臺灣博碩士論文加值系統

紫花地丁(堇菜科植物)廣泛的分布於臺灣、中國、中南半島、爪哇、菲律賓和琉球。在台灣作為民間用藥，用於鎮痛，發炎和退熱，根據文獻記載堇菜科的植物目前有關其化學成分之研究共發現數個化合物，如violaxanthin ester化合物是分離於V. tricolor，afzelin化合物是發現於V. yedoensis，kaempferol glycosides化合物是從V. diamantica所分離純化的。然而，紫花地丁的化學成分之研究目前仍無相關報導。此外，由於在抗血小板凝集活性測試中，發現紫花地丁的粗萃物是具有活性，故為了探討其活性成分，進而對此植物進行萃取及分離。
在這整個研究中，有二十六個化合物從此植物中分離出來，包括五個三萜類化合物: ursolic acid (1)、oleanoic acid (2)、uvaol (3)、pomolic acid (4)和11??-chloro-3??-hydroxy-oleanan-13,28??-olide (5)，兩個醯胺類化合物: N-icosanoyltyramine (6)和N-docosanoyltyramine (7)，一個glyceride: 9,16-dioxo-octadeca- 10,12,14-trienoic acid (8)，兩個雙胜肽類的化合物: aurantiamide acetate (9)和aurantiamide benzoate (10)，一個xanthone類化合物: 1,2,3,7-tetramethoxy xanthone (11)，四個香豆素: isoeuphorbetin (12)、scopoletin (13)、isoscopoletin (14)和 scoparone (15)，一個吲哚類化合物: indole-3-carboxylic acid methyl ester (16)，一個黃酮類化合物: apigenin (17)，一個苯環化合物: 4-methoxy phenol (18)，八個固醇纇化合物: stigmasta-5-ene-3??,7??-diol (19)、stigmasta-5-ene-3??,7??-diol (20)、(22E,24S)-stigmasta-5,22-dien- 3??,7??-diol (21)、(22E,24S)-stigmasta-5,22-dien-3??,7??-diol (22)、??-stigmasterol (23)和??-sitosterol (24)混合物、??-stigmasteryl- 3-O-??-D-glucoside (25)和??-sitosteryl-3-O-??-D-glucosid (26)混合物，這些化合物結構是以NMR光譜和質譜所確定的。在這些化合物之中，化合物5和6為新化合物。
在生物活性方面，化合物1、2、3、4、6和12具有微弱的細胞毒殺作用。此外，化合物13和15也具有顯著的抗血小板凝集活性。

Viola confusa (Violaceae) distributed throughout Taiwan, China, southeast Asia, Java, Philippines, and Ryukyu Islands, is used as a folk medicine in Taiwan with analgesis, anti-inflammatory, and antipyretic actions. Previously, phytochemical research revealed several compounds from Violaceous family, for example, violaxanthin ester from V. tricolor, afzelin from V. yedoensis and kaempferol glycosides from V. diamantica. The chemical constituents of V. confusa, however, are still remaining unknown. The crude extract of V. confusa showed moderate antiplatelet activity in our lab. In order to find out the bioactive components from this plant, the extraction and isolation of whole plant was proceeded.
In this study, twenty six compounds were isolated from this plant including five triterpenoids: ursolic acid (1), oleanoic acid (2), uvaol (3), pomolic acid (4) and 11??-chloro-3??-hydroxy- oleanan-13,28??-olide (5), two amides: N-icosanoyltyramine (6) and N-docosanoyltyramine (7), one glyceride: 9,16-dioxo-octadeca- 10,12,14-trienoic acid (8), two dipeptides: aurantiamide acetate (9) and aurantiamide benzoate (10), one xanthone: 1,2,3,7- tetramethoxyxanthone (11), four coumarins: isoeuphorbetin (12), scopoletin (13), isoscopoletin (14) and scoparone (15), one alkaloid: indole-3-carboxylic acid methyl ester (16), one flavonoid: apigenin (17), one benzenoid: 4-methoxy phenol (18) and eight steroids: stigmasta-5-ene-3β,7β-diol (19), stigmasta-5-ene-3β,7α-diol (20), (22E,24S)-stigmasta-5,22-dien-3??,7??-diol (21), (22E,24S)- stigmasta-5,22-dien-3??,7??-diol (22), a mixture of β-stigmasterol (23) and β-sitosterol (24), a mixture of β-stigmasteryl-3-O-β-D-glucoside (25) and β-sitosteryl-3-O-β-D-glucoside (26). The structures of these compounds were elucidated by analysis of NMR, and MS spectroscopic data. Among them, 5 and 6 are new compounds.
Compounds 1, 2, 3, 4, 6 and 12 showed weak cytotoxic activity, and then compounds 13 and 15 showed antiplatelet activity.

