進階搜尋


 
系統識別號 U0026-0812200911042882
論文名稱(中文) 天然藥物資源中新先導藥物之開發研究
論文名稱(英文) Discovery of New Lead Compound from Natural Medicinal Sources
校院名稱 成功大學
系所名稱(中) 化學系碩博士班
系所名稱(英) Department of Chemistry
學年度 92
學期 2
出版年 93
研究生(中文) 郭賓崇
研究生(英文) Ping-Chung Kuo
學號 l3888107
學位類別 博士
語文別 中文
論文頁數 316頁
口試委員 指導教授-吳天賞
口試委員-吳培琳
口試委員-莊治平
口試委員-郭悅雄
口試委員-郭盛助
口試委員-吳永昌
口試委員-陳益昇
中文關鍵字 抗瘧活性  細胞毒殺活性  抗氧化活性  稜果榕  東革阿里 
英文關鍵字 antioxidant and antityrosinase  dehydrozingerone  acridone  Eurycoma longifolia  Ficus septica 
學科別分類
中文摘要 從Eurycoma longifolia 根部分離得到69個化合物,經光譜分析與化學方法鑑定確認其結構,其中有10個為天然界首次分離得到之化合物,分別為n-pentyl -carboline-1-propionate、5-hydroxymethyl-9-methoxycanthin-6-one、1-hydroxy-9- methoxycanthin-6-one、eurycomalide A、eurycomalide B、13, 21-dihydroxy- eurycomanol、5, 14, 15-trihydroxyklaineanone、eurycomalin A、sodium vanilliate、sodium protocatechuate等,而除sodium protocatechuate之外,其餘均為首次報導之新化合物。由於本研究分離得到各種不同骨架的quassinoid二萜類,因此歸納整理出其光譜特徵,對於從事此類化合物的研究人員是一項很重要的參考工具。
從稜果榕(Ficus septica)莖部非生物鹼畫分分離得到22個化合物,經光譜分析鑑定確認其結構,包括7個三萜類化合物,2個木質素類化合物,及其他13個已知的化合物,而三萜類化合物中,13, 27-cycloursan-3-yl acetate為天然界首次分離得到之化合物,其所具有的13, 27-cycloursane骨架則為天然界中較少被報導的骨架。
在馬兜鈴酸之合成研究中,利用新的合成路徑,順利合成出1-溴-2, 3-二氧亞甲基-8-甲氧基菲,為馬兜鈴酸-A的前驅物,但產率偏低,仍需進一步改進。
在1, 2, 3, 7-tetrahydroxy-4, 6-dimethoxy-5-methyl-5H-acridin-10-one的合成研究中,順利合成出前驅物7, 11-dihydroxy-4, 6-dimethoxy-5-methyl-5H-[1, 3]dioxolo[4, 5-b]acridin-10-one、2, 3, 7-tribenzyloxy-1, 4, 6-trimethoxy-5-methyl-5H-acridin-10- one,與1-hydroxy-2, 3, 7-tribenzyloxy-4, 6-dimethoxy-5-methyl-5H-acridin-10-one,並將一系列具有acridone骨架的化合物送測生理活性,以評估此類化合物所特有的抗癌作用。
另一方面,採用Whiting方法,利用各種具有不同取代基的苯甲醛類化合物,在鹼性乙醇溶液下與丙酮進行醛醇縮合反應,可得到與天然的抗氧化成分zingerone與dehydrozingerone具有很高的結構相似度之各種不同取代基dehydrozingerone衍生
物。所得的各種不同取代基的dehydrozingerone衍生物,可利用來進行測試其抗氧化與抗酪胺酸酶活性,並送測其抗血小板凝集活性。
在acrovestone衍生物之合成研究部分,7個具有acrovestone類似骨架的化合物順利地利用不同取代的acetophenone類化合物與聚甲醛縮合得到,但經送測對A-549與MCF-7的癌細胞毒殺活性,並未發現其具有特別的細胞毒殺作用。
本研究亦進行了抗氧化與抗酪胺酸酶活性的測試,分別針對前述的各種不同取代基的dehydrozingerone衍生物,以及由黃柏屬植物所分離得到的部份成分,篩選其抗氧化與抗酪胺酸酶活性。除上述的兩種活性測試模式之外,dehydrozingerone衍生物亦進行抗血小板凝集活性測試;由Eurycoma longifolia所分離得到的部份成分與acrovestone衍生物亦測試其抗癌、抗瘧、與抗HIV病毒的活性。其中2', 3'-dihydroxydehydrozingerone具有比vitamin E還強的抗氧化活性;2', 4'-dihydroxy- dehydrozingerone具有比市售的美白化粧品主要成分kojic acid還強的抗酪胺酸酶活性。而由黃柏屬植物葉部所分離得到的主要成分,具有類黃酮骨架的amurensin,具有中等強度的抗氧化活性,值得進一步探討利用黃柏屬植物之葉部開發新的健康食品之可行性。而由Eurycoma longifolia所分離得到的成分eurycomalactone,6-dehydroxylongilactone,9-methoxycanthin-6-one,14, 15-dihydroxyklaineanone,與pasakbumin C對於A-549與MCF-7癌細胞具有很強的細胞毒殺活性;canthin-6-one,longilactone,與canthin-6-one 9-O--glucopyranoside對於A-549癌細胞具有很強的細胞毒殺活性;eurycomanone與pasakbumin B則對MCF-7癌細胞具有很強的細胞毒殺活性,且對於有抗藥性的P. falciparum具有比抗瘧藥物chloroquine更強的抗瘧活性。
英文摘要 Sixty-nine compounds were isolated from the roots of Eurycoma longifolia and they were characterized by comprehensive analyses of their 1D and 2D NMR and mass spectral data, and by chemical transformation studies. Among these isolates, ten compounds were reported for the first time from the natural sources, namely n-pentyl -carboline-1- propionate, 5-hydroxymethyl-9-methoxycanthin-6-one, 1-hydroxy-9-methoxycanthin-6- one, eurycomalide A, eurycomalide B, 13, 21-dihydroxyeurycomanol, 5, 14, 15-trihydroxyklaineanone, eurycomalin A, sodium vanilliate, and sodium protocatechuate. The thorough studies on the spectral characteristics of the different types of quassinoid diterpenoids provided a clear reference to distinguish the quassinoid types at an early stage for the scientists interested in this field.
Seven triterpenes, two lignans, together with thirteen known compounds were isolated from the non-alkaloidal fractions of stem of Ficus septica. Among these triterpenoids, a rare triterpene derivative with 13, 27-cycloursane skeleton, namely, 13, 27-cycloursan-3- yl acetate was isolated from natural sources for the first time. The structures of all these compounds were elucidated by spectroscopic methods.
The precursor of aristolochic acid A, namely, 1-bromo-3, 4-methylenedioxy-8- methoxyphenanthrene was successfully synthesized through a new pathway.
Acridone derivatives, 7, 11-dihydroxy-4, 6-dimethoxy-5-methyl-5H-[1, 3]dioxolo[4, 5-b]acridin-10-one, 2, 3, 7-tribenzyloxy-1, 4, 6-trimethoxy-5-methyl-5H-acridin-10-one, and 1-hydroxy-2, 3, 7-tribenzyloxy-4, 6-dimethoxy-5-methyl-5H-acridin-10-one were synthesized by the coupling of halogenated benzenoid moeity with amino benzoic acid moiety and their spectral data were compared with that of natural product isolated as constituent of Severinia buxifolia. The synthesized acridone derivatives were examined for the cytotoxicity to evaluate their cytotoxic potency.
