一种新型茶叶籽黄酮单体的分离鉴定及其抗氧化活性

doi:10.7506/spkx1002-6630-201321024

摘要/Abstract

摘要：

采用大孔吸附树脂HPD826、ODS柱和Sephadex LH-20分离纯化得到高纯度的茶叶籽黄酮单体化合物Ⅰ，通过紫外(UV)、红外(IR)、质谱(MS)、核磁共振(NMR)等方法鉴定其分子结构为柚皮素-7-O-(β-D-吡喃木糖基(1→6))(β-D-葡萄糖基(1→3)-α-L-鼠李糖基(1→2))-β-D-葡萄糖苷。对化合物Ⅰ及其同系物柚皮素和柚皮苷的抗氧化活性进行对比研究。结果表明：化合物Ⅰ在体外有一定的抗氧化能力，3种物质的抗氧化活性关系为柚皮素＞柚皮苷＞化合物Ⅰ，即黄酮苷元的抗氧化活性大于黄酮糖苷，黄酮二糖苷的抗氧化活性大于黄酮四糖苷。

关键词: 茶叶籽, 黄酮, 鉴定, 抗氧化

Abstract:

Using HPD826 resin, ODS and Sephadex LH-20 column chromatographies, compound Ⅰ, a flavanone
glycoside was obtained from the crude extract of tea seeds rich in flavonoids. The structure of compound Ⅰ was identified
by UV, IR, NMR and LC-MS as naringenin-7-O-[β-D-xylopyranosyl(1→6)][β-D-glucopyranosyl(1→3)-α-Lrhamnopyranosyl(
1→2)]-β-D-glucopyranoside. The antioxidant activity in vitro was measured, and compared with
reference standards of naringenin and naringin. Results showed that the antioxidant activity in vitro of these three
materials followed the order: naringenin ＞ naringin ＞ compound Ⅰ, suggesting that the antioxidant activity of the aglycon
flavanone was higher than that of the flavanone glycosides, and the antioxidant activity of diglycoside flavanone was higher than that of
flavanone with four glycosyl moieties. Therefore, the glycosyl moieties in flavanones can reduce antioxidant activity.

Key words: tea seed, flavonoids, identification, antioxidant activity

中图分类号:

TS201.2

侯留鑫，王华清，郑铁松*，吕丽爽. 一种新型茶叶籽黄酮单体的分离鉴定及其抗氧化活性[J]. 食品科学, 2013, 34(21): 115-120.

HOU Liu-xin，WANG Hua-qing，ZHENG Tie-song*，Lü Li-shuang. Isolation and Identification of a New Flavonoid from Tea (Camellia sinensis) Seeds and Its Antioxidant Activity[J]. FOOD SCIENCE, 2013, 34(21): 115-120.

参考文献

[1] 恽卓婷, 廖鲜艳, 翁新楚. 茶叶籽油与油茶籽油理化性质及脂肪酸组成比较[J]. 食品工业科技, 2011, 32(6): 136-138.

[2] 曾益坤. 茶叶籽制油及综合开发利用[J]. 中国油脂, 2006, 31(1): 69-71.

[3] 江和源, 柯昌强, 王川丕, 等. 茶籽饼粕中黄酮苷的HPLC分析、制备与MS鉴定[J]. 茶叶科学, 2005, 25(4): 289-294.

[4] PARK J S, RHO H S, KIM D H, et al. Enzymatic preparation of kaempferol from green tea seed and its antioxidant activity[J]. Journal of Agricultural and Food Chemistry, 2006, 54(8): 2951-2956.

[5] LI Bo, XU Yi, JIN Yuxia, et al. Response surface optimization of supercritical fluid extraction of kaempferol glycosides from tea seed cake[J]. Industrial Crops and Products, 2010, 32(2): 123-128.

[6] KISCH E S, JAFFE A, KNOLL E, et al. Role of the lipoxygenase pathway in angiotensinⅡ-induced vasoconstriction in the human placenta[J]. Hypertension, 1997, 29(3): 796-801.

[7] 岳庆磊, 郭效杰, 罗宗铭, 等. 黄酮类化合物抗氧化机理及其在医药中的应用[J]. 广州化工, 2003, 31(2): 10-12.

[8] 李桃园, 王昕, 赵旋. 柚皮素对四氯化碳致小鼠化学性肝损伤中氧化应激介质生成影响的实验研究[J]. 中国临床药理学杂志, 2010, 26(6): 420-423.

[9] ORUNO A, GARIA-PRIG D, FUSTER M D, et al. Flavanone and nootkatone levels in different varieties of grapefruit and pummelo[J]. Journal of Agricultural and Food Chemistry, 1995, 43(1): l-5.