目錄
目錄-----------------------------------------------------Ⅰ
圖表目錄-------------------------------------------------Ⅲ
中文摘要----------------------------------------------ⅩⅥ
英文摘要-----------------------------------------------ⅩⅧ
第一章、緒論--------------------------------------------1
第一節、前言------------------------------------1
第二節、文獻回顧--------------------------------7
第三節、植物型態及分佈--------------------------76
第四節、研究動機--------------------------------79
第二章、研究材料與方法----------------------------------81
第三章、化合物之結構證明--------------------------------88
第一節、Urasane和oleanane類化合物結構解析與比--88
第二節、Ursolic acid (1)結構鑑定------------------100
第三節、Oleanoic acid (2)結構鑑定-----------------107
第四節、Uvaol (3)結構鑑定------------------------113
第五節、Pomolic acid (4)結構鑑定------------------119
第六節、11??-Chloro-3??-hydroxy-oleanan-13,28??-olide (5)結構鑑定--------------------------------129

第七節、N-Icosanoyltyramine (6)結構鑑定-----------139
第八節、9,16-Dioxo-(10E,12Z,14E)-octadeca-trienoic acid (8)結構鑑定-----------------------------149
第九節、Auantiamide acetate (9)結構鑑定-----------159
第十節、Auantiamide benzoate (10) 結構鑑定-------168
第十一節、1,2,3,7-Tetramethoxy xanthone (11) -------176
第十二節、Isoeuphorbetin (12)---------------------184
第十三節、(24R)-Stigmasta-5-ene-3??,7??-diol (20)-----191
第四章、生物活性試驗--------------------------------197
第五章、結論------------------------------------------199
第六章、相關實驗部份--------------------------------217
第一節、儀器與材料-------------------------------217
第二節、植物材料與分離純化-----------------------219
第三節、生物活性試驗之實驗方法-------------------234
第四節、各化合物之物理與光譜數據總整理-----------237
第七章、參考文獻--------------------------------------263

1.Huang, T. C., Ed. In Flora of Taiwan, 2nd ed.; Lungwei Printing Co., Ltd Press: Taipei, 1993; Vol. 3, pp 805-833.
2.吳謙，「醫宗金鑑」，1742.
3.行政院衛生署中醫藥委員會編印，「台灣藥用植物資源名錄」，行政院衛生署中醫藥委員會出版，2003，pp 323.
4.Luo, H. Chinese medicinal composition for treating mastitis 2008.
5.Andrei, C. Antioxidant composition based on natural extracts for treating psoriasis. 2006.
6.Huo, Y.; Huo, H. Pharmaceuticals 2005.
7.Toiu, A.; Parvu Alina, E.; Oniga, I.; Tamas, M. Rev Med Chir Soc Med Nat Ias 2007, 111, 525-529.
8.Paoletti, S.; Ferrarese, L.; Santi, P.; Ghirardini, A. Cosmetic News 2001, 24, 156-161.
9.Deibel, M. A.; Colanese, J.; Nakata, C. Antioxidant activity in herbal extracts and isolated fractions. 2007.
10.Moon, H.-I.; Jung, J.-C.; Lee, J., Parasitol. Res. 2007, 100, 641-644.
11.Clarkson, C.; Maharaj, V. J.; Crouch, N. R. J. Ethnopharmacol. 2004, 92, 177-191.
12.Petelot, A., In Tome 1st ed 1952, Centre de Recherches Scientifiques et Techniques, I.D.E.O. Saigon.
13.Amer, A.; Mehlhorn, H. Parasitol. Res. 2006, 99, 478-490.
14.Schuele, S.; Lederman, R. J. Mov. Disord. 2004, 19, 43-48.
15.Lindholm, P.; Goransson, U.; Johansson, S. Mol. Cancer. Ther. 2002, 1, 365-369.
16.Carnat, A. P.; Carnet, A.; Fraisse, D.; Lamaison, J.-L. J. Nat. Prod. 1998, 61, 272-274.
17.Lee, Y. N. In Flora of Korea 1996, pp 126.
18.Molnar, P.; Szabolcs, J. Phytochemistry 1980, 19, 623-627.
19.Lee, S. W.; Chen, Z. T.; Chen, C. M. J. Chin. Chem. Soc. 1993, 40, 305-307.
20.Xie, C.; Veitch, N. C.; Houghton, P. J.; Simmonds, M. S. J. Chem. Pharm. Bull. 2003, 51, 1204-1207.
21.Flamini, G. Chemistry & Biodiversity 2007, 4, 139-144.
22.Moon, H.-I.; Lee, J.; Zee, O. P.; Chung, J. H., J. Ethnopharmacol. 2005, 101, 176-179.
23.Moon, H.-I.; Lee, J.; Kwak, J. H.; Zee, O. P.; Chung, J. H. Biol. Pharm. Bull. 2005, 28, 925-928.
