紫玉盘叶的化学成分研究
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摘要
自1998年我们首次报道多氧取代环己烯类化合物zeylenone及其抗肿瘤活性后,一直坚持研究该类成分。为了寻找新型抗肿瘤活性化合物,利用有关植物资源,本论文对该属植物紫玉盘(Uvaria microcarpa Champ. ex Benth)的叶进行了系统的化学成分研究。用70%乙醇回流提取紫玉盘叶三次,所得提取液浓缩后分别用石油醚、氯仿、乙酸乙酯、正丁醇萃取,得到四个部位。利用反复硅胶柱层析、Sephadex LH-20凝胶柱层析和制备HPLC等手段对这四分部位进行分离,得到25个化学成分,通过NMR、MS、IR、UV等光谱分析和理化常数,鉴定了22个化合物,分别为:硬脂酸(ZL-1)、乌苏酸(ZL-2)、β-谷甾醇(ZL-3)、蒲公英赛醇(ZL-4)、苯甲酸(ZL-5)、对羟基苯甲酸(ZL-6)、齐墩果酸(ZL-7)、咖啡酸(ZL-8)、阿魏酸(ZL-9)、3-甲氧基-4-羟基-苯甲酸(ZL-10)、Microcarpol A (ZL-11)、Microcarpol B (ZL-12)、延胡索乙素(ZL-13)、(E)-1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1 -one (ZL-14)、Zeylenol (ZL-15)、Ellipeiopsol B (ZL-16)、β-胡萝卜苷(ZL-17)、马兜铃内酰胺AⅡ(ZL-18)、槲皮素(ZL-19)、山奈酚(ZL-20)、山奈酚-3-O-β-D-芸香糖苷(ZL-21)、芦丁(ZL-22)。
其中,ZL-11、ZL-12为新化合物;ZL-15、ZL-16为多氧取代环己烯类化合物; ZL-7、ZL-8、ZL-10、ZL-14为首次从该属植物中分离得到的化合物。
此外,本文综述了紫玉盘属植物的化学成分和药理研究概况。
Our research group reported a new polyoxygenated cyclohexene-zeylenone and its antitumour activities for the first time in 1998, since then, we persisted in study on polyoxygenated cyclohexenes for several years. In order to research the resourse of Uvaria species and to discover more antitumor agents from nature, Uvaria microcarpa Champ. ex Benth growing in Guangxi province was subjected to phytochemical studies. The leaves were extracted with 70% EtOH three times under reflux. The EtOH extract was partitioned with petroleum ether, chloroform, ethyl acetate and n-butanol. Twenty-five compounds were isolated using silical gel, Sephedax LH-20 and semi-HPLC colomn chromatography and twenty-two were structurally identified by means of various modern spectroscopic techniques (NMR, MS, IR,UV and so on ) and their physical properties.They are as follows: stearic acid (ZL-1)、ursolicacid (ZL-2)、β-sitosterol (ZL-3)、taraxerol (ZL-4)、benzoic Acid (ZL-5)、hydroxybenzoic acid (ZL-6)、oleanolic Acid (ZL-7)、caffeic acid (ZL-8)、ferulic acid (ZL-9)、vanillic acid (ZL-10)、Microcarpol A (ZL-11)、Microcarpol B (ZL-12)、tetrahydropalmatie (ZL-13) (E)-1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one (ZL-14)、Zeylenol (ZL-15)、Ellipeiopsol B (ZL-16)、daucosterol (ZL-17)、Aristololactam AⅡ(ZL-18)、quercetin (ZL-19)、kaempferol (ZL-20)、kaempferol-3-O-β-D-rutinoside (ZL-21)、rutin (ZL-22)。
Among them, ZL-11 and ZL-12 were new compounds; ZL-15 and ZL-16 were polyoxygenated cyclohexenes compounds; ZL-7、ZL-8、ZL-10 and ZL-14 were isolated in Uvaria genus for the first time.
This thesis also reviewed advances of the chemical and pharmacological studies of Uvaria genus.
