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作者(中文):黃俊惟
作者(外文):Huang, Chun-Wei
論文名稱(中文):台灣產鷗蔓之娃兒藤生物鹼的分離與鑑定
論文名稱(外文):Isolation and Identification of Phenanthroindolizidine Alkaloids from Formosa Tylophora ovata
指導教授(中文):李秀珠
張晃猷
指導教授(外文):Lee, Shiow-Ju
Chang, Hwan-You
學位類別:碩士
校院名稱:國立清華大學
系所名稱:分子醫學研究所
學號:9680601
出版年(民國):98
畢業學年度:98
語文別:中文
論文頁數:163
中文關鍵詞:娃兒藤生物鹼(菲并吲哚啶生物鹼)製備級高效率液相層析印度娃兒藤鷗蔓(卵葉娃兒藤)娃兒藤鹼
外文關鍵詞:phenanthroindolizidine alkaloidspreparative HPLCT. indicaT. ovatatylophorine
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鷗蔓又稱卵葉娃兒藤,在分類學上屬於被子植物門、雙子葉綱、龍膽目、蘿摩科、娃兒藤屬(鷗蔓屬),為多年生藤蔓性植物。目前全世界已有60種以上的娃兒藤屬植物被鑑定出來,而這些娃兒藤屬植物大多含有娃兒藤生物鹼,又稱菲并吲哚啶生物鹼(phenanthroindolizidine alkaloids),此種化學成分首次於1935年從印度娃兒藤中分離出來,並命名為娃兒藤鹼(tylophorine),這些化合物多數具有抗癌、抗發炎等生物活性。本篇研究以台灣生鷗蔓做為研究材料,除了希望藉此開啟台灣娃兒藤植物所含活性成分的研究之外,也希望藉此尋找抗癌等生物活性更佳的娃兒藤生物鹼。首先經由甲醇萃取、酸鹼萃取、分配萃取,生物鹼成分會溶解在有機層,再經一系列管柱層析、製備級高效率液相層析(preparative high pressure liquid chromatography)實驗,以純化莖、葉所含的生物鹼成分。最後從葉部分離出10種化合物;從莖部則分離出7種,經由EI-MS、1H-NMR、13C-NMR、DEPT、2D-NMR,並輔以UV、IR、比旋光度等分析方法來確認化合物結構,共有12種不同的娃兒藤生物鹼被分離出來,分別是:(S)-(+)-tylophorine, (S)-(+)-septicine, (+)-tylophorinine, (-)-tylophorinicine, (+)-tylophorinicine , (S)-(+)-hispidine, (S)-(+)-2,6-didesmethoxyl-4-hydroxyl-septicine, (S)-(+)-6-desmethylsepticine, (S)-(+)-6-desmethyltylophorine, (S)-(+)-3-desmethyisotylocrebrine,
trans-(+)-3,14α-dihydroxy-4,6,7-trimethoxyphenanthroindolizidine, and
trans-(+)-3,14α-dihydroxy-6,7-dimethoxyphenanthroindolizidine.

關鍵詞:娃兒藤生物鹼(菲并吲哚啶生物鹼)、製備級高效率液相層析、印度娃兒藤、鷗蔓(卵葉娃兒藤)、娃兒藤鹼。
Tylophora ovata (T. ovata) belongs to phylum Magnoliophyta, class
Dicotyledoneae, order Gentianales, family Asclepiadaceae, and genus Tylophora. Up
to date, botanists have found about 60 species of Tylophora all over the world. Since
the first isolation of tylophorine from Tylophora indica in A.D. 1935, many kinds of
phenanthroindolizidine or phenanthroquinolizidine alkaloids have been isolated and
purified from Asclepiadaceae, especially from Tylophora and Cynanchum. These
alkaloids have been shown to exert anti-leukemia, anti-asthma, anti-anaphylactic,
anti-bacterial and other anti-inflammatory activities. Last decade, they have regained
attentions for development into therapeutic agents with well known cytotoxic activity
against a variety of cancer cell lines in vitro and in vivo. T. ovata is most commonly
distributed species of tylophora plants native to Taiwan than the other two species, T.
