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

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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 1–7 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.

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References

  • 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.

    Article  PubMed  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Yook, C.S. 1989. Medicinal Plants of Korea. Seoul: Jinmyeong Publishing Co.

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

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Acknowledgments

This research was supported by the Yeungnam University research grants in 2013.

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Authors and Affiliations

  1. College of Pharmacy, Yeungnam University, Gyeongsan, 712-749, Gyeongbuk, Korea

    Hyun Gyu Choi, Yeon Ho Choi, Ji Hyang Kim & Seung Ho Lee

  2. Laboratory of Immunotoxicology, Department of Pharmacology, School of Medicine, Kyungpook National University, Daegu, 700-422, Korea

    Hui-Hun Kim & Sang-Hyun Kim

  3. Research Institute of Pharmaceutical Science, College of Pharmacy, Kyungpook National University, Daegu, 702-701, Korea

    Jeong Ah Kim

  4. Korea Ginseng Corp., Central Research Institute, Daejeon, 305-805, Korea

    Sang Myung Lee

  5. College of Pharmacy, Chungnam National University, Daejeon, 305-764, Korea

    MinKyun Na

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  1. Hyun Gyu Choi
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  2. Yeon Ho Choi
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Correspondence to MinKyun Na or Seung Ho Lee.

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Choi, H.G., Choi, Y.H., Kim, J.H. et al. A new neolignan and lignans from the stems of Lindera obtusiloba Blume and their anti-allergic inflammatory effects. Arch. Pharm. Res. 37, 467–472 (2014). https://doi.org/10.1007/s12272-013-0239-7

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  • DOI: https://doi.org/10.1007/s12272-013-0239-7

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