其中,ZL-11、ZL-12为新化合物;ZL-15、ZL-16为多氧取代环己烯类化合物; ZL-7、ZL-8、ZL-10、ZL-14为首次从该属植物中分离得到的化合物。
此外,本文综述了紫玉盘属植物的化学成分和药理研究概况。
Our research group reported a new polyoxygenated cyclohexene-zeylenone and its antitumour activities for the first time in 1998, since then, we persisted in study on polyoxygenated cyclohexenes for several years. In order to research the resourse of Uvaria species and to discover more antitumor agents from nature, Uvaria microcarpa Champ. ex Benth growing in Guangxi province was subjected to phytochemical studies. The leaves were extracted with 70% EtOH three times under reflux. The EtOH extract was partitioned with petroleum ether, chloroform, ethyl acetate and n-butanol. Twenty-five compounds were isolated using silical gel, Sephedax LH-20 and semi-HPLC colomn chromatography and twenty-two were structurally identified by means of various modern spectroscopic techniques (NMR, MS, IR,UV and so on ) and their physical properties.They are as follows: stearic acid (ZL-1)、ursolicacid (ZL-2)、β-sitosterol (ZL-3)、taraxerol (ZL-4)、benzoic Acid (ZL-5)、hydroxybenzoic acid (ZL-6)、oleanolic Acid (ZL-7)、caffeic acid (ZL-8)、ferulic acid (ZL-9)、vanillic acid (ZL-10)、Microcarpol A (ZL-11)、Microcarpol B (ZL-12)、tetrahydropalmatie (ZL-13) (E)-1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one (ZL-14)、Zeylenol (ZL-15)、Ellipeiopsol B (ZL-16)、daucosterol (ZL-17)、Aristololactam AⅡ(ZL-18)、quercetin (ZL-19)、kaempferol (ZL-20)、kaempferol-3-O-β-D-rutinoside (ZL-21)、rutin (ZL-22)。
Among them, ZL-11 and ZL-12 were new compounds; ZL-15 and ZL-16 were polyoxygenated cyclohexenes compounds; ZL-7、ZL-8、ZL-10 and ZL-14 were isolated in Uvaria genus for the first time.
This thesis also reviewed advances of the chemical and pharmacological studies of Uvaria genus.
引文
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[3]杨向楠.紫玉盘的化学成分研究(硕士论文).第二军医大学, 2009.
[4] G. X. Zhou, R. Y. Chen, D. Q. Yu. New polyoxynated cyclohexennes from Uvaria calamistrata. J. Asia Nat. Prod. Res. , 1999, 1(3 ): 227-238.
[5]周光雄.番荔枝科植物刺果紫玉盘抗肿瘤化学成分研究(博士研究生毕业论文).中国医学科学院-中国协和医科大学,1999.
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[16] M. H. H. Nkunya, H.Weenen, N. J. Koyi, et al. Cyclohexene epoxides, (+)-pandoxide, (+)β-senepoxide and (-)-pipoxide, from Uvaria pandensis. Phytochemistry, 1987, 26(9): 2563-2565.
[17] M. H. H. Nkunya and H. Weenen. Two indolosesquiterpenes from Uvaria pandensis. Phytochemistry, 1989, 28(9): 2217-2218.
[18] M. Kodpinid, C. Sadavongvivad, C. Thebtaranonth, et a1. Benzyl benzoates from the root of Uvaria purpurea. Phytochemistry, 1989, 23 (1): 199-200.
[19] M. H. H. Nkunya, H. Weenen and N. J. Koyi. 3-Farnesylindole from Uvaria pandensis verdc. Phytochemistry, 1987, 26(8): 2402-2403.
[20] M. Kodpinid, C. Sadavongvivad, C. Thebtaranonth. Structures of p-senepoxide, tingtanoxide, and their dime precursors. Constituents of Uvaria ferruginea Tetrahedron Lett. , 1983, 24(19): 2019-2022.
[21] Y. H. Liao, Z. M. Zou, J. Guo, et al. Five polyoxygenated cyclohexenes from Uvaria grandiflora. Chin. Pharm. Sci. , 2000, 9(4): 170-173.
[22] I. Muhammad, C. M. Hasan, A. T. M. Anisuzzaman. Chemical and biological studies of benzylated indole alkaloids from Uvaria angolensisi stem bark. J. Bangladesh Acad. Sci. , 1987, 11(2): 195-203.
[23]廖永红,徐丽珍,杨世林.山椒子化学成分的研究.中草药, 1996, 27(9): 524-525.
[24] YH. Liao, L.Z. Xu, S.L. Yang, et al. Three cyclohexene oxides from Uvaria grandiflora. Phytochemistry, 1997, 45(4): 729-732
[25]潘锡平,秦永平,陈若芸,等.光叶紫玉盘多氧取代环己烯类成分研究[J].药学学报, 1998, 33(4): 278-281.
