, Qi Chen¹, Shihua Zhang¹, Haijing Li¹, Junlan Wu¹, Ping Wang¹, Penghui Li¹, Chengying Shi¹, Fengya Zheng², Jianbo Jian², Bei Huang¹, Dai Shan², Mingming Shi², Congbing Fang¹, Yi Yue¹, Fangdong Li¹, Daxiang Li¹, Shu Wei¹, Bin Han⁴, Chang-Jun Jiang¹, Ye Yin², Tao Xia¹, Zhengzhu Zhang¹, Jeffrey L. Bennetzen¹, Shancen Zhao², Xiaochun Wan¹ - Show less +39 more•Institutions (4)

Anhui Agricultural University¹, Beijing Genomics Institute², Shanghai Ocean University³, Chinese Academy of Sciences⁴

01 May 2018-Proceedings of the National Academy of Sciences of the United States of America

TL;DR: A high-quality genome assembly of Camellia sinensis var.

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Abstract: Tea, one of the world’s most important beverage crops, provides numerous secondary metabolites that account for its rich taste and health benefits. Here we present a high-quality sequence of the genome of tea, Camellia sinensis var. sinensis (CSS), using both Illumina and PacBio sequencing technologies. At least 64% of the 3.1-Gb genome assembly consists of repetitive sequences, and the rest yields 33,932 high-confidence predictions of encoded proteins. Divergence between two major lineages, CSS and Camellia sinensis var. assamica (CSA), is calculated to ∼0.38 to 1.54 million years ago (Mya). Analysis of genic collinearity reveals that the tea genome is the product of two rounds of whole-genome duplications (WGDs) that occurred ∼30 to 40 and ∼90 to 100 Mya. We provide evidence that these WGD events, and subsequent paralogous duplications, had major impacts on the copy numbers of secondary metabolite genes, particularly genes critical to producing three key quality compounds: catechins, theanine, and caffeine. Analyses of transcriptome and phytochemistry data show that amplification and transcriptional divergence of genes encoding a large acyltransferase family and leucoanthocyanidin reductases are associated with the characteristic young leaf accumulation of monomeric galloylated catechins in tea, while functional divergence of a single member of the glutamine synthetase gene family yielded theanine synthetase. This genome sequence will facilitate understanding of tea genome evolution and tea metabolite pathways, and will promote germplasm utilization for breeding improved tea varieties.

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586 citations

Cites background from "Recent studies of the volatile comp..."

...Prominent volatile compounds, crucial for tea aroma and flavor, are derived either by oxidation of lipids and carotenoids or from the terpenoid and shikimate pathways (19)....
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Journal Article•DOI•

Tea aroma formation

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Chi-Tang Ho, Xin Zheng¹, Shiming Li²•Institutions (2)

Rutgers University¹, Huanggang Normal University²

01 Mar 2015-Food Science and Human Wellness

TL;DR: In this article, the main aromas of green, black, and oolong tea are summarized and their formation in the manufacturing process is discussed. But, the authors focus on the formation mechanism of main aroma molecules during the tea manufacturing process.

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381 citations

Cites background from "Recent studies of the volatile comp..."

