Advertisement

Archives of Pharmacal Research

, Volume 38, Issue 4, pp 480–484 | Cite as

Chemical constituents from the leaves of Juglans mandshurica

  • Da Lei Yao
  • Chang Hao Zhang
  • Jie Luo
  • Mei Jin
  • Ming Shan Zheng
  • Jiong Mo Cui
  • Jong Keun Son
  • Gao LiEmail author
Research Article

Abstract

Two new (1 and 3) and two known diarylheptanoids (2 and 4), along with two tetralones (5 and 6), one naphthoquinone (7), four phenylpropanoids (811), and one phenol (12) were isolated from the leaves of Juglans mandshurica. Their structures were elucidated on the basis of spectral and chemical data. Compounds 2 and 10 are firstly isolated from this plant and 8 and 12 were isolated from the Juglans genus for the first time. Among these compounds, only 7 exhibited moderate cytotoxicities against cultured MGC-803, A549, K562, and HeLa tumor cell lines with IC50 values of 25.90, 28.60, 39.06, 44.90 μM, respectively.

Keywords

Juglans mandshurica Juglandaceae Diarylheptanoid Cytotoxicity Tetralone Phenylpropanoid 

Notes

Acknowledgments

This work was supported by the National Natural Science Foundation of China under Grant Numbers 30760291, 81160386, and 30911140276.

Supplementary material

12272_2014_398_MOESM1_ESM.doc (1.3 mb)
Supplementary material 1 (DOC 1370 kb)