A series of substituted (E)-4-phenyl-3-buten-2-ones were synthesized by Whiting method through aldol condensation of various substituted benzaldehydes with acetone in basic ethanolic solution, due to the structural similarity with the natural antioxidants, zingerone and dehydrozingerone. These synthetic analogues of dehydrozingerone were examined for their antioxidant and antityrosinase activities to evaluate the structure- activity relationships. In addition, the antiplatelet aggregation activities of some of these synthetic compounds were also screened.
Seven acrovestone derivatives were synthesized by condensation of acetophenones and paraformaldehyde. Their cytotoxicity toward A-549 and MCF-7 tumor cell lines were assayed, but no significant activities were found.
The third part of the thesis consists of bioassays of isolated and synthesized compounds to assess their efficacy as physiological active compound. The synthetic dehydrozingerone analogues and some of the isolates from the leaves of Phellodendron species were examined for their antioxidant and antityrosinase activities. In addition, the dehydrozingerone derivatives were also tested for their antiplatelet aggregation activity. Some of the isolates from the root of E. longifolia were screened for their cytotoxicity, antimalarial and anti-HIV activities in vitro. Among these bioactivity studies, 2', 3'-dihydroxydehydrozingerone exhibited stronger antioxidant activity than vitamin E, and 2', 4'-dihydroxydehydrozingerone displayed antityrosinase activity comparable with that of kojic acid, a commercially whitening agent. Amurensin, the main flavonoid component of the leaves of Phellodendron species, showed moderate antioxidant activity and support the use of Phellodendron species as natural health food. Eurycomalactone, 6-dehydroxy- longilactone, 9-methoxycanthin-6-one, 14, 15-dihydroxyklaineanone, and pasakbumin C displayed strong cytotoxicity toward human cancer cell lines A-549 and MCF-7. Canthin-6-one, longilactone, and canthin-6-one 9-O--glucopyranoside; eurycomanone, and pasakbumin B, exhibited strong cytotoxicity toward A-549 and MCF-7 tumor cell lines, respectively. Eurycomanone and pasakbumin B showed stronger antimalarial activity against the W2 P. falciparum clone than that of chloroquine, a clicnic antimalarial drug.
論文目次 目 錄

英文摘要…………………………………………………………………………………………I
中文摘要…………………………………………………………………………………………IV
誌謝………………………………………………………………………………………………VI
第一篇 緒論……………………………………………………………………………………1
第二篇 具有生理活性的天然物之成分分離研究……………………………………………3
第一章 Eurycoma longifolia根部之成分分離研究………………………………………4
第一節 E.longifolia之植物形態………………………………………………………4
第二節 Eurycoma屬植物之研究概況與藥理研究回顧…………………………………6
第三節 Eurycoma屬植物之成分研究回顧………………………………………………11
第四節 E.longifolia根部成分之抽取與分離…………………………………………20
第二章 E. longifolia根部成分之化學構造研究…………………………………………30
第一節 b-Carboline-1-propionic acid(43)之構造研究…………………………30
第二節 n-Pentylb-carboline-1-propionate(23)之構造研究……………………32
第三節 9-Methoxycanthin-6-one(12)之構造研究…………………………………36
第四節 5-Hydroxymethyl-9-methoxycanthin-6-one(29)之構造研究……………38
第五節 1-Hydroxy-9-methoxycanthin-6-one(30)之構造研究……………………42
第六節 Eurycomalactone(7)之構造研究……………………………………………46
第七節 Eurycomalide A(31)之構造研究……………………………………………49
第八節 Eurycomalide B(32)之構造研究……………………………………………55
第九節 Eurycomanone(60)之構造研究………………………………………………61
第十節 13,21-Dihydroxyeurycomanol(56)之構造研究……………………………64
第十一節 5, 14,15-Trihydroxyklaineanone(57)之構造研究……………………69
第十二節 Eurycomanol-2-O-b-D-glucopyranoside(59)之構造研究……………74
第十三節 Eurycomalin A(33)之構造研究…………………………………………79
第十四節 Sodium vanillate(58)之構造研究………………………………………85
第十五節 Sodium protocatechuate(65)之構造研究………………………………87
第十六節 其他化合物之構造決定………………………………………………………89
第十七節 非胺基酸劃分的鑑定…………………………………………………………91
第十八節 胺基酸劃分的鑑定……………………………………………………………92
第十九節 Quassinoid二萜類之光譜特徵歸納整理……………………………………93
第三章 稜果榕莖部之成分分離研究………………………………………………………95
第一節 稜果榕之植物形態………………………………………………………………95
第二節 台灣產榕屬植物之研究概況與藥理研究回顧…………………………………96
第三節 台灣產榕屬植物之成分研究回顧………………………………………………96
第四節 稜果榕莖部成分之抽取與分離………………………………………………125
第四章 稜果榕莖部成分之化學構造研究…………………………………………………129
第一節 13,27-Cycloursan-3-yl acetate(97)之構造研究………………………129
第二節 Simiarenol(98)之構造研究………………………………………………134
第三節 (+)-epi-Syringaresinol(109)之構造研究………………………………138
第四節 (+)-Syringaresinol(110)之構造研究……………………………………140
第五節 Tachioside(111)之構造研究………………………………………………142
第六節 其他化合物之構造決定………………………………………………………145
第三篇 具有生理活性的天然物之合成研究………………………………………………146
第一章 馬兜鈴酸之合成研究………………………………………………………………147
第一節 馬兜鈴酸之相關生理活性研究概況…………………………………………147
第二節 研究動機與合成策略…………………………………………………………148
第三節 結果與討論……………………………………………………………………150
第二章 1, 2, 3, 7-Tetrahydroxy-4, 6-dimethoxy-5-methyl-5H-acridin-10-one
之合成研究……………………………………………………………………………152
第一節 Acridone之相關生理活性研究概況…………………………………………152
第二節 研究動機與合成策略…………………………………………………………154
第三節 結果與討論……………………………………………………………………156
第三章 薑酮衍生物之合成研究……………………………………………………………164
第一節 薑酮之相關生理活性研究概況………………………………………………164
第二節 研究動機與合成策略…………………………………………………………164
第三節 薑酮衍生物之合成研究與構造修飾…………………………………………165
第四章 Acrovestone衍生物之合成研究…………………………………………………168
第一節 Acrovestone衍生物之相關生理活性研究概況………………………………168
第二節 研究動機與合成策略…………………………………………………………168
第三節 結果與討論……………………………………………………………………169
第四篇 生理活性試驗研究…………………………………………………………………173
第一章 抗酪胺酸酶活性試驗………………………………………………………………174
第一節 酪胺酸酶之生理活性與作用機制……………………………………………174
第二節 薑酮衍生物之抗酪胺酸酶活性試驗研究……………………………………174
第三節 黃柏屬植物葉部成分之抗酪胺酸酶活性試驗研究…………………………180
第二章 抗氧化活性試驗……………………………………………………………………182
第一節 薑酮衍生物之抗氧化活性試驗研究…………………………………………182
第二節 黃柏屬植物葉部成分之抗氧化活性試驗研究………………………………184
第三章 抗血小板凝集活性試驗……………………………………………………………187
第一節 薑酮衍生物之抗血小板凝集活性試驗研究…………………………………187
第四章 細胞毒殺活性試驗…………………………………………………………………189
第一節 E. longifolia根部成分之細胞毒殺活性試驗研究…………………………189
第二節 Acrovestone衍生物之細胞毒殺活性試驗研究………………………………190
第五章 抗瘧活性與抗HIV活性試驗………………………………………………………191
第一節 E. longifolia根部成分之抗瘧活性與抗HIV活性試驗研究………………191
第五篇 結論…………………………………………………………………………………194
第六篇 實驗部份……………………………………………………………………………196
第一章 本實驗所使用之儀器與藥品………………………………………………………196
第二章 植物的採集及鑑定…………………………………………………………………198
第三章 植物的萃取與分離…………………………………………………………………199
第一節 E. longifolia根部成分之萃取與分離………………………………………199
第二節 稜果榕莖部成分之萃取與分離………………………………………………204
第四章 合成部份之實驗步驟………………………………………………………………206
第一節 馬兜鈴酸合成研究之實驗步驟………………………………………………206
第二節 1, 2, 3, 7-Tetrahydroxy-4, 6-dimethoxy-5-methyl-5H-acridin-10-one
合成研究之實驗步驟………………………………………………………208
第三節 薑酮衍生物合成研究之實驗步驟……………………………………………217
第四節 Acrovestone衍生物合成研究之實驗步驟……………………………………218
第五章 生理活性試驗部份之實驗步驟…………………………………………………222
第一節 抗酪胺酸酶活性試驗…………………………………………………………222
第二節 抗氧化活性試驗………………………………………………………………222
第三節 抗血小板凝集活性試驗………………………………………………………223
第四節 細胞毒殺活性試驗……………………………………………………………224
第五節 抗瘧活性與抗HIV活性試驗……………………………………………………225
第六章 光譜數據…………………………………………………………………………226
第一節 由E. longifolia根部所分離得到的成分之光譜數據………………………226
第二節 由稜果榕莖部所分離得到的成分之光譜數據………………………………262
第三節 合成部份之光譜數據…………………………………………………………269
參考文獻…………………………………………………………………………………………298
參考文獻 參考文獻

1. 甘偉松,藥用植物學,第七版。中國醫藥研究所出版,台北,1986,p. 354。
2. L. M. Perry. Medicinal Plants of East and South East Asia: Attributed Properties and Uses; M. I. T. Press: Cambridge, Massachusetts, 1980; p 389.
