大瑶山甜茶正丁醇部位化学成分研究
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摘要
目的:研究大瑶山甜茶正丁醇部位中的二萜类化学成分,为探索其活性物质奠定基础。方法:采用95%乙醇提取药材,提取液回收至无醇味后溶于水中,依次用石油醚、乙酸乙酯和正丁醇萃取,减压干燥后获得相应萃取物,综合运用各种色谱技术对正丁醇萃取物进行分离纯化,获取二萜类化合物,通过NMR对得到的化合物进行结构鉴定。结果:从大瑶山甜茶中分离得到10个二萜类化合物,分别鉴定为7β, 17-dihydroxy-16β-ent-kauran-19-oic acid 19-O-β-D-glucopyranoside ester (1), 7β, 17-dihydroxy-entkaur-15-en-19-oic acid 19-O-β-D-glucopyranoside ester (2), 13-[(O-β-D-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-β-Dglucopyranosyl-β-D-glucopyranosyl ester (3), 12-α-[(2-O-β-D-glucopyranosyl-β-Dglucopyranosyl)oxy]ent-kaur-16-en-19-oic acidβ-Dglucopyranosyl ester (4), glaucocalyxin G (5),β-D-glucopyranosyl 17-hydroxy-ent-kauran-19-oate-16-O-β-D-glucopyranoside (6),cussoracosides E (7), 17-O-β-D-glucopyranosyl-16α-ent-kauran-19-oic acid (8),cussovantoside A (9),cussovantoside C (10)。结论:化合物1-10首次从大瑶山甜茶中分离得到。
Objective: To study the diterpenoids of n-butanol extract of Rubus suavissimus S. Lee., and to establish the foundation for its active substances. Methods: The medicinal materials were extracted by 95% Et OH. The extract was recovered to non-alcoholic taste and dissolved in water. The extract was successively extracted with petroleum ether, ethyl acetate and n-butanol. After drying under reduced pressure, the corresponding extract was obtained, and the n-butanol extract was separated and purified by various chromatographic techniques. Results: The structures of the compounds were established as 7β, 17-dihydroxy-16β-ent-kauran-19-oic acid19-O-β-D-glucopyranoside ester(1), 7 β, 17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-D-glucopyranoside ester(2), 13-[(O-β-Dglucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-β-D-glucopyranosyl-β-D-glucopyranosyl ester(3), 12-α-[(2-O-β-D-glucopyranosyl-β-Dglucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester(4), glaucocalyxin G(5), β-D-glucopyranosyl 17-hydroxyent-kauran-19-oate-16-O-β-D-glucopyranoside(6), cussoracosides E(7), 17-O-β-D-glucopyranosyl-16α-ent-kauran-19-oic acid(8),cussovantoside A(9), and cussovantoside C(10). Conclusion: Compounds 1-10 were obtained from Rubus suavissimus S. Lee firstly.
Objective: To study the diterpenoids of n-butanol extract of Rubus suavissimus S. Lee., and to establish the foundation for its active substances. Methods: The medicinal materials were extracted by 95% Et OH. The extract was recovered to non-alcoholic taste and dissolved in water. The extract was successively extracted with petroleum ether, ethyl acetate and n-butanol. After drying under reduced pressure, the corresponding extract was obtained, and the n-butanol extract was separated and purified by various chromatographic techniques. Results: The structures of the compounds were established as 7β, 17-dihydroxy-16β-ent-kauran-19-oic acid19-O-β-D-glucopyranoside ester(1), 7 β, 17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-β-D-glucopyranoside ester(2), 13-[(O-β-Dglucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-β-D-glucopyranosyl-β-D-glucopyranosyl ester(3), 12-α-[(2-O-β-D-glucopyranosyl-β-Dglucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester(4), glaucocalyxin G(5), β-D-glucopyranosyl 17-hydroxyent-kauran-19-oate-16-O-β-D-glucopyranoside(6), cussoracosides E(7), 17-O-β-D-glucopyranosyl-16α-ent-kauran-19-oic acid(8),cussovantoside A(9), and cussovantoside C(10). Conclusion: Compounds 1-10 were obtained from Rubus suavissimus S. Lee firstly.
