Title

金絲草成分之研究

Translated Titles

Studies on the constituents of Pogonatherum crinitum (Thunb.) Kunth

Authors

陳克君

Key Words

金絲草 ; luteolin 6-C-β-boivinopyranoside ; 6-trans-(2''''-O-α-rhamnopyranosyl)ethenyl-5,7,3'',4''-tetrahydroxyflavone ; 一氧化氮 ; 小鼠巨噬細胞株 ; Pogonatherum crinitum ; luteolin 6-C-β-boivinopyranoside ; 6-trans-(2''''-O-α-rhamnopyranosyl)ethenyl-5,7,3'',4''-tetrahydroxyflavone ; nitric oxide ; RAW 264.7

PublicationName

臺北醫學大學生藥學研究所學位論文

Volume or Term/Year and Month of Publication

2006年

Academic Degree Category

碩士

Advisor

李宗徽

Content Language

繁體中文

Chinese Abstract

金絲草 (Pogonatherum crinitum) 在傳統台灣民間用藥的使用上已行之有年,相關記載咸認其具有消炎、解熱、利尿及止血等主要功能,並已應用於尿道炎、膀胱炎、腎炎和肝炎等多種疾病的治療。過去,我們嘗試以脂多醣 (lipopolysaccharide, LPS) 刺激小鼠巨噬細胞株 (RAW 264.7) 產生大量NO之模式,對金絲草之萃取物進行篩檢,結果顯示金絲草的甲醇萃出物,在50μg/mL的濃度下,可完全抑制NO的產生,且不具任何細胞毒性。鑑於此,遂以金絲草為材料,針對其成分進行一系列的分析、分離、純化與構造解析,計分離、決定出十六個化合物,包括: 二個酚類化合物 (1, 16)、八個黃酮類化合物 (2–10)、一個雙倍半帖類化合物 (11)、一個二?類化合物 (12)、一個固醇類化合物 (13) 和二個去鎂葉綠酸鹽化合物 (14, 15)。其結構經各種光譜的解析鑑定為: 3,4-dihydroxy-cis-cinnamic acid methyl ester (1)、luteolin 6-C-β-fucopyranoside (2)、kaempferol 3-O-α-L-rhamnopyranoside (3)、luteolin 6-C-β-boivinopyranoside (4)、luteolin (5)、kaempferol (6)、luteolin 6-C-β-glucopyranoside (7)、rutin (8)、kaempferol 3-O-rutinoside (9)、6-trans-(2''-O-α-rhamnopyranosyl) ethenyl-5,7,3',4'-tetrahydroxyflavone (10)、3,7,11,15,19-pentamethyl-2 -cis-6-trans-eicosadien-l-ol (11)、trans-phytol (12)、β-sitosterol (13)、methyl pheophorbide a (14)、pheophytin a (15) 及1-(3',4' -dihydroxycinnamoyl)cyclopenta-2,3-diol (16),其中化合物4和10為新的化合物。此外,生物活性試驗的結果顯示化合物1、4和6對於脂多醣誘導小鼠巨噬細胞株產生NO有抑制效果,其半抑制濃度分別為13.81、34.29和13.22 μM。