3. J. D. Gimlette, J. W. Thomson. A Dictionary of Malayan Medicine; Oxford University Press: Kuala Lumpur, 1977; p 183.
4. K. L. Chan, S. P. Lee, K. H. Yuen. Chemical Prospecting in Malayan Forest; In Antipyretic activity of quassinoids from Eurycoma longifolia Jack, ed. by L. Ghazally, M. Murtedza, D. Laily. Pelanduk Publications: Selangor, 1995; p 219—224.
5. H. Itokawa, K. Takeya, Y. Hitotsuyanagi, H. Morita. Antitumor compounds isolated from higher plants. J. Biochem., Mol. Biol. Biophys. 2000, 4, 213-222.
6. K. L. Chan, M. J. O’Neil, J. D. Phillipson, D. C. Warhurst. Plants as sources of antimalarial drugs. Part 3 Eurycoma longifolia. Planta Med. 1986, 52, 105-107.
7. H. Morita, E. Kishi, K. Takeya, H. Itokawa, O. Tanaka. New quassinoids from the roots of Eurycoma longifolia. Chem. Lett. 1990, 749-752.
8. H. Tada, F. Yasuda, K. Otani, M. Doteuchi, Y. Ishihara, M. Shiro. New antiulcer quassinoids from Eurycoma longifolia. Eur. J. Med. Chem. 1991, 26, 345-349.
9. H. Itokawa, E. Kishi, H. Morita, K. Takeya, Y. Iitaka. A new squalene-type triterpene from the woods of Eurycoma longifolia. Chem. Lett. 1991, 2221-2222.
10. L. B. S. Kardono, C. K. Angerhofer, S. Tsauri, K. Padmawinata, L. M. Pezzuto, A. D. Kinghorn. Cytotoxic and antimalarial constituents of the roots of Eurycoma longifolia. J. Nat. Prod. 1991, 54, 1360-1367.
11. K. L. Chan, Y. Iitaka, H. Noguchi, H. Sugiyama, I. Saito, U. Sankawa. 6-Hydroxyeurycomalactone, a quassinoid from Eurycoma longifolia. Phytochemistry 1992, 31, 4295-4298.
12. H. Itokawa, E. Kishi, H. Morita, K. Takeya. Cytotoxic quassinoids and tirucallane-type triterpenoids from the woods of Eurycoma longifolia. Chem. Pharm. Bull. 1992, 40, 1053-1055.
13. H. Itokawa, E. Kishi, H. Morita, K. Takeya, Y. Iitaka. Novel squalene-type triterpene ethers and quassinoids from the woods of Eurycoma longifolia. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1992, 34th, 118-125.
14. H. Morita, E. Kishi, K. Takeya, H. Itokawa, Y. Iitaka. Highly oxygenated quassinoids from Eurycoma longifolia. Phytochemistry 1993, 33, 691-696.
15. H. Itokawa, X. R. Qin, H. Morita, K. Takeya. C18 and C19 quassinoids from Eurycoma longifolia. J. Nat. Prod. 1993, 56, 1766-1771.
16. H. Morita, E. Kishi, K. Takeya, H. Itokawa, Y. Iitaka. Squalene derivatives from Eurycoma longifolia. Phytochemistry 1993, 34, 765-771.
17. H. H. Ang, K. L. Chan, J. M. Mak. In vitro antimalarial activity of quassinoids from Eurycoma longifolia against Malaysian chloroquine-resistant Plasmodium falciparum isolates. Planta Med. 1995, 61, 177-178.
18. H. H. Ang, M. K. Sim. Eurycoma longifolia Jack enhances libido in sexually experienced male rats. Exp. Anim. 1997, 46, 287-290.
19. H. H. Ang, M. K. Sim. Eurycoma longifolia Jack and orientation activities in sexually experienced male rats. Biol. Pharm. Bull. 1998, 21, 153-155.
20. T. Iwai, T. Kinoshita, Y. Morimoto. Highly efficient total synthesis of cytotoxic meso polyether teurilene featuring diastereoselective method for construction of tetrahydrofuran rings by means of rhenium (VII) oxide. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1998, 40th, 277-282.
21. H. H. Ang, H. S. Cheang. Studies on the anxiolytic activity of Eurycoma longifolia Jack roots in mice. Jpn. J. Pharmacol. 1999, 79, 497-500.
22. H. H. Ang, H. S. Cheang, A. P. Md. Yusof. Effects of Eurycoma longifolia Jack (Tongkat Ali) on the initiation of sexual performance of inexperienced castrated male rats. Exp. Anim. 2000, 49, 35-38.
23. A. Adimoelja. Phytochemicals and the breakthrough of traditional herbs in the management of sexual dysfunctions. Int. J. Androl. 2000, 23, 82-84.
24. S. Jiwajinda, V. Santisopasri, A. Murakami, N. Hirai, H. Ohigashi. Quassinoids from Eurycoma longifolia as plant growth inhibitors. Phytochemistry 2001, 58, 959-962.
25. L. C. Lin, C. Y. Peng, H. S. Wang, K. W. Lee, P. S. Wang. Reinvestigation of the chemical constituents of Eurycoma longifolia. Chin. Pharm. J. 2001, 53, 97-106.
26. K. L. Chan, C. Y. Choo. The toxicity of some quassinoids from Eurycoma longifolia. Planta Med. 2002, 68, 662-664.
27. L. V. Thoi, N. N. Suong. Constituents of Eurycoma longifolia Jack. J. Org. Chem. 1970, 35, 1104-1109.
28. R. B. Bates, G. S. Linz, M. S. Tempesta. Structures of eurycomalactone and related terpenoids. J. Org. Chem. 1984, 49, 2820-2821.
29. H. H. Ang, Y. Hitotsuyanagi, H. Fukaya, K. Takeya. Quassinoids from Eurycoma longifolia. Phytochemistry 2002, 59, 833-837.
