Study on the Glycosidically Bound Volatiles and Aroma Constituents in the Processing of Wuyi Rougui

WU Zongjie; OU Xiaoxi; LIN Hongzheng; YU Xinru; CHEN Shouyue; WU Qingyang; LI Xinlei; SUN Yun

doi:10.13305/j.cnki.jts.2024.01.005

PDF(1428 KB)

Journal of Tea Science ›› 2024, Vol. 44 ›› Issue (1) : 84-100. DOI: 10.13305/j.cnki.jts.2024.01.005

Research Paper

Study on the Glycosidically Bound Volatiles and Aroma Constituents in the Processing of Wuyi Rougui

WU Zongjie^1,2, OU Xiaoxi^1,2, LIN Hongzheng^1,2, YU Xinru^1,2, CHEN Shouyue^1,2, WU Qingyang^1,2, LI Xinlei³, SUN Yun^1,2,*

Author information +

History +

Abstract

‘Rougui’, the main cultivar of Wuyi rock tea, is characterized by a rich floral and pungent cinnamon aroma. To elucidate the contribution of key aroma constituents and glycosidically bound volatiles (GBVs) to Wuyi Rougui rock tea, this study employed ultra-high-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF/MS) and headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) to investigate the dynamic changes of GBVs and aroma constituents during the processing of Wuyi Rougui rock tea. The results reveal that a total of 276 aroma constituents were identified from 11 different processing stages of Wuyi Rougui rock tea. These aroma constituents belong to various chemical classes, including esters, alcohols, heterocyclic constituents, ketones, aldehydes and terpenes, with heterocyclic constituents, esters, terpenes and alcohols being the predominant aroma components. Orthogonal partial least squares-discriminant analysis (OPLS-DA) identified 35 characteristic aroma constituents in Wuyi Rougui rock tea, as indicated by their Variable Importance in Projection (VIP) values and Odor Activity Values (OAV) greater than 1. Notably, the contents of constituents associated with green and grassy flavor, such as (Z)-3-hexen-1-ol, (E)-2-nonenal and hexanal, exhibited decreasing trends during the processing, while aroma constituents associated with floral or fruity aromas, like linalool, benzyl alcohol, benzaldehyde, eugenol and β-ocimene, displayed increasing trends. Furthermore, in fresh leaves of Wuyi Rougui rock tea, aroma constituents including linalool, benzyl alcohol, benzaldehyde, 2-ethoxy-3-methylpyrazine and (E,E)-3,5-octadien-2-one exhibited ACI values greater than 1, suggesting they are key aroma constituents during the processing of Wuyi Rougui rock tea. Constituents such as dehydrocinnamyl alcohol and α-ionone contributed to the characteristic cinnamon aroma of Wuyi Rougui rock tea. In addition, ten GBVs were identified. During the processing, the contents of glucosides showed an upward trend, while primeveroside showed trend. The total contents of GBVs remained relatively stable. During the late stages of fermentation, both GBVs demonstrated declining trends, particularly constituents like benzyl primeveroside, 2-phenylethyl primeveroside, geranyl glucoside, linayl primeveroside and benzyl glucoside. The results indicate that GBVs were involved in the development of the faint scent and floral-fruity notes of Wuyi Rougui rock tea. This study clarified the role of characteristic aroma constituents and GBVs in the aroma formation of Wuyi Rougui rock tea, in order to better improve the aroma quality of Wuyi Rougui rock tea.

Key words

aroma / glycosidically bound volatiles / metabolomics / processing procedure / Wuyi Rougui rock tea

Cite this article

EndNote

Ris (Procite)

Bibtex

Download Citations

WU Zongjie, OU Xiaoxi, LIN Hongzheng, YU Xinru, CHEN Shouyue, WU Qingyang, LI Xinlei, SUN Yun. Study on the Glycosidically Bound Volatiles and Aroma Constituents in the Processing of Wuyi Rougui[J]. Journal of Tea Science. 2024, 44(1): 84-100 https://doi.org/10.13305/j.cnki.jts.2024.01.005