English Abstract

Pogonatherum crinitum has long been used in folk medicine to treat urethritis, cystitis, nephritis, hepatitis and many other inflammatory diseases. It has been found that the whole plant MeOH extracts of P. crinitum inhibited 100% NO production in cultured murine macrophage RAW 264.7 cells stimulated with bacterial lipopolysaccharide (LPS) at a concentration of 50 μg/mL in our preliminary studies. Therefore, we investigated the chemical constituents of P. crinitum. Totally 16 compounds including two phenolics (1, 16), eight flavanoids (2 - 10), one sesterterpene (11), one diterpene (12), one steroid (13), and two pheophorbides (14, 15) were isolated and identified. Their structures were elucidated to be 3,4-dihydroxy-cis-cinnamic acid methyl ester (1), luteolin 6-C-β-fucopyranoside (2), kaempferol 3-O-α-L-rhamno pyranoside (3), luteolin 6-C-β-boivinopyranoside (4), luteolin (5), kaempferol (6), luteolin 6-C-β-glucopyranoside (7), rutin (8), kaempferol 3-O-rutinoside (9), 6-trans-(2''-O-α-rhamnopyranosyl)ethenyl-5,7,3',4' -tetrahydroxyflavone (10), 3,7,11,15,19-pentamethyl-2-cis-6-trans -eicosadien-l-ol (11), trans-phytol (12), β-sitosterol (13), methyl pheophorbide a (14), and pheophytin a (15), and 1-(3',4' -dihydroxycinnamoyl)cyclopenta-2,3-diol (16). Of these compounds identified, 4 and 10 are new. In addition, results of biological tests indicated that 1, 4 and 6 exhibited inhibitions of NO production in cultured murine macrophage RAW 264.7 cells stimulated by bacterial lipopolysaccharide (LPS). The IC50 values for each were 13.81, 34.29 and 13.22 μM, respectively.

