茶树2种酰基化黄酮苷的分布规律及加工变化特性研究

doi:10.3785/j.issn.1008-9209.2021.10.121

浙江大学学报（农业与生命科学版）

2022, Vol. 48

Issue (5): 573-582 DOI: 10.3785/j.issn.1008-9209.2021.10.121

园艺科学

茶树2种酰基化黄酮苷的分布规律及加工变化特性研究

黄艳梅¹(

),周菲菲¹,罗立民¹,黄海涛²,葛志伟³,杨江帆⁴,屠幼英¹,吴媛媛¹(

)

^1.浙江大学农业与生物技术学院茶学系，杭州 310058
^2.杭州市农业科学研究院茶叶研究所，杭州 310024
^3.浙江大学农生环测试中心，杭州 310058
^4.福建农林大学园艺学院/茶学福建省高校重点实验室，福州 350002

Distribution and processing characteristics of two acylated flavonol glycosides in Camellia sinensis

Yanmei HUANG¹(

),Feifei ZHOU¹,Limin LUO¹,Haitao HUANG²,Zhiwei GE³,Jiangfan YANG⁴,Youying TU¹,Yuanyuan WU¹(

)

^1.Tea Science Department, College of Agriculture and Biotechnology, Zhejiang University, Hangzhou 310058, China
^2.Tea Research Institute, Hangzhou Academy of Agricultural Sciences, Hangzhou 310024, China
^3.Analysis Center of Agrobiology and Environmental Sciences, Zhejiang University, Hangzhou 310058, China
^4.College of Horticulture/Key Laboratory of Tea Science at Universities in Fujian, Fujian Agriculture and Forestry University, Fuzhou 350002, China

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摘要：

本研究从茶叶中分离纯化出2种酰基化黄酮四糖苷{quercetin-3-O-[(E)-p-coumaroyl-(1→2)][α-L-arabinopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside，F₁；kaempferol-3-O-[(E)-p-coumaroyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside，F₂}，通过自主建立的高效液相色谱（high performance liquid chromatography, HPLC）定量检测方法，系统研究了F₁与F₂在茶树不同组织、叶位、品种中的分布特点，探究光照对F₁和F₂含量的影响，以及两者在乌龙茶加工过程中的动态变化。结果表明：F₁主要在叶和茎中分布，F₂仅存在于叶中；根中未检测到F₁与F₂。随着叶片成熟度的增加，F₁与F₂的含量呈先升高后降低的趋势。在42个茶树品种中，F₁和F₂含量范围分别为0～2.31、0～1.56 mg/g；F₁在‘黄金菊’中含量最高，在‘本山’和‘绿芽佛手’中未检测到；F₂在‘黄金菊’中含量最高，在‘绿芽佛手’‘金面奇兰’‘中黄2号’和‘本山’中未检测到。对3个茶树品种进行遮阴实验，发现遮阴处理组F₁含量显著降低，说明光照对其形成具有重要作用。选取‘福建水仙’鲜叶进行乌龙茶加工，F₁和F₂含量在整个加工过程中呈降低趋势，且在杀青工序中降幅最大，做青工序中降幅最小，表明不同加工工序对两者的含量存在不同程度的影响。

关键词： 酰基化黄酮苷; 茶树品种; 叶位; 组织; 遮阴处理; 乌龙茶加工

Abstract:

In this study, two acylated flavonol tetraglycosides {quercetin-3-O-[(E)-p-coumaroyl-(1→2)][α-L-arabinopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside，F₁；kaempferol-3-O-[(E)-p-coumaroyl-(1→2)]-[α-L-arabinopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside，F₂} were isolated and purified from Camellia sinensis, and the distribution characteristics of F₁ and F₂ in different tissues, leaf positions, and tea cultivars were systematically studied through the independent established high performance liquid chromatography (HPLC) method. The effect of light on the contents of F₁ and F₂, and the dynamic changes in the processing stages of oolong tea were also studied. The results showed that F₁ was mainly distributed in tea leaves and stems, and F₂ was only present in leaves; neither F₁ nor F₂ was detected in the roots. With the increase of leaf maturity, the contents of F₁ and F₂ firstly increased and then decreased. Among the 42 tea cultivars, the contents of F₁ and F₂ ranged from 0-2.31 mg/g and 0-1.56 mg/g, respectively. F₁ had the highest content in ‘Huangjinju’ and was not detected in ‘Benshan’ and ‘Lüyafoshou’ tea cultivars. F₂ had the highest content in ‘Huangjinju’ and was not detected in ‘Lüyafoshou’, ‘Jinmian Qilan’, ‘Zhonghuang No. 2’ and ‘Benshan’. Shading experiments were carried out on three tea cultivars, and it was found that the content of F₁ in the shading treatment group was significantly reduced, indicating that the light plays a significant role in the formation of F₁. The fresh leaves of ‘Fujian Shuixian’ were selected for the processing of oolong tea. The contents of F₁ and F₂ showed downward trends during the whole processing stages, and the largest decline was observed in the process of fixation, while the smallest was in the process of rotation, which shows that different processing operations have different degrees of influences on the contents of two substances.