30. H. Itokawa, X. R. Qin, H. Morita, K. Takeya, Y. Iitaka. Novel quassinoids from Eurycoma longifolia. Chem. Pharm. Bull. 1993, 41, 403-405.
31. E. Bedir, H. Abou-Gazar, J. N. Ngwendson, I. A. Khan. Eurycomaoside: a new quassinoid-type glycoside from the roots of Eurycoma longifolia. Chem. Pharm. Bull. 2003, 51, 1301-1303.
32. T. Kanchanapoom, R. Kasai, P. Chumsri, K. Yamasaki. Quassinoids from Eurycoma harmandiana. Phytochemistry 2001, 57, 1205-1208.
33. M. Darise, H. Kohda, K. Mizutani, O. Tanaka. Eurycomanone and eurycomanol, quassinoids from the roots of Eurycoma longifolia. Phytochemistry 1982, 21, 2091-2093.
34. M. Darise, H. Kohda, K. Mizutani, O. Tanaka. Revision of configuration of the 12-hydroxyl group of eurycomanone and eurycomanol, quassinoids from Eurycoma longifolia. Phytochemistry 1983, 22, 1514.
35. K. L. Chan, S. P. Lee, T. W. Sam, B. H. Han. A quassinoid glycoside from the roots of Eurycoma longifolia. Phytochemistry 1989, 28, 2857-2859.
36. K. L. Chan, S. P. Lee, T. W. Sam, S. C. Tan, H. Noguchi, U. Sankawa. 13, 18-Dihydroeurycomanol, a quassinoid from Eurycoma longifolia. Phytochemistry 1991, 30, 3138-3141.
37. N. N. Suong, S. Bhatnagar, J. Polonsky, M. Vuilhorgne, T. Prangé, C. Pascard. Structure of laurycolactone A and B, new C18-quassinoids from Eurycoma longifolia and revised structure of eurycomalactone (X-ray analysis). Tetrahedron Lett. 1982, 23, 5159-5162.
38. H. H. Ang, Y. Hitotsuyanagi, K. Takeya. Eurycolactones A-C, novel quassinoids from Eurycoma longifolia. Tetrahedron Lett. 2000, 41, 6849-6853.
39. K. Mitsunaga, K. Koike, T. Tanaka, Y. Ohkawa, Y. Kobayashi, T. Sawaguchi, T. Ohmoto. Canthin-6-one alkaloids from Eurycoma longifolia. Phytochemistry 1994, 35, 799-802.
40. T. Kanchanapoom, R. Kasai, P. Chumsri, Y. Hiraga, K. Yamasaki. Canthin-6-one and -carboline alkaloids from Eurycoma longifolia. Phytochemistry 2001, 56, 383-386.
41. H. Morita, E. Kishi, K. Takeya, H. Itokawa, Y. Biphenylneolignans from wood of Eurycoma longifolia. Phytochemistry 1992, 31, 3993-3995.
42. H. Morita, E. Kishi, K. Takeya, H. Itokawa, Y. Iitaka. Eurylene, a new squalene-type triterpene from Eurycoma longifolia. Tetrahedron Lett. 1991, 32, 1803-1804.
43. A. Oei-Koch, L. Kraus. Inhaltsstoffe von Eurycoma longifolia Jack. Planta Med. 1978, 34, 339-340.
44. N. B. H. A. Malek, D. I. Davies. The steroidal components of Eurycoma apiculatta. Sains Malays. 1982, 11, 87-103.
45. F. E. Wu, K. Koike, T. Nikaido, Y. Sakamoto, T. Ohmoto, K. Ikeda. New -carboline alkaloids from a Chinese medicinal plant, Arenaria kansuensis. Structures of Arenarines A, B, C, and D. Chem. Pharm. Bull. 1989, 37, 1808-1809.
46. T. Ohmoto, K. Koike, Y. Sakamoto. Studies on the constituents of Ailanthus altissima Swingle. II. Alkaloidal constituents. Chem. Pharm. Bull. 1981, 29, 390-395.
47. A. I. Scott. Interpretation of the Ultraviolet Spectra of the Natural Products; Pergamon Press: New York, 1964; p 119.
48. J. L. Ingham, S. Tahara, S. Z. Dziedzic. New 3-hydroxyflavanone (dihydroflavonol) phytoalexins from the papilionate legume Shuteria vestita. J. Nat. Prod. 1986, 49, 631-638.
49. H. B. Stegmann, K. Stolze, K. Scheffler. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1983, 38, 243-247.
50. T. S. Wu, D. M. Lin, L. S. Shi, A. G. Damu, P. C. Kuo, Y. H. Kuo. Cytotoxic anthraquinones from the stems of Rubia wallichiana Decne. Chem. Pharm. Bull. 2003, 51, 948-950.
51. C. Y. Chen, F. R. Chang, C. M. Teng, Y. C. Wu. Cheritamine, a new N-fatty acyl tryptamine and other constituents from the stems of Annona cherimola. J. Chin. Chem. Soc. 1999, 46, 77-86.
52. E. R. Fo., J. B. Fernandes, P. C. Vieira, M. F. Das G. F. Da Silva. Canthin-6-one alkaloids from Picrolemma granatensis. Phytochemistry 1992, 31, 2499-2501.
53. U. Mühlenbeck, A. Kortenbusch, W. Barz. Formation of hydroxycinnamoylamides and -hydroxyacetovanillone in cell cultures of Solanum khasianum. Phytochemistry 1996, 42, 1573-1579.
54. J. H. Li, J. K. Snyder. Selective oxidation of canthines to canthin-6-ones with triethylbenzylammonium permanganate. Tetrahedron Lett. 1994, 35, 1485-1488.
55. G. A. Cordell, M. Ogura, N. R. Farnsworth. Alkaloid constituentsof Alianthus excelsa (Simaroubaceae). J. Nat. Prod. 1978, 41, 166-168.
56. H. Tsukamoto, S. Hisada, S. Nishibe. Coumarins from bark of Fraxinus japonica and F. mandshurica var. japonica. Chem. Pharm. Bull. 1985, 33, 4069-4073.
57. E. Okuyama, K. Suzumura, M. Yamazaki. Pharmacologically active components of Todopon Puok (Fagraea racemosa), a medicinal plant from Borneo. Chem. Pharm. Bull. 1995, 43, 2200-2204.
58. H. Duan, Y. Takaishi, H. Momota, Y. Ohmoto, T. Taki. Immunosuppressive constituents from Saussurea medusa. Phytochemistry 2002, 59, 85-90.
59. T. Ohmoto, K. Koike. Studies on the constituents of Ailanthus altissima Swingle. III. The Alkaloidal constituents. Chem. Pharm. Bull. 1984, 32, 170-173.
60. Y. L. Lin, W. Y. Wang, Y. H. Kuo, C. F. Chen. Nonsteroidal constituents from Solanum incanum L. J. Chin. Chem. Soc. 2000, 47, 247-251.
61. H. Y. Li, K. Koike, T. Ohmoto. New alkaloids, picrasidines W, X and Y, from Picrasma quassioides and X-ray crystallographic analysis of Picrasidine Q. Chem. Pharm. Bull. 1993, 41, 1807-1811.
62. M. Màrton-Merész, J. Kuszmann, I. Pelczer, L. Pàrkànyi, T. Koritsànszky, A. Kàlmàn. Synthesis and reactions of 2', 3'-anhydro-1--D-ribofuranosyl-uracil derivatives: molecular structures of 3-methyl-2', 3'-anhydrouridine and 3, 5-dimethyl-2', 3':06, 5'-dianhydrouridine. Tetrahedron 1983, 39, 275-285.