24.Moon, H.-I.; Lee, J.; Zee, O. P.; Chung, J. H. Biol. Pharm. Bull. 2005, 28, 1123-1125.
25.Moon, H.-I.; Kim, J. E.; Lee, J.; Zee, O. P.; Chung, J. H. Bull. Korean Chem. Soc. 2005, 26, 451-453.
26.Moon, H.-I.; Kim, E. J.; Lee, J.; Lee, H. K.; Chung, J. H. J. Ethnopharmacol. 2006, 104, 12-17.
27.Moon, H.-I.; Kim, M. R.; Cho, M. K.; Park, S.; Chung, J. H. Phytother. Res. 2005, 19, 239-242.
28.Werkhoff, P.; Bretschneider, W.; Giintert, M.; Hopp, R.; Surburg, H. Z. Lebensm. Unters. Forsch. 1991, 192, 111-115.
29.Qin, B.; Chen, Q.-P.; Lou, Z.-C. J. Chinese Pharmaceutical Sci. 1994, 3, 91-96.
30.楊峻山主編，「實用天然產物手冊-萜類化合物」，2005，pp 300.
31.Radics, L.; Molnar, P.; Szabolcs, J. Phytochemistry 1983, 22, 306.
32.Molnar, P.; Szabolcs, J.; Radics, L. Phytochemistry 1986, 25, 195-199.
33.Göransson, U.; Svangard, E.; Claeson, P.; Bohlin, L. Current Protein and Peptide Science 2004, 5, 317-329.
34.Gran, L. Acta. Pharmacol. Toxicol. 1973, 33, 400-408.
35.Schöpke, T.; Hasan Agha, M. I.; Kraft, R.; Otto, A.; Hiller, K. Sci. Pharm. 1993, 61, 145-153.
36.Lindholm, P.; Göransson, U.; Johansson, S.; Claeson, P.; Gullbo, J.; Larsson, R.; Bohlin, L.; Backlund, A. Mol. Cancer.Ther 2002, 1, 365-369.
37.Svangård, E.; Göransson, U.; Hocaoglu, Z.; Gullbo, J.; Larsson, R.; Claeson, P.; Bohlin, L. J. Nat. Prod. 2004, 67, 144-147.
38.Tam, J. P.; Lu, Y. A.; Yang, J. L.; Chiu, K. W. Proc. Natl. Acad. Sci. USA 1999, 96, 8913-8918.
39.Jennings, C.; West, J.; Waine, C.; Craik, D. J.; Anderson, M. Proc. Natl. Acad. Sci. USA 2001, 98, 10614-10619.
40.Gustafson, K. R.; Sowder, R. C.; II, H., L. E.; ; Parsons, I. C.; Kashman, Y.; Cardellina, J. H.; II, M., J. B.; Buckheit, R. W.; Pannell, L. K.; Boyd, M. R. J. Am. Chem. Soc. 1994, 116, 9337-9338.
41.Gustafson, K. R.; Walton, L. K.; Sowder, R. C.; Johnson, D. G.; Pannell, L. K.; Cardellina, J. H.; Boyd, M. R. J. Nat. Prod 2000, 63, 176-178.
42.Hallock, Y. F.; Sowder, R. C.; Pannell, L. K.; Hughes, C. B.; Johnson, D. G.; Gulakowski, R.; Cardellina, J. H.; Boyd, M. R. J. Org. Chem. 2000, 65, 124-128.
43.Bokesch, H. R.; Pannell, L. K.; Cochran, P. K.; Sowder, R. C.; McKee, T. C.; Boyd, M. R. J. Nat. Prod. 2001, 64, 249-250.
44.Hernandez, J. F.; Gagnon, J.; Chiche, L.; Nguyen, T. M.; Andrieu, J. P.; Heitz, A.; Hong, T. T.; Pham, T. T. C.; Nguyen, D. L. Biochemistry 2000, 39, 5722-5730.
45.Craik, D. J.; Daly, N. L.; Waine, C. Toxicon. 2001, 39, 43-60.
46.Gran, L.; Sandberg, F.; Sletten, K. J. Ethnopharmacol. 2000, 70, 197-203.
47.Sletten, K.; Gran, L. Medd. Nor. Farm. Selsk. 1973, 35, 69-82.
48.Saether, O.; Craik, D. J.; Campbell, I. D.; Sletten, K., Juul, J.;; Norman, D. G. Biochemistry 1995, 34, 4147-4158.
49.Witherup, K. M.; Bogusky, M. J.; Anderson, P. S.; Ramjit, H.; Ransom, R. W.; Wood, T.; Sardana, M. J. Nat. Prod. 1994, 57, 1619-1625.