oshimae Hayata and T. taiwanensis Hatusima). In order to investigate the tylophorine
analogous ingredients from T. ovata, we collected T. ovata plant materials for
isolation and purification of tylophorine analogues. The air-dried leaves and stems
were extracted with MeOH at boiling point under reflux and then concentrated to
green-brown gummy residues, respectively. The residues in 0.5% HCl-soluble
portions were filtered. The filtrates were made alkaline with 25% NH4OH (pH=9),
and extracted repeatedly with CHCl3 until the organic layer exhibited Dragendorff test
was negative. Subsequently, a series of chromatography including open silica gel
column and preparative high pressure liquid chromatography were applied for
purification. EI-MS, 1H-NMR, 13C-NMR, DEPT, 2D-NMR, IR, and [α] were
exploited to identify the structures of the 12 compounds from the leaves and the stems
of T. ovata. They are (S)-(+)-tylophorine, (S)-(+)-septicine, (+)-tylophorinine,
(+)-tylophorincine, (-)-tylophorincine, (S)-(+)-hispidine,
(S)-(+)-2,6-didesmethoxyl-4-hydroxyl-septicine, (S)-(+)-6-desmethylsepticine,
(S)-(+)-6-desmethyltylophorine, (S)-(+)-3-desmethyisotylocrebrine,
trans-(+)-3,14α-dihydroxy-4,6,7-trimethoxyphenanthroindolizidine, and
trans-(+)-3,14α-dihydroxy-6,7-dimethoxyphenanthroindolizidine.
目 錄
第一章前言 -p1
第一節鷗蔓(Tylophora ovata)的簡介 -p1
第二節娃兒藤生物鹼的簡介 -p2
第三節研究鷗蔓的動機 -p3
第二章文獻回顧 -p4
第一節鷗蔓之娃兒藤生物鹼成分概述 -p4
第二節鷗蔓屬植物之娃兒藤生物鹼成分概述 -p5
第三章實驗材料、儀器與藥品 -p12
第一節植物材料 -p12
第二節儀器與藥品 -p14
第四章萃取及分離流程 -p16
第五章實驗數據 -p25
第六章結構鑑定 -p48
第一節TOL-c1 -p49
第二節TOL-c2 -p56
第三節TOL-c3 -p63
第四節TOL-c4 -p67
第五節TOL-c5 -p74
第六節TOL-c6 -p81
第七節TOL-c7 -p88
第八節TOL-c8 -p95
第九節TOL-c9 -p102
第十節TOL-c10 -p109
第十一節TOS-c1 -p116
第十二節TOS-c2 -p119
第十三節TOS-c3 -p121
第十四節TOS-c4 -p128
第十五節TOS-c5 -p134
第十六節TOS-c6 -p141
第十七節TOS-c7 -p148
第七章實驗討論 -p155
參考文獻 -p160

表目錄
表一:Phenanthroindolizidine alkaloids of T. ovata -p5
表二:Phenanthroindolizidine alkaloids of T. indica -p6
表三:Phenanthroindolizidine alkaloids of T. crebriflora -p7
表四:Phenanthroindolizidine alkaloids of T. hirsuta -p8
表五:Phenanthroindolizidine alkaloids of T. tanakae -p10
表五-1:Phenanthroindolizidine alkaloids of Ideopsis similis -p10
表六:Phenanthroindolizidine alkaloids of T. atrofolliculata -p11
表七-1a:1H-NMR spectra data of the isolated compounds (TOL-c1~c5) from leaves -p41
表七-1b: 1H-NMR spectra data of the isolated compounds (TOL-c6~c10) from leaves -p42
表七-2a: 1H-NMR spectra data of the isolated compounds (TOS-c1~c4) from stems -p43
表七-2b: 1H-NMR spectra data of the isolated compounds (TOS-c5~c7) from stems -p44
表八-1a: 13C-NMR spectra data of the isolated compounds (TOL-c1, c2, c4, c5) from leaves -p45
表八-1b: 13C-NMR spectra data of the isolated compounds (TOL-c6~c10) from leaves -p46
表八-2: 13C-NMR spectra data of the isolated samples (TOS-c3~c7) from stems -p47
