Archives of Pharmacal Research

, Volume 37, Issue 4, pp 467–472

A new neolignan and lignans from the stems of Lindera obtusiloba Blume and their anti-allergic inflammatory effects

  • Hyun Gyu Choi
  • Yeon Ho Choi
  • Ji Hyang Kim
  • Hui-Hun Kim
  • Sang-Hyun Kim
  • Jeong Ah Kim
  • Sang Myung Lee
  • MinKyun Na
  • Seung Ho Lee
Research Article

Abstract

A new neolignan, linderin A (1), together with six known lignans, (+)-xanthoxyol (2), pluviatilol (3), actiforin (4), (+)-syringaresinol (5), (+)-(7S,8R,8′R)-acuminatolide (6), and (+)-9′-O-trans-feruloyl-5,5′-dimethoxylariciresinol (7) were isolated from the stems of Lindera obtusiloba Blume (Lauraceae). Their chemical structures were elucidated by a combination of spectroscopic analysis and chemical reaction, and the absolute configuration of 1 was determined by Mosher’s esterification. The effect of compounds 17 on tumor necrosis factor (TNF)-α, interleukin(IL)-6, and their inhibitory activity of histamine release were examined using human mast cells. Among the lignans tested, compounds 1, 3, 4, 6, and 7 inhibited release of histamine from mast cells. Especially, compounds 1 and 4 suppressed the gene expressions of pro-inflammatory cytokines, TNF-α, and IL-6 in human mast cells. Our findings suggest that the lignan constituents in L. obtusiloba may contribute to its anti-allergic inflammatory effects.

Keywords:

Lindera obtusiloba Lignan Linderin A Anti-allergic effect 

References

  1. Choi, E.J., S. Lee, H.H. Kim, T.S.K. Singh, J.K. Choi, H.G. Choi, W.M. Suh, S.H. Lee, and S.H. Kim. 2011. Suppression of dust mite extract and 2,4-dinitrochlorobenzene-induced atopic dermatitis by the water extract of Lindera obtusiloba. Journal of Ethnopharmacology 137: 802–807.PubMedCrossRefGoogle Scholar
  2. Hironobu, T., Y. Seiko, K. Shoichi, A. Hiroshi, and F. Yoshiyasu. 2002. Lignans and sesquiterpenes from Magnolia praecocissima. Chemical and Pharmaceutical Bulletin 50: 541–543.CrossRefGoogle Scholar
  3. Kim, S.H., C.D. Jun, K. Suk, B.J. Choi, H. Lim, S. Park, S.H. Lee, H.Y. Shin, D.K. Kim, and T.Y. Shin. 2006. Gallic acid inhibits histamine release and pro-inflammatory cytokine production in mast cells. Toxicological Sciences 91: 123–131.PubMedCrossRefGoogle Scholar
  4. Kim, S.H., S. Lee, K. Suk, H. Bark, C.D. Jun, D.K. Kim, C.H. Choi, and T. Yoshimura. 2007. Discoidin domain receptor 1 mediates collagen-induced nitric oxide production in J774A.1 murine macrophages. Free Radical Biology and Medicine 42: 343–352.PubMedCrossRefGoogle Scholar
  5. Kubo, I., Jamalamadaka, V., Kamisawa, T., Takahashi, K., Tabata, K., Kusumi, K. 1996. Absolute stereochemistry of tanabalin, an insect antifeedant clerodane from Tanacetum balsamita. Chemistry Letters, 441–442.Google Scholar
  6. Kuo, P.C., M.C. Lin, G.F. Chen, T.J. Yiu, and J.T.C. Tzen. 2011. Identification of methanol-soluble compounds in sesame and evaluation of antioxidant potential of its lignans. Journal of Agriculture and Food Chemistry 59: 3214–3219.CrossRefGoogle Scholar
  7. Kwon, H.C., S.U. Choi, J.O. Lee, K.H. Bae, O.P. Zee, and K.R. Lee. 1999. Two new lignans from Lindera obtusiloba Blume. Archives of Pharmacal Research 22: 417–422.PubMedCrossRefGoogle Scholar
  8. Kwon, H.C., N.I. Baek, S.U. Choi, and K.R. Lee. 2000. New cytotoxic butanolides from Lindera obtusiloba. Chemical and Pharmaceutical Bulletin 48: 614–616.PubMedCrossRefGoogle Scholar
  9. Lee, J., E.K. Seo, D.S. Jang, T.J. Ha, J.P. Kim, J.W. Nam, G. Bae, Y.M. Lee, D.S. Yang, and J.S. Kim. 2009. Two new stereoisomers of neolignan and lignan from the flower buds of Magnolia fargesii. Chemical and Pharmaceutical Bulletin 57: 298–301.PubMedCrossRefGoogle Scholar
  10. Yook, C.S. 1989. Medicinal Plants of Korea. Seoul: Jinmyeong Publishing Co.Google Scholar
  11. Park, J.C., Y.B. Yu, and J.H. Lee. 1996. Isolation and structure elucidation of flavonoid glycosides from Lindera obtusiloba Blume. J. Korean. Soc. Food Nutr. 25: 76–79.Google Scholar
  12. Su, B.N., E.J. Park, Z.H. Mbwambo, B.D. Santarsiero, A.D. Mesecar, H.H.S. Fong, J.M. Pezzuto, and A.D. Kinghon. 2002. New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes. Journal of Natural Products 65: 1278–1282.PubMedCrossRefGoogle Scholar
  13. Takanu, N., D.H. Choi, K. Mikame, T. Okunishi, S. Suzuki, H. Ohashi, T. Umezawa, and M. Shimada. 2001. Lignans of Chamaecyparis obtusa. Journal of Wood Science 47: 476–482.CrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 2013

Authors and Affiliations

  • Hyun Gyu Choi
    • 1
  • Yeon Ho Choi
    • 1
  • Ji Hyang Kim
    • 1
  • Hui-Hun Kim
    • 2
  • Sang-Hyun Kim
    • 2
  • Jeong Ah Kim
    • 3
  • Sang Myung Lee
    • 4
  • MinKyun Na
    • 5
  • Seung Ho Lee
    • 1
  1. 1.College of PharmacyYeungnam UniversityGyeongsanKorea
  2. 2.Laboratory of Immunotoxicology, Department of Pharmacology, School of MedicineKyungpook National UniversityDaeguKorea
  3. 3.Research Institute of Pharmaceutical Science, College of PharmacyKyungpook National UniversityDaeguKorea
  4. 4.Korea Ginseng Corp., Central Research InstituteDaejeonKorea
  5. 5.College of PharmacyChungnam National UniversityDaejeonKorea

Personalised recommendations