攀茎钩藤茎枝的化学成分研究
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摘要
目的研究攀茎钩藤Uncaria scandens茎枝的化学成分。方法利用硅胶、Sephadex LH-20、RP_(18)和HPLC等对其化学成分进行分离和纯化,根据波谱数据和理化性质对化合物的结构进行鉴定。利用高效液相色谱法测定了其中钩藤碱和异钩藤碱的含量。结果从攀茎钩藤茎枝的95%乙醇提取物中分离得到17个化合物,分别鉴定为5α-carboxystrictosidine(1)、3β-异二氢卡丹宾碱(2)、异长春花苷内酰胺(3)、3α-二氢卡丹宾碱(4)、帽柱叶碱(5)、恩卡林碱F(6)、3β-异二氢卡丹宾碱4-氧化物(7)、异二氢卡丹宾碱(8)、nauclefine(9)、卡丹宾碱(10)、calyxamine B(11)、绿原酸甲酯(12)、3,4,5-三甲氧基苯酚(13)、托可醌(14)、喹诺瓦酸(15)、咖啡酸甲酯(16)、金丝桃苷(17)。攀茎钩藤中钩藤碱和异钩藤碱的质量分数分别为0.72和0.38μg/g。结论化合物7～9、11～14为首次从该属植物中分离得到;化合物1～6、16、17为首次从该植物中分离得到。攀茎钩藤中钩藤碱和异钩藤碱的含量较低,其在部分地区作为钩藤使用的合理性有待进一步验证。
Objective To study the chemical constituents from the stems of Uncaria scandens. Methods The compounds were isolated and purified by silica gel column chromatography, Sephadex LH-20, RP_(18), and HPLC. The structures were identified by spectroscopic methods and physicochemical properties. The contents of rhynchophylline and isorhynchophylline were detected by HPLC method. Results Seventeen compounds were isolated and identified from 95% ethanol extract of the stems of U. scandens and characterized as 5α-carboxystrictosidine(1), 3β-isodihydrocadambine(2), strictosamide(3), 3α-dihydrocadambine(4), mitraphylline(5), uncarine F(6), 3β-isodihydrocadambine 4-oxide(7), isodihydrocdambine(8), nauclefine(9), cadambine(10), calyxamine B(11),methyl chlorogenate(12), 3,4,5-trimethoxyphenol(13), α-tocopherylquinone(14), quinovic acid(15), methyl caffeate(16), and hyperoside(17). The contents of rhynchophylline and isorhynchophylline from U. scandens were 0.72 and 0.38 μg/g. Conclusion Compounds 7—9 and 11—14 are isolated from Uncaria genus for the first time. Compounds 1—6 and 16, 17 are isolated from U.scandens for the first time. The contents of rhynchophylline and isorhynchophylline is low and the reasonable use of them as U.scandens in some areas needs to be further verified.
Objective To study the chemical constituents from the stems of Uncaria scandens. Methods The compounds were isolated and purified by silica gel column chromatography, Sephadex LH-20, RP_(18), and HPLC. The structures were identified by spectroscopic methods and physicochemical properties. The contents of rhynchophylline and isorhynchophylline were detected by HPLC method. Results Seventeen compounds were isolated and identified from 95% ethanol extract of the stems of U. scandens and characterized as 5α-carboxystrictosidine(1), 3β-isodihydrocadambine(2), strictosamide(3), 3α-dihydrocadambine(4), mitraphylline(5), uncarine F(6), 3β-isodihydrocadambine 4-oxide(7), isodihydrocdambine(8), nauclefine(9), cadambine(10), calyxamine B(11),methyl chlorogenate(12), 3,4,5-trimethoxyphenol(13), α-tocopherylquinone(14), quinovic acid(15), methyl caffeate(16), and hyperoside(17). The contents of rhynchophylline and isorhynchophylline from U. scandens were 0.72 and 0.38 μg/g. Conclusion Compounds 7—9 and 11—14 are isolated from Uncaria genus for the first time. Compounds 1—6 and 16, 17 are isolated from U.scandens for the first time. The contents of rhynchophylline and isorhynchophylline is low and the reasonable use of them as U.scandens in some areas needs to be further verified.
引文
[1]贾敏如,李星炜.中国民族药志要[M].北京:中国医药科技出版社,2005.
[2]中国药典[S].一部.2015.
[3]史晓龙.藏药攀茎钩藤化学成分及生物活性研究[D].兰州:兰州理工大学,2015.
[4]马大勇,汪冶,晏晨,等.攀茎钩藤化学成分的研究[J].中国医药工业杂志,2008,39(7):507-509.