...Sugar moieties of glycosides are typically monosaccharides or disaccharides (Table 4) [6,25]....
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...During the manufacturing process, injured tea leaf tissues release enzymes into cell walls or cavities to hydrolyze glycosidic bonds liberating volatile aromas, such as monoterpene alcohols (linalool, linalool oxides, and geraniol) or aromatic alcohols (benzyl alcohol and phenylethanol) [25,3032]....
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...Formation of geraniol and linalool [25]...
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...Formation of β-damascenone from glycoside precursors [12] Page 20 of 36 Ac ce pt ed M an us cr ip t 20 linalool oxide III √ √ [25,38,39] linalool oxide IV √ √ [38,39] (Z)-3-hexenol √ √ √ [35] 8-hydroxygeraniol √ [46,49] 1-phenylethanol √ √ √ [43] benzyl alcohol √ √ √ [38,46,49] (Z)-3-hexenol √ √ √ [38,45,46,49] 2-phenylethanol √ √ [25,38] methyl salicylate √ √ [25,34] geraniol √ √ [25,38] linalool oxide I √ √ [25,38] linalool oxide II √ √ [25,38] linalool oxide III √ [25,38] linalool oxide IV √ [25,38] β-damascenone √ [9] DMHF √ [42] β-DGlucopyranoside 1-phenylethanol √ √ √ [43] linalool oxide III √ [46,49] linalool oxide IV √ [46,49] β-Acuminoside 3-hydroxy-7,8dihydro-β-ionol √ √ √ [25,51] β-Vicianoside geraniol √ √ [38,52]...
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...Main tea aromas and their precursors of formation Compounds Precursors Type of tea identified Aroma quality Odor Threshold (ppb in water) Reference β-Ionone Carotenoids Green, Oolong, Black tea Woody, violet 0.007 [7,22] Nerolidiol Carotenoids Green, Oolong, Black tea flowery [7,50] Theaspirone Carotenoids Black tea flowery [8] α-Ionone Carotenoids Black tea Woody, hay-like [78,79] β-Damascone Carotenoids Green tea sweet hay-like [78] Sarfranal Carotenoids Green, Oolong, Black tea herbal [79] Geranylacetone Carotenoids Green, Oolong, Black tea Floral, hay-like [78,79] β-Damascenone Carotenoids Glycosides Green, Black tea fruity, apple-like 0.002 [12,14] (Z)-3-hexenol Lipids, Glycosides Green, Oolong, Black tea green 13 [6,34] Hexanal Lipids Green tea, Oolong tea, Black tea grassy, green 10 [22,50] Pentanal Lipids Green tea pungent, malt, almond [50] (Z)-1,5-octadien3-one Lipids Green tea geranium-like [78] Jasmine Lipids Green tea jasmine-like [50] (E,Z)-2,6nonadienal Lipids Green tea cucumber-like 0.03 [50] 1-octen-3-one Lipids Green tea mushroom-like [78] Page 31 of 36 Ac ce pt ed M an us cr ip t 31 cis-Jasmone Lipids Green, Oolong, Black tea floral, jasmine-like [22,34,50] (Z)-4-heptanal Lipids Green, Oolong, Black tea hay-like 0.06 [50] 1-penten-3-ol Lipids Oolong tea butter, green [22] (E)-2-hexenal Lipids Green tea, Black tea green 190 [22] (E,E)-2,4hexadienal Lipids Black tea fatty [22] (E,E)-2,4decadienal Lipids Green tea, Black tea fatty, fried 0.16 [78] (Z)-3-hexenal Lipids Green tea, Black tea green [22] Methyl jasmonate Lipids Green, Oolong, Black tea floral [34] Hexanoic acid Lipids Black tea Sweaty, green 890 [78,79] 2,3-butanedione Lipids Green tea butter 10 [78.79] (E)-geraniol Glycosides Green, Oolong, Black tea rose-like 3.2 [22,50] Linalool Carotenoids Glycosides Green, Oolong, Black tea floral 6 [22,50] Linalool Oxide I II III IV Glycosides Green, Oolong, Black tea earthy, floral, creamy [38] Hotrienol Glycosides Oolong tea flowery 110 [25] Methyl salicylate Glycosides Green, Oolong, Black tea minty [22,50] Benzyl alcohol Glycosides Green, Oolong, Black tea burning taste, faint aromatic [22,50] 2-Phenyl ethanol Glycosides Oolong tea, Black tea honey-like 1000 [22] 4-hydroxy-2,5dimethyl-3(2H)furanone Glycosides Black tea caramel-like 60 [42] dimethyl disulfide Maillard reaction Green tea, Oolong tea garlic-like 7.6 [22.50] trimethylsulfide Maillard reaction Black tea putrid 0.01 [78] 2-acetyl-3methylpyrazine Maillard reaction Black tea roasty [78] 2-ethyl-3,5dimethylpyrazine Maillard reaction Black tea nutty 0.04 [78] 5-ethyl-2,3dimethylpyrazine Maillard reaction Black tea nutty 0.09 [78] Indole Maillard reaction Green tea, Oolong tea animal-like [22,33] 2-acetyl-2thiazoline Maillard reaction Black tea popcorn-like 1.3 [22] 2-acetyl-1pyrroline Maillard reaction Black tea popcorn-like 0.1 [22] Phenylacetaldehyde Maillard reaction Oolong tea, Black tea honey-like 4 [22] 4-methyl-2methyl-2butanethiol Maillard reaction Green tea meaty 0.00002 [78] 4-mercapto-4methyl-2pentanone Maillard reaction Green tea meaty 0.0001 [78] Methional Maillard Green, Black tea potato-like 0.2 [78] Page 32 of 36 Ac ce pt ed M an us cr ip t 32 reaction...
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Journal Article•DOI•

