| 研究生: |
邱智揚 Chiu, Chih-Yang |
|---|---|
| 論文名稱: |
日本黃柏葉部之成分研究 The Constituents of the leaves of Phellodendron japonicum Maxim. |
| 指導教授: |
吳天賞
Wu, Tian-Shung |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2004 |
| 畢業學年度: | 92 |
| 語文別: | 中文 |
| 論文頁數: | 126 |
| 中文關鍵詞: | 日本黃柏 |
| 外文關鍵詞: | Phellodendron japonicum Maxim. |
| 相關次數: | 點閱:128 下載:5 |
| 分享至: |
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將陰乾的日本黃柏(Phellodendron japonicum Maxim.)葉部,以甲醇熱迴流萃取、過濾,濾液經減壓濃縮後,再利用氯仿與水進行分配萃取,得到氯仿層及水層。各劃分層利用管柱層析、薄層層析、高效能液相層析及再結晶等方法分離純化。目前共分離得到36個化合物,其中33個化合物經光譜分析,確定其化學結構為:Flavonoids:phellamurin、amurensin、quercetin、(2R)-phellodensin-F、phellodensin-A、phellodensin-B、6'-O-acetyl amurensin、6'-O-acetyl phellamurin等8個化合物;Coumarins:umbelliferone、scopoletin、scoparone、esculetin、columbianetin等5個化合物;Benzenoids:benzoic acid、vanillic acid、methylparaben、methyl p-anisate、p-hydroxybenzoic acid、p-coumaric acid、methyl p-hydroxycinnamate、methyl caffeate、p-hydroxybenzaldehyde、caffeic acid、phellojaponin-A等11個化合物;Triterpenoids:lupenone、3-epilupeol、friedelin、β-sitosterol等4個化合物;Amides:N-p-coumaroyltyramine、N-trans-cinnamoyltyramine等2個化合物;Alkaloids:rutaecarpine、3-formylindole等2個化合物;Ionone:grasshopperketone等1個化合物。其中6'-O-acetyl amurensin、6'-O-acetyl phellamurin、(2R)-phellodensin-F、phellojaponin-A等四個為天然界首次分離得到之新化合物。
Four new compounds, 6'-O-acetyl amurensin, 6'-O-acetyl phellamurin, (2R)-phello- densin-F and phellojaponin-A, together with twenty-nine known compounds: Flavonoids: amurensin, phellamurin, quercetin, phellodensin-A, phellodensin-B; Coumarins: umbelliferone, columbianetin, scopoletin, scoparone, esculetin; Benzenoids: benzoic acid, vanillic acid, methylparaben, methyl p-anisate, p-hydroxybenzoic acid, p-coumaric acid, methyl p-hydroxycinnamate, methyl caffeate, p-hydroxybenzaldehyde, caffeic acid; Triterpenoids: lupenone, 3-epilupeol, friedelin, β-sitosterol; Alkaloids: rutaecarpine, 3-formylindole; Amides: N-p-coumaroyltyramine, N-trans-cinnamoyltyramine and Ionone: grasshopperketone were isolated from the leaves of Phellodendron japonicum Maxim. Their structures were determined by 1H-, 13C-, 2D-NMR and MS spectroscopic analyses.
1. 北村四郎, 村田源共著; “原色日本植物圖鑑”; 本木編[I]; 1989; p.314; 保育社; 日本。
2. 國家中醫藥管理局中華本草編委會; “中華本草”; 第四冊; 1999; p.949; 上海科學技術出版社; 上海。
3. http://www.bbg.org/index.html.
4. Yang, H. C.; Chang, H. H.; Weng, T. C.; “Influence of several Chinese drugs on the growth of some pathologic organisms”; J. Formosan Med. Assoc.; 52; 1953; 109-112.(C.A. 47:8175c; 1953)
5. Hsu, H. Y.; “Antibacterial activities of the non-alkaloidal portion of the aqueous extracts of Huang-Lien and Huang-Pai (Phellodendron wilsonii)”; J. Taiwan Pharm. Assoc.; 6; 1954; 2-6.(C.A. 50:1217b; 1954)
6. Kurokawa, M.; Nagasaka, K.; Hirabayashi, T.; Uyama, S.; Sato, H.; Kageyama, T.; Kadota, S.; Ohyama, H.; Hozumi, T.; “Efficacy of traditional herbal medicines in combination with acyclovir against herpes simplex virus type 1 infection in vitro and in vivo”; Antiviral Res.; 27; 1995; 19-37.