表九:Summary of Tylophorine analogs from the leaves of T. ovata -p158
表十:Summary of Tylophorine analogs from the stems of T. ovata -p159

圖目錄
圖一:娃兒藤生物鹼基本架構分解圖 -p2
圖二:2005/12/08,鷗蔓的葉、莖及果實。楊政偉先生攝。-p12
圖三:2005/12/08,鷗蔓的果實與具白絹種芒的卵形種子。楊政偉先生攝。-p13
圖四:2006/07/10,鷗蔓的花。攝自實驗室培養箱,楊政偉先生攝。 -p13
圖五:Flow chart for 1st separation and isolation from dry leaves of T.ovata -p18
圖六:Flow chart for 2nd separation and isolation from dry leaves of T.ovata -p21
圖七:Flow chart for separation and isolation from dry stems of T.ovata -p23
圖1-1:UV spectrum of TOL-c1 -p50
圖1-2: IR spectrum of TOL-c1 -p50
圖1-3: EI-MS spectrum of TOL-c1 -p51
圖1-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c1 -p52
圖1-5: 13C-NMR (600 MHz, CDCl3) spectrum of TOL-c1 -p53
圖1-6: DEPT spectrum of TOL-c1 -p53
圖1-7: COSY spectrum of TOL-c1 -p54
圖1-8: HSQC spectrum of TOL-c1 -p54
圖1-9: HMBC spectrum of TOL-c1 -p55
圖1-10: NOESY spectrum of TOL-c1 -p55
圖2-1: UV spectrum of TOL-c2 -p57
圖2-2: IR spectrum of TOL-c2 -p57
圖2-3: EI-MS spectrum of TOL-c2 -p58
圖2-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c2 -p59
圖2-5: 13C-NMR (600 MHz, CDCl3) spectrum of TOL-c2 -p60
圖2-6: DEPT spectrum of TOL-c2 -p60
圖2-7: COSY spectrum of TOL-c2 -p61
圖2-8: HSQC spectrum of TOL-c2 -p61
圖2-9: HMBC spectrum of TOL-c2 -p62
圖2-10: NOESY spectrum of TOL-c2 -p62
圖3-1: LC/MS spectrum of TOL-c3 -p63
圖3-2: 1H-NMR (400 MHz, CDCl3) of TOL-c3 -p64
圖3-3: 1H-NMR (600 MHz, CDCl3) of TI-379 -p65
圖3-4: 1H-NMR (400 MHz, CDCl3) of TI-379-OAc -p66
圖4-1: UV spectrum of TOL-c4 -p68
圖4-2: IR spectrum of TOL-c4 -p69
圖4-3: EI-MS spectrum of TOL-c4 -p69
圖4-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c4 -p70
圖4-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOL-c4 -p71
圖4-6: DEPT spectrum of TOL-c4 -p71
圖4-7: COSY spectrum of TOL-c4 -p72
圖4-8: HSQC spectrum of TOL-c4 -p72
圖4-9: HMBC spectrum of TOL-c4 -p73
圖4-10: NOESY spectrum of TOL-c4 -p73
圖5-1: UV spectrum of TOL-c5 -p75
圖5-2: IR spectrum of TOL-c5 -p76
圖5-3: EI-MS spectrum of TOL-c5 -p76
圖5-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c5 -p77
圖5-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOL-c5 -p78
圖5-6: DEPT spectrum of TOL-c5 -p78
圖5-7: COSY spectrum of TOL-c5 -p79
圖5-8: HSQC spectrum of TOL-c5 -p79
圖5-9: HMBC spectrum of TOL-c5 -p80
圖5-10: NOESY spectrum of TOL-c5 -p80
圖6-1: UV spectrum of TOL-c6 -p82
圖6-2: IR spectrum of TOL-c6 -p83
圖6-3: EI-MS spectrum of TOL-c6 -p83
圖6-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c6 -p84
圖6-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOL-c6 -p85
圖6-6: DEPT spectrum of TOL-c6 -p85
圖6-7: COSY spectrum of TOL-c6 -p86
圖6-8: HSQC spectrum of TOL-c6 -p86
圖6-9: HMBC spectrum of TOL-c6 -p87
圖6-10: NOESY spectrum of TOL-c6 -p87
圖7-1: UV spectrum of TOL-c7 -p89