[5]张俊杰,杨敏超,彭伟,等.攀茎钩藤化学成分的研究[J].海南师范大学学报,2016,29(2):189-191.
[6]张俊杰.云南钩藤和攀茎钩藤两种药用植物化学成分的研究[D].昆明:云南师范大学,2016.
[7]邹澄,张荣平,孙晓豫,等.攀枝钩藤中的化学成分[J].中国民族民间医药,1998(1):41-42.
[8]Yang A M,Shi X L,Zheng Z S,et al.Chemical constituents of Uncaria scandens[J].Chem Nat Compd,2018,54(4):793-794.
[9]Ferrari F,Messana I,Botta B.Constituents of Guettarda platypoda[J].J Nat Prod,1986,49(6):1150-1151.
[10]韦宏.团花树皮的吲哚生物碱成分[J].广西科学院学报,1999,15(2):52-55.
[11]Takayama H,Tsutsumi S I,Kitajima M,et al.Gluco-indole alkaloids from Nauclea cadamba in Thailand and transformation of 3α-dihydrocadambine into the indolopyridine alkaloid,16-carbomethoxynaufoline[J].Chem Pharm Bull,2003,51(2):232-233.
[12]Raja P B,Qureshi A K,Rahim A A,et al.Neolamarckia cadamba alkaloids as eco-friendly corrosion inhibitors for mild steel in 1 M HCI media[J].Corros Sci,2013,69(2):292-301.
[13]杨龄,肖春贵,金亚菊,等.倒挂金钩茎枝的化学成分研究[J].中草药,2018,49(5):2365-2371.
[14]辛文波,俞桂新,王峥涛.钩藤生物碱类成分研究[J].中草药,2009,40(2):204-207.
[15]Seki H,Takayama H,Aimi N,et al.A nuclear magnetic resonance study on the eleven stereoisomers of heteroyohimbine-type oxindole alkaloids[J].Chem Pharm Bull,1993,41(12):2077-2086.
[16]Zhou H,He H P,Kong N C,et al.Indole alkaloids from the leaves of Anthocephalus chinensis[J].Helv Chim Acta,2010,91(11):2148-2152.
[17]Endo K,Oshima Y,Kikuchi H,et al.Hypotensive principles of Uncaria hooks[J].Planta Med,1983,49(11):188-190.
[18]Abreu P,Pereira A.A new indole aikaloid from Sarcocephalus latifollus[J].Heterocycles,1998,29(48):885-891.
[19]Rodriguez A D,Cobar O M,Padilla O L,et al.Calyxamines A and B,novel piperidine alkaloids from the caribbean sea sponge Calyx podatypa[J].J Nat Prod,1997,60(12):1331-1333.
[20]孔娜娜,方圣涛,刘莺.罗布麻叶中非黄酮类化学成分研究[J].中草药,2013,44(22):3114-3118.
[21]李薇,梅文莉,王昊,等.白木香树干的化学成分研究[J].中国中药杂志,2013,38(17):2826-2831.
[22]刘晖晖,于永明,张涛,等.半边铁角蕨化学成分研究[J].中国药学杂志,2017,52(2):100-104.
[23]孙敬勇.胆木和山香圆化学成分及其生物活性研究[D].济南:山东大学,2008.
[24]关永霞,杨小生,佟丽华,等.苗药地瓜藤化学成分的研究[J].中草药,2007,38(3):342-344.
[25]王强,徐芳辉.衡山金丝桃地上部分乙酸乙酯部位化学成分研究[J].中药材,2013,36(10):1611-1613.
[26]Zhang F,Sun A S,Yu L M,et al.Effects of isorhynchophylline on angiotensin II-induced proliferation in rat vascular smooth muscle cells[J].JPharm Pharmacol,2008,60(12):1673-1678.
[27]邓岳,刘阿娜,王小明,等.UPLC法同时测定钩藤提取物中4种生物碱类成分的含量[J].中药材,2016,39(4):819-821.
[28]杨秀娟,洪燕龙,吴飞,等.HPLC测定钩藤中钩藤碱和异钩藤碱的方法学探讨[J].中国中药杂志,2013,38(5):720-723
[29]Heitzman M E,Neto C C,Winiarz E,et al.Ethnobotany,phytochemistry and pharmacology of Uncaria(Rubiaceae)[J].Phytochemistry,2005,66(1):5-29.
[2]中国药典[S].一部.2015.
[3]史晓龙.藏药攀茎钩藤化学成分及生物活性研究[D].兰州:兰州理工大学,2015.
