青钱柳叶醇提物的化学成分研究

doi:10.5246/jcps.2025.03.015

中国药学(英文版) ›› 2025, Vol. 34 ›› Issue (3): 195-209.DOI: 10.5246/jcps.2025.03.015

• 【研究论文】 • 下一篇

青钱柳叶醇提物的化学成分研究

许海龙¹^,², 杨娇¹^,², 王天霞²^,³, 邓改改¹^,^*(), 张友波²^,^*()

^1. 三峡大学健康医学院, 三峡大学国家中医药管理局中药药理科研三级实验室, 湖北宜昌 443002
^2. 北京大学药学院天然药物学系, 天然药物及仿生药物全国重点实验室, 北京 100191
^3. 兰州理工大学甘肃省高校中藏药筛选评价及深加工省级重点实验室, 甘肃兰州 730050

收稿日期:2024-12-31 修回日期:2025-01-10 接受日期:2025-01-12 出版日期:2025-03-31 发布日期:2025-04-01
通讯作者: 邓改改, 张友波

Study on chemical constituents from ethanol extract of Cyclocarya paliurus

Hailong Xu¹^,², Jiao Yang¹^,², Tianxia Wang²^,³, Gaigai Deng¹^,^*(), Youbo Zhang²^,^*()

¹ College of Medicine and Health Sciences,China Three Gorges University; Third-grade Pharmacological Laboratory on Traditional Chinese Medicine, State Administration of Traditional Chinese Medicine, China Three Gorges University, Yichang 443002, Hubei, China
² State Key Laboratory of Natural and Biomimetic Drugs, Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
³ School of Life Science and Engineering, Lanzhou University of Technology; University of Technology Gansu Provincial Key Laboratory for Screening, Evaluation and Deep Processing of Tibetan Medicine in Universities, Lanzhou 730050, Gansu, China

Received:2024-12-31 Revised:2025-01-10 Accepted:2025-01-12 Online:2025-03-31 Published:2025-04-01
Contact: Gaigai Deng, Youbo Zhang

摘要/Abstract

摘要：

本研究旨在对青钱柳叶醇提物的乙酸乙酯和正丁醇萃取部位的化学成分进行提取和鉴定。运用硅胶、D101大孔吸附树脂、Sephadex LH-20等柱色谱和高效液相色谱分离和纯化青钱柳叶醇提物的化学成分, 并运用核磁共振、高分辨质谱等谱学技术鉴定所得化合物的结构。从青钱柳叶醇提物的乙酸乙酯和正丁醇萃取部位分离得到黄酮及其苷类、糖类、香豆素和有机酸等类化合物28个, 分别鉴定为山奈酚(1)、拟雌内酯(2)、山柰酚-3-O-β-D-葡萄糖苷(3)、绿原酸甲酯(4)、黄连醛碱(5)、五味子苷(6)、山柰酚-3-O-α-L-鼠李糖苷(7)、绿原酸乙酯(8)、槲皮素(9)、木犀草素(10)、原儿茶酸(11)、山奈酚-3-O-α-L-呋喃阿拉伯糖(12)、反式对羟基肉桂酸(13)、蔗糖(14)、彼西丹醇(15)、绿原酸(16)、吡哆醇(17)、槲皮素-3-O-β-D-葡萄糖醛酸苷(18)、山奈酚-3-O-β-D-葡萄糖醛酸苷(19)、异槲皮苷(20)、mururin A(21)、柑橘苷A(22)、苄基-6-O-α-L-阿拉伯呋喃糖基-β-D-吡喃葡萄糖苷(23)、(+)-(6S,9R)-9-O-β-D-吡喃葡萄糖苷-6-羟基-3-O-α-紫罗兰醇(24)、杨梅素-3-O-β-D-葡萄糖苷(25)、蚱蜢酮(26)、槲皮素-3-O-α-L-鼠李糖苷(27)和3, 5-O-二咖啡酰奎尼酸(28)。其中化合物2, 5, 6, 15, 21, 22, 23, 24, 26和28均系首次从青钱柳叶中分离得到。

关键词: 青钱柳叶, 化学成分, 醇提物, 乙酸乙酯, 正丁醇

Abstract:

The aim of this study is to isolate and identify the chemical compounds in ethanol extract of Cyclocarya paliurus. Some purification and analysis techniques like silica gel, D101-macroporous adsorptive resins, and Sephadex LH-20 column chromatographies as well as high-performance liquid chromatography were used to isolate and analyze the compounds from ethanol extract of Cyclocarya paliurus. The structures of these constituents were identified by spectroscopic techniques such as nuclear magnetic resonance and high-resolution mass spectrometries. Twenty-eight compounds, including flavonoids and their glycoside, carbohydrate, coumarin and organic acid, were isolated from ethyl acetate and n-butanol fractions in ethanol extract of Cyclocarya paliurus, and they were identified as kaempferol (1), coumestrol (2), kaempferol 3-O-β-D-glucoside (3), methyl caffeoylquinic acid (4), coptichic aldehyde (5), schizandriside (6), kaempferol 3-O-α-L-rhamnoside (7), 3-caffeoylquinic acid ethyl ester (8), quercetin (9), luteolin (10), protocatechuic acid (11), kaempferol-3-O-α-L-furan arabinose (12), trans-p-hydroxy-cinnamic acid (13), α-D-glucopyranosido-β-D-fructofuranoside, sucrose (14), peucedanol (15), chlorogenic acid (16), pyridoxine (17), quercetin-3-O-β-D-glucuronide (18), kaempferol-3-O-β-D-glucuronide (19), isoquercitrin (20), mururin A (21), citroside A (22), benzyl-6-O-α-L-arabinofuranosyl-β-D-glucopyranoside (23), (+)-(6S,9R)-9-O-β-D-glucopyranosyl-6-hydroxy-3-O-α-ionol (24), myricetin-3-O-β-D-glucopyranoside (25), (4R)-4-(3-Oxo-1-buten-1-ylidene)-3α,5,5-trimethylcyclohexane-1α,3β-diol (26), quercetin-3-O-α-L-rhamnopyranosyl (27) and 3,5-O-dicaffeoylquinic acid (28). Compounds 2, 5, 6, 15, 21, 22, 23, 24, 26 and 28 were isolated from Cyclocarya paliurus for the first time.

Key words: Cyclocarya paliurus, Components, Ethanol extract, Ethyl acetate, n-Butanol

Supporting:

许海龙, 杨娇, 王天霞, 邓改改, 张友波. 青钱柳叶醇提物的化学成分研究[J]. 中国药学(英文版), 2025, 34(3): 195-209.

Hailong Xu, Jiao Yang, Tianxia Wang, Gaigai Deng, Youbo Zhang. Study on chemical constituents from ethanol extract of Cyclocarya paliurus[J]. Journal of Chinese Pharmaceutical Sciences, 2025, 34(3): 195-209.