63. M. Johnson, J. Lind, T. Reitberger, T. E. Eriksen, G. Merenyi. Free radical combination reactions involving phenoxyl radicals. J. Phys. Chem. 1993, 97, 8229-8233.
64. N. Motohashi, Y. Saito. Competitive measurement of rate constants for hydroxyl radical reactions using radiolytic hydroxylation of benzoate. Chem. Pharm. Bull. 1993, 41, 1842-1845.
65. Y. Furukawa, M. Honjo. A novel method for the synthesis of purine nucleosides using Friedel-Crafts catalysts. Chem. Pharm. Bull. 1968, 16, 1076-1080.
66. M. M. Alauddin, P. S. Conti. Selective alkylation of pyrimidyl dianions II: synthesis, characterization, and comparative reactivity of 3', 5'-O-bis-tetrahydropyranyl, trimethylsilyl and tert-butyldimethylsilyl derivatives of 5-bromo-2'-deoxyuridine. Tetrahedron 1994, 50, 1699-1706.
67. H. Otsuka, M. Takeuchi, S. Inoshiri, T. Sato, K. Yamasaki. Phenolic compounds from Coix lachrymal-jobi var. ma-yuen. Phytochemistry 1989, 28, 883-886.
68. M. DellaGreca, A. Fiorentino, P. Monaco, L. Previtera. Enantioselective synthesis of phenylpropanetriols. Synth. Commun. 1998, 28, 3693-3700.
69. K. Miki, T. Takehara, T. Sasaya, A. Sakakibara. Lignans of Larix leptolepis. Phytochemistry 1980, 19, 449-453.
70. H. Aono, K. Koike, J. Kaneko, T. Ohmoto. Alkaloids and quassinoids from Alianthus malabarica. Phytochemistry 1994, 37, 579-584.
71. L. C. Lin, C. J. Chou, Y. C. Kuo. Cytotoxic Principles from Ventilago leiocarpa. J. Nat. Prod. 2001, 64, 674-676.
72. P. Abreu, A. Pereira, A. Relva. Characterisation of a sugar fraction from Sarcocephalus latifolius stem bark extract. Carbohydrate Polymers 2001, 45, 155-160.
73. M. de C. Sanchez-Mata, M. Camara-Hurtado, C. Diez-Marques. Identification and quantification of soluble sugars in green beans by HPLC. Eur. Food Res. Technol. 2002, 214, 254-258.
74. P. C. Kuo, A. G. Damu, K. H. Lee, T. S. Wu. Cytotoxic and antimalarial constituents from the roots of Eurycoma longifolia. Bioorg. Med. Chem. 2004, 12, 537-544.
75. 甘偉松,台灣藥用植物誌,第一卷。中國醫藥出版社印行,台北,1967,p. 86。
76. 邱年永,張光雄,原色台灣藥用植物圖鑑(2)。台北南天書局發行,台北,1986,p. 19。
77. 江一民,正榕氣根之成分研究。國立台灣大學化學研究所博士論文,2001,p. 1。
78. J. C. Liao. Moraceae in Flora of Taiwan, 2nd ed; Editorial Committee of the Flora of Taiwan: Taipei, Taiwan, R. O. C., 1996; Vol II, p. 145-188.
79. 許雅雯,台灣產天仙果莖部細胞毒及化學成分之研究。高雄醫學大學天然藥物研究所碩士論文,2003,p. 28-140。
80. C. T. Chen, C. Y. Chang. Studies in natural products. (17). Constituents of Ficus beecheyana Hook. et Arn. Bull. Inst. Chem., Acad. Sin. 1977, 24, 47-49.【C.A. 87: 19026f(1977)】
81. T. H. Lee, Y. C. Kuo, G. J. Wang, Y. H. Kuo, C. I. Chang, C. K. Lu, C. K. Lee. Five new phenolics from the roots of Ficus beecheyana. J. Nat. Prod. 2002, 65, 1497-1500.
82. N. V. Tuyen, D. S. H. L. Kim, H. S. Fong, D. D. Soejarto, T. C. Khanh, M. V. Tri, L. T. Xuan. Structure elucidation of two triterpenoids from Ficus fistulosa. Phytochemistry 1999, 50, 467-469.
83. Y. C. Li, Y. H. Kuo. Two new isoflavones from the bark of Ficus microcarpa. J. Nat. Prod. 1997, 60, 292-293.
84. Y. H. Kuo, Y. C. Li. Constituents of the bark of Ficus microcarpa L. f. J. Chin. Chem. Soc. 1997, 44, 321-325.
85. M. Higa, K. Yokota, K. Ogihara, S. Yogi. Studies on the constituents of Ficus microcarpa L. f. II. Bull. Coll. Sci., Univ. Ryukyus 1996, 62, 45-52.【C.A. 126: 314828p(1977)】
86. Y. C. Li, Y. H. Kuo. A monoterpenoid and two simple phenols from heartwood of Ficus microcarpa. Phytochemistry 1998, 49, 2417-2419.
87. Y. H. Kuo, Y. C. Li. Three new compounds, ficusone, ficuspirolide, and ficusolide from the heartwood of Ficus microcarpa. Chem. Pharm. Bull. 1999, 47, 299-301.
88. Y. C. Li, Y. H. Kuo. Four new compounds, ficusal, ficusesquilignan A, B, and ficusolide diacetate from the heartwood of Ficus microcarpa. Chem. Pharm. Bull. 2000, 48, 1862-1865.
89. M. Higa, S. Yogi, K. Hokama. Studies on the constituents of Ficus microcarpa L. f. I. Triterpenoids from the leaves. Bull. Coll. Sci., Univ. Ryukyus 1988, 44, 75-86.【C.A. 109: 18730p(1988)】
90. Y. H. Kuo, Y. M. Chiang. Five new taraxastane-type triterpenes from the aerial roots of Ficus microcarpa. Chem. Pharm. Bull. 1999, 47, 498-500.
91. Y. M. Chiang, Y. H. Kuo. Taraxastane-type triterpenes from the aerial roots of Ficus microcarpa. J. Nat. Prod. 2000, 63, 898-901.
92. Y. H. Kuo, Y. M. Chiang. Six new ursane- and oleanane-type triterpenes from the aerial roots of Ficus microcarpa. Chem. Pharm. Bull. 2000, 48, 593-596.
93. Y. M. Chiang, Y. H. Kuo. New peroxy triterpenes from the aerial roots of Ficus microcarpa. J. Nat. Prod. 2001, 64, 436-439.
94. Y. M. Chiang, J. K. Su, Y. H. Liu, Y. H. Kuo. New cyclopropyl-triterpenoids from the aerial roots of Ficus microcarpa. Chem. Pharm. Bull. 2001, 49, 581-583.
95. Y. M. Chiang, Y. H. Kuo. Novel triterpenoids from the aerial roots of Ficus microcarpa. J. Org. Chem. 2002, 67, 7656-7661.
96. Y. M. Chiang, Y. H. Kuo. Two novel -tocopheroids from the aerial roots of Ficus microcarpa. Tetrahedron Lett. 2003, 44, 5125-5128.
97. L. Pistelli, E. E. Chiellini, I. Morelli. Flavonoids from Ficus pumila. Biochem. Syst. Ecol. 2000, 28, 287-289.【C.A. 132: 234345n(2000)】
98. K. F. Ts’eng, T. Y. Yao. Chinese drug PI-LI (Ficus pumila). Yao Hsueh Hsueh Pao 1965, 12, 577-583.【C.A. 64: 17353b(1966)】
99. E. A. Yarosh, G. K. Nikonov. Ficus genus coumarins. Khim. Prir. Soedin. 1973, 269-270.【C.A. 79: 40005t(1973)】
100. J. Kitajima, K. Kimizzuka, M. Arai, Y. Tanaka. Constituents of Ficus pumila leaves. Chem. Pharm. Bull. 1998, 46, 1647-1649.