圖7-2: IR spectrum of TOL-c7 -p90
圖7-3: EI-MS spectrum of TOL-c7 -p90
圖7-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c7 -p91
圖7-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOL-c7 -p92
圖7-6: DEPT spectrum of TOL-c7 -p92
圖7-7: COSY spectrum of TOL-c7 -p93
圖7-8: HSQC spectrum of TOL-c7 -p93
圖7-9: HMBC spectrum of TOL-c7 -p94
圖7-10: NOESY spectrum of TOL-c7 -p94
圖8-1: UV spectrum of TOL-c8 -p96
圖8-2: IR spectrum of TOL-c8 -p97
圖8-3: EI-MS spectrum of TOL-c8 -p97
圖8-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c8 -p98
圖8-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOL-c8 -p99
圖8-6: DEPT spectrum of TOL-c8 -p99
圖8-7: COSY spectrum of TOL-c8 -p100
圖8-8: HSQC spectrum of TOL-c8 -p100
圖8-9: HMBC spectrum of TOL-c8 -p101
圖8-10: NOESY spectrum of TOL-c8 -p101
圖9-1: UV spectrum of TOL-c9 -p103
圖9-2: IR spectrum of TOL-c9 -p103
圖9-3: EI-MS spectrum of TOL-c9 -p104
圖9-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c9 -p105
圖9-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOL-c9 -p106
圖9-6: DEPT spectrum of TOL-c9 -p106
圖9-7: COSY spectrum of TOL-c9 -p107
圖9-8: HSQC spectrum of TOL-c9 -p107.
圖9-9: HMBC spectrum of TOL-c9 -p108
圖9-10: NOESY spectrum of TOL-c9 -p108
圖10-1: UV spectrum of TOL-c10 -p110
圖10-2: IR spectrum of TOL-c10 -p111
圖10-3: EI-MS spectrum of TOL-c10 -p111
圖10-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOL-c10 -p112
圖10-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOL-c10 -p113
圖10-6: DEPT spectrum of TOL-c10 -p113
圖10-7: COSY spectrum of TOL-c10 -p114
圖10-8: HSQC spectrum of TOL-c10 -p114
圖10-9: HMBC spectrum of TOL-c10 -p115
圖10-10: NOESY spectrum of TOL-c10 -p115
圖11-1: UV spectrum of TOS-c1 -p116
圖11-2: IR spectrum of TOS-c1 -p117
圖11-3: LC/MS spectrum of TOS-c1 -p117
圖11-4: 1H-NMR (400 MHz, CDCl3) spectrum of TOS-c1 -p118
圖12-1: LC/MS spectrum of TOS-c2 -p119
圖12-2: 1H-NMR (400 MHz, CDCl3) spectrum of TOS-c2 -p120
圖13-1: UV spectrum of TOS-c3 -p122
圖13-2: IR spectrum of TOS-c3 -p123
圖13-3: EI-MS spectrum of TOS-c3 -p123
圖13-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOS-c3 -p124
圖13-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOS-c3 -p125
圖13-6: DEPT spectrum of TOS-c3 -p125
圖13-7: COSY spectrum of TOS-c3 -p126
圖13-8: HSQC spectrum of TOS-c3 -p126
圖13-9: HMBC spectrum of TOS-c3 -p127
圖13-10: NOESY spectrum of TOS-c3 -p127
圖14-1: EI-MS spectrum of TOS-c4 -p129
圖14-2: 1H-NMR (600 MHz, CDCl3) spectrum of TOS-c4 -p130
圖14-3: 13C-NMR (150 MHz, CDCl3) spectrum of TOS-c4 -p131
圖14-4: DEPT spectrum of TOS-c4 -p131
圖14-5: COSY spectrum of TOS-c4 -p132
圖14-6: HSQC spectrum of TOS-c4 -p132
圖14-7: HMBC spectrum of TOS-c4 -p133
圖14-8: NOESY spectrum of TOS-c4 -p133
圖15-1: UV spectrum of TOS-c5 -p135
圖15-2: IR spectrum of TOS-c5 -p136