图/表 2

参考文献 33

[1]	Tang, M.; Zhao, L.C.; Hu, Z.Y.; Zhang, Q.H. Chemical constituents and pharmacological activities of cyclocarya paliurus (Batal.) iljinskaja: research advances. J. Int. Pharm. Res. 2017, 44, 851–859.
[2]	Yuan, C.J.; Liu, N.; Xie, T.; Huang, A.X.; Wu, Y.H.; Ding, F.J. Research Progress on the Active Components and Influencing Factors of Cyclocarya paliurus Leaves. Guizhou Forestry Sci. Technol. 2021, 49, 48–53.
[3]	Li, L.Y.; Luo, R.H.; Xu, M.J.; Wu, Y.W.; Zhao, D.; Pan, Q.L.; Jin, J.Y.; Zhao, T.T.; Xu, T.H.; Zheng, X.J.; Jiang, C.X.; Zhu, Y.D. Chemical Constituents from Leaves of Cyclocarya paliurus. Mod. Chin. Med. 2021, 23, 1705–1709.
[4]	Gao, Y.; Lu, Y.F., Zhang, Y.X.; Pang, J.L.; Zhang, C.P. Study on the Chemical Constituents of Flavonoids from Potentilla Discolor Bge. and Their Hypoglycemic Activity. Guangzhou Chem. Ind. 2021, 49, 103–106.
[5]	Peng, X.J.; Zhong, L.; Wu, C.T.; Long, L.; Li, Q.; Tang, S.H. Effects of polysaccharides and flavonoids from Cyclocarya paliurus on blood metabolism parameters and liver pathological changes in nonalcoholic fatty liver disease rats with type 2 diabetes mellitus. Chin. J. Pathophysiol. 2021, 37, 1838–1847.
[6]	Hou, X.L.; Liu, X.X.; Wang, S.; Zhou, X.L.; Wei, F.; Miao, J.H. Effect of the flavonoids from Cyclocarya paliurus on spontaneous hypertension rats. Pharmacol. Clin. Chin. Mater. Med. 2014, 30, 62–69.
[7]	Lu, Q.Q. M.S thesis, Guizhou University. 2021.
[8]	Pan, K.; Tan, X.M.; Zhao, L.C.; Zhong, Y.J.; Yang, Y.T. Molecular Identification and Antimicrobial Activity of Endophytic Fungi From Cyclocarya paliurus (Batal.) Iljinsk. North. Hortic. 2022, 10, 95–101.
[9]	Zhou, R.G. M.S thesis, Guizhou Normal University. 2018.
[10]	Yao, Y.; Yan, L.J.; Chen, H.; Wu, N.; Wang, W.B.; Wang, D.S. Cyclocarya paliurus polysaccharides alleviate type 2 diabetic symptoms by modulating gut microbiota and short-chain fatty acids. Phytomedicine. 2020, 77, 153268.
[11]	Chen, Z.L.; Jian, Y.Q.; Wu, Q.; Wu, J.; Sheng, W.B.; Jiang, S.; Shehla, N.; Aman, S.; Wang, W. Cyclocarya paliurus (batalin) iljinskaja: botany, ethnopharmacology, phytochemistry and pharmacology. J. Ethnopharmacol. 2022, 285, 114912.
[12]	Li, J.; Huang, X.S.; Lu, Y.Y.; Zhang, Y.J.; Su, X.J. Chemical constituents of cyclocarya paliums. Chin. Tradit. Pat. Med. 2008, 30, 238–240.
[13]	Yuk, H.J.; Lee, J.H.; Curtis-Long, M.J.; Lee, J.W.; Kim, Y.S.; Ryu, H.W.; Park, C.G.; Jeong, T.S.; Park, K.H. The most abundant polyphenol of soy leaves, coumestrol, displays potent α-glucosidase inhibitory activity. Food Chem. 2011, 126, 1057–1063.
[14]	Peng, L.Y.; Mei, S.X.; Jiang, B.; Zhou, H.; Sun, H.D. Constituents from lonicera Japonica. Fitoterapia. 2000, 71, 713–715.
[15]	Qian, P.; Yang, X.W. Five new alkaloids from Coptidis Rhizoma–Euodiae Fructus couple and their cytotoxic activities against gastrointestinal cancer cells. Fitoterapia. 2014, 93, 74–80.
[16]	Jing, W.G.; Zhao, Y.; Zhang, K.X.; Zhang, J.; Liu, A. Study on the chemical constituents from aqueous extract of polygonum capitatum Buch.-ham. ex D. don. Lishizhen Med. Mater. Med. Res. 2015, 26, 47–50.
[17]	Ni, F.Y. M.S thesis, Suzhou University. 2013.
[18]	Yang, Y.X.; Jin, Y.S.; Chen, H.S. Chemical constituents from polygonum paleaceum. Chin. Med. Mater. 2016, 39, 110–112.
[19]	Chen, L.; Du Li-jun, Ding, Y.; Xing, D.M.; Wang, W. Studies on chemical constituents from flowers of Apocynum venetum. China J. Chin. Mater. Med. 2005, 30, 1340–1342.
[20]	Wang, K.H.; Zhang, Y.T.; Yang, X.W.; Xu, W.; Zhang, P.; Gong, Y.; Liu, N.F. Chemical constituents from fukeqianjin formula. China J. Chin. Mater. Med. 2018, 43, 2300–2312.
[21]	Xiao, Y.H.; Xu, Z.; Du, Z.P. Chemical constituents and antioxidant activity of Cyclocarya paliurus. Food Sci. Technol. 2019, 44, 223.
[22]	Du, S.S.; Zhang, W.S.; Wu, C.; Xu, Y.C.; Wei, L.X. Study on Chemical Components of Geranium sibiricum. China J. Chin. Mater. Med. 2003, 28, 625–626.
[23]	Xiao, M.T.; Ye, J.; Hong, B.B.; Zan, K.; Tu, P.F. Study on chemical constituents of artemisia lactiflora. Chin. Pharm. J. 2011, 46, 414–417.
[24]	Zhang, Y.F.; Wei, D.; Guo, S.Y.; Chen, F.; Du, N.S. Studies on chemical constituents of poacynum hendersonii. Nat. Prod. Res. Dev. 2006, 18, 954–957.
[25]	Liu, J.H.; Chen, Y.P.; Xu, S.X.; Yao, X.S.; Tan, Y. Study on the Chemical Components of Angelica pubescens. Chin. Tradit. Herb. Drugs. 1994, 06, 288–291.
[26]	Zhang, Y.F. M.S thesis, Nanjing Normal University. 2013.
[27]	Liu, S.Z.; Mou, M.X. New synthetic route of vitamin B6. World. Clin. Drugs. 1980, 04, 1.
[28]	Takashima, J.; Asano, S.; Ohsaki, A. Mururins A-C, three new lignoids from Brosimum acutifolium and their protein kinase inhibitory activity. Planta Med. 2002, 68, 621–625.
[29]	Long, C.L. Chemical constituents from the stems of dipteronia dyeriana henry. Nat. Prod. Res. 2012, 24, 1007.
[30]	Yang, D.; Xie, H.H. Aromatics and Flavonoids from Strawberry cv. Falandi. J. Trop. Subtrop. Bot. 2017, 25, 617.
[31]	Zhao, M.; Chen, C.C.; Yang, S.Q.; Zhang, S.J. Chemical constituents from leaves of Morus alba Linn. Chin. Tradit. Pat. Med. 2012, 34, 1126–1131.
[32]	Li, Z.; Wang, J.L.; Ruan, Y.J.; Huang, P.J.; Wang, T.; Zhang, Y. Isolation and identification of phenols from Eurycoma longifolia leaves. J. Shenyang Pharm. Univ. 2020, 37, 1071–1077.
[33]	Hu, J.; Wang, Z.Y.; Kang, M.; Zhang, B.; Deng, Y. Chemical constituents of Ardisia faberi. Chin. Tradit. Herb. Drugs. 2015, 46, 2048–2051.

青钱柳叶醇提物的化学成分研究

Study on chemical constituents from ethanol extract of Cyclocarya paliurus

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