[10] AUNER B, WIRTH M, VALENTA C. Antioxidative activity and eytotoxicity of four different fiavonoids for dermal applieations[J]. Journal of Drug Delivery Science and Technology. 2005, 15(3): 227-232.

[11] JEON S M, BOK S H, JANG M K, et al. Comparison of antioxidant effects of naringin and probucol in cholesterol-fed rabbits[J]. Clinica Chimica Acta, 2002, 317(1-2): 181-190.

[12] OZYURT D, DEMIRATA B, APAK R. Determination of total antioxidant capacity bya new spectrophotometric method based on Ce (IV) reducing capacity measurement[J]. Talanta, 2007, 71(3): 1155-1165.

[13] 王巧能. 枳实中黄酮类化合物的提取、分离、鉴定与生物活性研究[D]. 杭州, 浙江工商大学, 2008.

[14] 王克勤. 芹菜黄酮类物质的分离纯化与药理功能研究[D]. 长沙: 湖南农业大学, 2009.

[15] LI Ning, MORIKAWA T, MATSUDA H, et al. New flavanone oligoglycosides, theaflavanosides I, II, III,and IV, with hepatoprotective activity from the seeds of tea plant (camellia sinensis) [J]. Heterocycles, 2007, 71(5): 1193-1201.

[16] CHEN Junghui, LIAU Bingchung, JONG Tingting, et al. Extraction and purification of flavanone glycosides and kaemferol glycosides from defatted Camellia oleifera seeds by salting-out using hydrophilic isopropanol[J]. Separation and purification technology, 2009, 67(1): 31–37.

[17] 谭晓荣. 不同干旱方式对小麦幼苗可溶性蛋白含量及总抗氧化力的影响[J]. 河南工业大学学报(自然科学版), 2008, 29(l): 42-47.

[18] 赵继红, 梁宇, 颜达予. 黄酮类化合物抗氧化活性的结构因素[J]. 北方工业大学学报, 2001, 13(1): 36-44.

[19] 应龙彬, 池玉梅. 植物药黄酮苷类化合物的分离及其构效关系研究进展[J]. 中国中医药信息杂志, 2007, 14(12): 100-102.

[20] BEYELE S, TESTA B, PERRISSOUD D. Flavonoids as inhibitors of rat liver monooxygenase activities [J]. Biochemical Pharmacology, 1988, 37(10): 1971-1979.

[21] HODNICK W F, KUNG F S, ROETTGER W J. Inhibition of mitochondrial respiration and production of toxic oxygen radicals by flavonoids: A structure-activity study [J]. Biochemical Pharmacology, 1986, 35(14): 2315-2357.

[22] RICE-EVANS C A, MILLER N J, PAGANGA G. Structure-antioxidant activity relationships of flavonoids and phenolic acids[J]. Free Radical Biology and Medicine, 1996, 20(7): 933–956.

[23] LAI H H, YEN G C. Inhibitory effect of isoflavones on peroxynitrite-mediated low-density lipoprotein oxidation[J]. Bioscience, Biotechnology, and Biochemistry, 2002, 66(1): 22-28.

[24] HAGERMAN A E, RIEDL K M, JONES G A, et al. High molecular weight plant polyphenolics (tannins) as biological antioxidants[J]. Journal of Agricultural and Food Chemistry, 1998, 46(5): 1887–1892.

[25] RATTY A K, DAS N P. Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship[J]. Biochemical Medicine and Metabolic Biology, 1988, 39(1): 69–79.

[26] GAO Zhonghong, HUANG Kaixun, YANG Xiangliang, et al. Free radical scavenging and antioxidant activities of flavonoids extracted from the radix of Scutellaria baicalensis Georgi[J]. Biochimica et Biophysica Acta (BBA) - General Subjects, 1999, 1472 (3): 643–650.

[27] VAN ACKER S A B E, VAN DEN BERG D J, TROMP M N J L, et al. Structural aspects of antioxidant activity of flavonoids[J]. Free Radical Biology and Medicine, 1996, 20(3): 331–342.

[28] WOLFE K L, LIU Ruihai. Structure-activity relationships of flavonoids in the cellular antioxidant activity assay[J]. Journal of Agricultural and Food Chemistry, 2008, 56(29): 8404–8411.

[29] VAN ACKER S A B E, DE GROOT M J, VAN DEN BERG D J, et al. A quantum chemical explanation of the antioxidant activity of flavonoid[J]. Chemical Research in Toxicology, 1996, 9(8): 1305-1312.

[30] BORS W, HELLER W, MICHEL C, et al. Flavonoids as antioxidants: determination of radical-scavenging efficiencies[J]. Methods Enzymol, 1990, 186: 343-355.

[31] 蒋柳云, 刘玉明. 黄酮类化合物抗氧化活性的构效关系研究[J]. 化学研究与应用, 2004, 16(4): 510-512.