Key words: acylated flavonol glycosides tea cultivar leaf position tissue shading treatment oolong tea processing

收稿日期: 2021-10-12 出版日期: 2022-11-02

CLC:

S 571.1

基金资助: 福建省“2011中国乌龙茶产业协同创新中心”项目（〔2015〕No. 75）;浙江省重点研发计划项目(2018C02012);浙江省农业新品种茶树选育重大科技专项(2021C02067)

通讯作者: 吴媛媛 E-mail: hym18273120704@163.com;yywu@zju.edu.cn

作者简介: 黄艳梅（https://orcid.org/0000-0002-6905-0765)，E-mail：hym18273120704@163.com

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引用本文:

黄艳梅,周菲菲,罗立民,黄海涛,葛志伟,杨江帆,屠幼英,吴媛媛. 茶树2种酰基化黄酮苷的分布规律及加工变化特性研究[J]. 浙江大学学报（农业与生命科学版）, 2022, 48(5): 573-582.

Yanmei HUANG,Feifei ZHOU,Limin LUO,Haitao HUANG,Zhiwei GE,Jiangfan YANG,Youying TU,Yuanyuan WU. Distribution and processing characteristics of two acylated flavonol glycosides in Camellia sinensis. Journal of Zhejiang University (Agriculture and Life Sciences), 2022, 48(5): 573-582.

链接本文:

https://www.zjujournals.com/agr/CN/10.3785/j.issn.1008-9209.2021.10.121 或 https://www.zjujournals.com/agr/CN/Y2022/V48/I5/573

表1 HPLC洗脱梯度

表2 对照品F1和F2溶液质量浓度 (mg/mL)

图1 2种酰基化黄酮苷的分子结构及HPLC图谱A. F1的分子结构；B. F2的分子结构；C. 2种酰基化黄酮苷的HPLC图谱（λ=360 nm）。

图2 2种酰基化黄酮苷的标准曲线

表3 2种酰基化黄酮苷在茶树不同组织部位的含量分布 (mg/g)

图3 2种酰基化黄酮苷在不同叶位中的含量分布及含量比值1：第1叶；2：第2叶；3：第3叶；4：第4叶；5：老叶。短栅上不同小写字母表示同种酰基化黄酮苷在不同叶位间在P＜0.05水平差异有统计学意义。n=3。

图4 2种酰基化黄酮苷在不同茶树品种中的含量分布n=3。

表4 2种酰基化黄酮苷的含量分组及组间变异系数

图5 遮阴处理对2种酰基化黄酮苷含量的影响N26：‘福建水仙’；N8：‘龙井1号’；N3：‘政和大白’。*表示在P＜0.05水平差异有统计学意义，ns表示差异无统计学意义；n=3。下同。

图6 2种酰基化黄酮苷遮阴处理后的含量变化率

图7 2种酰基化黄酮苷含量在乌龙茶加工过程中的动态变化以鲜叶中F1和F2的含量为基准，将其分别定为100%，其他各加工过程中的含量表示与鲜叶含量的比值。XY：鲜叶；WD：萎凋；ZQ1、ZQ2、ZQ3、ZQ4：做青1、做青2、做青3、做青4；SQ：杀青；RN：揉捻；GZ：干燥。n=3。

表5 2种酰基化黄酮苷在乌龙茶加工过程中的含量降低幅度 (%)