References

[1] 毕婉君, 魏子淳, 郑玉成, 等. 基于ATD-GC-MS技术检测铁观音做青过程环境挥发性成分的动态变化[J]. 食品科学, 2023, 44(8): 201-211.
Bi W J, Wei Z C, Zheng Y C, et al.Using automatic thermal desorption gas chromatography-mass spectrometry to detect dynamic changes of environmental volatile components in Tieguanyin oolong tea during fine manipulation[J]. Food Science, 2023, 44(8): 201-211.
[2] 魏子淳, 庄加耘, 孙志琳, 等. 不同摊叶厚度晾青对武夷岩茶品质的影响[J]. 食品工业科技, 2023, 44(7): 97-106.
Wei Z C, Zhuang J Y, Sun Z L, et al.Effects on the quality of Wuyi rock tea with different airing thicknesses[J]. Science and Technology of Food Industry, 2023, 44(7): 97-106.
[3] 钟秋生, 彭佳堃, 戴伟东, 等. 基于UHPLC-Q-Exactive/MS的不同烘焙处理岩茶化学成分差异分析[J]. 食品科学, 2023, 44(20): 268-282.
Zhong Q S, Peng J K, Dai W D, et al.Analysis of differences in chemical constituents of Rougui rock tea with different roasting degrees by ultra-high performance liquid chromatography-quadrupole orbitrap mass spectrometry[J]. Food Science, 2023, 44(20): 268-282.
[4] 周子维, 刘宝顺, 武清扬, 等. 基于LOX-HPL途径的武夷肉桂加工中香气物质的形成与调控[J]. 食品与生物技术学报, 2021, 40(1): 100-111.
Zhou Z W, Liu B S, Wu Q Y, et al.Formation and regulation of aroma-related volatiles during the manufacturing process of wuyi rougui tea via LOX-HPL pathway[J]. Journal of Food Science and Biotechnology, 2021, 40(1): 100-111.
[5] Yang Z Y, Baldermann S, Watanabe N.Recent studies of the volatile compounds in tea[J]. Food Research International, 2013, 53(2): 585-599.
[6] 黄慧清, 郑玉成, 胡清财, 等. 基于SBSE-GC-O-MS技术的三个代表性乌龙茶品种关键香气成分分析[J]. 食品科学, 2023: 1-13. [2023-11-05]. http://kns.cnki.net/kcms/detail/11.2206.ts.20230830.0954.011.html.
Huang H Q, Zheng Y C, Hu Q C, et al. Study on key aroma components of three representative oolong tea varieties based on SBSE-GC-O-MS technology [J]. Food Science, 2023: 1-13. [2023-11-05]. http://kns.cnki.net/kcms/detail/11.2206.ts.20230830.0954.011.html.
[7] Wang B S, Yu M G, Tang Y, et al.Characterization of odor-active compounds in Dahongpao Wuyi rock tea (Camellia sinensis) by sensory-directed flavor analysis[J]. Journal of Food Composition and Analysis, 2023, 123(3): 105612. doi: 10.1016/j.jfca.2023.105612.
[8] Ma C Y, Li J X, Chen W, et al.Study of the aroma formation and transformation during the manufacturing process of oolong tea by solid-phase micro-extraction and gas chromatography-mass spectrometry combined with chemometrics[J]. Food Research International, 2018, 108: 413-422.
[9] Zeng L T, Watanabe N, Yang Z Y.Understanding the biosyntheses and stress response mechanisms of aroma compounds in tea (Camellia sinensis) to safely and effectively improve tea aroma[J]. Critical Reviews in Food Science and Nutrition, 2019, 59(14): 2321-2334.
[10] Liu H F, Li S F, Zhong Y M, et al.Study of aroma compound formations and transformations during Jinxuan and Qingxin oolong tea processing[J]. International Journal of Food Science & Technology, 2021, 56(11): 5629-5638.
[11] Ho C T, Zheng X, Li S M.Tea aroma formation[J]. Food Science & Human Wellness, 2015, 4(1): 9-27.
[12] Guo X Y, Ho C T, Wan X C, et al.Changes of volatile compounds and odor profiles in Wuyi rock tea during processing[J]. Food Chemistry, 2021, 341: 128230. doi: 10.1016/j.foodchem.2020.128230.
[13] Guo X Y, Schwab W, Ho T C, et al.Characterization of the aroma profiles of oolong tea made from three tea cultivars by both GC-MS and GC-IMS[J]. Food Chemistry, 2022, 376: 131933. doi: 10.1016/j.foodchem.2021.131933.
[14] 欧阳珂, 张成, 廖雪利, 等. 基于感官组学分析玉米香型南川大茶树工夫红茶特征香气[J]. 茶叶科学, 2022, 42(3): 397-408.