101. C. Y. Ragasa, E. Juan, J. A. Rideout. A triterpene from Ficus pumila. J. Asian Nat. Prod. Res. 2000, 1, 269-275.【C.A. 132: 119846q(2000)】
102. J. Kitajima, K. Kimizzuka, M. Arai, Y. Tanaka. New sterols and triterpenoids of Ficus pumila fruit. Chem. Pharm. Bull. 1998, 46, 1408-1411.
103. J. Kitajima, K. Kimizzuka, Y. Tanaka. New dammarane-type acetylated triterpenoids and their related compounds of Ficus pumila fruit. Chem. Pharm. Bull. 1999, 47, 1138-1140.
104. J. Kitajima, K. Kimizzuka, Y. Tanaka. Three new sesquiterpenoid glucosides of Ficus pumila fruit. Chem. Pharm. Bull. 2000, 48, 77-80.
105. E. A. Juan, J. A. Rideout, C. Y. Ragasa. Bioactive furanocoumarin derivatives from Ficus pumila. Philipp. J. Sci. 1998, 126, 143-153.【C.A. 128: 292758c(1998)】
106. M. Aida, Y. Hano, T. Nomura. Ficusins A and B, two new cyclic-monoterpene-substituted isoflavones from Ficus septica Burm. f. Heterocycles 1995, 41, 2761-2768.
107. B. Baumgartner, C. A. J. Erdelmeier, A. D. Wright, T. Rali, O. Sticher. An antimicrobial alkaloid from Ficus Septica. Phytochemistry 1990, 29, 3327-3330.
108. I. L. Tsai, J. H. Chen, C. Y. Duh, I. S. Chen. Chemical constituents from the leaves of Formosan Ficus septica. Chin. Pharm. J. 2000, 52, 195-201.
109. A. K. Chakravarty, B. Das, K. Masuda, Y. Arai, K. Shiojima. Peracid induced oxidative rearrangements of triterpenoids: products of new skeleton from bauerenyl acetate. Tetrahedron 1998, 54, 6065-6078.
110. R. Tanaka, S. Matsunaga. Triterpene constituents from Euphorbia supina. Phytochemistry 1988, 27, 3579-3584.
111. C. Y. Chen, T. Y. Wu, F. R. Chang, Y. C. Wu. Lignans and kauranes from the stem of Annona cherimola. J. Chin. Chem. Soc. 1998, 45, 629-634.
112. X. N. Zhong, H. Otsuka, T. Ide, E. Hirata, Y. Takeda. Hydroquinone diglycoside acyl esters from the leaves of Myrsine seguinii. Phytochemistry 1999, 52, 923-927.
113. T. S. Wu, Y. L. Leu, Y. Y. Chan, F. W. Lin, C. Y. Li, L. S. Shi, S. C. Kuo, C. F. Chen, Y. C. Wu. Severibuxine, a new quinolin-2, 4-dione and other constituents from Severinia buxifolia. Phytochemistry 1998, 49, 1467-1470.
114. Y. Y. Chan, Y. L. Leu, F. W. Lin, C. Y. Li, Y. C. Wu, L. S. Shi, M. J. Liou, T. S. Wu. A secoiridoid and other constituents of Gonocaryum calleryanum. Phytochemistry 1998, 47, 1073-1077.
115. S. R. Kim, Y. C. Kim. Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. Phytochemistry 2000, 54, 503-509.
116. S. Rasmussen, C. Wolff, H. Rudolph. 4′-O-β-D-Glucosyl-cis-p-coumaric acid-a natural constituent of Sphagnum fallax cultivated in bioreactors. Phytochemistry 1996, 42, 81-87.
117. T. S. Wu, L. S. Shi, S. C. Kuo. Alkaloids and other constituents from Tribulus terrestris. Phytochemistry 1999, 50, 1411-1415.
118. T. S. Wu, Z. J. Tsang, P. L. Wu, F. W. Lin, C. Y. Li, C. M. Teng, K. H. Lee. New constituents and antiplatelet aggregation and anti-HIV principles of Artemisia capillaris. Bioorg. Med. Chem. 2001, 9, 77-84.
119. K. Ingkaninan, A. P. Ijzerman, T. Taesotikul, R. Verpoorte. Isolation of opioid-active compounds from Tabernaemontana pachysiphon leaves. J. Pharm. Pharmacol. 1999, 51, 1441-1446.
120. R. A. Holton, C. Somoza, H. B. Kim, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. S. Zhang, K. K. Murthi, L. N. Gentile, J. H. Liu. First total synthesis of taxol. 1. functionalization of the B Ring. J. Am. Chem. Soc. 1994, 116, 1597-1598.
121. R. A. Holton, H. B. Kim, C. Somoza, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. S. Zhang, K. K. Murthi, L. N. Gentile, J. H. Liu. First total synthesis of taxol. 2. Completion of the C and D rings. J. Am. Chem. Soc. 1994, 116, 1599-1600.
122. J. N. Denis, A. E. Greene, D. GuEnard, F. GuEritte-Voegelein, L. Mangatal, P. Potier. Highly efficient, practical approach to natural taxol. J. Am. Chem. Soc. 1988, 110, 5917-5919.
123. D. Hou. Flora of Taiwan, 2nd ed; Editorial Committee of the Flora of Taiwan: Taipei, Taiwan, R. O. C., 1996; Vol II, p. 636-642.
124. N. Y. Chiu, K. H. Chang. The Illustrated Medicinal Plants of Taiwan; Southern Materials Center, Inc.: Taipei, Taiwan, 1983; Vol 1, p. 23.
125. D. Bensky, A. Gamble, T. Kaptchuk, L. L. Bensky. Chinese Herbal Medicine: Materia Medica, revised ed.; Eastland Press: Washington, 1993; p. 136.
126. W. Tang, G. Eisenbrand. Chinese Drugs of Plant Origin-Chemistry, Pharmacology, and Uses in Traditional and Modern Medicine; Springer-Verlag: Berlin, 1992; p. 145.
127. L. X. He, W. H. Wang, H. Z. Xue. Studies on contraceptive constituents of Aristolochia mollissima. Yao Hsueh Tung Pao 1980, 15, 44.
128. T. S. Wu, L. F. Ou, C. M. Teng. Aristolochic acids, aristolactam alkaloids and amides from Aristolochia kankauensis. Phytochemistry 1994, 36, 1063-1068.
129. L. Lajide, P. Escoubas, J. Mizutani. Antifeedant activity of metabolites of Aristolochia albida against the tobacco cutworm, Spodoptera litura. J. Agric. Food Chem. 1993, 41, 669-673.
130. C. Moretti, M. Rideau, J. C. Chénieux, C. Viel. Isolation of aristolochic acid from two Madagascar Aristolochiaceae. Determination of its toxicity on vegetal cells. Comparison with animal cells. Planta Med. 1979, 35, 360-365.
131. W. H. Wang, J. H. Zheng. Pregnancy-terminating effect and toxicity of an active component of Aristolochia mollissima Hance, aristolochic acid A. Yaoxue Xuebao 1984, 19, 405-409.
132. H. Z. Xue, J. Zhang, L. X. He. Isolation and identification of the constituents soluble in petroleum ether from Aristolochia versicolar. Nanjing Yaoxueyuan Xuebao 1985, 16, 7-9.
133. J. Hinou, C. Demetzos, C. Harvala, C. Roussakis. Cytotoxic and antimicrobial principles from the roots of Aristolochia longa. Int. J. Crude Drug Res. 1990, 28, 149-151.