The Reference Genome of Tea Plant and Resequencing of 81 Diverse Accessions Provide Insights into Its Genome Evolution and Adaptation.

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En-Hua Xia¹, Wei Tong¹, Yan Hou¹, Yanlin An¹, Linbo Chen, Qiong Wu¹, Yun-Long Liu², Jie Yu¹, Fangdong Li¹, Ruopei Li¹, Penghui Li¹, Huijuan Zhao¹, Ruoheng Ge¹, Jin Huang¹, Ali Inayat Mallano¹, Yanrui Zhang¹, Shengrui Liu¹, Wei-Wei Deng¹, Chuankui Song¹, Zhaoliang Zhang¹, Jian Zhao¹, Shu Wei¹, Zhengzhu Zhang¹, Tao Xia¹, Chaoling Wei¹, Xiaochun Wan¹ - Show less +22 more•Institutions (2)

Anhui Agricultural University¹, Chinese Academy of Sciences²

06 Jul 2020-Molecular Plant

TL;DR: A high-quality reference genome of the tea plant consisting of 15 pseudo-chromosomes, 70.38% of which are LTR retrotransposons is presented, showing the evidence that LTR-RTs play critical roles in the genome size expansion and transcriptional diversification of tea plant genes through preferential gene insertions in promoter regions and introns.

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194 citations

Journal Article•DOI•

Tea aroma formation from six model manufacturing processes

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Zhihui Feng¹, Yifan Li¹, Ming Li¹, Yijun Wang¹, Liang Zhang¹, Xiaochun Wan¹, Xiaogen Yang¹ - Show less +3 more•Institutions (1)

Anhui Agricultural University¹

01 Jul 2019-Food Chemistry

TL;DR: This study investigated the impact of manufacturing processes on the aroma composition of tea to identify volatile compounds formed mainly from four precursor groups: carotenoids, fatty acids, glycosides, and amino acids/sugars.

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176 citations

Journal Article•DOI•

Comparison of Aroma-Active Volatiles in Oolong Tea Infusions Using GC–Olfactometry, GC–FPD, and GC–MS

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Jiancai Zhu¹, Feng Chen¹, Feng Chen², LingYing Wang, Yunwei Niu¹, Dan Yu¹, Chang Shu¹, Chen Hexing¹, HongLin Wang¹, Zuobing Xiao¹ - Show less +6 more•Institutions (2)

Shanghai Institute of Technology¹, Clemson University²

19 Aug 2015-Journal of Agricultural and Food Chemistry

TL;DR: The aroma profile of oolong tea infusions (Dongdingwulong, DDWL; Tieguanyin, TGY; Dahongpao, DHP) was investigated in this study, and forty-seven aroma compounds were at concentrations higher than their corresponding odor thresholds.

