Antioxidative Activities of Diarylheptanoids from Alnus japonica and Their Structural Relationship

오리나무에서 분리된 Diarylheptanoid의 항산화작용 및 구조상관활성

  • Published : 2003.06.30

Abstract

Anitioxidative activities againt 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were evaluated for ten diarylheptanoids, $1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-{\beta}-D-glucopyranosyl(1{\rightarrow}3)-{\beta}-D-xylopyranoside(1)$, $1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-{\beta}-D-apiofuranosyl(1{\rightarrow}6)-{\beta}-D-glucopyranoside(2)$, $1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-{\beta}-D-glucopyranoside(3)$, 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane(4), $1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-{\beta}-D-glucopyranoside(5)$, oregonin(6), hirsutanonol(7), hirsutenone(8), $1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-{\beta}-D-xylopyranoside(9)$ and platyphylloside(10), which were isolated from Alnus japonica. Aglycones (4,7 and 8) and mono glycosides (3,6 and 9) showed more strong antioxidative activities than diglycosides (1 and 2) against the DPPH radical. Especially, hirsutenone(8) showed superior activity among ten diarylheptanoid.

Keywords

References

  1. 이우철(1996) 한국식물명고, 154, 아카데미서적, 서울
  2. (1985) 中藥大辭典 (3권), 3042,小學館
  3. Lee, S. J. (1966) 40, Korean Folk Medicine, 서울
  4. Terazawa, M., Okuyama, H. and Miyake, M. (1974) Isolation of Hirsutanonol and Hirsutenone, Two new diarylheptanoids from the green bark of keyamahannoki, Alnus hirsuta Turcz, Mokuzai gakkaish; 19: 45-46
  5. Karches. J. J., Laever. M. L., Barofsky, D. F. and Barofsky, E. (1974) Structureof oregonin, a Natural DiarylheptanoidXyloside. J. C. S. Chem. Comm.: 649-650
  6. Lee, M., W., Tanaka, T., Nonaka, G. and Nishioka, I. (1992) Hirsunin, an ellagitannin with a diarylheptanoid moiety from Alnus hitsuta var. microphylla, Phytochemistry, 31: 967-970 https://doi.org/10.1016/0031-9422(92)80049-K
  7. Tori, M., Hashimoto, A., Hirose, K. and Asakawa, Y. (1995) Diarylheptanoids, flavonoids, stilbenoids, sesquiterpenoids and a phenanthrene from Alnus maximowiczii. Phytochemistry, 40: 1263-1264 https://doi.org/10.1016/0031-9422(95)00439-E
  8. Wada, H., Tachibana, H., Fuchino, H. and Tanaka, N. (1998) Three new diarylheptanoid glycosides from Alnus japonica, Chem. Pharm. Bull.. 46: 1054-1055 https://doi.org/10.1248/cpb.46.1054
  9. Gonzalez-Laredo, R. F., Chem, J., Karchesy, Y. M. and Karchesy. J. J. (1999) Four New Diarylheptanoid Glycosides from Alnus Rubra Bark, Nat. Prod. Lett., 13: 75 https://doi.org/10.1080/10575639908048826
  10. Suga, T., Iwata, N. and Asakawa, Y.(1972), Chemical constituents of the male Flower of Alnus pendula (Betu1aceae), Bull. Chem. Soc. Jpn., 45: 2058-2067 https://doi.org/10.1246/bcsj.45.2058
  11. Asakawa, Y.(1971) Chemical constituents of Alnus sieboldiana (Betu1aceae) II. The isolation and structure of flavonoids and sti1benes, Bull. Chem. Soc. Japan, 44: 2761-2766 https://doi.org/10.1246/bcsj.44.2761
  12. Stikhin, V. A., Ban'kovskii, A. I., G1yzin, V. I. and Kir'yanova, I. A. (1974) Quercetin-3-sophoroside from Alnus glutinosa and Fraxinus lanceolata pollens, Chem. Nat. Comp., 10: 526 https://doi.org/10.1007/BF00563830
  13. Lee, M. W., Jeong, D. W., Lee, Y. A., Park, M. S. and Tob, S. H. (1999) Flavonoids from the Leaves of Alnus hirsuta, Yakhak Hoeji, 43: 547-552
  14. Ahn, K. W., Toh, S. H., Jeong, D. W., Kim, J. S., Cho, S. M. and Lee, M. W. (2000) Flavonoids from the Leaves of Alnus maximowiczii Call, Yakhak Hoeji, 44: 41-46
  15. Lee, M. W., Park, M. S., Jeong, D. W., Kim, K. H. and Toh, S. H. (2000) Diarylheptanoids from the Leaves of Alnus hirsuta Torcz, Arch. Pharm. Res., 23: 50-53 https://doi.org/10.1007/BF02976466
  16. Lee, M. W., Kim, N. Y., Park, M. S., Ahn, K. H., Toh, S. H., Hahn, D. R., Kim, Y. C. and Chung, H. T. (2000) Diarylheptanoids with In vitro Inducible Nitric Oxide Synthesis Inhibitory Activity from Ainus hirsuta, Planta Med., 66(6): 551-553 https://doi.org/10.1055/s-2000-8606
  17. Lee, M. W., Kim, J. H., Jeong, D. W., Ahn, K. H., Toh, S. H. and Such, Y. J. (2000) Inhibition of Cyclooxygenase-2 Expression by Diarylheptanoids from the Bark of Alnus hirsuta var. sibirica Biol. Pharm. Bull., 23(4): 517-518 https://doi.org/10.1248/bpb.23.517
  18. Lee, D. I., Chang, J. K., Lee, M. W. and Hong, S. G. (1998) Effects of Oregonin, diarylheptanoid derivative from plant on antitumor, Chung-Ang J. Pharm. Sci., 12: 50 https://doi.org/10.1126/science.ns-12.287.50
  19. Lee, Y. A., Kim, K. H., Kim, J. S., Cho, S. M., Kim, S. W. and Lee, M. W. (2000) Antioxidative Effects of Diarylheptanoids from Alnus hirsuta, Yakhak Hoeji, 44: 193-196
  20. Submitted
  21. Hatano, T., Edamatsu, R., Hiramatsu, M., Mori,A., Fujita, Y., Yasuhara, T., Yoshida, T. and Okuda, T. (1989), Effects of the interaction of tannins with co-existing substances.. Effects of tannins and ralated polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical, Chem. Pharm. Bull. 37: 2016 https://doi.org/10.1248/cpb.37.2016