134. S. M. Kupchan, H. C. Wormser. Tumor inhibitors. X. Photochemical synthesis of phenanthrenes. Synthesis of aristolochic acid and related compounds. J. Org. Chem. 1965, 30, 3792-3800.
135. L. Liu, B. Yang, T. J. Katz, M. K. Poindexter. Improved methodology for photocyclization reactions. J. Org. Chem. 1991, 56, 3769-3775.
136. 陳建茂,海南島產酒餅勒根皮部與台灣土防己根莖部成份及生物活性研究。國立成功大學化學研究所碩士論文,2000,p. 136。
137. C. E. Chang. Flora of Taiwan; Epoch. Publishing Co., Ltd. Taiwan: Taipei, Taiwan, 1977; Vol III, p. 525.
138. S. Sasaki. Khoyo Taiwan minkan yakuyo shokubutsu shi, (khobunkan), Taipei; 1924, p. 36.
139. W. M. Tin, R. W. Scora, J. Kumanoto. Constituents of Severinia buxifolia. Lloydia 1972, 35, 183-185.
140. W. M. Tin, S. Bonomo, R. W. Scora. Isolation of mexoticin from Severinia buxifolia. Planta Med. 1979, 37, 379-380.
141. D. L. Dreyer. Structure of zapotin. Tetrahedron 1967, 23, 4607-4613.
142. T. S. Wu, M. Niwa, H. Furukawa. Sesquiterpenes from Severinia buxifolia. Phytochemistry 1984, 23, 595-597.
143. T. S. Wu, C. S. Kuoh, H. Furukawa. Acridone alkaloids from Severinia buxifolia. Phytochemistry 1982, 21, 1771-1773.
144. T. S. Wu, Y. L. Leu, Y. Y. Chan, P. L. Wu, C. S. Kuoh, S. J. Wu, Y. Wang. Tetranortriterpenoid insect antifeedants from Severinia buxifolia. Phytochemistry 1997, 45, 1393-1398.
145. D. K. Qin. New acridone alkaloid from Chinese drug Tung-Feng-Jie (Atalantia buxifolia). Yaoxue Xuebao 1986, 21, 683-685.
146. G. M. Gu. Studies on the chemical constituents of Atalantia buxifolia. Yaoxue Xuebao 1987, 22, 886-888.
147. G. H. Svoboda, G. A. Poore, P. J. Simpson, G. B. Boder. Alkaloids of Acronychia baueri Schott. I. Isolation of the alkaloids and a study of the antitumor and other biological properties of acronycine. J. Pharm. Sci. 1966, 55, 758-768.
148. T. C. Chou, C. C. Tzeng, T. S. Wu, A. W. Kyoichi, T. L. Su. Inhibition of cell growth and macromolecule biosynthesis of human promyelocytic leukemic cell by acridone alkaloids. Phytotherapy Res. 1989, 3, 237-242.
149. T. L. Su, K. Dziewiszek, T. S. Wu. Synthesis of glyfoline, a constituent of Glycosmis citrifolia (Willd.) Lindl. and a potential anticancer agent. Tetrahedron Lett. 1991, 32, 1541-1544.
150. 呂彥禮,酒餅簕根皮的成分及生物活性研究。國立成功大學化學研究所碩士論文,1994,p. 54-57。
151. B. Weniger, B. H. Um, A. Valentin, A. Estrada, A. Lobstein, R. Anton, M. Maillé, M. Sauvain. Bioactive acridone alkaloids from Swinglea glutinosa. J. Nat. Prod. 2001, 64, 1221-1223.
152. C. Tringali, C. Spatafora, V. Calì, M. S. J. Simmonds. Antifeedant constituents from Fagara macrophylla. Fitoterapia 2001, 72, 538-543.
153. J. Forrest. The Ullmann biaryl synthesis. Part I. Atypical products of syntheses of 2, 4-dinitrobiphenyl and related compounds. J. Chem. Soc. 1960, 566-573.
154. J. Forrest. The Ullmann biaryl synthesis. Part III. The influence of diluents on the reaction between iodobenzene and copper. J. Chem. Soc. 1960, 581-588.
155. G. K. Hughes, K. G. Neill, E. Ritchie. The synthesis of melicopicine and some trimethoxy-10-methylacridones. Aust. J. Sci. Res. Ser. A 1950, 3, 497-503.
156. R. Olivera, R. SanMartin, F. Churruca, E. Dominguez. Revisiting the Ullmann-ether reaction: a concise and amenable synthesis of novel dibenzoxepino[4, 5-d]pyrazoles by intramolecular etheration of 4, 5-(o, o'-halohydroxy)arylpyrazoles. J. Org. Chem. 2002, 67, 7215-7225.
157. M. Watanabe, A. Kurosaki, S. Furukawa. Acridones from the reaction of N-lithio anthranilates with benzynes, a short synthesis of acronycine. Chem. Pharm. Bull. 1984, 32, 1264-1267.
158. K. Takahashi, A. Brossi, K. Diseases. Heterocycles 1982, 19, 691-695.
159. M. A. Rizzacasa, M. V. Sargent. The structure and synthesis of nepenthone-A, a naphthoquinone from Nepenthes rafflesiana. J. Chem. Soc. Perkin Trans. I 1987, 2017-2022.
160. H. Nomura, L. K. Pearson, F. A. Royle. The pungent principles of ginger. I. A new ketone, zingerone (4-hydroxy-3-methoxyphenylethyl methyl ketone), occurring in ginger. J. Chem. Soc. 1917, 111, 769-776.
161. E. K. Nelson. Gingerol and paradol. J. Am. Chem. Soc. 1917, 39, 1466-1469.
162. J. C. William. Zingerone. U.S.Pat. 1945, 2,381,210, Aug. 7.
163. N. Pravatoroff. Ginger. The properties and chemistry of some natural spicy compounds. Mfg. Chem. Aerosel News 1967, 38, 40-41.
164. T. Muramora, M. Shinohara, M. Miyamoto. Isolation of hexahydrocurcumin, dihydrogingerol and two additional pungent principles from ginger. Chem. Pharm. Bull. 1972, 20, 2291-2292.
165. Y. Masada, T. Inoue, K. Hashimoto, M. Fujioka, K. Shiraki. Studies on the pungent principles of Ginger (Zingiber officinale Roscoe) by GC-MS. J. Pharm. Soc. Japan 1973, 93, 318-321.
166. Y. Masada, T. Inoue, K. Hashimoto, M. Fujioka, C. Uchino. Studies on the constituents of Ginger (Zingiber officinale Roscoe) by GC-MS. J. Pharm. Soc. Japan 1974, 94, 735-738.
167. H. Nomura, S. Tsurumi. Synthesis of the homologs of zingerone. II. Science Repts. Tohoku Imp. Univ. 1927, 16, 565-579.【C.A. 21: 3623(1927)】
168. T. Kobayasi, T. Iwasaki. Condensation of methylzingerone. Science Repts. Tohoku Imp. Univ., First Ser. 1940, 28, 297-303.【C.A. 34: 40639(1940)】
169. T. Yamagishi, K. Hayashi, H. Mitsuhashi. Synthesis of D, L-gingerol. Chem. Pharm. Bull. 1972, 20, 2287-2289.
170. P. Denniff, D. A. Whiting. Synthesis of (±)-[6]-gingerol (pungent principle of ginger) and relatives via directed aldol reactions. J. Chem. Soc., Chem. Commun. 1976, 712-713.
171. P. Denniff, D. A. Whiting. Synthesis of (±)-[n]-gingerols and related compounds through regioselective aldol condensation: relative pungency assays. J. Chem. Soc, Perkin Trans. I 1981, 82-87.