圖15-3: EI-MS spectrum of TOS-c5 -p136
圖15-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOS-c5 -p137
圖15-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOS-c5 -p138
圖15-6: DEPT spectrum of TOS-c5 -p138
圖15-7: COSY spectrum of TOS-c5 -p139
圖15-8: HSQC spectrum of TOS-c5 -p139
圖15-9: HMBC spectrum of TOS-c5 -p140
圖15-10: NOESY spectrum of TOS-c5 -p140
圖16-1: UV spectrum of TOS-c6 -p142
圖16-2: IRspectrum of TOS-c6 -p143
圖16-3: EI-MS spectrum of TOS-c6 -p143
圖16-4: 1H-NMR (600 MHz, CDCl3) spectrum of TOS-c6 -p144
圖16-5: 13C-NMR (150 MHz, CDCl3) spectrum of TOS-c6 -p145
圖16-6: DEPT spectrum of TOS-c6 -p145
圖16-7: COSY spectrum of TOS-c6 -p146
圖16-8: HSQC spectrum of TOS-c6 -p146
圖16-9: HMBC spectrum of TOS-c6 -p147
圖16-10: NOESY spectrum of TOS-c6 -p147
圖17-1: UV spectrum of TOS-c7 -p149
圖17-2: IR spectrum of TOS-c7 -p150
圖17-3: EI-MS spectrum of TOS-c7 -p150
圖17-4: 1H-NMR (600 MHz, DMSO-d6) spectrum of TOS-c7 -p151
圖17-5: 13C-NMR (150 MHz, DMSO-d6) spectrum of TOS-c7 -p152
圖17-6: DEPT spectrum of TOS-c7 -p152
圖17-7: COSY spectrum of TOS-c7 -p153
圖17-8: HSQC spectrum of TOS-c7 -p153
圖17-9: HMBC spectrum of TOS-c7 -p154
圖17-10: NOESY spectrum of TOS-c7 -p154
圖八:Irradiation of 6,7-Bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one -p155
1. 北京人民衛生出版社. 全國中草藥匯編. 1990.
2. 林柏昌、林有義. 蝴蝶食草圖鑑. 2008.
3. 中華民國行政院衛生署中醫藥委員會. 臺灣原住民藥用植物彙編. 2003.
4. 中華民國行政院農委會. 臺灣維管束植物簡誌. 2003.
5. Ratnagiriswaran, A. N.; Venkatachalam, K. The chemical examination of
Tylophora asthmatica and isolation of the alkaloids tylophorine and tylophorinine.
Indian J Med Res 1935, 22, 433-441.
6. Yang, C. W.; Chen, W. L.; Wu, P. L.; Tseng, H. Y.; Lee, S. J. Anti-inflammatory
mechanisms of phenanthroindolizidine alkaloids. Mol Pharmacol 2006, 69, 749-58.
7. Ganguly, T.; Sainis, K. B. Inhibition of cellular immune responses by Tylophora
indica in experimental models. Phytomedicine 2001, 8, 348-55.
8. Gore, K. V.; Rao, A. K.; Guruswamy, M. N. Physiological studies with
Tylophora asthmatica in bronchial asthma. Indian J Med Res 1980, 71, 144-8.
9. Gopalakrishnan, C.; Shankaranarayanan, D.; Nazimudeen, S. K.; Kameswaran, L.
Effect of tylophorine, a major alkaloid of Tylophora indica, on immunopathological
and inflammatory reactions. Indian J Med Res 1980, 71, 940-8.
10. Gopalakrishnan, C.; Shankaranarayan, D.; Kameswaran, L.; Natarajan, S.
Pharmacological investigations of tylophorine, the major alkaloid of Tylophora indica.
Indian J Med Res 1979, 69, 513-20.
11. Gao, W.; Lam, W.; Zhong, S.; Kaczmarek, C.; Baker, D. C.; Cheng, Y. C. Novel
mode of action of tylophorine analogs as antitumor compounds. Cancer Res 2004, 64,
678-88.
12. Zhen, Y. Y.; Huang, X. S.; Yu, D. Q.; Yu, S. S. Antitumor Alkaloids Isolated from
Tylophora ovata. Acta Botanica Sinica 2002, 44, 349-353.