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Abstract: The aroma profile of oolong tea infusions (Dongdingwulong, DDWL; Tieguanyin, TGY; Dahongpao, DHP) were investigated in this study. Gas chromatography-olfactometry (GC-O) with the method of aroma intensity (AI) was employed to investigate the aroma-active compounds in tea infusions. The results presented forty-three, forty-five, and forty-eight aroma-active compounds in the TGY, DHP, and DDWL infusions, including six, seven, and five sulfur compounds, respectively. In addition, the concentration of volatile compounds in the tea infusions was further quantitated by solid phase microextraction-gas chromatography (SPME)-GC-MS and SPME-GC-flame photometric detection (FPD). Totally, seventy-six and thirteen volatile and sulfur compounds were detected in three types of tea infusions, respectively. Quantitative results showed that forty-seven aroma compounds were at concentrations higher than their corresponding odor thresholds. On the basis of the odor activity values (OAVs), 2-methylpropanal (OAV: 230-455), 3-methylbutanal (1-353), 2-methylbutanal (34-68), nerolidol (108-184), (E)-2-heptenal (148-294), hexanal (134-230), octanal (28-131), β-damascenone (29-59), indole (96-138), 6-methyl-5-hepten-2-one (34-67), (R)-(-)-linalool (63-87), and dimethyl sulfide (7-1320) presented relatively higher OAVs than those of other compounds, indicating the importance of these compounds in the overall aroma of tea infusions.

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146 citations

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References

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Journal Article•DOI•

Plant terpenoid synthases: Molecular biology and phylogenetic analysis

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JÃ¶rg Bohlmann¹, Gilbert Meyer-Gauen, Rodney Croteau•Institutions (1)

Max Planck Society¹

14 Apr 1998-Proceedings of the National Academy of Sciences of the United States of America

TL;DR: This review focuses on the monoterpene, sesquiterpenes, and diterpene synthases of plant origin that use the corresponding C10, C15, and C20 prenyl diphosphates as substrates to generate the enormous diversity of carbon skeletons characteristic of the terpenoid family of natural products.

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Abstract: This review focuses on the monoterpene, sesquiterpene, and diterpene synthases of plant origin that use the corresponding C10, C15, and C20 prenyl diphosphates as substrates to generate the enormous diversity of carbon skeletons characteristic of the terpenoid family of natural products. A description of the enzymology and mechanism of terpenoid cyclization is followed by a discussion of molecular cloning and heterologous expression of terpenoid synthases. Sequence relatedness and phylogenetic reconstruction, based on 33 members of the Tps gene family, are delineated, and comparison of important structural features of these enzymes is provided. The review concludes with an overview of the organization and regulation of terpenoid metabolism, and of the biotechnological applications of terpenoid synthase genes.

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1,011 citations

Journal Article•DOI•

Biosynthesis of plant-derived flavor compounds.

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Wilfried Schwab¹, Rachel Davidovich-Rikanati², Efraim Lewinsohn²•Institutions (2)

Technische Universität München¹, Agricultural Research Organization, Volcani Center²

01 May 2008-Plant Journal

TL;DR: Modification of flavor by genetic engineering is dependent on the knowledge and availability of genes that encode enzymes of key reactions that influence or divert the biosynthetic pathways of plant-derived volatiles.

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Abstract: Plants have the capacity to synthesize, accumulate and emit volatiles that may act as aroma and flavor molecules due to interactions with human receptors. These low-molecular-weight substances derived from the fatty acid, amino acid and carbohydrate pools constitute a heterogenous group of molecules with saturated and unsaturated, straight-chain, branched-chain and cyclic structures bearing various functional groups (e.g. alcohols, aldehydes, ketones, esters and ethers) and also nitrogen and sulfur. They are commercially important for the food, pharmaceutical, agricultural and chemical industries as flavorants, drugs, pesticides and industrial feedstocks. Due to the low abundance of the volatiles in their plant sources, many of the natural products had been replaced by their synthetic analogues by the end of the last century. However, the foreseeable shortage of the crude oil that is the source for many of the artificial flavors and fragrances has prompted recent interest in understanding the formation of these compounds and engineering their biosynthesis. Although many of the volatile constituents of flavors and aromas have been identified, many of the enzymes and genes involved in their biosynthesis are still not known. However, modification of flavor by genetic engineering is dependent on the knowledge and availability of genes that encode enzymes of key reactions that influence or divert the biosynthetic pathways of plant-derived volatiles. Major progress has resulted from the use of molecular and biochemical techniques, and a large number of genes encoding enzymes of volatile biosynthesis have recently been reported.