[26] I. Muhammad, P. G. Waterman. Chemistry of the Annonaceae, Part 18. Benzylated Indoles and Dihydrochalcones in Uvaria angolensis from Tanzania. J. Nat. Prod. , 1985, 48(4): 571-580.
[27]陈瑛.两种番荔枝科植物东京紫玉盘和长叶哥纳香中抗肿瘤化学成分研究(博士研究生毕业论文).中国医学科学院-中国协和医科大学, 1997.
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[29] V. S. Parmar, O. D. Tyagi, A. Malhotra, et al. Novel constituents of Uvaria species Nat. Prod. Rep. , 1994(11): 219 -224.
[30] M. H. H. Nkunya, et al, Med. , 1991, 57, 341.
[31] L. Huang, et at. , J. Nat. Prod. 1998, 61, 446.
[32] Y. Chen, and D. Q. Yu. Tonkinelin, a novel annonaceous acetogenin from Uvaric tonkinesis. Planta Med, 1996, 62(6): 512-514.
[33] Y. Chen, et al. , Phytochemistry, 1996, 43 (4): 793.
[34] Y. Chen and D. Q. Yu. Tonkinecin, a novel bioactive annonaceous acetogenin from Uvaria tonkinesis J. Nat. Prod, 1996, 59(5): 507-509.
[35] A. Hisham, L. A. C. Pieters, M. Claeys, et al. Squamocin-28-one and panalicin, two acetogenins from Uvaria narum Phytochemistry, 1990, 30(2): 545-548.
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[38]余冬蕾,郭剑,廖永红等.紫玉盘中的新内酰胺.植物学报, 1999, 41(10): 1104-1107.
[39] Lu YP, Mu L, Zheng SL, et al. Two new constituents from Uvaria microcarpa. Chin Chem Lett, 1995, 6(9): 775-778.
[40] Polyoxygenated cyclohexene derivatives from Ellipeiopsis cherrevensis. Anake Kijjoa, Julia Bessa, Madalena M. M. Pinto, et al. Phytochemistry 2002, 59: 543-549.
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[2]王嗣.景洪哥纳香和大叶紫玉盘根抗肿瘤化学成分研究(博士论文).中国医学科学院-中国协和医科大学:2002.
[3]杨向楠.紫玉盘的化学成分研究(硕士论文).第二军医大学, 2009.
[4] G. X. Zhou, R. Y. Chen, D. Q. Yu. New polyoxynated cyclohexennes from Uvaria calamistrata. J. Asia Nat. Prod. Res. , 1999, 1(3 ): 227-238.
[5]周光雄.番荔枝科植物刺果紫玉盘抗肿瘤化学成分研究(博士研究生毕业论文).中国医学科学院-中国协和医科大学,1999.
[6]潘锡平.紫玉盘属两种植物抗肿瘤化学成分研究(博士研究生毕业论文).中国医学科学院-中国协和医科大学,1996.
[7]吕子明,黄龙江,陈若芸等.黄花紫玉盘枝、叶化学成分的研究.中国中药杂志,2009, 34(17): 2203-2205.
[8] S. D. Jolad, J. J. Hoffmann, J. R. Cole, et al. 1-Epizeylenol from Uvaria zeylanica roots. Phytochemistry, 1984, 23(4): 935-936.
[9] G. R. Schulte, B. Gn Chantrapromma, M. Kodpinid, et al. The structure of ferrudiol. A highly oxidized constituent of uvaria ferruginea. Tetrahedron Lett. , 1983, 23(3): 289-292.
[10] R. Hollands, D. Becher, A. Gaudemer, et al. Etude des constituants des fruits d Uvaria catocarpa (Annonacae): Structure du senepoxyde et du seneol. Tetrahedron, 1968, 24(4): 1633-1650.
[11] S. D. Jolad, J. J. Hoffman, K. H. Schram, et al. Uvaricin, a new antitumor agent from Uvaria accuminata (Annonaceae). J. Org. Chem. , 1982, 47(16): 3151-3153.
[12] YH. Liao, Z. M. Zou, J. Guo, et al. Five polyoxygenated cyclohexenes from Uvaria grandiflora. Chin. Pharm.Sci. , 2000, 9(4): 170-173.
[13] I. Muhammad, C. M.Hasan, A. T. M. Anisuzzaman. Chemical and biological studies of benzylated indole alkaloids from Uvaria angolensisi stem bark. J. Bangladesh Acad. Sci. , 1987, 11(2): 195-203.
[14]刘安,徐丽珍.乌藤和对叶豆化学成分的研究及Zeylenone其类似物全合成研究.博士研究生学位论文. 2004.