Ouyang K, Zhang C, Liao X L, et al.Characterization of the key aroma in corn-scented congou black tea manufactured from Camellia nanchuanica by sensory omics techniques[J]. Journal of Tea Science, 2022, 42(3): 397-408.
[15] Yang P, Yu M G, Song H L, et al.Characterization of key aroma-active compounds in rough and moderate fire Rougui Wuyi Rock tea (Camellia sinensis) by sensory-directed flavor analysis and elucidation of the influences of roasting on aroma[J]. Journal of Agricultural and Food Chemistry, 2022, 70(1): 267-278.
[16] 李朋亮. 基于修饰代谢组学的绿茶中糖苷类品质成分研究[D]. 武汉: 华中农业大学, 2018.
Li P L.Study on the glycosidic flavor constituents in green tea based on modification-specific metabolomics approach[J]. Wuhan: Huazhong Agricultural University, 2018.
[17] Gui J D, Fu X M, Zhou Y, et al.Does enzymatic hydrolysis of glycosidically bound volatile compounds really contribute to the formation of volatile compounds during the oolong tea manufacturing process?[J]. Journal of Agricultural and Food Chemistry, 2015, 63(31): 6905-6914.
[18] 路欣, 陈丽, 肖凌, 等. 凤凰单丛香气及糖苷类香气前体变化研究[J]. 食品安全质量检测学报, 2018, 9(11): 2808-2816.
Lu X, Chen L, Xiao L, et al.Changes of volatile and glycosidically aroma precursors of Fenghuang Dancong[J]. Journal of Food Safety & Quality, 2018, 9(11): 2808-2816.
[19] 谢运海, 郑德勇, 叶乃兴, 等. 漳平水仙茶加工过程中香气前体含量的变化[J]. 茶叶科学, 2016, 36(1): 11-17.
Xie Y H, Zheng D Y, Ye N X, et al.Analysis on the contents of Zhangping Shuixian tea's aroma precursors during manufacturing processes[J]. Journal of Tea Science, 2016, 36(1): 11-17.
[20] Cui J L, Katsuno T, Totsuka K, et al.Characteristic fluctuations in glycosidically bound volatiles during tea processing and identification of their unstable derivatives[J]. Journal of Agricultural and Food Chemistry, 2016, 64(5): 1151-1157.
[21] Li P L, Zhu Y, Lu M L, et al.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[J]. Food Chemistry, 2018, 279: 80-87.
[22] Wang D M, Kubota K, Kobayashi A, et al.Analysis of glycosidically bound aroma precursors in tea leaves. 3. Change in the glycoside content of tea leaves during the oolong tea manufacturing process[J]. Journal of Agricultural & Food Chemistry, 2001, 49(11): 5391-5396.
[23] Dai W D, Yin P Y, Zeng Z D, et al.Nontargeted modification-specific metabolomics study based on liquid chromatography-high-resolution mass spectrometry[J]. Analytical Chemistry, 2014, 86(18): 9146-9153.
[24] Chen D, Sun Z, Gao J J, et al.Metabolomics combined with proteomics provides a novel interpretation of the compound differences among chinese tea cultivars (Camellia sinensis var. sinensis) with different manufacturing suitabilities[J]. Food Chemistry, 2022, 377: 131976. doi: 10.1016/j.foodchem.2021.131976.
[25] Yuan H L, Cao G P, Hou X D, et al.Development of a widely targeted volatilomics method for profiling volatilomes in plants[J]. Molecular Plant, 2022, 15(1): 189-202.
[26] 王梦琪, 朱荫, 张悦, 等. 茶叶挥发性成分中关键呈香成分研究进展[J]. 食品科学, 2019, 40(23): 341-349.
Wang M Q, Zhu Y, Zhang Y, et al.A review of recent research on key aroma compounds in tea[J]. Food Science, 2019, 40(23): 341-349.
[27] 王赞, 郭雅玲. 做青工艺对乌龙茶特征香气成分影响的研究进展[J]. 食品安全质量检测学报, 2017, 8(5): 1603-1609.
Wang Z, Guo Y L.Research progress on influence of green-making process on characteristic aroma components of oolong tea[J]. Journal of Food Safety & Quality, 2017, 8(5): 1603-1609.
[28] 陈林, 陈键, 陈泉宾, 等. 做青工艺对乌龙茶香气组成化学模式的影响[J]. 茶叶科学, 2014, 34(4): 387-395.