1	ZUCHOWSKI J, PECIO L, MARCINIAK B, et al. Unusual isovalerylated flavonoids from the fruit of sea buckthorn (Elaeagnus rhamnoides) grown in Sokolka, Poland[J]. Phytochemistry, 2019, 163: 178-186. DOI:10.1016/j.phytochem.2019.03.001 doi: 10.1016/j.phytochem.2019.03.001
2	LI K K, LI S S, XU F, et al. A novel acylated quercetin glycoside and compounds of inhibitory effects on α-glucosidase from Panax ginseng flower buds[J]. Natural Product Research, 2020, 34(18): 2559-2565. DOI:10.1080/14786419.2018.1543685 doi: 10.1080/14786419.2018.1543685
3	SHKONDROV A M, KRASTEVA I N. HIGH resolution LC-MS/MS screening for secondary metabolites in Bulgarian species of genus Astragalus L.[J]. Quimica Nova, 2021, 44: 683-688. DOI:10.21577/0100-4042.20170730 doi: 10.21577/0100-4042.20170730
4	WANG Y X, XIE X, LIU L N, et al. Four new flavonol glycosides from the leaves of Ginkgo biloba [J]. Natural Product Research, 2021, 35(15): 2520-2525. DOI:10.1080/14786419.2019.1684282 doi: 10.1080/14786419.2019.1684282
5	WU X L, ZHAO Y, HAYTOWITZ D B, et al. Effects of domestic cooking on flavonoids in broccoli and calculation of retention factors[J]. Heliyon, 2019, 5(3): e01310. DOI:10.1016/j.heliyon.2019.e01310 doi: 10.1016/j.heliyon.2019.e01310
6	NIELSEN J K, OLSEN C E, PETERSEN M K. Acylated flavonol glycosides from cabbage leaves[J]. Phytochemistry, 1993, 34(2) :539-544.
7	FERRERES F, CASTANER M, TOMASBARBERAN F A. Acylated flavonol glycosides from spinach leaves (Spinacia oleracea)[J]. Phytochemistry, 1997, 45(8): 1701-1705.
8	SAID R B, RAHALI S, AISSA M A B, et al. Fingerprinting profile of flavonol glycosides from Bassia eriophora using negative electrospray ionization, computational studies and their antioxidant activities[J]. Journal of Molecular Structure, 2021, 1241: 130689. DOI:10.1016/j.molstruc.2021.130689 doi: 10.1016/j.molstruc.2021.130689
9	LORENZ P, BUNSE M, KLAIBER I, et al. Comprehensive phytochemical characterization of herbal parts from Kidney Vetch (Anthyllis vulneraria L.) by LC/MS(n) and GC/MS[J]. Chemistry and Biodiversity, 2020, 17(10): e2000485. DOI:10.1002/cbdv.202000485 doi: 10.1002/cbdv.202000485
10	FAVRE G, GONZALEZ-NEVES G, PICCARDO D, et al. New acylated flavonols identified in Vitis vinifera grapes and wines[J]. Food Research International, 2018, 112: 98-107. DOI:10.1016/j.foodres.2018.06.019 doi: 10.1016/j.foodres.2018.06.019
11	MIHARA R, MITSUNAGA M, FUKUI Y, et al. A novel acylated quercetin tetraglycoside from oolong tea (Camelia sinensis) extracts[J]. Tetrahedron Letters, 2004, 45(26): 5077-5080. DOI:10.1016/j.tetlet.2004.04.192 doi: 10.1016/j.tetlet.2004.04.192
12	TOHGE T, WENDENBURG R, ISHIHARA H, et al. Characterization of a recently evolved flavonol-phenylacyltransferase gene provides signatures of natural light selection in Brassicaceae[J]. Nature Communications, 2016, 7: 12399. DOI:10.1038/ncomms12399 doi: 10.1038/ncomms12399
13	AMEN Y M, MARZOUK A M, ZAGHLOUL M G, et al. A new acylated flavonoid tetraglycoside with anti-inflammatory activity from Tipuana tipu leaves[J]. Natural Product Research, 2015, 29(6): 511-517. DOI:10.1080/14786419.2014.952233 doi: 10.1080/14786419.2014.952233
14	MANIR M M, KIM J K, LEE B G, et al. Tea catechins and flavonoids from the leaves of Camellia sinensis inhibit yeast alcohol dehydrogenase[J]. Bioorganic and Medicinal Chemistry, 2012, 20(7): 2376-2381. DOI:10.1016/j.bmc.2012.02.002 doi: 10.1016/j.bmc.2012.02.002