References

  1. Fujioka, T., K. Furumi, H. Fujii, H. Okabe, K. Mihashi, Y. Nakano, H. Matsunaga, M. Katano, and M. Mori. 1999. Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica. Chemical & Pharmaceutical Bulletin 47: 96–100.CrossRefGoogle Scholar
  2. Joe, Y.K., J.K. Son, S.H. Park, I.J. Lee, and D.C. Moon. 1996. New naphthalenyl glucosides from the roots of Juglans mandshurica. Journal of Natural Products 59: 159–160.CrossRefGoogle Scholar
  3. Ju, S.M., H.Y. Song, S.J. Lee, W.Y. Seo, D.H. Sin, A.R. Goh, Y.H. Kang, I.J. Kang, M.H. Won, J.S. Yi, D.J. Kwon, Y.S. Bae, S.Y. Choi, and J. Park. 2009. Suppression of thymus- and activation-regulated chemokine (TARC/CCL17) production by 1,2,3,4,6-penta-O-galloyl-β-d-glucose via blockade of NF-kappaB and STAT1 activation in the HaCaT cells. Biochemical and Biophysical Research Communications 387: 115–120.CrossRefPubMedGoogle Scholar
  4. Kim, S.H., K.S. Lee, J.K. Son, G.H. Je, J.S. Lee, C.H. Lee, and C.J. Cheong. 1998. Cytotoxic compounds from the roots of Juglans mandshurica. Journal of Natural Products 61: 643–645.CrossRefPubMedGoogle Scholar
  5. Lal, C., A.S.M. Raja, P.K. Pareek, D.B. Shakyawar, K.K. Sharma, and M.C. Sharma. 2011. Juglans nigra: Chemical constitution and its application on Pashmina (Cashmere) fabric as a dye. Journal of Natural Product and Plant Resources 1: 13–19.Google Scholar
  6. Lee, K.S., G. Li, S.H. Kim, C.S. Lee, M.H. Woo, S.H. Lee, Y.D. Jhang, and J.K. Son. 2002. Cytotoxic diarylheptanoids from the roots of Juglans mandshurica. Journal of Natural Products 65: 1707–1708.CrossRefPubMedGoogle Scholar
  7. Lee, S.W., K.S. Lee, and J.K. Son. 2000. New naphthalenyl glycosides from the roots of Juglans mandshurica. Planta Medica 66: 184–186.CrossRefPubMedGoogle Scholar
  8. Li, G., J.M. Cui, Y.J. Kwon, C.S. Seo, C.S. Lee, M.H. Woo, E.S. Lee, Y.D. Jahng, H.W. Chang, S.H. Lee, and J.K. Son. 2005. Two new diarylheptanoids from Juglans mandshurica. Bulletin of the Korean Chemical Society 26: 1878–1880.CrossRefGoogle Scholar
  9. Li, G., S.Y. Lee, K.S. Lee, S.W. Lee, S.H. Kim, S.H. Lee, C.S. Lee, M.H. Woo, and J.K. Son. 2003a. DNA topoisomerases I and II inhibitory activity of constituents isolated from Juglans mandshurica. Archives of Pharmacal Research 26: 466–470.CrossRefPubMedGoogle Scholar
  10. Li, G., C.S. Seo, S.H. Lee, Y.D. Jahng, H.W. Chang, C.S. Lee, M.H. Woo, and J.K. Son. 2004. Diarylheptanoids from the roots of Juglans mandshurica. Bulletin of the Korean Chemical Society 25: 397–399.CrossRefGoogle Scholar
  11. Li, G., M.L. Xu, H.G. Choi, S.H. Lee, Y.D. Jahng, C.S. Lee, D.C. Moon, M.H. Woo, and J.K. Son. 2003b. Four new diarylheptanoids from the roots of Juglans mandshurica. Chemical & Pharmaceutical Bulletin 51: 262–264.CrossRefGoogle Scholar
  12. Li, Z.B., J.Y. Wang, B. Jiang, X.L. Zhang, L.J. An, and Y.M. Bao. 2007. Benzobijuglone, a novel cytotoxic compound from Juglans mandshurica, induced apoptosis in HeLa cervical cancer cells. Phytomedicine 14: 846–852.CrossRefPubMedGoogle Scholar
  13. Li, Z.B., J.Y. Wang, J. Yang, X.L. Zhang, L.J. An, and Y.M. Bao. 2009. Apoptosis of BGC823 cell line induced by p-hydroxymethoxybenzobijuglone, a novel compound from Juglans mandshurica. Phytotherapy Research 23: 551–557.CrossRefPubMedGoogle Scholar
  14. Lin, H., Y.W. Zhang, Y.L. Bao, Y. Wu, L.G. Sun, C.L. Yu, Y.X. Huang, E.B. Wang, and Y.X. Li. 2013. Secondary metabolites from the stem bark of Juglans mandshurica. Biochemical Systematics and Ecology 51: 184–188.CrossRefGoogle Scholar
  15. Liu, L.J., W. Li, T. Sasaki, Y. Asada, and K. Koike. 2010. Juglanone, a novel α-tetralonyl derivative with potent antioxidant activity from Juglans mandshurica. Journal of Natural Medicines 64: 496–499.CrossRefPubMedGoogle Scholar
  16. Liu, L., W. Li, K. Koike, S. Zhang, and T. Nikaido. 2004. New α-tetralonyl glucosides from the fruit of Juglans mandshurica. Chemical & Pharmaceutical Bulletin 52: 566–569.CrossRefGoogle Scholar
  17. Machida, K., E. Matsuoka, T. Kasahara, and M. Kikuchi. 2005. Studies on the constituents of Juglans species. I. Structural determination of (4S)- and (4R)-4-hydroxy-alpha-tetralone derivatives from the fruit of Juglans mandshurica MAXIM. var. sieboldiana MAKINO. Chemical & Pharmaceutical Bulletin 53: 934–937.CrossRefGoogle Scholar
  18. Min, B.S., H.K. Lee, S.M. Lee, Y.H. Kim, K.H. Bae, T. Otake, N. Nakamura, and M. Hattori. 2002. Anti-human immunodeficiency virus-type 1 activity of constituents from Juglans mandshurica. Archives of Pharmacal Research 25: 441–445.CrossRefPubMedGoogle Scholar
  19. Min, B.S., S.Y. Lee, J.H. Kim, J.K. Lee, T.J. Kim, D.H. Kim, Y.H. Kim, H. Joung, H.K. Lee, N. Nakamura, H. Miyashiro, and M. Hattori. 2003. Anti-complement activity of constituents from the stem-bark of Juglans mandshurica. Biological and Pharmaceutical Bulletin 26: 1042–1044.CrossRefPubMedGoogle Scholar