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837 citations

Journal Article•DOI•

Solvent assisted flavour evaporation – a new and versatile technique for the careful and direct isolation of aroma compounds from complex food matrices

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Wolfgang Engel, Wolfgang Bahr, Peter Schieberle

01 Jan 1999-European Food Research and Technology

TL;DR: In this article, a solvent assisted flavour evaporation (SAFE) method was proposed for the isolation of volatiles from either solvent extracts, aqueous foods, such as milk or beer, or even matrices with a high oil content.

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Abstract: A compact and versatile distillation unit was developed for the fast and careful isolation of volatiles from complex food matrices. In connection with a high vacuum pump (5×10–3 Pa), the new technique, designated solvent assisted flavour evaporation (SAFE), allows the isolation of volatiles from either solvent extracts, aqueous foods, such as milk or beer, aqueous food suspensions, such as fruit pulps, or even matrices with a high oil content. Application of SAFE to model solutions of selected aroma compounds resulted in higher yields from both solvent extracts or fatty matrices (50% fat) compared to previously used techniques, such as high vacuum transfer. Direct distillation of aqueous fruit pulps in combination with a stable isotope dilution analysis enabled the fast quantification (60 min including MS analysis) of compounds such as the very polar and unstable 4-hydroxy-2,5-dimethyl-3(2H)-furanone in strawberries (3.2 mg/kg) and tomatoes (340 μg/kg). Furthermore, the direct distillation of aqueous foods, such as beer or orange juice, gave flavourful aqueous distillates free from non-volatile matrix compounds.

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814 citations

Journal Article•DOI•

Jasmonic acid distribution and action in plants: regulation during development and response to biotic and abiotic stress

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Robert A. Creelman¹, John E. Mullet•Institutions (1)

Texas A&M University¹

09 May 1995-Proceedings of the National Academy of Sciences of the United States of America

TL;DR: In soybean leaves that had been dehydrated to cause a 15% decrease in fresh weight, JA levels increased approximately 5-fold within 2 h and declined to approximately control levels by 4 h and a lag time of 1-2 h occurred before abscisic acid accumulation reached a maximum.

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Abstract: Jasmonic acid (JA) is a naturally occurring growth regulator found in higher plants. Several physiological roles have been described for this compound (or a related compound, methyl jasmonate) during plant development and in response to biotic and abiotic stress. To accurately determine JA levels in plant tissue, we have synthesized JA containing 13C for use as an internal standard with an isotopic composition of [225]:[224] 0.98:0.02 compared with [225]:[224] 0.15:0.85 for natural material. GC analysis (flame ionization detection and MS) indicate that the internal standard is composed of 92% 2-(+/-)-[13C]JA and 8% 2-(+/-)-7-iso-[13C]JA. In soybean plants, JA levels were highest in young leaves, flowers, and fruit (highest in the pericarp). In soybean seeds and seedlings, JA levels were highest in the youngest organs including the hypocotyl hook, plumule, and 12-h axis. In soybean leaves that had been dehydrated to cause a 15% decrease in fresh weight, JA levels increased approximately 5-fold within 2 h and declined to approximately control levels by 4 h. In contrast, a lag time of 1-2 h occurred before abscisic acid accumulation reached a maximum. These results will be discussed in the context of multiple pathways for JA biosynthesis and the role of JA in plant development and responses to environmental signals.

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741 citations

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Carotenoids and their cleavage products: Biosynthesis and functions

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Michael H. Walter¹, Dieter Strack¹•Institutions (1)

Leibniz Institute for Neurobiology¹

23 Mar 2011-Natural Product Reports

TL;DR: This review focuses on plant Carotenoids, but it also includes progress made on microbial and animal carotenoid metabolism to better understand the functions and the evolution of these structurally diverse compounds with a common backbone.

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450 citations