Topic Category 醫藥衛生 > 藥理醫學
藥學院 > 生藥學研究所
Reference
  1. 3. Suzuki, R.; Okada, Y.; Okuyama, T. J. Nat. Prod. 2003, 66, 564
    連結:
  2. 4. Ceska, O.; Styles, E.D. Phytochemistry 1984, 23, 1822.
    連結:
  3. 5. Elliger, C. A.; Chan, B.G.; Waiss, A. C.; Lundin, R. E.; Haddon, W. F. Phytochemistry 1980, 19,293.
    連結:
  4. 8. Nabeta, K.; Kadota, G.; Tanj, T. Phytochemistry 1977, 16, 1112.
    連結:
  5. 11. Matsunaga, K.; Shibuya, M.; Ohizumi, Y. J. Nat. Prod. 1994, 57, 1183.
    連結:
  6. 16. Deshmane, S. S.; Dev, S. Tetrahedron 1971, 27, 1109.
    連結:
  7. 22. Kluge, M.; Grambow, H. J.; Sicker, D. Phytochemistry 1997, 44,639.
    連結:
  8. 23. Chung, H. S.; Woo, W.S. J. Nat. Prod. 2001, 64, 1579.
    連結:
  9. 28. Matsunaga, K.; Shibuya, M.; Ohizumi, Y. J. Nat. Prod. 1994, 57, 1734.
    連結:
  10. 29. Praznik, W.; Spies, T.; Hofinger, A. Carbohydr. Res. 1992, 235,231.
    連結:
  11. 31. Ukita, T.; Tamimura, A. Chem. Pharm. Bull. 1961, 9,43.
    連結:
  12. 33. Yoon, J.S.; Lee, M. K.; Sung, S. H.; Kim, Y. C. J. Nat. Prod. 2006, 69,290.
    連結:
  13. 34. Matsunaga, K.; Shibuya, M.; Ohizumi, Y. J. Nat. Prod. 1995, 58,138.
    連結:
  14. 41. Marletta, M. A. J. Biol. Chem. 1993, 268, 12231.
    連結:
  15. 43. Hawiger, J. Immunol. Res. 2001, 23,99.
    連結:
  16. 48. Jackson, D. E.; Dewick, P. M. Phytochemistry 1984, 23, 1029.
    連結:
  17. 50. Ju, Y.; Sacalis J. N.; Still, C. C. J. Agric. Food Chem. 1998, 46, 3785.
    連結:
  18. 55. Chang, Y. C.; Chang, F. R.; Wu, Y. C. J. Chin. Chem. Soc. 2000, 47,373.
    連結:
  19. 57. Wang, P. H.; Lee, S. S. J. Chin. Chem. Soc. 1999, 46,215.
    連結:
  20. 60. Martos, I.; Ferreres, F.; Tomas-Barberan, F. A. J. Agric. Food Chem. 2000, 48, 1498.
    連結:
  21. 61. Deng, Y. R.; Song, A. X.; Wang, H. Q. J. Chin. Chem. Soc. 2004, 51,629.
    連結:
  22. 62. Senatore, F.; D'Agostino, M.; Dini, I. J. Agric. Food Chem. 2000, 48, 2659.
    連結:
  23. 66. Rastrelli, L.; Saturnino, P.; Schettino, O.; Dini, A. J. Agric. Food Chem. 1995, 43, 2020.
    連結:
  24. 67. Kazuma, K; Noda, N; Suzuki, M. Phytochemistry 2003, 62,229.
    連結:
  25. 70. Banthorpe, D. V.; Bilyard, H.; Watson, D. G. Phytochemistry 1985, 24, 2677.
    連結:
  26. 71. Banthorpe, D. V.; Bilyard, H.; Brown, G. D. Phytochemistry 1989, 28, 2109.
    連結:
  27. 74. Gupta M. M.; Shukla Y. N. Phytochemistry 1986, 25, 1423.
    連結:
  28. 76. Lee, C. K.; Lu, C. K.; Kuo, Y. H.; Chen, J. Z.; Sun, G. Z. J. Chin. Chem. Soc. 2004, 51,437.
    連結:
  29. 78. Cheng, H. H.; Wang, H. K.; Ito, J.; Bastow, K. F.; Tachibana, Y.; Nakanishi, Y.; Xu, Z.; Luo, T. Y.; Lee, K. H. J. Nat. Prod. 2001, 64,915.
    連結:
  30. 83. Lin, H. Y.; Shen, S. C.; Chen, Y. C. J Cell Physiol. 2005, 202,579.
    連結:
  31. 86. Du, X.; Low, M. G. Infect Immun. 2001, 69, 3214.
    連結:
  32. 89. O'Brien, J.; Wilson, I.; Orton, T.; Pognan, F. Eur. J. Biochem. 2000, 267, 5421.
    連結:
  33. 參考文獻