13. Institute of Medical and Pharmaceutical Science of Kwangsi Chunang
Autonomous Region, N. Experimental studies on antitumour agents of Tylophora
ovata (Lindl.) Hook. ET Steud.(Asclepiadaceae). Acta Biochimica et Biophysica
Sinica 1977, 9, 131-145.
14. Suffness, M.; Douros, J. Anticancer agents based on natural product models.
Medicinal chemistry 1980, 16, 465-487.
15. Govindachari, T. R.; Pai, B. R.; Ragade, I. S.; Rajappa, S. Chemical examination
of Tylophora Asthmatica-V. Tetrahedron 1961, 14, 288-295.
16. Govindachari, T. R.; Lakshmikantham, M. V.; Rajappa, S. Chemical examination
of Tylophora Asthmatica-IV. Tetrahedron 1961, 14, 284-287.
17. Govindachari, T. R.; Lakshmikantham, M. V.; Pai, B. R.; Rajappa, S. Chemical
examination of Tylophora Asthmatica-III. Tetrahedron 1960, 9, 53-57.
18. Govindachari, T. R.; Lakshmikantham, M. V.; Nagarajan, K. Chemical
examination of Tylophora Asthmatica-II. Tetrahedron 1958, 4, 311-324.
19. Wadhawan, V. K.; Sikka, S. K.; Mulchandani, N. B. Minor alkaloids of
Tylophora Asthmatica (X-ray analysis of Tylophorinidine). Tetrahedron letters 1973,
5091-5094.
20. Govindachari, T. R.; Viswanethan, N.; Radhakrishnan, J.; Pai, B. R.; Natarajan,
S.; S., S. P. Minor alkaloids of tylophora asthmatica (revised structure of
tylophorinidine). Tetrahedron 1973, 29, 891-897.
21. Ali, M.; Bhutani, K. K. Alkaloids from Tylophora Indica. Phytochemistry 1989,
28, 3513-3517.
22. Rao, K. V.; Wilson, R.; Cummings, B. Alkaloids of Tylophora I: Isolation of six
new alkaloids. J Pharm Sci 1970, 59, 1501-1502.
23. Bhutani, K. K.; Ali, M.; Atal, C. K. Alkaloids from Tylophora Hirsuta.
Phytochemistry 1984, 23, 1765-1769.
24. Bhutani, K. K.; Ali, M.; Atal, C. K. 13a-Hydroxytylophorine from Tylophora
Hirsuta. Phytochemistry 1985, 24, 2778-2780.
25. Ali, M.; Bhutani, K. K. Minor Akaloids of Tylophora Hirsuta. Phytochemistry
1987, 26, 2089-2092.
26. Abe, F.; Iwase, Y.; Yamauchi, T.; Honda, K.; Hayashi, N. Phenanthroindolizidine
Alkaloids From Tylophora Tanakae. Phytochemistry 1995, 39, 695-699.
27. Abe, F.; Hirokawa, M.; Yamauchi, T.; Honda, K.; Hayashi, N.; Ishii, M.;
Imagawa, S.; Iwahana, M. Futher Investigation of Phenanthroindolizidine Alkaloids
from Tylophora tanakae. Chem. Pharm. Bull. 1998, 46, 767-769.
28. Ohyama, M.; Komatsu, H.; Watanabe, M.; Enya, T.; Koyama, K.; Sugimura, T.;
Wakabayashi, K. Cytotoxic phenanthroindolizidine alkaloids in Tylophora tanakae
against human gastric carcinoma cells. Proceedings of the Japan Academy 2000, 76,
161-165.
29. Komatsu, H.; Watanabe, M.; Ohyama, M.; Enya, T.; Koyama, K.; Kanazawa, T.;
Kawahara, N.; Sugimura, T.; Wakabayashi, K. Phenanthroindolizidine alkaloids as
cytotoxic substances in a Danaid butterfly, Ideopsis similis, against human cancer
cells. J Med Chem 2001, 44, 1833-6.
30. Koyama, K.; Baba, M.; Watanabe, M.; Takahashi, H.; Ishiyama, H.; Sugimura, T.;
Wakabayashi, K. Cytotoxic agent against human gastric carcinoma cells from a kind
of Danaidae and its host plant. Proceedings of the Japan Academy 1999, 75, 7-9.