7. Namba, T.; Shiraki, K.; Kurokawa, M.; “Development of antiviral agents from traditional medicines”; Int. Congr. Ser.; 1157; 1998; 67-87.(C.A. 130:242197; 1999 )
8. Park, K. S.; Kang, K. C.; Kim, J. H.; Adams, D. J.; Johng, T. N.; Paik, Y. K.; “Differential inhibitory effects of protoberberines on sterol and chitin biosyntheses in Candida albicans”; J. Antimicrob. Chemother.; 43; 1999; 667-674.
9. Kim, D. H.; Song, M. J.; Bae, E. A.; Han, M. J.; “Inhibitory effect of herbal medicines on rotavirus infectivity”; Biol. Pharm. Bull.; 23; 2000; 356-358.
10. Xian, G.; Liang, B.; “Experimental observation on bactericidal efficacy of compound disinfectant solution of Chinese drugs and chlorhexidine”; Zhongguo Xiaoduxue Zazhi; 17; 2000; 229-231.
11. Wang, S.; Fan, M.; Bian, Z.; “Study of bacteriostatic activity of Chinese herbal medicines on primary cariogenic bacteria in vitro”; Zhonghua Kouqiang Yixue Zazhi; 36; 2001; 385-387.
12. Wang, L.; Hu, Y.; Tu, P.; Wu, Z.; Zheng, J.; Guo, D.; “Antifungal activity screening on 13 crude drug extracts and chemical constituents”; Zhongcaoyao; 32; 2001; 241-244.
13. Huang, Y.; Xie, S.; Zhang, Y.; “Lotion for treating tinea pedis”; Zhongcayao; 32; 2001; 127-128.
14. He, Q.; Guo, G.; Guo, Y.; Zhao, B.; Chen, W.; “Studies on extraction process for preparation of eczema spray”; Zhongcayao; 32; 2001; 503-506.
15. Guo, Z.; Guo, S.; He, K.; Liu, H.; Pan, S.; “Determination of contents of flavonol glycosides in the leaves of Phellodendron chinense Schneid. and study of their fungistasis”; Jinan Daxue Xuebao; 23; 2002; 64-66.
16. Furusawa, Y.; Kurosawa, Y.; Chuman, I.; “Trypsin inhibitor in oriental drug plants and its antiinflammatory effect”; Nippon Nogei Kagaku Kaishi; 47; 1973; 359-365.(C.A. 80:240e; 1973)
17. Otsuka, H.; Tsukui, M.; Matsuoka, T.; Goto, M.; Fujimura, H.; Hiramatsu, Y.; Sawada, T.; “Antiinflammatory screening by a fertile egg method”; Yakugaku Zasshi; 94; 1974; 796-801.
18. Moon, C. K.; Sim, K. S.; Lee, S. H.; Park, K. S.; Yun,
Y. P.; Ha, B. J.; Lee, C. C.; “Antitumor activity of some phytobased polysaccharides and their effects on the immune function”; Arch. Pharmacol. Res.; 6; 1983; 123-131.(C.A. 100:132269n; 1983)
19. Kondo, Y.; Suzuki, H.; “Suppression of tumor cell growth by berberrubine, a pyrolyzing artifact of berberine”; Shoyakugaku Zasshi; 45; 1991; 35-39.(C.A. 115:84983b; 1991)
20. Piungki, M.; “Experimental investigation on the influence of the drugs employed in Chinese medicine as antidiabetica on the blood sugar of rabbits”; Folia Pharmacol. Japan.; 11; 1930; 181-187.(C.A. 25:12862; 1930)
21. Noriyuki, S.; Shigeo, H.; “The mechanism of the blood
sugar reducing action of Phellodendron lactone”; Keijo J. Med.; 3; 1932; 333-339.(C.A. 26:60705; 1932)
22. Li, L.; Ye, J.; “Expectorant activity of volatile oil and myrcene in the fruit of Phellodendron amurense”; Yaoxue Tongbao; 17; 1982; 304-305.