  34. 1. Huang, T. C.; Ed. Flora of Taiwan; National Science Council of the Republic of China: Taipei, 2000; Vol. 2, pp. 570-571.
  35. 2. 邱年永著,原色台灣藥用植物圖鑑,南天書局,p.231。
  36. 6. Jain, N.; Ahmad, M.; Kamil, M.; Ilyas, M. Phytochemistry 1991, 30, 1345.
  37. 7. Wenzig, E.; Kunert, O.; Ferreira, D.; Schmid, M.; Schuhly, W.; Bauer, R.; Hiermann, A. J. Nat. Prod. 2005, 68,289.
  38. 9. Colombo, R.; Yariwake, J.H.; Queiroz, E. F.; Ndjoko, K.; Hostettmann, K. J. Chromatogr. A 2005, 29,51.
  39. 10. Besson, E.; Dellamonica, G.; Chopin, J.; Markham, K. R.; Kim, M.; Koh, H. S.; Fukami, H. Phytochemistry 1985, 24, 1061.
  40. 12. Liu, X. T.; Pan, Q.; Shi, Y.; Williams, I. D.; Sung, H. H.; Zhang, Q.; Liang, J. Y.; Ip, N. Y.; Min, Z. D. J. Nat. Prod. 2006, 69,255.
  41. 13. Sharma, S. C.; Tandon, J. S.; Dhar, M. M. Phytochemistry 1975, 14, 1055.
  42. 14. Hanson, S. W.; Crawford, M.; Koker, M. E. S.; Menezes, F. A. Phytochemistry 1976, 15, 1074.
  43. 15. Nishimoto, K.; Ito, M.; Natori, S.; Ohmoto, T. Tetrahedron 1968, 24,735.
  44. 17. Kondo, Y.; Nakajima, K.; Nozoe, S.; Suzuki, S. Chem. Pharm. Bull. 1988, 36, 3147.
  45. 18. 簡雅琳,國立台灣大學食品科技研究所碩士論文,1998。
  46. 19. 林方宜,國立台灣大學食品科技研究所碩士論文,1999。
  47. 20. Fielder, D. A.; Collins, F. W.; Blackwell, B. A.; Bensimon, C.; ApSimon J. W. Tetrahedron lett. 1994, 35,521.
  48. 21. Nagao, T.; Otusta, H.; Kohda, H.; Sato, T.; Yamasaki, K. Phytochemistry 1985, 24, 2959.
  49. 24. Spendley, P. J.; Bird, P. M.; Ride, J. P.; Leworthy D. P. Phytochemistry 1982, 21, 2403.
  50. 25. Seca, A. M.; Cavaleiro, J. A.; Domingues, F. M.; Silvestre, A. J.; Evtuguin, D.; Neto, C. P. J. Agric. Food. Chem. 2000, 48,817.
  51. 26. Matsunaga, K.; Ikeda, M.; Shibuya, M.; Ohizumi, Y. J. Nat. Prod. 1994, 57, 1290.
  52. 27. Otsuka, H.; Takeuchi, M.; Inoshiri, S.; Sato, T.; Yamasaki, K. Phytochemistry 1989, 28,883.
  53. 30. Takahashi, M.; Konno, C.; Hikino, H. Planta Med. 1986, 52,64.
  54. 32. ToKUda, H.; Mastsumto, M.; Konoshima, T.; Kozuka, M.; Nishino, H.; Iwashima, A. Planta Med. 1990, 56,653.
  55. 35. Jain, N.; Alam, M. S.; Kamil, M.; Ilyas, M.; Ali, M. Phytochemistry 1991, 30, 3826.
  56. 36. Dimberg, L. H.; Andersson, R. E.; Gohil, S.; Bryngelsson, S.; Lundgren, L. N. Phytochemistry 2001, 56,843.
  57. 37. Miles, D. H.; Tunsuwan, K.; Chittawong, V.; Hedin, P. A.; Kokpol, U.; Ni, C. Z.; Clardy, J. J. Nat. Prod. 1993, 56, 1590.
  58. 38. Hibbs, J. B.; Taintor, R. R.; Vavrin, Z. Science 1987, 235,473.
  59. 39. Chen, Y. C.; Lin-Shiau, S. Y.; Lin, J. K. J. Cell Physiol. 1998, 177,324.
  60. 40. Gao, P. S.; Kawada, H.; Kasamatsu, T.; Mao, X. Q.; Roberts, M. H.; Miyamoto, Y.; Yoshimura, M.; Saitoh, Y.; Yasue, H.; Nakao, K.; Adra, C. N.; Kun, J. F.; Moro-oka, S.; Inoko, H.; Ho, L. P.; Shirakawa, T.; Hopkin, J. M. Biochem. Biophys. Res. Commun. 2000, 267,761.
  61. 42. Reiling, N.; Ulmer, A. J.; Duchrow, M.; Ernst, M.; Flad, H. D.; Hauschildt, S. Eur. J. Immunol. 1994, 24, 1941.