31. College, J. N. M. Dictionary of Chinese Traditional Medicine. In Shanghai:
Science and Technology Publishing House, 1977.
32. Huang, X. S.; Yu, S. S.; Liang, X. T. Two Phenanthroindolizidine Alkaloids from
Tylophora atrofolliculata. Chinese Chemical Letters 2002, 13, 61-64.
33. Huang, X. S.; Gao, S.; Fan, L.; Yu, S. S.; Liang, X. T. Cytotoxic alkaloids from
the roots of Tylophora atrofolliculata. Planta Med 2004, 70, 441-445.
34. Chuang, T. H.; Lee, S. J.; Yang, C. W.; Wu, P. L. Expedient synthesis and
structure-activity relationships of phenanthroindolizidine and phenanthroquinolizidine
alkaloids. Org Biomol Chem 2006, 4, 860-7.
35. Zeng, W.; Chemler, S. R. Total synthesis of (S)-(+)-tylophorine via
enantioselective intramolecular alkene carboamination. J. Org. Chem. 2008, 73,
6045-6047.
36. Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T.
Phenanthroindolizidine and related alkaloids: synthesis of tylophorine, septicine, and
deoxytylophorine. J. Chem. Soc. Perkin Trans. I 1982, 2477-2485.
37. Rao, K. V. Alkaloids of Tylophora. II. Structural studies. J Pharm Sci 1970, 59,
1608-11.
38. Comins, D. L.; Chen, X.; Morgan, L. A. Enantiopure N-Acyldihydropyridones as
Synthetic Intermediates: Asymmetric Synthesis of (-)-Septicine and (-)-Tylophorine. J
Org Chem 1997, 62, 7435-7438.
39. Staerk, D.; Lykkeberg, A. K.; Christensen, J.; Budnik, B. A.; Abe, F.; Jaroszewski,
J. W. In vitro cytotoxic activity of phenanthroindolizidine alkaloids from Cynanchum
vincetoxicum and Tylophora tanakae against drug-sensitive and multidrug-resistant
cancer cells. J Nat Prod 2002, 65, 1299-302.
40. Mulchandani, N. B.; Venkatachalam, S. R. Tylophorinicine, a
phenanthroindolizidine alkaloid from Tylophora Asthmatica and Pergularia Pallida.
Phytochemistry 1984, 23, 1206.
41. Venkatachalam, S. R.; Mulchandani, N. B. Isolation of phenanthroindolizidine
alkaloids and a novel biphenylhexahydroindolizine alkaloid from Ficus hispida.
Naturwissenschafteu 1982, 69, 287-288.
42. Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. General synthesis of
phenanthroindolizidine, phenanthroquinolizidine, and related allkaloids: Preparation
of tylophorine, cryptopleurine, septicine, and julandine. J. Org. Chem. 1984, 49,
2412-2418.
43. Buckley III, T. F.; Rapoport, H. alpha-Amino acids as chiral educts for
asymmertric products. Chirally specific syntheses of tylophorine and cryptopleurine. J.
Org. Chem. 1983, 48, 4222-4232.
44. Gellert, E.; Rudzats, R.; Craig, T. C.; Roy, S. K.; Woodard, R. W. The absolute
configuration of cryptopleurine and tylocrebrine. Aust. J. Chem. 1978, 31, 2095-2097.
45. Nordlander, J. E.; Njoroge, F. G. A short synthesis of (S)-(+)-tylophorine. J. Org. Chem. 1987, 52, 1627-1630.
46. Bielory, L.; Lupoli, K. Herbal interventions in asthma and allergy. J Asthma.
1999, 36, 1-65.
47. Shivpuri, D. N.; Menon, M. P.; Prakash, D. A crossover double-blind study on
Tylophora indica in the treatment of asthma and allergic rhinitis. J Allergy. 1969, 43,
145-150.
48. Chopra, R. N.; Chakerburty, M. The pharmacological action of tylophorine: The
alkaloid occurring in Tylophora Asthmaticus. Indian J Med Res 1935, 23, 263-269.
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