Abstract
A high-purity compound was extracted by solvent extraction, liquid-liquid separation, silica gel chromatography and high-performance liquid semi-preparative chromatography by using seeds of Camellia semiserrata Chi. as raw materials. The compound was identified as kaempferol-3-O-\[α-L-rhamnopyranosyl-(1-3)- 2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1-6)\]-β-D-glucopyranoside, an acetyl flavonoid glycoside, by physical and chemical properties, mass spectrometry and nuclear magnetic resonance. Two-dimensional nuclear magnetic resonance (2D-NMR) techniques including H-H COSY, HSQC, HMBC and TOCSY were used to affiliate its 1H and 13C NMR chemical shift and explain the structure.
Publication Date
5-28-2017
First Page
21
Last Page
24,58
DOI
10.13652/j.issn.1003-5788.2017.05.004
Recommended Citation
Qingming, CAO; Fang, LAN; Weijie, WANG; Liyuan, BAO; and Haiyan, ZHONG
(2017)
"Structure determination on a new acetyl flavonoid glycoside in seeds of Camellia semiserrata Chi. by NMR spectroscopy,"
Food and Machinery: Vol. 33:
Iss.
5, Article 4.
DOI: 10.13652/j.issn.1003-5788.2017.05.004
Available at:
https://www.ifoodmm.cn/journal/vol33/iss5/4
References
[1] 师江, 刘兴勇. 基于营养成分的变化确定油茶最佳采摘期[J]. 食品与机械, 2014, 30(1): 71-74.
[2] 郑德勇, 常玉玺, 叶乃兴, 等. 茶籽成熟过程中主要功能成分变化规律研究[J]. 茶叶科学, 2013, 33(3): 253-260.
[3] 李好, 方学智, 钟海雁, 等. 油茶籽成熟过程中油脂及营养物质变化的研究[J]. 林业科学研究, 2014, 27(1): 86-91.
[4] 曹永庆, 姚小华, 任华东, 等. 油茶果实矿质元素含量和油脂积累的相关性[J]. 中南林业科技大学学报, 2013, 33(10): 38-41.
[5] 朱勇, 王湘莹, 马锦林, 等. 不同物种油茶籽仁含油率及其茶油的脂肪酸组成[J]. 经济林研究, 2013, 31(2): 134-137.
[6] 陈轲, 刘零怡, 徐翔, 等. 基于离子迁移谱法对橄榄油与油茶籽油区分鉴别的研究[J]. 中国粮油学报, 2016(11): 130-134.
[7] 柏云爱, 宋大海, 张富强, 等. 油茶籽油与橄榄油营养价值的比较[J]. 中国油脂, 2008, 33(3): 39-41.
[8] 李好, 钟海雁, 方学智, 等. 油茶籽成熟过程中抗氧化物质的变化规律[J]. 食品与机械, 2013, 29(5): 6-9.
[9] DU Li-chun, WU Bei-li, CHEN Jian-min. Flavonoid triglycos-ides from the seeds of Camellia oleifera Abel.[J]. Chinese Chemical Letters, 2008, 19(11): 1 315-1 318.
[10] 曹清明, 邬靖宇, 钟海雁. 油茶叶提取物中两种联苄化合物的分离与鉴别[J]. 中国食品学报, 2015, 15(9): 206-214.
[11] 曹清明, 钟海雁, 邬靖宇, 等. 液相制备油茶叶提取物组分及其结构鉴定[J]. 经济林研究, 2015, 33(3): 68-74.
[12] 侍银宝, 钟海雁. 油茶果皮多酚粗提物对DNA氧化损伤的影响[J]. 食品与机械, 2013, 29(6): 143-146.
[13] 张微微, 于大永, 史丽颖, 等. 南山茶果皮化学成分的研究[J]. 广西植物, 2012, 32(5): 698-700.
[14] 彭凌, 朱必凤, 刘主. 油茶肉质果和肉质叶提取液降血糖及抗氧化作用的实验研究[J]. 中国药理学通报, 2007, 23(12): 1 679-1 680.
[15] YE Y, XING H T, GUO Y. Hypolipidemic effect of a novel biflavonoid from shells of Camellia oleifera (Abel.)[J]. Indian Journal of Experimental Biology, 2013, 51(6): 458-463.
[16] ZHANG Liang-liang, WANG Yong-mei, WU Dong-mei, et al. Microwave-assisted extraction of polyphenols from Camellia oleifera fruit hull[J]. Molecules, 2011, 16(6): 4 428-4 437.
[17] 刘应珍, 邹天才. 贵州山茶属植物资源及其开发利用探讨[J]. 贵州科学, 2008, 26(2): 75-81.
[18] 田晔林. 湖南省山茶属红山茶组植物分类及园林应用研究[D]. 长沙: 中南林学院, 2001.
[19] YE Yong, GUO Ya, LUO Yue-ting, et al. Isolation and free radical scavenging activities of a novel biflavonoid from the shells of Camellia oleifera Abel.[J]. Fitoterapia, 2012, 83(8): 1 585-1 589.
[20] MORIKAWA T, NINOMIYA K, MIYAKE S, et al. Flavonol glycosides with lipid accumulation inhibitory activity and simultaneous quantitative analysis of 15 polyphenols and caffeine in the flower buds of Camellia sinensis from different regions by LCMS[J]. Food Chemistry, 2013, 140(1/2): 353-360.
[21] WU Xiao-Juan, TANG Ling, LIN Hong-jing, et al. Flavonoids from Seeds of Camellia semiserrata Chi. and Their Estrogenic Activity[J]. Bioscience, Biotechnology, and Biochemistry. 2008, 72(9): 2 428-2 431.
[22] YE Yong, GUO Ya, LUO Yue-ting. Anti-Inflammatory and Analgesic Activities of a Novel Biflavonoid from Shells of Camellia oleifera[J]. International journal of molecular sciences, 2012, 13(10): 12 401-12 411.
[23] 漆龙霖, 吕芳德, 李克瑞, 等. 湖南山茶属植物种质资源调查、收集和利用的研究[J]. 武汉植物学研究, 1989, 7(3): 275-284.
[24] 孙佩光. 广宁红花油茶种质特性与变异研究[D]. 北京: 北京林业大学, 2012.
[25] SUN L, LIAO Z, LI X S, et al. Flavonoids from the fruits of Camellia oleifera.[J]. Asian Journal of Chemistry, 2012, 24(11): 4 892-4 894.
[26] 包莉圆, 钟海雁, 王蔚婕, 等. 南山茶饼中乙醇提取物5个多酚化合物的分离纯化[J]. 食品与机械, 2017, 33(4): 133-138.
[27] TENG Xi-feng, YANG Jia-yue, YANG Chong-ren, et al. Five New Flavonol Glycosides from the Fresh Flowers of Camellia reticulata[J]. Helvetica Chimica Acta, 2008, 91(7): 1 305-1 312.