三七花中1个新的多烯炔型大环内酯  

A new polyenyne macrolide from flower buds of Panax notoginseng

作　　者：李欣馨 王新欣 廖彭莹 尚佳欢 杨杏芝 白雪[1] 朱宏涛[1] 张颖君[1] LI Xinxin;WANG Xinxin;LIAO Pengying;SHANG Jiahuan;YANG Xingzhi;BAI Xue;ZHU Hongtao;ZHANG Yingjun(Key Laboratory of Phytochemistry and Natural Medicines,Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201,China;University of Chinese Academy of Sciences,Beijing 100049,China;School of Traditional Chinese Medicine,Shenyang Pharmaceutical University,Shenyang 110016,China;College of Pharmacy,Gangxi University of Chinese Medicine,Nanning 530200,China)

机构地区：[1]植物化学与天然药物重点实验室(中国科学院),中国科学院昆明植物研究所,云南昆明650201 [2]中国科学院大学,北京100049 [3]沈阳药科大学中药学院,辽宁沈阳110016 [4]广西中医药大学药学院,广西南宁530200

出　　处：《中草药》2024年第14期4643-4649,共7页Chinese Traditional and Herbal Drugs

基　　金：云南省科技厅重点研发计划(202203AC100008);植物化学与西部植物资源持续利用国家重点实验室开放课题(P2022-KF15);广西中医药大学杰出青年基金项目(2022JQ001)。

摘　　要：目的研究三七Panax notoginseng花的化学成分。方法采用65%乙醇水热回流提取,石油醚、醋酸乙酯与正丁醇萃取,运用大孔吸附树脂Diaion HP-20、硅胶、MCI gel CHP 20P、Sephadex LH-20等柱色谱及半制备液相色谱等方法进行分离纯化,根据化合物的理化性质和波谱数据进行结构鉴定,并对部分化合物进行肿瘤细胞毒和抗氧化活性评价。结果从三七花正丁醇部位分离得到11个化合物,包括大环内酯类1个、酚酸类2个、木脂素类3个、黄酮类5个,分别鉴定为(11Z,10R,17R)-17-乙烯基-10-羟基氧杂环十七烷-11-烯-13,15-二炔-2-酮(1)、反式对羟基肉桂酸(2)、3-O-对香豆酰基奎宁酸(3)、(-)-芝麻素(4)、2-甲氧基芝麻素(5)、ecbolin B(6)、槲皮素(7)、槲皮素-3-O-β-D-吡喃葡萄糖苷(8)、槲皮素-3-O-β-D-吡喃木糖基-(1→2)-β-D-吡喃半乳糖苷(9)、槲皮素-3-O-β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃半乳糖苷(10)、山柰酚-3-O-β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃半乳糖苷(11)。结论化合物1为新的多烯炔型大环内酯,命名为三七花大环内酯。化合物2~6、8为首次从人参属植物中分离得到,化合物2~9为首次从三七花中分离得到。化合物4对白血病HL-60细胞的体外肿瘤生长具有弱的抑制作用。化合物7~10表现出较强的清除DPPH自由基活性。Objective To study the chemical constituents of the flower buds of Sanqi [Panax notoginseng(Burk.) F.H.Chen].Methods Heat reflux extraction by 65% aqueous ethanol,successive solvent extraction by petroleum ether,ethyl acetate and nbutanol,various column chromatography by Diaion HP-20 macroporous adsorption resin,silica gel,MCI gel CHP 20P,Sephadex LH-20 gel,as well as semi-preparative liquid chromatography,were used for isolation and purification of target compounds.The structures of the compounds were identified based on physicochemical properties and spectroscopic data,some of them were evaluated for cytotoxic and antioxidant activities.Results Eleven compounds were isolated from n-butanol part of the flower buds of P.notoginseng,including one macrolide,two phenolic acids,three lignans and five flavonoids.Their structures were identified as(11Z,10R,17R)-17-ethenyl-10-hydroxyoxacycloheptadec-11-ene-13,15-diyn-2-one(1),(E)-p-hydroxycinnamic acid(2),3-O-pcoumaroylquinic acid(3),(-)-sesamin(4),2-methoxysesamin(5),ecbolin B(6),quercetin(7),quercetin-3-O-β-D-glucopyranoside(8),quercetin-3-O-β-D-xylopyranosyl-(1→2)-β-D-galactopyranoside(9),quercetin-3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside(10),kaempferol-3-O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside(11).Conclusion Compound 1 is a new polyenyne macrolide named floraolide.Compounds 2—6 and 8 were firstly isolated from Panax,while 2—9 were isolated from the flower buds of P.notoginseng for the first time.Compound 4 has a weak inhibitory effect on tumor growth of leukemia HL-60 cells in vitro.Compounds 7—10showed strong DPPH scavenging activity.

关 键 词：三七 酚酸类 木脂素类 黄酮类 三七花大环内酯 (-)-芝麻素 槲皮素-3-O-β-D-吡喃木糖基-(1→2)-β-D-吡喃半乳糖苷 肿瘤细胞毒活性 抗氧化活性 

分 类 号：R284.1[医药卫生—中药学]