50.Broussalis, A. M.; Göransson, U.; Coussio, J. D.; Ferraro, G.; Martino, V.; Claeson, P. Phytochemistry 2001, 58, 47-51.
51.Claeson, P.; Göransson, U.; Johansson, S.; Luijendijk, T.; Bohlin, L. J. Nat. Prod. 1998, 61, 77-81.
52.Göransson, U.; Luijendijk, T.; Johansson, S.; Bohlin, L.; Claeson, P. J. Nat. Prod. 1999, 62, 283-286.
53.Craik, D. J.; Daly, N. L.; Bond, T.; Waine, C. J. Mol. Biol. 1999, 294, 1327-1336.
54.Svangård, E.; Göransson, U.; Smith, D.; Verma, C.; Backlund, A.; Bohlin, L.; Claeson, P. Phytochemistry 2003, 64, 135-142.
55.Göransson, U.; Broussalis, A. M.; Claeson, P. Anal. Biochem. 2003, 318, 107-117.
56.Felizmenio-Quimio, M. E.; Daly, N. L.; Craik, D. J. J. Biol. Chem. 2001, 276, 22875-22882.
57.Craik, D. J.; Daly, N. L.; Trabi, M.; Plan, M. P.; Mulvenna, J. Curr. Prot. & Pept. Sci. 2004, 5, 297-315.
58.Herrmann, A.; Burman, R.; Mylne, J. S.; Karlsson, G.; Gullbo, J.; Craik, D. J.; Clark, R. J.; Go¨ransson, U. Phytochemistry 2008, 69, 939-952.
59.Wang, C. K. L.; Colgrave, M. L.; Gustafson, K. R.; Ireland, D. C.; Goransson, U.; Craik, D. J. J. Nat. Prod. 2008, 71, 47-52.
60.Gran, L. Lloydia 1973, 36, 207-208.
61.Loomis, W. D.; Battaile, J. Phytochemistry 1966, 5, 423-438.
62.Burns, J. A.; Butler, J. C.; Moran, J.; Whitesides, G. M. J. Org. Chem. 1991, 56, 2648-2650.
63.Göransson, U.; Craik, D. J. J. Biol. Chem. 2003, 278, 48188-48196.
64.Chen, B.; Colgrave, M. L.; Wang, C.; Craik, D. J. J. Nat. Prod. 2006, 69, 23-28.
65.Simonsen, S. M.; Sando, L.; Ireland, D. C.; Colgrave, M. L.; Bharathi, R.; Gö ransson, U.; Craik, D. J. The Plant Cell 2005, 17, 3176-3189.
66.Flamni, G.; Cioni, P. L.; Morelli, I. Annals of Botany 2003, 91, 493-497.
67.Mazza, F. Abbadia S. Salvatore, Siena, Italy: Stampa 2000. 2000.
68.Santi, G. Pisa, Italy: Prosperi. 1795.
69.Caruel, T. Firenze, Italy: Le Monnier 1860.
70.Arcangeli, G. Nuovo Giornale Botanico Italiano 1889, 21, 119.
71.Bertoloni, A. Flora Italica 1889, Bologna, Italy: Masi.
72.Terracciano, A. Nuovo Giornale Botanico Italiano 1889, 21, 320-331.
73.Parlatore, F. Flora Italiana. 1890, Firenze, Italy: Le Monnier.
74.Fiori, A. In Nuova Flora Analitica Italiana. 1924, Bologna: Edagricole, Ristampa anastatica 1974.
75.Valentine, D. H.; Merzmüller, H.; Schmidt, A. In: Tutin TG, eds. Flora Europaea. Cambridge: Cambridge University Press. 1968.
76.Zangheri, P. In Flora Italica 1976, Padova, Italy: Cedam.
77.Foggi, B.; Di Fazio, L.; Selvi, F.; Clauser, M. Giornale Botanico Italiano 1993, 127, 755-763.
78.Werkhoff, P.; Bretschneider, W.; Guentert, M.; Hopp, R.; Surburg, H. 6th Flavour Science and Technology Symposium 1990, Chichester, UK.
79.Selvi, F.; Foggi, B.; Di Fazio, L. Candollea 1995, 50, 309-319.
80.Dunlop, P. J.; Bignell , C. M.; Hibbert, D. B. Australian Journal of Botany 1997, 45, 1-13.
81.Akashi, T.; Furuno, T.; Takehashi, T.; Ayabe, S. Phytochemistry 1994, 36, 303-308.
82.Mahato, S. B.; Kundu, A. P. Phytochemistry 1994, 37, 1517-1575.
83.Zander, J. M.; Caspi, E.; Pandey, G. N.; Mitra, C. R. Phytochemistry 1969, 8, 2265-2267.
84.Shiojima, S.; Msuda, K.; Suzuki, H.; Lin, T.; Ooishi, Y.; Ageta, H. Chem. Pharm. Bull. 1995, 43, 1634-1639.
