Diarylheptanoids from the Bark of Alnus pendula Matsumura

  • 투고 : 2012.04.17
  • 심사 : 2012.05.24
  • 발행 : 2012.06.30

초록

Diarylheptanoids, (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-one-5-O-${\beta}$-D-xylopyranoside (1, Oregonin), 1,7-bis-(3,4-dihydroxyphenyl)-4-heptene-3-one (2, Hirsutenone), (5S)-7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxyphenyl)-3-heptanone-5-O-${\beta}$-D-xylopyranoside (3, Alnuside A), (5S)-1-(3,4-dihydroxyphenyl)-5-hydroxy-7-(4-hydroxyphenyl)-3-heptanone-5-O-${\beta}$-D-xylopyranoside (4, Alnuside B), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-on-5-O-${\beta}$-D-glucopyranoside (5) and 1,7-bis-(4-hydroxyphenyl)-5-hydroxyheptane-3-on-5-O-${\beta}$-D-glucopyranoside (6, Platyphylloside) were isolated from the bark of Alnus pendula Matsumura. The structures of these compounds were identified based on the spectral and physicochemical data.

키워드

참고문헌

  1. Choi, S.E., Jeong, M.S., Kang, M.J., Lee, D.I., Joo, S.S., Lee, C.S., Bang, H., Lee, M.K., Myung, S.C., Choi, Y.W., Lee, K., Seo, S.J., and Lee, M.W., Effect of topical application and intraperitoneal injection of oregonin on atopic dermatitis in NC/Nga mice. Exp. Dermatol, 19, e37-e43 (2010).
  2. Jeong, D.W., Kim, J.S., Cho, S.M., Lee, Y.A., Kim, K.H., Kim, S.W., and Lee, M.W., Diarylheptanoids from the stem bark of Alnus hirsuta var. sibirica. Kor. J. Pharmacogn., 31, 28-33 (2000).
  3. Kim, H.J., Kim, K.H., Yeom, S.H., Kim, M.K., Shim, J.G., Lim, H.W., and Lee, M.W., New diarylheptanoid from the barks of Alnus japonica Steudel. Chin. Chem. Lett., 16, 1337-1340 (2005a).
  4. Kim, H.J., Yeom, S.H., Kim, M.K., Shim, J.G., Peak, I.N., and Lee, M.W., Nitric oxide and prostaglandin E2 synthesis inhibitory activities of diarylheptanoids from the barks of Alnus japonica Steudel. Arch. Pharm. Res. 28, 177-179 (2005b). https://doi.org/10.1007/BF02977711
  5. Kuroyanagi, M., Shimomae, M., Nagashima, Y., Muto, N., Okuda, T., Kawahara, N., Nakane, T., and Sano, T., New diarylheptanoids from Alnus japonica and their antioxidative activity. Chem. Pharm. Bull. 53, 1519-1523 (2005). https://doi.org/10.1248/cpb.53.1519
  6. Lee, M.W., Kim, J.H., Jeong, D.W., Ahn, K.H., Toh, S.H., and Surh, Y.J., Cyclooxygenase-2 inhibitory effect of diarylheptanoids from the barks of Alnus hirsuta var. sibirica. Biol. Pharm. Bull. 23, 517-518 (2000a). https://doi.org/10.1248/bpb.23.517
  7. 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., Diarylheptanoids with in vitro inducible nitric oxide synthesis inhibitory activity from Alnus hirsuta. Planta Med. 66, 551-553 (2000b). https://doi.org/10.1055/s-2000-8606
  8. Lee, M.W., Park, M.S., Jeong, D.W., Kim, K.H., Kim, H.H., and Toh, S.H., Diarylheptanoids from the leaves of Alnus hirsuta Turcz. Arch. Pharm. Res. 23, 50-53 (2000c). https://doi.org/10.1007/BF02976466
  9. Lee, M.W., Tanaka, T., Nonaka, G., and Nishioka, I., Hirsunin, an ellagitannin with a diarylheptanoid moiety from Alnus hirsuta var. Microphylla. Phytochemistry 31, 967-970 (1992). https://doi.org/10.1016/0031-9422(92)80049-K
  10. Lee, S.J., Korea Folk Medicine. Seoul National University Publishing Center Press., Seoul., pp. 40 (1966).
  11. Lee, Y.A., Jeong, D.W., Kim, K.H., Kim, J.S., Kim, S.W., and Lee, M.W., Antioxidant activity of diarylheptanoids from the leaves of Alnus hirsute. Yakhak Hoeji 44, 193-196 (2000d).
  12. Lim, H.W., Kim, M.K., Kim, H.J., Shim, J.G., Kim, G.H., Choi, H.K., and Lee, M.W., Quantitative determination of diarylheptanoid compounds from korean Alnus. Kor. J. Pharmacogn. 35, 384-387 (2004).
  13. Nomura, M., Tokoroyama, T., and Kubota, T., Biarylheptanoids and other constituents from wood of Alnus japonica. Phytochemistry 20, 1097 - 1104 (1981). https://doi.org/10.1016/0031-9422(81)83035-X
  14. Smite, E., Lundgren, L.N., and Anderson, R., Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula. Phytochemistry 32, 365-369 (1993). https://doi.org/10.1016/S0031-9422(00)94995-1