The Structure of Phenolic Compounds and Their Antibiotic Activities in Umbilicaria vellea

Umbilicaria vellea 중 페놀성 화합물의 구조 및 항균활성

  • 민태진 (동국대학교 이과대학 화학과) ;
  • 배강규 (동국대학교 이과대학 화학과)
  • Published : 19960900

Abstract

In order to identify antibiotic substances in the extract of a lichen, Umbilicaria vellea, the extract was chromatographed and two compounds were isolated. Compound I which showed antifungal and antibacterial activities, melted around 129∼132$^{\circ}C$ and showed UV absorption at 217, 265 and 300 nm. It showed a molecular ion at m/z 196. Its molecular formular was confirmed to be $C_{10}H_{12}O_4$ from elemental analysis. From its IR and NMR data it was identified to be ethyl 2,4-dihydroxy-6-methyl benzoate. Compound II melted around 58∼59$^{\circ}C$ and showed UV absorption at 212, 276 and 282 nm. It showed a molecular ion at m/z 124 and molecular formular was confirmed to be $C_7H_8O_2.$ From the analysis of its IR and NMR spectra it was identified to be 5-methyl-1,3-benzenediol.

지의류에 속하는 Umbiliciaria vellea 중 에탄올 분획의 항균활성 물질을 규명하기 위하여 silica겔 컬럼 크로마토그래피 및 재결정법으로 화합물 I과 II를 순수히 분리정제하여 그 구조와 항균활성을 측정하였다. 정제된 화합물I은 Cryptococcus neoformance 등의 균에 대한 항진균활성과, Pseudomonas aeruginosa등의 균에 대한 항세균 활성이 있었다. 이 물질의 녹는점은 129~132$^{\circ}C$였고, 217, 265 및 330 nm의 UV 최대흡광을 보였다. 그리고 EI-mass에서 측정된 분자이온은 m/z 196이었고, 원소분석 결과 분자식은 $C_{10}H_{12}O_4$였으며 IR 및 NMR 스펙트라로부터 이 물질이 ethyl 2,4-dihydroxy-6-methyl benzoate임을 확인하였다. 화합물 II의 녹는점은 58~59$^{\circ}C$였고, 212, 276 및 282 nm의 UV 최대흡광을 보였다. 이 물질의 분자이온은 m/z 124였고, $C_7H_8O_2$의 분자식을 갖는 5-methyl-1,3-benzenediol임을 확인하였다.