85.Tanaka, R.; Matsunaga, S. Phytochemistry 1992, 31, 3535-3539.
86.Shao, M.; Yang, Y.; Gao, H.; Wu, B.; Wang, L.; Wu, L. Shenyang Yaoke Daxue Xuebao 2005, 22, 100-102.
87.Lee, S.; Paek, S. H.; Kim, S.-K.; Kim, B.-K.; Shin, K. H. Nat. Prod. Sci. 2004, 10, 306-309.
88.Sengupta, P.; Ghosh, S. J. Indian Chem. Soc. 1965, 42, 543-546.
89.Tao, J.; Morikawa, T.; Toguchida, I.; Ando, S.; Matsuda, H.; Yoshikawa, M. Bioorg. Med. Chem. 2002, 10, 4005-4012.
90.Merfort, I.; Buddrus, J.; Nawwar, M. A. M.; Lambert, J. Phytochemistry 1992, 31, 4031-4032.
91.Chakravarty, A. K.; Mukhopadhyay, S.; Das, B. Phytochemistry 1991, 30, 4087-4092.
92.Shiojima, K.; Arai, Y.; Masuda, K.; Hirohara, M.; Zuzuki, H.; Ageta, H. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1989, 31st, 554-561.
93.Siddiqui, S.; Hafeez, F.; Begum, S.; Siddiqui, B. S. J. Nat. Prod. 1986, 1086-1090.
94.Numata, A.; Yang, P.; Takahashi, C.; Fujiki, R.; Nabae, M.; Fujita, E. Chem. Pharm. Bull. 1989, 37, 648—651
95.Katai, M.; Terai, T.; Meguri, H. Chem. Pharm. Bull. 1983, 31, 1567-1571.
96.Achenbac, H.; Hubner, H.; Brandt, W.; Reiter, M. Phytochemistry 1994, 35, 1527-1543.
97.Herz, W.; Kulanthaivel, P. Phytochemistry 1984, 23, 1453-1459.
98.Ishiguro, K.; Nagata, S.; Fukumoto, H.; Yamaki, M.; Takagi, S.; Isoi, K. Phytochemistry 1991, 30, 3639-3641.
99.Isobe, T.; Doe, M.; Morimoto, Y.; Nagata, K.; Masuoka, N.; Ohsaki, A. Yakugaku zasshi 2007, 127, 389-395.
100.Ishiguro, K.; Nagata, S.; Fukumoto, H.; Yamaki, M.; Takagi, S.; Isoi, K. Phytochemistry 1991, 30, 3639-3641.
101.Isobe, T.; Doe, M.; Morimoto, Y.; Nagata, K.; Masuoka, N.; Ohsaki, A. Yakugaku zasshi 2007, 127, 389-395.
102.Ikeya, Y.; Sugama, K.; Okada, M.; Mitsuhashi, H. Phytochemistry 1991, 30, 2061-2065.
103.Dutta, P. K.; Banerjee, D.; Dutta, N. L. Indian Journal of Chemistry 1973, 11, 831-832.
104.Chauras, N.; Wichtl, M. J. Nat. Prod. 1987, 50, 881-885.
105.Caterina, M. J.; Schumacher, M. A.; Tominaga, M.; Rosen, T. A.; Levine, J. D.; Julis, D. Nature 1997, 389, 816-824.
106.Szallasi, A.; Blumberg, P. M. Pharmacol. Rev. 1999, 51 159-211.
107.Zygmunt, P. M.; Petersson, J.; Andersson, D. A.; Chuang, H.; Sorgard, M.; Di Marzo, V.; Julius, D.; Hogestatt, E. D. Nature 1999, 400, 452-457.
108.Szallasi, A.; Blumberg, P. M. Pain 1996, 68, 195-208.
109.Ryu, C. H.; Jang, M. J.; Jung, J. W.; Park, J. H.; Choi, H. Y.; Suh, Y.; Oh, U.; Park, H.; Lee, J.; Koh, H.; Mo, J. H.; Joo, Y. H.; Park, Y. H.; Kim, H. D. Bioorg. Med. Chem. Lett. 2003, 13, 1549-1552.
110.Krane, S. M.; Simon, L. S. Med. Clin. North Am. 1986, 70 263-284.
111.Schwartz, L. B. Curr. Opin. Immunol. 1994, 691-697.
112.Sashidhara, K. V.; Rosaiah, J. N.; Tyagi, E.; Shukla, R.; Raghubir, R.; Rajendran, S. M. Eur. J. Med. Chem. In Press, Corrected Proof 2008, 1-5.
113.Sastri, B. N., The Wealth of India, Council of Scientific and Industrial Research, New Delhi 1962, p. 425.