  62. 44. Seatter, S. C.; Li, M. H.; Bubrick, M. P.; West, M. A. Shock. 1995, 3,252.
  63. 45. 高木村著,台灣民間藥 (1),南天書局,p.32。
  64. 46. 徐順裕著,救人青草藥,元氣齋出版社,p.123。
  65. 47. Silva, F. A.; Borges, F.; Guimaraes, C.; Lima, J. L.; Matos, C.; Reis, S. J. Agric. Food Chem. 2000, 48, 2122.
  66. 49. Sugama, K.; Hayashi, K.; Nakagawa, T.; Mitsuhashi H.; Yoshida, N. Phytochemistry 1983, 23, 1619.
  67. 51. Ahn, M. J.; Kim, C. Y.; Yoon, K. D.; Ryu, M. Y.; Cheong, J. H.; Chin, Y. W.; Kim, J. J. Nat. Prod. 2006, 69,360.
  68. 52. Hua, Y.; Du, Y.; Yu, G.; Chu, S. Carbohydr. Res. 2004, 339, 2083.
  69. 53. Gaidi, G.; Miyamoto, T.; Ramezani, M.; Lacaille-Dubois, M. A. J. Nat. Prod. 2004, 67, 1114.
  70. 54. Mareck, U.; Herrmann, K.; Galensa, R.; Wray, V. Phytochemistry 1991, 30, 3486.
  71. 56. Braca, A.; Politi, M.; Sanogo, R.; Sanou, H.; Morelli, I.; Pizza, C.; De Tommasi, N. J. Agric. Food Chem. 2003, 51, 6689.
  72. 58. Nakamura, T.; Goda, Y.; Sakai, S.; Kondo, K.; Akiyama, H.; Toyada, M. Phytochemistry 1998, 49, 2097.
  73. 59. Gil. R. R.; Lin, L. Z.; Chai, H. B.; Pezzuto, J. M.; Cordell, G. A. J. Nat. Prod. 1995, 58,848.
  74. 63. Kumazawa, T.; Kimura, T.; Matsuba, S.; Sato, S.; Onodera, J. Carbohydr. Res. 2001, 334,183.
  75. 64. Calzada, F.; Cedillo-Rivera, R.; Mata, R. J. Nat. Prod. 2001, 64,671.
  76. 65. Sang, S.; Cheng, X.; Zhu, N.; Stark, R. E.; Badmaev, V.; Ghai, G.; Rosen, R.T.; Ho, C. T. J. Agric. Food Chem. 2001, 49, 4478.
  77. 68. Sang, S.; Lapsley, K.; Jeong, W. S.; Lachance, P. A.; Ho, C. T.; Rosen, R. T. J. Agric. Food Chem. 2002, 50, 2459.
  78. 69. Ding, Z.; Zhou, J.; Tan, N.; Planta Med. 1999, 65,578.
  79. 72. Toyoda, M.; Asahina, M.; Fukawa, H.;Shimizu, T. Tetrahedron lett. 1965, 55, 4879.
  80. 73. Itoh, D.; Kawano, K.; Nabeta, K. J. Nat. Prod. 2003, 66,332.
  81. 75. Chiang, Y. M.; Liu, H. K.; Lo, J. M.; Chien, S.C.; Chan, Y. F.; Lee, T. H.; Su, J. K.; Kuo, Y. H. J. Chin. Chem. Soc. 2003, 50,161.
  82. 77. Ma, L.; Dolphin, D Tetrahedron. 1996, 52, 849
  83. 79. Kobayashi, M.; Ishida, K.; Terabayashi, S.; Mitsuhashi, H. Chem. Pharm. Bull. 1991, 39, 3348.
  84. 80. Wang, H.; Nair, M. G.; Strasburg, G. M.; Booren, A. M.; Gray, J. I. J. Nat. Prod. 1999, 62,86.
  85. 81. Kim, H. K.; Cheon, B. S.; Kim, Y. H.; Kim, S. Y.; Kim, H. P. Biochem Pharmacol. 1999, 58,759.
  86. 82. Cimanga, R. K.; Kambu, K.; Tona, L.; Hermans, N.; Apers, S.; Totte, J.; Pieters, L.; Vlietinck, A. J. J. Ethnopharmacol. 2006,28. (in press)
  87. 84. Kim, J. S.; Lee, H. J.; Lee, M. H.; Kim, J.; Jin, C.; Ryu, J. H. Planta Med. 2006, 72,65.
  88. 85. Schroder, N. W.; Opitz, B.; Lamping, N.; Michelsen, K. S.; Zahringer, U.; Gobel, U. B.; Schumann, R. R. J Immunol. 2000, 165, 2683.
  89. 87. Gupta, S.; Afaq, F.; Mukhtar, H. Oncogene. 2002, 21, 3727.
  90. 88. Kim, S. J.; Park, H.; Kim, H. P. Arch Pharm Res. 2004, 27,937.
Times Cited
  1. 詹桂榕(2007)。白頭翁素抑制人類正常黑色素細胞內酪氨酸酵素活性與酪氨酸相關酵素表現。臺北醫學大學醫學科學研究所學位論文。2007。1-73。