[15] G. R. Schulte, M. Kodpinid, C. Thebtaranonth, et al. Studies on highly oxidized cyclohexanes. Constitution of a new key metabolic intermediate. Tetrahedron Lett., 1982, 23(42): 4303-4304.
[16] M. H. H. Nkunya, H.Weenen, N. J. Koyi, et al. Cyclohexene epoxides, (+)-pandoxide, (+)β-senepoxide and (-)-pipoxide, from Uvaria pandensis. Phytochemistry, 1987, 26(9): 2563-2565.
[17] M. H. H. Nkunya and H. Weenen. Two indolosesquiterpenes from Uvaria pandensis. Phytochemistry, 1989, 28(9): 2217-2218.
[18] M. Kodpinid, C. Sadavongvivad, C. Thebtaranonth, et a1. Benzyl benzoates from the root of Uvaria purpurea. Phytochemistry, 1989, 23 (1): 199-200.
[19] M. H. H. Nkunya, H. Weenen and N. J. Koyi. 3-Farnesylindole from Uvaria pandensis verdc. Phytochemistry, 1987, 26(8): 2402-2403.
[20] M. Kodpinid, C. Sadavongvivad, C. Thebtaranonth. Structures of p-senepoxide, tingtanoxide, and their dime precursors. Constituents of Uvaria ferruginea Tetrahedron Lett. , 1983, 24(19): 2019-2022.
[21] Y. H. Liao, Z. M. Zou, J. Guo, et al. Five polyoxygenated cyclohexenes from Uvaria grandiflora. Chin. Pharm. Sci. , 2000, 9(4): 170-173.
[22] I. Muhammad, C. M. Hasan, A. T. M. Anisuzzaman. Chemical and biological studies of benzylated indole alkaloids from Uvaria angolensisi stem bark. J. Bangladesh Acad. Sci. , 1987, 11(2): 195-203.
[23]廖永红,徐丽珍,杨世林.山椒子化学成分的研究.中草药, 1996, 27(9): 524-525.
[24] YH. Liao, L.Z. Xu, S.L. Yang, et al. Three cyclohexene oxides from Uvaria grandiflora. Phytochemistry, 1997, 45(4): 729-732
[25]潘锡平,秦永平,陈若芸,等.光叶紫玉盘多氧取代环己烯类成分研究[J].药学学报, 1998, 33(4): 278-281.
[26] I. Muhammad, P. G. Waterman. Chemistry of the Annonaceae, Part 18. Benzylated Indoles and Dihydrochalcones in Uvaria angolensis from Tanzania. J. Nat. Prod. , 1985, 48(4): 571-580.
[27]陈瑛.两种番荔枝科植物东京紫玉盘和长叶哥纳香中抗肿瘤化学成分研究(博士研究生毕业论文).中国医学科学院-中国协和医科大学, 1997.
[28]张海玲.番荔枝科植物大叶紫玉盘抗肿瘤化学成分研究(硕士研究生毕业论文).中国医学科学院-中国协和医科大学, 2001.
[29] V. S. Parmar, O. D. Tyagi, A. Malhotra, et al. Novel constituents of Uvaria species Nat. Prod. Rep. , 1994(11): 219 -224.
[30] M. H. H. Nkunya, et al, Med. , 1991, 57, 341.
[31] L. Huang, et at. , J. Nat. Prod. 1998, 61, 446.
[32] Y. Chen, and D. Q. Yu. Tonkinelin, a novel annonaceous acetogenin from Uvaric tonkinesis. Planta Med, 1996, 62(6): 512-514.
[33] Y. Chen, et al. , Phytochemistry, 1996, 43 (4): 793.
[34] Y. Chen and D. Q. Yu. Tonkinecin, a novel bioactive annonaceous acetogenin from Uvaria tonkinesis J. Nat. Prod, 1996, 59(5): 507-509.
[35] A. Hisham, L. A. C. Pieters, M. Claeys, et al. Squamocin-28-one and panalicin, two acetogenins from Uvaria narum Phytochemistry, 1990, 30(2): 545-548.
[36]全国中草药汇编编写组.全国中草药汇编下册[M].北京:人民卫生出版社, 1992: 623-623.
[37]陈文森,姚祝军,吴毓林.紫玉盘种子中的番荔枝内酯类成分研究.化学学报,1997, 55: 723-728.
[38]余冬蕾,郭剑,廖永红等.紫玉盘中的新内酰胺.植物学报, 1999, 41(10): 1104-1107.
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