23. Hohin, G.; “The pharmacological action of the lactone obtained from Phellodendron amurense”; Keijo J. Med.; 3; 1932; 60-87.(C.A. 26:48812; 1932)
24. Noriyuki, S.; Shigeo, H.; “The blood pressure depressant action of Phellodendron lactone”; Keijo J. Med.; 3; 1932; 160-174.(C.A. 26:48815; 1932)
25. Wada, K.; Yagi, M.; Matsumura, A.; Sasaki, K.; Sakata, M.; Haga, M.; “Isolation of limonin and obacunone from Phellodendri cortex shorten the sleeping time induced by α-chloralose-urethane”; Chem. Pharm. Bull.; 38; 1990; 2332-
2334.
26. Hino, K.; Yamaguchi, S.; Ida, Y.; Satoh, Y.; Maoka, T.; Itoh, Y.; “Antioxidative activities of constituents in Phellodendron amurense bark”; Igaku to Seibutsugaku; 131; 1995; 59-62.(C.A. 124:719; 1995)
27. Wu, T. S.; Hsu, M. Y.; Kuo, P. C.; Sreenivasulu, B.; Damu, A. G.; Su, C. R.; Li, C. Y.; Chang, H. C.; “Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity”; J. Nat. Prod.; 66; 2003; 1207-1211.
28. Haller, H. L.; “Insecticidal properties of the fruit of Phellodendron spp.”; J. Econ. Entomol.; 33; 1940; 941.(C.A. 35:15732; 1940)
29. Sullivan, W. N.; Schechter, M. S.; Haller, H. L.; “Insecticidal tests with Phellodendron amurense extractive and several of its fraction”; J. Econ. Entomol.; 36; 1943; 937-938.(C.A. 38:30496; 1943)
30. Schechter, M. S.; Haller, H. L.; “The insecticidal principle in the fruit of the Amur cork tree”; J. Org. Chem.; 8; 1943; 194-197.
31. Kazutaka, Y.; Takeshi, S.; Akihito, K.; Manabu, S.; Suzukichi, I.; “A general method of detecting effective fraction and its application to 24 species of insecticidal plants”; Botyu. Kagaku.; 15; 1950; 62-70.(C.A. 44:10245h; 1950)
32. Kawaguchi, H.; Kim, M.; Ishida, M.; Ahn, Y. J.; Yamamoto, T.; Yamaoka, R.; Kozuka, M.; Goto, K.; Takahashi, S.; “Several antifeedants from Phellodendron amurense against Reticulitermes speratus”; Agric. Biol. Chem.; 53; 1989; 2635-2640.
33. Su, R. H.; Kim, M.; Yamamoto, T.; Takahashi, S.; “Antifeeding constituents of Phellodendron chinense fruit against Reticulitermes speratus”; Nippon Noyaku Gakkaishi; 15; 1990; 567-572.(C.A. 114:160748; 1990)
34. Su, R. H.; Kim, M.; Nakajima, S.; Takahashi, S.; Liu, M.; “Amides from the fruits of Phellodendron chinense”; Zhiwu Xuebao; 36; 1994; 817-820.
35. Miyazawa, M.; Fujioka, J.; Ishikawa, Y.; “Insecticidal compounds from Phellodendron amurense active against Drosophila melanogaster”; J. Sci. Food Agric.; 82; 2002; 830-833.
36. Ki, K. B.; Tanaka, M.; Maehara, T.; Jung, C. C.; “Effects of cortex Phellodendri and berberine on experimental liver injury in mice”; Wakan Iyaku Gakkaishi; 5; 1988; 406-407.(C.A. 111:70924; 1988)
37. Mori, H.; Fuchigami, M.; Inoue, N.; Nagai, M.; Koda, A.; Nishioka, I.; “Principle of the bark of Phellodendron amurense to suppress the cellular immune response”; Planta Med.; 60; 1994; 445-449.
38. Yotsumoto, H.; Yanagita, T.; Yamamoto, K.; Ogawa, Y.; Cha, J. Y.; Mori, Y.; “Inhibitory effects of Oren-gedoku-to and its components on cholesteryl ester synthesis in cultured human hepatocyte HepG2 cells. Evidence from the cultured HepG2 cells and in vitro assay of ACAT”; Planta Med.; 63; 1997; 141-145.
39. Bonte, F.; Dumas, M.; Saunois, A.; Meybeck, A.; “Phospholipase A2 inhibition by alkaloid compounds from Phellodendron amurense Bark”; Pharm. Biol.; 37; 1999; 77-79.