[4]马大勇,汪冶,晏晨,等.攀茎钩藤化学成分的研究[J].中国医药工业杂志,2008,39(7):507-509.
[5]张俊杰,杨敏超,彭伟,等.攀茎钩藤化学成分的研究[J].海南师范大学学报,2016,29(2):189-191.
[6]张俊杰.云南钩藤和攀茎钩藤两种药用植物化学成分的研究[D].昆明:云南师范大学,2016.
[7]邹澄,张荣平,孙晓豫,等.攀枝钩藤中的化学成分[J].中国民族民间医药,1998(1):41-42.
[8]Yang A M,Shi X L,Zheng Z S,et al.Chemical constituents of Uncaria scandens[J].Chem Nat Compd,2018,54(4):793-794.
[9]Ferrari F,Messana I,Botta B.Constituents of Guettarda platypoda[J].J Nat Prod,1986,49(6):1150-1151.
[10]韦宏.团花树皮的吲哚生物碱成分[J].广西科学院学报,1999,15(2):52-55.
[11]Takayama H,Tsutsumi S I,Kitajima M,et al.Gluco-indole alkaloids from Nauclea cadamba in Thailand and transformation of 3α-dihydrocadambine into the indolopyridine alkaloid,16-carbomethoxynaufoline[J].Chem Pharm Bull,2003,51(2):232-233.
[12]Raja P B,Qureshi A K,Rahim A A,et al.Neolamarckia cadamba alkaloids as eco-friendly corrosion inhibitors for mild steel in 1 M HCI media[J].Corros Sci,2013,69(2):292-301.
[13]杨龄,肖春贵,金亚菊,等.倒挂金钩茎枝的化学成分研究[J].中草药,2018,49(5):2365-2371.
[14]辛文波,俞桂新,王峥涛.钩藤生物碱类成分研究[J].中草药,2009,40(2):204-207.
[15]Seki H,Takayama H,Aimi N,et al.A nuclear magnetic resonance study on the eleven stereoisomers of heteroyohimbine-type oxindole alkaloids[J].Chem Pharm Bull,1993,41(12):2077-2086.
[16]Zhou H,He H P,Kong N C,et al.Indole alkaloids from the leaves of Anthocephalus chinensis[J].Helv Chim Acta,2010,91(11):2148-2152.
[17]Endo K,Oshima Y,Kikuchi H,et al.Hypotensive principles of Uncaria hooks[J].Planta Med,1983,49(11):188-190.
[18]Abreu P,Pereira A.A new indole aikaloid from Sarcocephalus latifollus[J].Heterocycles,1998,29(48):885-891.
[19]Rodriguez A D,Cobar O M,Padilla O L,et al.Calyxamines A and B,novel piperidine alkaloids from the caribbean sea sponge Calyx podatypa[J].J Nat Prod,1997,60(12):1331-1333.
[20]孔娜娜,方圣涛,刘莺.罗布麻叶中非黄酮类化学成分研究[J].中草药,2013,44(22):3114-3118.
[21]李薇,梅文莉,王昊,等.白木香树干的化学成分研究[J].中国中药杂志,2013,38(17):2826-2831.
[22]刘晖晖,于永明,张涛,等.半边铁角蕨化学成分研究[J].中国药学杂志,2017,52(2):100-104.
[23]孙敬勇.胆木和山香圆化学成分及其生物活性研究[D].济南:山东大学,2008.
[24]关永霞,杨小生,佟丽华,等.苗药地瓜藤化学成分的研究[J].中草药,2007,38(3):342-344.
[25]王强,徐芳辉.衡山金丝桃地上部分乙酸乙酯部位化学成分研究[J].中药材,2013,36(10):1611-1613.
[26]Zhang F,Sun A S,Yu L M,et al.Effects of isorhynchophylline on angiotensin II-induced proliferation in rat vascular smooth muscle cells[J].JPharm Pharmacol,2008,60(12):1673-1678.
[27]邓岳,刘阿娜,王小明,等.UPLC法同时测定钩藤提取物中4种生物碱类成分的含量[J].中药材,2016,39(4):819-821.
[28]杨秀娟,洪燕龙,吴飞,等.HPLC测定钩藤中钩藤碱和异钩藤碱的方法学探讨[J].中国中药杂志,2013,38(5):720-723
[29]Heitzman M E,Neto C C,Winiarz E,et al.Ethnobotany,phytochemistry and pharmacology of Uncaria(Rubiaceae)[J].Phytochemistry,2005,66(1):5-29.