  20. Min, B.S., N. Nakamura, H. Miyashiro, Y.H. Kim, and M. Hattori. 2000. Inhibition of human immunodeficiency virus type 1 reverse transcriptase and ribonuclease H activities by constituents of Juglans mandshurica. Chemical & Pharmaceutical Bulletin 48: 194–200.CrossRefGoogle Scholar
  21. Moore, R.E., and P.J. Scheuer. 1966. Nuclear magnetic resonance spectra of substituted naphthoquinones. Influence of substituents on tautomerism, anisotropy, and stereochemistry in the naphthazarin system. Journal of Organic Chemistry 31: 3272–3283.CrossRefPubMedGoogle Scholar
  22. Morihara, M., N. Sakurai, T. Inoue, K. Kawai, and M. Nagai. 1997. Two novel diarylheptanoid glucosides from Myrica gale var. tomentosa and absolute structure of plane-chiral galeon. Chemical and Pharmaceutical Bulletin 28: 820–823.CrossRefGoogle Scholar
  23. Ngoc, T.M., T.M. Hung, P.T. Thuong, J.C. Kim, J.S. Choi, K. Bae, M. Hattori, C.S. Choi, J.S. Lee, and B.S. Min. 2008. Antioxidative activities of galloyl glucopyranosides from the stem-bark of Juglans mandshurica. Bioscience, Biotechnology, and Biochemistry 72: 2158–2163.CrossRefPubMedGoogle Scholar
  24. Park, G.H., D.S. Jang, and M.S. Oh. 2012. Juglans mandshurica leaf extract protects skin fibroblasts from damage by regulating the oxidative defense system. Biochemical and Biophysical Research Communications 421: 343–348.CrossRefPubMedGoogle Scholar
  25. Park, G., and M.S. Oh. 2014. Inhibitory effects of Juglans mandshurica leaf on allergic dermatitis-like skin lesions-induced by 2,4-dinitrochlorobenzene in mice. Experimental and Toxicologic Pathology 66: 97–101.CrossRefPubMedGoogle Scholar
  26. Rebelo, S.L.H., M.M.Q. Simoes, M.G.P.M. Neves, A.M.S. Silva, P. Tagliatesta, and J.A.S. Cavaleiro. 2005. Oxidation of bicyclic arenes with hydrogen peroxide catalysed by Mn(III) porphyrins. Journal of Molecular Catalysis A: Chemical 232: 135–142.CrossRefGoogle Scholar
  27. Son, J.K. 1995. Isolation and structure determination of a new tetralone glucoside from the roots of Juglans mandshurica. Archives of Pharmacal Research 18: 203–205.CrossRefGoogle Scholar
  28. Tian, H., L. Ip, H. Luo, D.C. Chang, and K.Q. Luo. 2007. A high throughput drug screen based on fluorescence resonance energy transfer (FRET) for anticancer activity of compounds from herbal medicine. British Journal of Pharmacology 150: 321–334.CrossRefPubMedCentralPubMedGoogle Scholar
  29. Wan, C., T. Yuan, A.L. Cirello, and N.P. Seeram. 2012. Antioxidant and α-glucosidase inhibitory phenolics isolated from highbush blueberry flowers. Food Chemistry 135: 1929–1937.CrossRefPubMedGoogle Scholar
  30. Xin, N., M. Hasan, W. Li, and Y. Li. 2014. Juglans mandshurica Maxim extracts exhibit antitumor activity on HeLa cells in vitro. Molecular Medicine Reports 9: 1313–1318.PubMedGoogle Scholar
  31. Xu, H.L., X.F. Yu, S.C. Qu, R. Zhang, X.R. Qu, Y.P. Chen, X.Y. Ma, and D.Y. Sui. 2010. Anti-proliferative effect of Juglone from Juglans mandshurica Maxim on human leukemia cell HL-60 by inducing apoptosis through the mitochondria-dependent pathway. European Journal of Pharmacology 645: 14–22.CrossRefPubMedGoogle Scholar
  32. Xu, H.L., X.F. Yu, S.C. Qu, and D.Y. Sui. 2013. Juglone, isolated from Juglans mandshurica Maxim, induces apoptosis via down-regulation of AR expression in human prostate cancer LNCaP cells. Bioorganic and Medicinal Chemistry Letters 23: 3631–3634.CrossRefPubMedGoogle Scholar
  33. Yang, H.J., S.H. Sung, J.W. Kim, and Y.C. Kim. 2011. Neuroprotective diarylheptanoids from the leaves and twigs of Juglans sinensis against glutamate-induced toxicity in HT22 cells. Planta Medica 77: 841–845.CrossRefPubMedGoogle Scholar
  34. Yang, H., A.J. Hou, B. Jiang, Z.W. Lin, and H.D. Sun. 2000. Serratumin A, a novel compound from Clerodendrum serratum. Acta Botanica Yunnanica 22: 75–80.Google Scholar
  35. Yao, Y., Y.W. Zhang, L.G. Sun, B. Liu, Y.L. Bao, H. Lin, Y. Zhang, L.H. Zheng, Y. Sun, C.L. Yu, Y. Wu, G.N. Wang, and Y.X. Li. 2012. Juglanthraquinone C, a novel natural compound derived from Juglans mandshurica Maxim, induces S phase arrest and apoptosis in HepG2 cells. Apoptosis 17: 832–841.CrossRefPubMedGoogle Scholar
  36. Yoshioka, T., T. Inokuchi, S. Fujioka, and Y. Kimura. 2004. Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia. Zeitschrift fur Naturforschung. C, Journal of biosciences 59: 509–514.PubMedGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 2014

Authors and Affiliations

  • Da Lei Yao
    • 1
  • Chang Hao Zhang
    • 1
  • Jie Luo
    • 1
  • Mei Jin
    • 1
    • 2
  • Ming Shan Zheng
    • 1
  • Jiong Mo Cui
    • 1
  • Jong Keun Son
    • 3
  • Gao Li
    • 1
    Email author
  1. 1.Key Laboratory of Natural Resources of the Changbai Mountain and Functional Molecules, Ministry of EducationYanbian University College of PharmacyYanjiPeople’s Republic of China
  2. 2.Yanbian University HospitalYanjiChina
  3. 3.College of PharmacyYeungnam UniversityGyeongsanKorea

Personalised recommendations