114.Chopra, R. N.; Nayar, S. L.; Chopra, I. C. Glossary of Indian Medicinal Plants, Council of Scientific and Industrial Research, New Delhi. 1956, p. 170.
115.Udupa, S. L.; Udupa, A. L.; Kulkarni, D. R. Fitoterapia 1994, 65, 119-123.
116.A.P. Guevara; C. Vargas; M. Uy, Philipp. J. Sci. 1996, 125, 175-184.
117.Ruckmani, K.; Kavimani, S.; Anandan, R.; Jaykar, B. Indian J. Pharm. Sci. 1998, 60, 33-35.
118.Rao, C. V.; Ojha, S. K.; Mehrotra, S. In Proceedings of the Second World Congress on Biotechnological Developments of Herbal Medicine, Lucknow, India 2003, p. 42.
119.Basu, B. D.; Kirtikar, K. R. Indian Medicinal Plants, 2nd ed. 1980, Vol. 1, Dehradun, pp. 676-683.
120.Vaidyaratnam, P. S. V. Indian Medicinal Plants: A Compendium of 500 Species, 1994, Vol. 4, Orient Longman Ltd., Madras, pp. 59-64.
121.Ezeamuzie, I. C.; Ambakederemo, A. W.; Shode, F. O.; Ekwebelem, S. C. J. Pharmacogn. 1996, 34 207-212.
122.Tetlow, L. C.; Woolley, D. E. Ann. Rheum. Dis. 1995, 54, 896-903.
123.Tsai, P.-L.; Wang, J.-P.; Chang, C.-W.; Kuo, S.-C.; Chao, L. P.-D. Phytochemistry 1998, 49 1663-1666.
124.Manez, S.; Recio, M. C.; Giner, R. M.; Rios, J. L. Eur. J. Pharmacol. 1997, 334, 103–105.
125.Liu, J. J. Ethnopharmacol. 1995, 49, 57-68.
126.Ikeda, Y.; Murakami, A.; Ohigashi, H. Mol. Nutr. Food Res. 2008, 52, 26-42.
127.Croteau, R.; Kutchan, T. M.; Lewis, N. G. In Buchanan, B., Gruissem, W., Jones, R. (Eds.), Biochemistry and Molecular Biology of Plants. American Society of Plant Biologists, Rockville, 2000, pp. 1250-1268.
128.Chappell, J. Curr. Opin. Plant Biol. 2002, 5, 151-157.
129.McGarvey, D. J.; Croteau, R. Plant Cell 1995, 7, 1015-1026.
130.Chappell, J. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1995, 46, 521-547.
131.Novotny, L.; Vachalkova, A.; Biggs, D. Neoplasma 2001, 48, 241-246.
132.Flesch, G.; Rohmer, M. Eur. J. Biochem. 1988, 175, 405 -411.
133.Rohmer, M.; Knani, M.; Simonin, P.; Sutter, B.; Sahm, H. Biochem. J. 1993, 295 (Pt 2), 517-524.
134.Price, K. R.; Johnson, I. T.; Fenwick, G. R. Crit. Rev. Food Sci. Nutr. 1987, 26, 27-135.
135.Mahato, S. B.; Sarkar, S. K.; Poddar, G. Phytochemistry 1988, 27, 3037 -3067.
136.Wang, B.; Jiang, Z. Chin. Pharm. J. 1992, 27, 393-397.
137.Rousseau, J. Archives de Folklore 1947, 11, 145 -182.
138.Chandler, R. F.; Freeman, L.; Hooper, S. N. J. Ethnopharmacol. 1979, 1, 49-68.
139.Gunther, E., Ethnobotany of Western Washington University of Washington Press 1973.
140.Burgesse, J. A. Primitive Man 1944, 17, 1-18.
141.Turner, N. J.; Bouchard, R.; Kennedy, D. I. D. Ethnobotany of the Okanagan-Colville Indians of British Columbia and Washington British Columbia Provincial Museum 1980.
142.Ismaili, H.; Tortora, S.; Sosa, S.; Fkih-Tetouani, S. J. Pharm. Pharmacol. 2001, 53, 1645 -1652.
143.Ismaili, H.; Sosa, S.; Brkic, D.; Fkih-Tetouani, S. J. Pharm. Pharmacol. 2002, 54, 1137-1140.
144.Samuelsen, A. B. J. Ethnopharmacol. 2000, 71, 1-21.
145.Ohigashi, H.; Takamura, H.; Koshimizu, K.; Tokuda, H.; Ito, Y. Cancer Lett. 1986, 30, 143-151.
146.Tokuda, H.; Ohigashi, H.; Koshimizu, K.; Ito, Y. Cancer Lett. 1986, 33, 279-285.
147.Nishino, H.; Nishino, A.; Takayasu, J.; Hasegawa, T. Cancer Res. 1988, 48, 5210 -5215.