40. Park, J. I.; Shim, J. K.; Do, J. W.; Kim, S. Y.; Seo, E. K.; Kwon, H. J.; Lee, T. K.; Kim, J. K.; Choi, D. Y.; Kim, C. H.; “Immune-stimulating properties of polysaccharides from Phellodendri cortex (Hwangbek)”; Glycoconjugate J.; 16; 1999; 247-252.
41. Chen, H. Y.; Wu, T. S.; Hou, Y. C.; Kuo, S. C.; Chao, P. L.; “Determination and disposition kinetics of phellamurin metabolites in rat brain”; J. Food Drug Anal.; 9; 2001; 127-131.
42. Chen, H. Y.; Wu, T. S.; Su, S. F.; Kuo, S. C.; Chao, P. D.; “Marked decrease of cyclosporin absorption caused by phellamurin in rats”; Planta Med.; 68; 2002; 138-141.
43. Ikuta, A.; Nakamura, T.; Urabe, H.; “Indolopyridoquinazoline, furoquinoline and canthinone type alkaloids from Phellodendron amurense callus tissues”; Phytochemistry; 48; 1998; 285-291.
44. Ikuta, A.; Urabe, H.; Nakamura, T.; “A new indolopyridoquinazoline-type alkaloid from Phellodendron amurense callus tissues”; J. Nat. Prod.; 61; 1998; 1012-1014.
45. Kunitomo, J. I.; “Alkaloids of Phellodendron amurense
var. japonicum”; Yakugaku Zasshi; 81; 1961; 1370-1372.
46. Wu, T. S.; Hsu, M. Y.; Damu, A. G.; Kuo, P. C.; Su, C. R.; Li, C. Y.; Sun, H. D.; “Constituents of leaves of Phellodendron chinense var. glabriusculum”; Heterocycles; 60; 2003; 397-404.
47. Sheridan, H.; Bhandari, P.; “Cathin-6-one from the root bark of Phellodendron chinense”; Planta Med.; 58; 1992; 299.
48. Miyaichi, Y.; Segi, H.; Tomimori, T.; “Constituents of the leaves of Phellodendron japonicum Maxim.”; Yakugaku Zasshi; 114; 1994; 186-199.
49. Ida, Y.; Satoh, Y.; Ohtsuka, M.; Nagasao, M.; Shoji, J.; “Phenolic constituents of Phellodendron amurense bark”; Phytochemistry; 35; 1994; 209-215.
50. Su, R.; Kim, M.; Kawaguchi, H.; Yamamoto, T.; Goto, K.; Taga, T.; Miwa, Y.; Kozuka, M.; Takahashi, S.; “Triterpenoids from the fruits of Phellodendron chinense Schneid.: the stereostructure of niloticin”; Chem. Pharm. Bull.; 38; 1990; 1616-1619.
51. Kishi, K.; Yoshikawa, K.; Arihara, S.; ”Limonoids and protolimonoids from the fruits of Phellodendron amurense”; Phytochemistry; 31; 1992; 1335-1338.
52. Gray, A. I.; Bhandari, P.; Waterman, P. G.; “New protolimonoids from the fruits of Phellodendron chinense”; Phytochemistry; 27; 1998; 1805-1808.
53. Miyake, M.; Inaba, N.; Ayano, S.; Ozaki, Y.; Maeda, H.; Ifuku, Y.; Hasegawa, S.; “Limonoids in Phellodendron amurense”; Yakugaku Zasshi; 112; 1992; 343-347.
54. Bodalski, T.; Lamer, E.; “Hyperoside occurrence in the leaves of Phellodendron japonicum”; Dissertationes Pharm.; 16; 1964; 67-70.(C.A. 62:817d; 1962)
55.呂建興; “關黃柏葉部之成分研究”; 國立成功大學化學研究所碩士論文; 2002。
56. Wu, W. N.; Mitscher, L. A.; Beal, J. L.; “A note on the isolation and identification of the quaternary alkaloids of Phellodendron wilsonii”; Lloydia; 39; 1976; 249-252.
57. Ikuta, A.; Nakamura, T.; “Canthin-6-one from the roots of Phellodendron amurense”; Planta Med.; 61; 1995; 581-582.
58. Su, R.; Kim, M.; Kawaguchi, H.; Takahashi, S.; Liu, M.; “A new triterpenoid in the fruits of Phellodendron chinense Schneid.”; Zhiwu Xuebao; 33; 1991; 801-806.
