油樟叶水提物化学成分分离鉴定和抗肝癌活性研究

doi:10.3969/j.issn.0253-2417.2022.06.001

林产化学与工业 ›› 2022, Vol. 42 ›› Issue (6): 1-10.doi: 10.3969/j.issn.0253-2417.2022.06.001

油樟叶水提物化学成分分离鉴定和抗肝癌活性研究

周文娟¹(), 邱远望², 贝佳炎¹, 王煜洲¹, 阮诗琪¹, 倪林¹^,³^,*()

1. 福建农林大学生物农药与化学生物学教育部重点实验室，福建福州 350002
2. 福建中益制药有限公司，福建泉州 362700
3. 自然生物资源保育利用福建省高校工程研究中心，福建福州 350002

收稿日期:2021-09-26 出版日期:2022-12-28 发布日期:2023-01-07
通讯作者: 倪林 E-mail:1200215008@fafu.edu.cn;nilin_fjau@126.com
作者简介:倪林，副教授，博士，硕士生导师，主要从事天然药物活性物质的开发与利用；E-mail: nilin_fjau@126.com
周文娟(1998—)，女，浙江义乌人，硕士生，研究方向为天然药物活性物质的开发与利用；E-mail: 1200215008@fafu.edu.cn
基金资助:
国家级大学生创新创业训练计划项目(202110389039X);央财政林业科技推广示范项目(闽【2022】TG16号)

Separation and Identification of Aqueous Extracts of Cinnamomum longe-paniculatum Leaves and Their Anti-hepatocellular-cancer Activity

Wenjuan ZHOU¹(), Yuanwang QIU², Jiayan BEI¹, Yuzhou WANG¹, Shiqi RUAN¹, Lin NI¹^,³^,*()

1. Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China
2. Fujian Zhongyi Pharmaceutical Co., Ltd., Quanzhou 362700, China
3. Conversation and Utilization of Natural Biological Resources Fujian University Engineering Research Center, Fuzhou 350002, China

Received:2021-09-26 Online:2022-12-28 Published:2023-01-07
Contact: Lin NI E-mail:1200215008@fafu.edu.cn;nilin_fjau@126.com

摘要/Abstract

摘要：

对油樟叶水提物的化学成分进行研究，采用大孔吸附树脂、PRP-512A树脂和Sephadex LH-20等色谱分离技术分离纯化得到24个化合物，利用UV、MS和NMR等波谱学手段对化合物结构进行鉴定。研究结果表明24个化合物分别为：6-甲氧基-7-羟基香豆素(1)、异嗪皮啶(2)、甲基牛蒡酚(3)、(+)-表芝麻酮(4)、(7R, 7'S, 8R, 8'R)-3, 4-亚甲二氧基-3'-甲氧基-4'-羟基-7, 9': 7', 9-双环氧木脂烷(5)、(+)-表松脂醇(6)、(+)-松脂醇(7)、(+)-松脂素单甲基醚(8)、(+)-O-去甲基木兰木脂素(9)、连翘脂素(10)、(2R, 3S)-4'-羟基-5, 7, 3'-三甲氧基黄烷-3-醇(11)、(2S, 3S)-4'-羟基-5, 7, 3'-三甲氧基黄烷-3-醇(12)、槲皮素(13)、黑麦草内酯(14)、2, 6-二甲氧基对苯醌(15)、邻苯二酚(16)、香草酸(17)、3-甲氧基-4-羟基苯乙醇(18)、二氢松柏醇(19)、3, 5-二甲氧基- 4-羟基苯丙醇(20)、2-羟基-1-(4-羟基-3, 5-二甲氧基苯基)-1-丙酮(21)、丁香酸甲酯(22)、1-(4-乙基苯基)-1, 2-乙二醇(23)和对羟基苯乙酮(24)。化合物2、5~6、9~12、14~16和18~24这17个化合物均为首次从樟属植物中分离得到。抗肝癌活性结果显示：化合物2、5和13对人肝癌细胞HepG2具有中等抑制活性，半数抑制浓度(IC₅₀)分别为33.43、107.40和71.43 μmol/L，其中化合物5的抗肝癌活性为首次报道，化合物2、13分属香豆素类和黄酮类化合物，在抗肿瘤药物研究方面具有良好应用前景。

关键词: 油樟, 化学成分, 结构鉴定, 抗肝癌

Abstract:

This chemical constituents of the aqueous extract of leaves of Cinnamomum longepaniculatum(Gamble) N. Chao ex H.W.Li were studied. Twenty-four compounds were isolated and purified by macroporous resin, PRP-512A resin, Sephadex LH-20, and etc. The structures of the compounds were identified by spectroscopic methods of UV, MS and NMR as 7-hydroxy-6-methoxy-coumarin(1), isofraxidin(2), dimethylmatairesinol(3), (+)-episesaminone(4), horsfieldin(5), (+)-epipinoresinol(6), (+)-pinoresinol(7), (+)-pinoresinol monomethyl ether(8), (+)-de-O-methylmagnolin(9), phillyrin(10), (2R, 3S)-4'-hydroxy-5, 7, 3'-trimethoxyflavan-3-ol(11), (2S, 3S)-4'-hydroxy-5, 7, 3'-trimethoxyflavan-3-ol(12), quercetin(13), loliolide(14), 2, 6-dimethoxy-1, 4-benzoquinone(15), pyrocatechol(16), vanillic acid(17), 3-methoxy-4-hydroxyphenylethanol(18), dihydroconifery alcohol(19), 3, 5-dimethoxy-4-hedroxyphenylpropynol(20), 2-hydroxy-1-(4-hydroxy-3, 5-dimethoxyphenyl)propan-1-one(21), methyl syringate(22), 1-(4-ethylphenyl)-1, 2-ethanediol(23), p-hydroxyacetophenone(24). Compounds 2, 5-6, 9-12, 14-16 and 18-24 were all isolated from Cinnamomum for the first time. The results of anti-hepatocellular-activity showed that compounds 2, 5 and 13 had moderate inhibitory activity effects on human liver cancer(HepG2) cells, with the half inhibitory concentrations(IC₅₀) values of 33.43, 107.40, and 71.43 μmol/L, respectively. Among them, the anti-hepatocellular-activity of compound 5 was reported for the first time. Compounds 2 and 13 belong to coumarins and flavonoids, which have good application prospects in the research of anti-tumor drugs.

Key words: Cinnamomum longepaniculatum, chemical constituents, structural identification, anti-hepatocellular

中图分类号:

TQ35

周文娟, 邱远望, 贝佳炎, 王煜洲, 阮诗琪, 倪林. 油樟叶水提物化学成分分离鉴定和抗肝癌活性研究[J]. 林产化学与工业, 2022, 42(6): 1-10.

Wenjuan ZHOU, Yuanwang QIU, Jiayan BEI, Yuzhou WANG, Shiqi RUAN, Lin NI. Separation and Identification of Aqueous Extracts of Cinnamomum longe-paniculatum Leaves and Their Anti-hepatocellular-cancer Activity[J]. Chemistry and Industry of Forest Products, 2022, 42(6): 1-10.

图/表 1

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Separation and Identification of Aqueous Extracts of Cinnamomum longe-paniculatum Leaves and Their Anti-hepatocellular-cancer Activity

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