Chen L, Chen J, Chen Q B, et al.Effects of green-making technique on aroma pattern of oolong tea[J]. Journal of Tea Science, 2014, 34(4): 387-395.
[29] 刘彬彬. 新品系“606”乌龙茶加工中主要呈味物质动态变化及FOMT基因表达研究[D]. 福州: 福建农林大学, 2020.
Liu B B.Study on the dynamic changes of main taste substances and FOMT gene expression in the processing of new strain "606" oolong tea [D]. Fuzhou: Fujian Agriculture and Forestry University, 2020.
[30] Ma C Y, Li J X, Chen W, et al.Study of the aroma formation and transformation during the manufacturing process of oolong tea by solid-phase micro-extraction and gas chromatography-mass spectrometry combined with chemometrics[J]. Food Research International, 2018, 108: 413-422.
[31] 杨云, 刘彬彬, 周子维, 等. 新品系‘606’乌龙茶加工过程中呈味物质的变化与品质分析[J]. 食品工业科技, 2021, 42(23): 311-318.
Yang Y, Liu B B, Zhou Z W, et al.Changes of taste compounds and quality analysis during the manufacturing process of a new tea line ‘606’ oolong tea[J]. Science and Technology of Food Industry, 2021, 42(23): 311-318.
[32] Ruther J.Retention index database for identification of general green leaf volatiles in plants by coupled capillary gas chromatography-mass spectrometry[J]. Journal of Chromatography A, 2000, 890(2): 313-319.
[33] Liu Z B, Chen F C, Sun J Y, et al.Dynamic changes of volatile and phenolic components during the whole manufacturing process of Wuyi rock tea (Rougui)[J]. Food Chemistry, 2022, 367: 130624. doi: 10.1016/j.foodchem.2021.130624.
[34] Yue C, Cao H L, Zhang S R, et al.Aroma characteristics of Wuyi rock tea prepared from 16 different tea plant varieties[J]. Food Chemistry: X, 2023, 17: 100586. doi: 10.1016/j.fochx.2023.100586.
[35] 佐明兴, 闫瑞, 封子旋, 等. 基于代谢组学分析铁观音乌龙茶包揉过程中代谢物动态变化[J]. 食品科学, 2023, 44(22): 353-365.
Zuo M X, Yan R, Feng Z X, et al.Metabolomics analysis of dynamic changes in metabolites in tieguanyin oolong tea during wrapping-twisting[J]. Food Science, 2023, 44(22): 353-365.
[36] 陈倩莲, 刘仕章, 占仕权, 等. 基于HS-SPME-GC-MS和OAV鉴定4种武夷岩茶关键呈香物质[J]. 食品工业科技, 2023, 44(14): 296-303.
Chen Q L, Liu S Z, Zhan S Q, et al.Identification of four kind key aroma components of Wuyi rock tea based on HS-SPME-GC-MS and OAV[J]. Science and Technology of Food Industry, 2023, 44(14): 296-303.
[37] Zheng Y C, Hu Q C, Wu Z J, et al.Volatile metabolomics and coexpression network analyses provide insight into the formation of the characteristic cultivar aroma of oolong tea (Camellia sinensis)[J]. LWT, 2022, 164: 113666. doi: doi.org/10.1016/j.lwt.2022.113666.
[38] Guo X Y, Song C K, Ho C, et al.Contribution of L-theanine to the formation of 2,5-dimethylpyrazine, a key roasted peanutty flavor in oolong tea during manufacturing processes[J]. Food Chemistry, 2018, 263: 18-28.
[39] Zhang Y, Kang S Y, Yan H, et al.Insights into characteristic volatiles in wuyi rock teas with different cultivars by chemometrics and gas chromatography olfactometry/mass spectrometry[J]. Foods, 2022, 11(24): 4109. doi: 10.3390/foods11244109.
[40] Mizutani M, Nakanishi H, Ema J I, et al.Cloning of β-primeverosidase from tea leaves, a key enzyme in tea aroma formation[J]. Plant Physiology, 2002, 130(4): 2164-2176.
[41] Ohgami S, Ono E, Horikawa M, et al.Volatile glycosylation in tea plants: sequential glycosylations for the biosynthesis of aroma β-primeverosides are catalyzed by two Camellia sinensis glycosyltransferases[J]. Plant Physiology, 2015, 168(2): 464-477.
[42] 张正竹. 绿茶主要香气物质的糖苷类前体研究[D]. 长沙: 湖南农业大学, 2000.
Zhang Z Z.Study on glycoside precursors of main aroma substances in green tea [D]. Changsha: Hunan Agricultural University, 2000.