59. Tomita, M.; Nakano, T.; “Alkaloids of Phellodendron amurense”; Chem. Pharm. Bull.; 5; 1957; 10-12.(C.A. 51:15063d; 1957)
60.王美玲; “台灣黃柏莖皮成分之研究”; 靜宜女子文理學院應用化學研究所碩士論文; 1989。
61. Lu, S. T.; J. Taiwan Pharm. Assoc.; 14; 1962; 9.
62. Glyzin, V. I.; Bankovskii, I. A.; Sheichenko, V. I.; “New flavonol glycosides from Phellodendron lavallei and Phellodendron amurense”; Khim. Prir. Soedin.; 6; 1970; 762-763.(C.A. 74:108104d; 1970)
63. Shevchuk, O. I.; Maksyutina, N. P.; Litvinenko, V. I.; “The flavonoids of Phellodendron sachalinense and Phellodendron amurense”; Khim. Prir. Soedin.; 4; 1968; 77-
82.(C.A. 69:41709f; 1968)
64. Bodalski, T.; Lamer, E.; “Phellodendron occurrence in Phellodendron amurense leaves”; Acta Polon. Pharm.; 22; 1965; 281.(C.A. 63:16767b; 1965)
65.徐美玉; “台灣黃柏、淨禿黃柏及川黃柏葉部之成分研究”; 國立成功大學化學研究所碩士論文; 1998。
66. Nishioka, I.; “Sterols from Phellodendron amurense. Isolation of 7-dehydrostigma- sterol”; Yakugaku Zasshi; 78; 1958; 1432-1434.(C.A. 53:8198c; 1958)
67. Nelson, E. K.; J. Am. Chem. Soc.; 60; 1938; 920-921.
68. Shimo, K.; Chem. Zentralbl.; 93; 1922; 361.
69. Kunitomo, J.; “Alkaloids of Phellodendron amurense”; Yakugaku Zasshi; 82; 1962; 611-613.(C.A. 57:4760d; 1962)
70. Wu, T. S.; “The constituents of the leaves of Phellodendron wilsonii Hayata et Kanehira”; J. Chin. Chem. Soc.; 26; 1979; 25-28.
71. Nishioka, T.; Watanabe, J.; Kawabata, J.; “Isolation and activity of N-p-coumaroyltyr- amine, an α-glucosidase inhibitor in Allium fistulosum”; Biosci. Biotech. Biochem.; 61; 1997; 1138-1141.
72. Mabry, T. J.; Markham, K. R.; Thomas, M. B.; “The systematic identification of flavonoids”; Springer Verlag; New York; 1970.
73. Webb, K. S.; Ruszkay, S. J.; ”Oxidation of aldehydes with oxone in aqueous acetone”; Tetrahedron; 54; 1998; 401-410.
74. Iwagawa, T.; Takahashi, H.; Munesada, K.; Hase, T.; “A phenol alloside from Viburnum wrightii”; Phytochemistry; 23; 1984; 468-469.
75. Bolzani, V. S.; Trevisan, M. V.; Young, M. C.; “Caffeic acid esters and triterpenes of Alibertia macrophylla”; Phytochemistry; 30; 1991; 2089-2091.
76. Waterman, P. G.; Ampofo, S.; “Dammarane triterpenes from the stem bark of Commiphora dalzielii”; Phytochemistry; 24; 1985; 2925-2928.
77. Stermitz, F. R.; Sharifi, I. A.; “Alkaloids of Zanthoxylum monophyllum and Zanthoxylum punctatum”; Phytochemistry; 16; 1977; 2003-2006.
78. 徐任生編; “天然產物化學”; 1993; p.649-651; 科學出版社; 北京。
79. Miyase, T.; Ueno, A.; Takizawa, N.; Kobayashi, H.; Karasawa, H.; “Studies on the glycosides of Epimedium grandiflorum var. thunbergianum”; Chem. Pharm. Bull.; 35; 1987; 1109-1117.
80. Frolova, V. I.; Bankovski, A. I.; Volynskaya, M. B.; “Chemical study of the alkaloids of Phellodendron lavallei”; Med. Prom.; 12; 1958; 16-18. (C.A. 53:11536e; 1958)
81. Tomita, M.; Kunitomo, J.; “Alkaloids of Phellodendron amurense var. sachalinense”; Chem. Pharm. Bull.; 5; 1957; 1444-1447.(C.A. 53:7219a; 1957)