172. T. Mukaiyama, J. Inoue. New cross-aldol reaction via vinyloxyboranes. Chem. Lett. 1976, 559-562.
173. S. J. Sheu, Y. J. Chang, Y. P. Chen, H. Y. Hsu. Synthetic and pharmacological studied on the pungent principles of ginger and related compounds. J. Taiwan Pharm. Assoc. 1979, 31, 40-46.
174. Y. C. Huang, B. N. Wu, J. L. Yeh, S. J. Chen, J. C. Liang, Y. C. Lo, I. J. Chen. A new aspect of view in synthesizing new type -adrenoceptor blockers with ancillary antioxidant activities. Bioorg. Med. Chem. 2001, 9, 1739-1746.
175. S. Shirota, K. Miyazaki, R. Aiyama, M. Ichioka, T. Yokokura. Tyrosinase inhibitors from crude drugs. Biol. Pharm. Bull. 1994, 17, 266-269.
176. F. N. Lahey, R. Hutchins. Acrovestone-new phenolic ketone. Symp. Phytochem. Proc. Meeting Univ. Hong Kong 1961, 121-122.【C.A. 61: 14573f(1964)】
177. V. Kumor, V. Karunaratne, M. R. Meegalle, K. Sanath. 1-[2', 4'-Dihydroxy-3', 5'-di-(3"-methylbut-2"-enyl)-5'-methoxy]phenylethanone from Acronychia pedunculata root bark. Phytochemistry 1989, 28, 1278-1279.
178. F. Zhou, Z. Min. Chemical constituents of Acronychia pedunculata (L.). Zhongguo Zhongyao Xaxhi 1989, 14, 94-95.【C.A. 110: 189445c(1989)】
179. T. S. Wu, M. L. Wang, T. T. Jong, A. T. Mcphail, R. Donald, K. H. Lee. X-ray crystal structure of acrovestone, a cytotoxic principle from Acronychia pedunculata. J. Nat. Prod. 1989, 52, 1284-1289.
180. G. K. Hughes, F. N. Lahey, J. R. Price, L. J. Wedd. Alkaloids of the Australian Rutaceae. Nature 1948, 162, 223-224.【C.A. 43: 648g(1948)】
181. B. S. Balgir, L. N. Mander, S. T. K. Mander. A revision of the structures proposed for the Melicope extractives, melicopol and methylmelicopol. Aust. J. Chem. 1973, 26, 2459-2472.
182. H. Obara, J. Onodera, T. Shibata, K. Shibayama. Synthesis of 1,2,3,6,7,8-, 1,3,4,5,6,8-, and 1,2,3,5,6,8-hexamethoxyxanthene. Bull. Chem. Soc. Jpn. 1981, 54, 1261-1262.
183. C. F. Carvalho, M. V. Sargent. Naturally occurring dibenzofurans. Part 4. Synthesis of dibenzofurandiols by annelation of benzofurans. J. Chem. Soc., Perkin Trans. I 1984, 1605-1612.
184. H. S. Raper. The aerobic oxidases. Physiol. Rev. 1928, 8, 245-282.
185. H. S. Mason, E. W. Peterson. Melanoproteins. I. Reactions between enzyme-generated quinones and amino acids. Biochim. Biophys. Acta 1965, 111, 134-146.
186. P. Bernard, J. Y. Berthon. Resveratrol: an original mechanism on tyrosinase inhibition. Inter. J. Cosmet. Sci. 2000, 22, 219-226.
187. N. H. Shin, S. Y. Ryu, E. J. Choi, S. H. Kang, I. M. Chang, K. R. Min, Y. S. Kim. Oxyresveratrol as the potent inhibitor on dopa oxydase activity of mushroom tyrosinase. Biochim. Biophys. Res. Commun. 1998, 243, 801-803.
188. T. S. Wu, M. Y. Hsu, A. G. Damu, P. C. Kuo, C. R. Su, C. Y. Li, H. D. Sun. Constituents of leaves of Phellodendron chinense var. glabriusculum. Heterocycles 2003, 60, 397-404.
189. T. S. Wu, M. Y. Hsu, P. C. Kuo, B. Sreenivasulu, A. G. Damu, C. R. Su, C. Y. Li, H. C. Chang. Constituents of leaves of Phellodendron amurense var. wilsonii. and their bioactivity. J. Nat. Prod. 2003, 66, 1207-1211.
190. P. C. Kuo, M. Y. Hsu, A. G. Damu, C. R. Su, C. Y. Li, H. D. Sun, T. S. Wu. Flavonoids and coumarins from leaves of Phellodendron chinense. Planta Med. 2004, 70, 183-185.
191. I. Fridovich. The biology of oxygen radicals. Science 1978, 201, 875-880.
192. N. C. Cook, S. Samman. Flavonoids-chemistry, metabolism, cardioprotective effects, and dietary sources. J. Nutr. Biochem. 1996, 7, 66-76.
193. M. T. Huang, C. T. Ho, C. Y. Lee. ACS Symposium Series 507, American Chemical Society, Washington, DC, 1992.
194. F. N. Ko, C. H. Liao, Y. H. Kuo, Y. L. Lin. Antioxidant properties of demethyl-diisoeugenol. Biochim. Biophys. Acta 1995, 1258, 145-152.
195. A. Mellors, A. L. Tappel. The inhibition of mitochondrial peroxidation by ubiquinone and ubiquinol. J. Biol. Chem. 1966, 241, 4353-4356.
196. J. M. Braughler, S. Philip, R. L. Barton, J. F. Chase, E. J. Pregenzer, F. J. Jacobsen, J. M. T. Van Doornik, E. A. Donald, L. B. Gordon. Novel membrane localized iron chelators as inhibitors of iron-dependent lipid peroxidation. Biochem. Pharmacol. 1988, 37, 3853-3860.
197. C. M. Teng, W. Y. Chen, W. C. Ko, C. Ouyang. Antiplatelet effect of butylidene-phthalide. Biochim. Biophys. Acta 1987, 924, 375-382.
198. J. R. O'Brien. Platelet aggregation Part II. Some results from a new method of study. J. Chin. Path. 1962, 15, 452.
199. L. V. Rubinstein, R. H. Shoemaker, K. D. Paull, R. M. Simon, S. Tosini, P. Skehan, D. A. Scudiero, A. Monks, M. R. Boyd. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J. Natl. Cancer Inst. 1990, 82, 1113-1118.
200. J. Guan, D. E. Kyle, L. Gerena, Q. Zhang, W. K. Milhous, A. J. Lin. Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum. J. Med. Chem. 2002, 45, 2741-2748.
201. R. E. Desjardins, C. J. Canfield, D. E. Haynes, J. D. Chulay. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 1979, 16, 710-718.
202. W. K. Milhous, N. F. Weatherly, J. H. Bowdre, R. E. Desjardins. In vitro activities and mechanisms of resistance to antifol antimalarial drugs. Antimicrob. Agents Chemother. 1985, 27, 525-530.
203. J. Ito, F. R. Chang, H. K. Wang, Y. K. Park, M. Ikegaki, N. Kilgore, K. H. Lee. Anti-AIDS agents. 48. Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian Propolis. J. Nat. Prod. 2001, 64, 1278-1281.
論文全文使用權限
  • 同意授權校內瀏覽/列印電子全文服務,於2007-04-12起公開。
  • 同意授權校外瀏覽/列印電子全文服務,於2009-04-12起公開。


  • 如您有疑問,請聯絡圖書館
    聯絡電話:(06)2757575#65773
    聯絡E-mail:etds@email.ncku.edu.tw