Keywords

References

  1. The Korean Society of Mycology News Letter v.5 no.1 Jung, H. S.
  2. Kor. J. Mycol. v.18 no.4 Lee, T. S.
  3. The Korean Mushrooms Park, W. H.
  4. Dongeibogam Namsandang Hu, J.
  5. Mushroom Chemistry and Biochemistry Mizuno, T.
  6. Kor. J. Mycol. v.20 no.2 Ahn, D. K.
  7. Plants in the World Asahi Newpaper Co. Ito, T.
  8. Pro. Natl. Acad. Sci. USA v.35 Kavanagh, F.;Hervey, A.;Robbins, W. J.
  9. J. Antibiotics v.33 no.5 Anke, T.;Kupka, J.;Schramm, G.;Steglich, W.
  10. J. Chem. Soc. Jones, E. R. H.;Stephenson, J. S.;Turner, W. B.;Whiting, M. C.
  11. J. Chem. Soc. Cambie, R. C.;Hirschberg, A.;Jones, E. R. H.;Lowe, G.
  12. J. Am. Chem. Soc. v.89 no.5 Kepler, J. A.;Wall, M. E.;Mason, J. E.;Basset, C.;McPhail, A. T.;Sim, G. A.
  13. Can. J. Microbiol. v.17 Allbutt, A. D.;Ayer, W. A.;Brodie, H. J.;Johri, B. N.;Taube, H.
  14. J. Antibiotics v.30 no.3 Anke, T.;Oberwinkler, F.
  15. J. Antibiotics v.28 no.1 Umezawa, H.;Takeuchi, T.;Iinuma, H.;Ito, M.;Ishizuka, M.;Kurakata, Y.;Umeda, Y.;Nakanish, Y.;Nakamura, T.;Obayashi, A.;Tanabe, O.
  16. J. Antibiotics v.30 no.10 Anke, T.;Oberwinkler, F.
  17. J. Antibiotics v.31 no.8 Quack, W.;Anke, T.;Oberwinkler, F.
  18. J. Antibiotics v.32 no.11 Anke, T.;Hecht, H. J.;Schramm, G.;Steglich, W.
  19. J. Antibiotics v.32 no.2 Kupka, J.;Anke, T.;Oberwinkler, F.
  20. Tetrahedron Lett. v.23 Midland, S. L.;Izac, R. R.;Wing, R. M.;Zaki, A. I.;Munnecke, D. E.;Sims, J. J.
  21. J. Antibiotics v.36 no.4 Iinuma, H.;Nakamura, H.;Naganawa, H.;Masuda, T.;Takano, S.;Takeuchi, T.;Umezawa, H.;Iitaka, Y.;Obayashi, A.
  22. J. Antibiotics v.39 no.4 Kida, T.;Shibai, H.;Seto, H.
  23. J. Antibiotics v.40 no.2 Hara, M.;Yoshida, M.;Morimoto, M.;Nakano, H.
  24. J. Antibiotics v.41 no.12 Heim, J.;Anke, T.
  25. Chem. Pharm. Bull. v.36 no.7 Takahashi, A.;Kusano, G.;Ohta, T.;Nozoe, S.
  26. J. Antibiotics v.45 no.1 Erkel, G.;Anke, T.
  27. Chem. Pharm. Bull. v.22 Nishikawa, Y.;Ohki, K.;Takahashi, K.;Fukuoka, F.;Emori, M.
  28. Chem. Pharm. Bull. v.29 no.11 Nishikawa, Y.;Ohno, H.
  29. Iwate Igaku Zasshi v.34 no.4 Kim, C. H.
  30. Iwate Igaku Zasshi v.34 no.5 Kim, C. H.
  31. Kor. J. Nutr. v.16 no.1 Kim, C. H.
  32. Kor. J.Nutr. v.20 no.1 Kim, C. H.;Hiroyasu, F.
  33. Chem. Express v.6 no.8 Nakatani, N.;Kim, C. H.;Kikuzaki, H.;Muroi, T.;Matsumura, Y.
  34. Yakugaku Zasshi v.90 no.12 Fujikawa, F.;Hihayama, T.;Nakamura, Y.;Suzuk, M.;Dio, M.;Niki, C.
  35. Yakugaku Zasshi v.90 no.10 Fujikawa, F.;Hirai, K.
  36. Kor. J. Mycol. v.23 no.1 Min, T. J.;Kim,E. M.;Lee, S. J.;Bae, K. G.
  37. Kor. J. Mycol. v.23 no.1 Park, S. S.;Lee, K. D.;Min, T. J.
  38. Kor. J. Mycol. v.23 no.1 Lee, K. D.;Su, Y. C.;Park, S. S.;Min, T.
  39. Kor. J. Mycol. v.23 no.1 Yoon, J. O.;Min, T. J.;Yoon, H.
  40. Kor. J. Mycol. v.23 no.2 Park, S. S.;Lee, K. D.;Min, T. J.
  41. Kor. J. Mycol. v.24 no.1 Min, T. J.;Kim, E. M.;You, S. H.
  42. Am. J. Clin. Pathol. v.45 no.4 Bauer, A.;Kirby, W.;Sherris, J.;Turck, M.
  43. Diagnostic Microbiology(4th Ed.) Koneman, E.;Allen, S.;Janda, W.;Schreckenberger, P.;Winn, W.
  44. Antibiotics in Laboratory Medicine(3rd Ed.) Lorian, V.
  45. Hwang, S. C.
  46. The Merk Index(11th Ed.) Budavari, S.
  47. Yakugaku Zasshi v.59 Fujikawa, F.
  48. Yakugaku Zasshi v.59 Fujikawa, F.
  49. Yakugaku Zasshi v.76 Fujikawa, F.;Hitosa, Y.;Yagi, Y.;Yasuda, K.
  50. Yakugaku Zasshi v.76 Fujikawa, F.;Hitosa, Y.;Yagi, Y.;Nakazawa, S.;Omatsu, T.
  51. The Merk Index(11th Ed.) Budavari, S.
  52. Naturforsch. v.26 Lennartz, T. Z.