15	BAI W X, WANG C, WANG Y J, et al. A novel acylated flavonol tetraglycoside with inhibitory effect on lipid accumulation in3T3-L1 cells from Lu’an Guapian tea and quantification of flavonoid glycosides in six major processing types of tea[J]. Journal of Agricultural and Food Chemistry, 2017, 65(14): 2999-3005. DOI:10.1021/acs.jafc.7b00239 doi: 10.1021/acs.jafc.7b00239
16	顾莹婕.福建水仙茶两种黄酮糖苷的分离鉴定及其抑制口腔致病菌功能的研究[D].杭州:浙江大学,2019. GU Y J. Studies on isolation and identification of two flavonol glycosides from Fujian Shuixian tea and their inhibition of oral pathogenic bacteria[D]. Hangzhou: Zhejiang University, 2019. (in Chinese with English abstract)
17	陆英,钟晓红,操君喜,等.茯砖茶中黄酮类化合物的分离与鉴定[J].现代食品科技,2017,33(3):285-294. DOI:10.13982/j.mfst.1673-9078.2017.3.043 LU Y, ZHONG X H, CAO J X, et al. Isolation and identification of flavones from Fuzhuan tea[J]. Modern Food Science and Technology, 2017, 33(3): 285-294. (in Chinese with English abstract) doi: 10.13982/j.mfst.1673-9078.2017.3.043
18	LU Y, HE Y J, ZHU S H, et al. New acylglycosides flavones from Fuzhuan brick tea and simulation analysis of their bioactive effects[J]. International Journal of Molecular Sciences, 2019, 20(3): 494. DOI:10.3390/ijms20030494 doi: 10.3390/ijms20030494
19	HSIEH S K, LIN H Y, CHEN C J, et al. Promotion of myotube differentiation and attenuation of muscle atrophy in murine C2C12 myoblast cells treated with teaghrelin[J]. Chemico-Biological Interactions, 2020, 315: 108893. DOI:10.1016/j.cbi.2019.108893 doi: 10.1016/j.cbi.2019.108893
20	TIAN Y Z, LIU X, LIU W, et al. A new anti-proliferative acylated flavonol glycoside from Fuzhuan brick-tea[J]. Natural Product Research, 2016, 30(23): 2637-2641. DOI:10.1080/14786419.2015.1136911 doi: 10.1080/14786419.2015.1136911
21	KEHR J, YOSHITAKE S, IJIRI S, et al. Ginkgo biloba leaf extract (EGb 761 (R)) and its specific acylated flavonol constituents increase dopamine and acetylcholine levels in the rat medial prefrontal cortex: possible implications for the cognitive enhancing properties of EGb 761 (R)[J]. International Psychogeriatrics, 2012, 24: S25-S34. DOI:10.1017/S1041610212000567 doi: 10.1017/S1041610212000567
22	MIHARA R, MITSUNAGA M, FUKUI Y, et al. A novel acylated quercetin tetraglycoside from oolong tea (Camelia sinensis) extracts[J]. Tetrahedron Letters, 2004, 45: 5077-5080. DOI:10.1016/j.tetlet.2004.04.192 doi: 10.1016/j.tetlet.2004.04.192
23	HUA F, ZHOU P, WU H Y, et al. Inhibition of α-glucosidase and α‍-amylase by flavonoid glycosides from Lu’an Guapian tea: molecular docking and interaction mechanism[J]. Food and Function, 2018, 9(8): 4173-4183. DOI:10.1039/c8fo00562a doi: 10.1039/c8fo00562a
24	MONOBE M, NOMURA S, EMA K, et al. Quercetin glycosides-rich tea cultivars (Camellia sinensis L.) in Japan[J]. Food Science and Technology Research, 2015, 21(3): 333-340. DOI:10.3136/fstr.21.333 doi: 10.3136/fstr.21.333
25	FORREST G I, BENDALL D S. Distribution of polyphenols in tea plant (Camellia sinensis L.)[J]. Biochemical Journal, 1969, 113(5): 741-755.
26	MATUS J T, LOYOLA R, VEGA A, et al. Post-veraison sunlight exposure induces MYB-mediated transcriptional regulation of anthocyanin and flavonol synthesis in berry skins of Vitis vinifera [J]. Journal of Experimental Botany, 2009, 63(3): 853-867. DOI:10.1093/jxb/ern336 doi: 10.1093/jxb/ern336
27	LENG P S, SU S C, WANG T H, et al. Effects of light intensity and light quality on photosynthesis, flavonol glycoside and terpene lactone contents of Ginkgo biloba L.seedlings[J]. Journal of Plant Resources and Environment, 2002, 11(1): 1-4.

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