148.Najid, A.; Simon, A.; Cook, J.; Chable-Rabinovitch, H. FEBS Lett. 1992, 299, 213 -217.
149.Huang, M. T.; Ho, C. T.; Wang, Z. Y.; Ferraro, T. Cancer Res. 1994, 54, 701-708.
150.He, X.; Liu, R. H. J. Agric. Food Chem. 2007, 55, 4366-4370.
151.Chiang, L. C.; Ng, L. T.; Cheng, P. W.; Chiang, W.; Lin, C. C. Clin. Exp. Pharmacol. Physiol. 2005, 32, 811-816.
152.Neto, C. C. Mol. Nutr. Food Res. 2007, 51, 652 -664.
153.Begum, S.; Hassan, S. I.; Ali, S. N.; Siddiqui, B. S. Nat. Prod. Rep. 2004, 18, 135-140.
154.Jung, H. A.; Chung, H. Y.; Jung, J. H.; Choi, J. S. Chem. Pharm. Bull. (Tokyo). 2004, 52, 157-159.
155.Dufour, D.; Pichette, A.; Mshvildadze, V.; Bradette-Hebert, M. E. et al. J. Ethnopharmacol. 2007, 111, 22-28.
156.Zhou, C.; Chen, K.; Sun, C.; Chen, Q. Biomed. Chromatogr. 2007, 21, 755-761.
157.Young, H. S.; Chung, H. Y.; Lee, C. K.; Park, K. Y. Biol. Pharm. Bull. 1994, 17, 990-992.
158.Andrikopoulos, N. K.; Kaliora, A. C.; Assimopoulou, A. N.; Papapeorgiou, V. P. J. Med. Food 2002, 5, 1-7.
159.Somova, L. I.; Shode, F. O.; Ramnanan, P.; Nadar, A. J. Ethnopharmacol. 2003, 84, 299-305.
160.Chinou, I.; Liolios, C.; Moreau, D.; Roussakis, C. Fitoterapia 2007, 78, 342-344.
161.Goun, E. C., G.;; Solodnikov, S.; Krasnykch, O.; Miles, H. Fitoterapia 2002, 73, 692-694.
162.Heo, H. J.; Cho, H. Y.; Hong, B.; Kim, H. K. Mol. Cells 2002, 13, 5-11.
163.Chen, G.; Lu, H.; Wang, C.; Yamashita, K. Clin. Chim. Acta 2002, 320, 11-16.
164.Recio, M. C.; Giner, R. M.; Manez, S.; Gueho, J. Planta Med. 1995, 61, 9-12.
165.Altinier, G.; Sosa, S.; Aquino, R. P.; Mencherini, T. J. Agric. Food Chem. 2007, 55, 1718-1723.
166.Balanehru, S.; Nagarajan, B. Biochem. Int. 1991, 24, 981-990.
167.Balanehru, S.; Nagarajan, B. Biochem. Int. 1992, 28, 735-744.
168.Bokoch, G. M. Trends Cell Biol. 1995, 5, 109-113.
169.Vuillaume, M. Mutat. Res. 1987, 186, 43 -72.
170.Hussain, S. P.; Hofseth, L. J.; Harris, C. C. Nat. Rev. 2003, 3, 276-285.
171.Witztum, J. L. Lancet 1994, 344, 793-795.
172.Dijkstra, G.; Moshage, H.; van Dullemen, H. M.; de Jager-Krikken, A. J. Pathol. 1998, 186, 416 -421.
173.Andreadis, A. A.; Hazen, S. L.; Comhair, S. A.; Erzurum, S. C. Free Radic. Biol. Med. 2003, 35, 213 -225.
174.Bauerova, K.; Bezek, A. Gen. Physiol. Biophys. 1999, 18 Spec No, 15-20.
175.Saravanan, R.; Pugalendi, V. Pharmacol. Rep. 2006, 58, 41-47.
176.Saravanan, R.; Viswanathan, P.; Pugalendi, K. V. Life Sci. 2006, 78, 713-718.
177.Senthil, S.; Chandramohan, G.; Pugalendi, K. V. Int. J. Cardiol. 2007, 119, 131-133.
178.Lu, J.; Zheng, Y. L.; Wu, D. M.; Luo, L. et al. Biochem. Pharmacol. 2007, 74, 1078-1090.
179.Shih, Y. H.; Chein, Y. C.; Wang, J. Y.; Fu, Y. S. Neurosci. Lett. 2004, 362, 136-140.
180.Behl, C.; Davis, J. B.; Lesley, R.; Schubert, D. Cell 1994, 77, 817-827.
181.Dalgleish, A. G.; O''Byrne, K. J. Adv. Cancer Res. 2002, 84, 231-276.