引文
[1]李树刚.甜茶,悬钩子属一新种[J].广西植物,1981,1(4):19-21
[2]郑华,苏志恒.广西甜茶的药理学研究进展[J].广西医科大学学报2015,8(1):149-151
[3]马建春,何伟,伍振峰.甜茶素的研究进展[J].食品与药品,2008,10(5):73-75
[4]Nhiem N X,Hien NTT,Tai B H,et al.New ent-kauranes from the fruits of Annona glabra,and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages[J].Bioorganic&Medicina Chemistry Letters,2014,25(2):254-258
[5]Mohamed A Ibrahim,Douglas L Rodenburg,Kamilla Alves,et al Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana[J]Journal of Natural Products,2014,77:1231-1235
[6]Xiang Z B,Wang G L,Huang L Z,et al.A new ent-kaurane diterpenoid glycoside from Isodon japonica var.glaucocalyx[J]Journal of Asian Natural Products Research,2013,15(5):574-578
[7]Harinantenaina L,Kasai R,Yamasaki K.A new ent-kaurane diterpenoid glycoside from the leaves of Cussonia bojeri,a Malagasy endemic plant[J].Chemical&Pharmaceutical Bulletin,2002,50(8):1122
[8]Harinantenaina L,Kasai R,Yamasaki K.Ent-kaurane diterpenoid glycosides from the leaves of Cussonia racemosa,a Malagasy endemic plant[J].Chemical&Pharmaceutical Bulletin,2002,50(2):268-271
[9]Qin J J,Zhu J X,Zhang W D,et al.A new ent-kaurane type diterpenoid glycoside from Inula japonica Thunb[J].Archives of Pharmacal Research,2009,32(10):1369-1372
[10]Harinantenaina L,Kasai R,Yamasaki K.ent-Kaurane diterpenoid glycosides from a Malagasy endemic plant,Cussonia vantsilana[J].Phytochemistry,2002,61(4):367-372
[11]柳俊辉,周小雷,翁铭钻,等.广西甜茶多酚对四氧嘧啶致糖尿病小鼠的降血糖作用[J].中药药理与临床,2014,30(6):51-54
[12]韩碧群,谭芳,张鑫瑶,等.甜茶的应用历史与研究现状[J].中国现代中药,2014,16(7):582-587
[13]Liu Z,Schwimer J,Liu D,et al.Gallic acid is partially responsible for the antiangiogenic activitives of Rubus leaf extract[J].Phyother Res,2006,20(9):806-813
[14]滕昭玉,崔紫姣,杜莹,等.甜茶总多酚的纯化及其抗氧化活性[J].安徽农业科学,2016,44(1):36-39
[15]Xia X L,Jin H Z,Yan S K,et al.Analysis of the bioactive constituents of Chansu in rat plasma by high Performance liquid chromatography with mass spectrometric detection[J].J Pharm Biomed Anal,2010,53(3):646-654
[16]王硕,侯小利,周小雷,等.甜茶多酚对高脂血症大鼠的降血脂作用及其机制研究[J].中国药学杂志,2015,50(20):1811-1815
[17]闫志刚,蒙淑洁,韦荣昌,等.广西甜茶研究与应用现状[J].中草药,2017,48(12):2572-2588
[18]李莉,王玉波,陈岱韻,等.甜茶皂甙对变形链球菌抑龋性的研究[J].泰山医学学报,2014,35(12):1252-1253
[19]谭冬明,石相莉,罗星晔,等.广西甜茶化学成分、提取工艺及生物活性研究进展[J].中成药,2017,39(6):1252-1255
[20]Hoesel B,Schmid JA.The complexity of NF-κB signaling in inflammation and cancer[J].Mol Cancer,2013,12:86-100
[22]Rico-Martinez M,Medina FG,Marrero JG,et al.Biotransformation of Diterpenes[J].Rsc Advances,2014,4(21):2046-2069
[23]海广范,张慧,郭兰青.二萜类化合物药理学作用研究进展[J].新乡医学院学报,2015,32(1):77-80
[24]金海峰,吕宾,戴金锋,等.温郁金二萜类化合物C抗胃癌作用的实验研究[J].中国中西医结合杂志,2015,35(2):216-221
[25]Bhatti HN,Khera RA.Biotransformations of diterpenoids and triterpenoids:a review[J].J Asian Nat Prod Res,2014,16(1):70-104
[26]吴亦晴,虞劲祥,程志红.二萜类化合物微生物转化研究进展[J].中国生化药物杂志,2016,36(3):9-14
[27]Wang HB,Wang XY,Liu LP,et al.Tigliane diterpenoids from the Euphorbiaceae and Thymelaeaceae families[J].Chem Rev,2015,115(9):2975-3011
[28]Liu Z,Zhang F,Koh G Y,et al.Cytotoxic and antiangiogenic paclitaxel solubilized and permeation-enhanced by natural product nanoparticles[J].Anticancer Drugs,2015,26(2):167-179
[29]颜小捷,卢凤来,李典鹏.甜茶化学成分及药理作用研究进展[J].广西植物,2013,33(1):136-142
