藏药香芸火绒草化学成分及抗菌活性研究
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摘要
为对香芸火绒草(Leontopodium haplophylloides)的化学成分进行分离纯化及抗炎活性研究,本实验通过正、反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱,从香芸火绒草的中分离得到17个化合物,并运用现代波谱技术(1H NMR、13C NMR)分别鉴定为:咖啡酸(1)、咖啡酸-β-苯乙醇酯(2)、原儿茶酸(3)、tyrosol(4)、对羟基苯甲酸(5)、邻苯二甲酸二丁酯(6)、异莨菪亭(7)、7-(2,3-epoxy-3-methyl-3-butyloxy)-6-methoxycoumarin(8)、洋芹素(9)、牡荆素(10)、5-羟基-4',7-二甲氧基-6,8-二甲基黄酮(11)、5,7-二羟基-8-甲氧基黄酮(12)、百蕊草素Ⅲ(13)、methyl flavogallonate(14)、3,5,7,3',4'-pentahydroxyflavone (15)、木犀草素(16)、高良姜素(17),其中化合物1～16为首次从该植物中分离得到;经抗菌筛选发现发化合1、2、4～6、9、10、13～17对大肠杆菌、金黄色葡萄球菌及蜡状芽孢菌有抑制作用。
This paper reported the chemical constituents and anti-bacterial activties of Leontopodium haplophylloides Hand.-Mazz.Seventeen compounds were isolated fromLeontopodium haplophylloides by column chromatography on silica gel,ODS,Sephadex LH20 and identified by chemical and special analysis.Their structures were elucidated as caffeic acid(1),phenethyl caffeate(2),protocatechuic acid(3),tyrosol(4),p-hydroxybenzoic acid(5),dibutyl phthalate(6),isoscopoletin(7),7-(2,3-epoxy-3-methyl-3-butyloxy)-6-methoxycoumarin(8),apigenin(9),vitexin(10),5-hydroxy-4',7-dimethoxy-6,8-dimethyl flavones(11),5,7-dihydroxy-8-methoxyflavone(12),kaempferol 3-glucorhamnoside(13),methyl flavogallonate(14),3,5,7,3',4'-pentahydroxyflavone(15),luteolin(16),galangin(17),among which compounds 1-16 were obtained from this plant for the first time.After antibacterial test,1,2,4-6,9,10 and 13-17 have strong inhibitory effects on E.coli,Staphylococcus aureus,and Bacillus subtilis.
This paper reported the chemical constituents and anti-bacterial activties of Leontopodium haplophylloides Hand.-Mazz.Seventeen compounds were isolated fromLeontopodium haplophylloides by column chromatography on silica gel,ODS,Sephadex LH20 and identified by chemical and special analysis.Their structures were elucidated as caffeic acid(1),phenethyl caffeate(2),protocatechuic acid(3),tyrosol(4),p-hydroxybenzoic acid(5),dibutyl phthalate(6),isoscopoletin(7),7-(2,3-epoxy-3-methyl-3-butyloxy)-6-methoxycoumarin(8),apigenin(9),vitexin(10),5-hydroxy-4',7-dimethoxy-6,8-dimethyl flavones(11),5,7-dihydroxy-8-methoxyflavone(12),kaempferol 3-glucorhamnoside(13),methyl flavogallonate(14),3,5,7,3',4'-pentahydroxyflavone(15),luteolin(16),galangin(17),among which compounds 1-16 were obtained from this plant for the first time.After antibacterial test,1,2,4-6,9,10 and 13-17 have strong inhibitory effects on E.coli,Staphylococcus aureus,and Bacillus subtilis.
引文
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2 Zhou JS,Mei Q.A study on chemical constituent of essential oil from Leontopodium haplophylloides[J].Acta Bot BorealiOccident Sin(西北植物学报),2002,22:1482-1484.
3 Gao F.The study on extraction,chemical constituent and bioactivity of L.haplophylloides Hand-Mazz Volatile oil[D].Chengdu:Sichuan University(四川大学),2007.
4 Cai F,Tan DP,Yan QX.Chemical constituents in herbs of Prunella vulgaris[J].Nat Prod Res Dev(天然产物研究与开发),2016,28:18-20.
5 Xiang CY.Synthesis of caffeic acidβ-phenethyl ester analogues and study on their anti-tumor activity[D].Chongqing:Southwest University(西南大学),2012.
6 Yun XJ,Shu HM,Chen GY,et al.Chemical constituents from barks of Lannea coromaruielica[J].Chin Herb Med,2014,6(1):65-69.
7 Li NX,Fan QF,Song QS.Chemical constituents from bark of Gmelina arborea and Sambucus chinensis[J].Nat Prod Res Dev(天然产物研究与开发),2017,29:11-17.
8 Olaleye O,Li SS,Liu HT,et al.Study on chemical constituents and DPPH free radical scavenging activity of Carthamus tinctorius L.[J].Nat Prod Res Dev(天然产物研究与开发),2014,26:60-63.
9 Huang Y,Zheng JY,Yang GJ,et al.Chemical constituents in roots of Ilex kudingcha[J].Chin Tradit Herb Drugs(中草药),2015,46:2371-2376.
10 Wang QJ,Wang YS,He L,et al.Study on chemical constituents from Ipomoea Pes-caprae(L.)Sweet(Ⅰ)[J].Chin JMar Drugs(中国海洋药物),2006,25(3):15-17.
11 Stein AC,Fritz D,Lima L FP,et al.Distribution of coumarins in the tribe plucheeae,genus Pterocaulon[J].Chem Nat Compd,2007,43:691-693.
12 Liu Y,Li XF,Liu AL,et al.Chemical constituents from leaves of Elsholtzia rugulosa[J].Chin Tradit Herb Drugs(中草药),2009,40:1356-1359.
13 Fang ZF,Ling ZQ,Shi L,et al.Studies on chemical constituents from twigs and leaves of Illicium majus[J].Chin Tradit Herb Drugs(中草药),2018,3:1019-1024.
14 Sui XL.Studies on chemical constituents of Fruits of Eucalyptus globulus Labill.[D].Ji'nan:Shandong University(山东大学),2011.
15 Li WJ,Cheng XL,Liu J,et al.Phenolic compounds and antioxidant activities of Liriope muscari[J].Molecules,2012,17:1797-1808.
16 Hu XL,Zhu H,Liu CR,et al.Study on the chemical constituents of the flowers of Impatiens balsamina L.[J].Chin Tradit Patent Med 25:833-834.
17 Marzouk MS,El-Toumy SA,Moharram FA,et al.Pharmacologically active ellagitannins from Terminalia myriocarpa[J].Planta Medica,2002,68:523-527.
18 Dong JY,Jia ZJ.Study on chemical constituents of flavonids in Hypericum attenuatum[J].Chin Pharm J(中国药学杂志),2005,39:897-899.
19 Lv XH,Li ZL,Liu SX,et al.Chemical constituents from leaves of Adinandra nitida(Ⅱ)[J].Chin Tradit Herb Drugs(中草药),2018,3:1272-1276.
20 Rajibul AL,Ismail S,Nayan R,et al.Antioxidant activity of Indian propolis and its chemical constituents[J].Food Chem,2010,122:233-237.