182.Coussens, L. M.; Werb, Z. Nature 2002, 420, 860-867.
183.Thun, M. J.; Henley, S. J.; Gansler, T. Novartis Found. Symp. 2004, 256, 6-21.
184.Cominelli, F., Kam, L. Curr. Opin. Gastroenterol. 1993, 9, 534–543.
185.Ishiguro, Y. J. Gastroenterol. 1999, 34, 66-74.
186.Ryu, S. Y.; Oak, M. H.; Yoon, S. K.; Cho, D. I. Planta Med. 2000, 66, 358-360.
187.Subbaramaiah, K.; Michaluart, P.; Sporn, M. B. Cancer Res. 2000, 60, 2399-2404.
188.Winter, C. A.; Risley, E. A.; Nuss, G. W. Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547.
189.Della Loggia, R.; Tubaro, A.; Dri, P.; Zilli, C.; Del Negro, P. Prog. Clin. Biol. Res. 1986, 213, 481-484.
190.Alcaraz, M. J.; Jimenez, M. J. Fitoterapia 1988, 59, 25-38.
191.Chattopadhyay, D.; Arunachalam, G.; Mandal, A. B.; Sur, T. K. J. Ethnopharmacol. 2002, 82, 229-237.
192.Miceli, N.; Taviano, M. F.; Giuffrida, D.; Trovato, A. J. Ethnopharmacol. 2005, 97, 261-266.
193.Deepak, M.; Handa, S. S. Phytother. Res. 2000, 14, 463-465.
194.Suh, N.; Honda, T.; Finlay, H. J.; Barchowsky, A. Cancer Res. 1998, 58, 717-723.
195.Ringbom, T.; Segura, L.; Noreen, Y.; Perera, P.; Bohlin, L. J. Nat. Prod. 1998, 61, 1212-1215.
196.Diaz, A. M.; Abad, M. J.; Fernandez, L.; Recuero, C. Biol. Pharm. Bull. 2000, 23, 1307-1313.
197.Huang, J.; Sun, Y.; Lu, S. Chinese journal of integrated traditional and Western medicine (in Chinese) 1999, 19, 296-298.
198.Liu, X. S.; Jiang, J. Planta Med. 2007, 73, 1192 -1194.
199.Andersson, D.; Liu, J. J.; Nilsson, A.; Duan, R. D. Anticancer Res. 2003, 23, 3317-3322.
200.Zhang, G. P.; Lu, Y. Y.; Lv, J. C.; Ou, H. J. China journal of Chinese materia medica (in Chinese) 2006, 31, 141-144.
201.Zhang, W.; Li, Y.; Zhang, G. P.; Lu, J.; Ou, H. Journal of Chinese medicinal materials (in Chinese) 2005, 28, 297-301.
202.Hsu, Y. L.; Kuo, P. L.; Lin, C. C. Life Sci. 2004, 75, 2303-2316.
203.Lai, M. Y.; Leung, H. W.; Yang, W. H.; Chen, W. H.; Lee, H. Z. Anticancer Res. 2007, 27, 145 -153.
204.Kassi, E.; Papoutsi, Z.; Pratsinis, H.; Aligiannis, N. J. Cancer Res. Clin. Oncol. 2007, 133, 493-500.
205.Harmand, P. O.; Duval, R.; Delage, C.; Simon, A. Int. J. Cancer 2005, 114, 1-11.
206.Kim, D. K.; Baek, J. H.; Kang, C. M.; Yoo, M. A. Int. J. Cancer 2000, 87, 629-636.
207.Liu, J.; Liu, Y.; Klaassen, C. D. J. Ethnopharmacol. 1994, 42, 183-191.
208.Liu, J.; Liu, Y.; Mao, Q.; Klaassen, C. D. Fundam. Appl. Toxicol. 1994, 22, 34-40.
209.Lin, C. N.; Chung, M. I.; Gan, K. H. Planta Med. 1988, 54, 222.
210.You, H. J.; Choi, C. Y.; Kim, J. Y.; Park, S. J. FEBS Lett. 2001, 509, 156-160.
211.Ikeda, Y.; Murakami, A.; Ohigashi, H. Biochem. Pharmacol. 2005, 70, 1497-1505.
212.Ishida, M.; Okubo, T.; Koshimizu, K.; Daito, H. Chemical Abs. 1990, 113, 12173.
213.Ikeda, Y.; Murakami, A.; Fujimura, Y.; Tachibana, H. J. Immunol. 2007, 178, 4854 -4864.
214.Moon, P.-D.; Lee, B.-H.; Jeong, H.-J.; An, H.-J.; Park, S.-J.; Kim, H.-R.; Ko, S.-G.; Um, J.-Y.; Hong, S.-H.; Kim, H.-M. Eur. J. Pharmacol. 2007, 555, 218-225.