[2]郑华,苏志恒.广西甜茶的药理学研究进展[J].广西医科大学学报2015,8(1):149-151
[3]马建春,何伟,伍振峰.甜茶素的研究进展[J].食品与药品,2008,10(5):73-75
[4]Nhiem N X,Hien NTT,Tai B H,et al.New ent-kauranes from the fruits of Annona glabra,and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages[J].Bioorganic&Medicina Chemistry Letters,2014,25(2):254-258
[5]Mohamed A Ibrahim,Douglas L Rodenburg,Kamilla Alves,et al Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana[J]Journal of Natural Products,2014,77:1231-1235
[6]Xiang Z B,Wang G L,Huang L Z,et al.A new ent-kaurane diterpenoid glycoside from Isodon japonica var.glaucocalyx[J]Journal of Asian Natural Products Research,2013,15(5):574-578
[7]Harinantenaina L,Kasai R,Yamasaki K.A new ent-kaurane diterpenoid glycoside from the leaves of Cussonia bojeri,a Malagasy endemic plant[J].Chemical&Pharmaceutical Bulletin,2002,50(8):1122
[8]Harinantenaina L,Kasai R,Yamasaki K.Ent-kaurane diterpenoid glycosides from the leaves of Cussonia racemosa,a Malagasy endemic plant[J].Chemical&Pharmaceutical Bulletin,2002,50(2):268-271
[9]Qin J J,Zhu J X,Zhang W D,et al.A new ent-kaurane type diterpenoid glycoside from Inula japonica Thunb[J].Archives of Pharmacal Research,2009,32(10):1369-1372
[10]Harinantenaina L,Kasai R,Yamasaki K.ent-Kaurane diterpenoid glycosides from a Malagasy endemic plant,Cussonia vantsilana[J].Phytochemistry,2002,61(4):367-372
[11]柳俊辉,周小雷,翁铭钻,等.广西甜茶多酚对四氧嘧啶致糖尿病小鼠的降血糖作用[J].中药药理与临床,2014,30(6):51-54
[12]韩碧群,谭芳,张鑫瑶,等.甜茶的应用历史与研究现状[J].中国现代中药,2014,16(7):582-587
[13]Liu Z,Schwimer J,Liu D,et al.Gallic acid is partially responsible for the antiangiogenic activitives of Rubus leaf extract[J].Phyother Res,2006,20(9):806-813
[14]滕昭玉,崔紫姣,杜莹,等.甜茶总多酚的纯化及其抗氧化活性[J].安徽农业科学,2016,44(1):36-39
[15]Xia X L,Jin H Z,Yan S K,et al.Analysis of the bioactive constituents of Chansu in rat plasma by high Performance liquid chromatography with mass spectrometric detection[J].J Pharm Biomed Anal,2010,53(3):646-654
[16]王硕,侯小利,周小雷,等.甜茶多酚对高脂血症大鼠的降血脂作用及其机制研究[J].中国药学杂志,2015,50(20):1811-1815
[17]闫志刚,蒙淑洁,韦荣昌,等.广西甜茶研究与应用现状[J].中草药,2017,48(12):2572-2588
[18]李莉,王玉波,陈岱韻,等.甜茶皂甙对变形链球菌抑龋性的研究[J].泰山医学学报,2014,35(12):1252-1253
[19]谭冬明,石相莉,罗星晔,等.广西甜茶化学成分、提取工艺及生物活性研究进展[J].中成药,2017,39(6):1252-1255
[20]Hoesel B,Schmid JA.The complexity of NF-κB signaling in inflammation and cancer[J].Mol Cancer,2013,12:86-100
[22]Rico-Martinez M,Medina FG,Marrero JG,et al.Biotransformation of Diterpenes[J].Rsc Advances,2014,4(21):2046-2069
[23]海广范,张慧,郭兰青.二萜类化合物药理学作用研究进展[J].新乡医学院学报,2015,32(1):77-80
[24]金海峰,吕宾,戴金锋,等.温郁金二萜类化合物C抗胃癌作用的实验研究[J].中国中西医结合杂志,2015,35(2):216-221
[25]Bhatti HN,Khera RA.Biotransformations of diterpenoids and triterpenoids:a review[J].J Asian Nat Prod Res,2014,16(1):70-104
[26]吴亦晴,虞劲祥,程志红.二萜类化合物微生物转化研究进展[J].中国生化药物杂志,2016,36(3):9-14
[27]Wang HB,Wang XY,Liu LP,et al.Tigliane diterpenoids from the Euphorbiaceae and Thymelaeaceae families[J].Chem Rev,2015,115(9):2975-3011
[28]Liu Z,Zhang F,Koh G Y,et al.Cytotoxic and antiangiogenic paclitaxel solubilized and permeation-enhanced by natural product nanoparticles[J].Anticancer Drugs,2015,26(2):167-179
[29]颜小捷,卢凤来,李典鹏.甜茶化学成分及药理作用研究进展[J].广西植物,2013,33(1):136-142