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Constituents from Zhuyeqing Liquor with hepatoprotective effect on alcohol-induced HepaG 2 toxicity

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Abstract

An unprecedented new skeleton compound (1R, 10R, 11S)-10,11-dimethyl-4-formyl-2,9-dioxa-bicyclo [5.4.0] undeca-4,6-dien-3-one (1), monoterpenoids and monoterpene glycoside picrocrocinic ester (2), epijasminoside B (3) and 6′-O-(3-methoxyl-4-hydroxyl-coumaroyl)-epijasminoside B (4), along with 26 known compounds, were obtained from Zhuyeqing Liquor. These compounds were identified mainly by analyzing their NMR, HR-ESI–MS and CD data. The isolated compounds were screened against alcohol induced HepaG 2 toxicity for hepatoprotective assay. Compounds 10, 19, 21 and 26 displayed the highest potency against alcohol induced HepaG 2 toxicity with the cell viability ratio 41.21, 56.91, 67.69 and 70.32 % respectively.

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References

  • Anh, N.T.H., T.V. Sung, K. Franke, and L.A. Wessjohann. 2003. Phytochemical studies of Rehmannia glutinosa rhizomes. Pharmazie 58: 593–595.

    CAS  PubMed  Google Scholar 

  • Chen, Q.C., U.J. Youn, B.S. Min, and K.H. Bae. 2008. Pyronane monoterpenoids from the fruit of Gardenia jasminoides. Journal of Natural Product 71: 995–999.

    Article  CAS  Google Scholar 

  • Dinda, B., D. Roy Chowdhury, and B.C. Mohanta. 2009. Naturally occurring iridoids, secoiridoids and their bioactivity. An updated review, part 3. Chemical & Pharmaceutical Bulletin 57: 765–796.

    Article  CAS  Google Scholar 

  • Dinda, B., S. Debnath, and R. Banik. 2011. Naturally occurring iridoids and secoiridoids. An updated review, part 4. Chemical & Pharmaceutical Bulletin 59: 803–833.

    Article  CAS  Google Scholar 

  • Djerassi, C., R. Riniker, and B. Riniker. 1956. Optical rotatory dispersion studies. VII. Apllication to problems of absolute configuration. Journal of the American Chemical Society 78: 6362–6377.

    Article  CAS  Google Scholar 

  • Evidente, A., S. Superchi, A. Cimmino, G. Mazzeo, L. Mugnai, D. Rubiales, A. Andol, and A.M. Villegas-Fernández. 2011. Configuration/phytotoxicity relationship. European Journal of Organic Chemistry 28: 5564–5570.

    Article  Google Scholar 

  • Fiorentino, A., B. DiAbrosca, M. DellaGreca, A. Izzo, A. Natale, M.T. Pascarella, S. Pacifico, A. Zarrelli, and P. Monaco. 2008. Chemical characterization of new oxylipins from Cestrum parqui, and their effects on seed germination and early seedling growth. Chemistry & Biodiversity 5: 1780–1791.

    Article  CAS  Google Scholar 

  • Fu, Z.H., Y.M. Zhang, N.H. Tan, H.B. Chu, and C.J. Ji. 2008. Chemical constituents of Keteleeria evelyniana. Natural Product Research and Development 20: 257–261.

    CAS  Google Scholar 

  • Gu, Q.K., X.Q. Zhou, Z.M. Bi, P. Li, and L. Yang. 2009. Chemical constituents of the fruits of Gardenia jasminoides form grandiflora (Lour.) Makino. Linchan Huaxue Yu Gongye 29: 61–64.

    Google Scholar 

  • Kai, N.K. 1977. Shin Jikken Kagaku Koza 13, Yuki kozo (II), 821–830. Tokyo: Maruzen.

    Google Scholar 

  • Kim, H.J., E.J. Kim, S.H. Seo, C.G. Shin, C. **, and Y.S. Lee. 2006. Vanillic acid glycoside and quinic acid derivatives from gardeniae fructus. Journal Natural Product 69: 600–603.

    Article  CAS  Google Scholar 

  • Li, Z.Y., and H.B. Liu. 2010. Fragrant zhuyeqing Liquor. Liquor Making 37: 79–80.

    CAS  Google Scholar 

  • Liu, X.M., Y. Jiang, Y.Q. Sun, X.W. Xu, and P.F. Tu. 2011. Chemical constituent study of Herba Cistanches. Chinese Journal of Pharmaceuticals 46: 1053–1058.

    CAS  Google Scholar 

  • Ma, Z.T., X.W. Yang, and G.Y. Zhong. 2009. A new flavonoid glucoside from Huanglian jiedutang decoction. China Journal of Chinese Materia Medica 34: 1097–1100.

    CAS  PubMed  Google Scholar 

  • Machida, K., R. Onodera, K. Furuta, and M. Kikuchi. 1998. Studies of the constituents of gardenia species. I, Monoterpenoids from Gardeniae Fructus. Chemical & Pharmaceutical Bulletin 46: 1295–1300.

    Article  CAS  Google Scholar 

  • Machida, K., K. Oyama, M. Ishii, R. Kakuda, Y. Yaoita, and M. Kikuchi. 2000. Studies of the constituents of gardenia species. II. Terpenoids from Gardeniae Fructus. Chemical & Pharmaceutical Bulletin 48: 746–748.

    Article  CAS  Google Scholar 

  • Machida, K., E. Takehara, H. Kobayashi, and M. Kikuchi. 2003. Studies on the constituents of gardenia species. III. New iridoid glycosides from the leaves of Gardenia jasminoides cv. fortuneana HARA. Chemical & Pharmaceutical Bulletin 51: 1417–1419.

    Article  CAS  Google Scholar 

  • Mahato, S.B., and A.P. Kundu. 1994. 13C NMR spectra of pentacyclic triterpenoids a compilation and some salient features. Phytochemistry 37: 1517–1575.

    Article  CAS  Google Scholar 

  • Mazzeo, G., E. Santoro, A. Andol, A. Cimmino, P. Troselj, A.G. Petrovic, S. Superchi, A. Evidente, and N. Berova. 2013. Absolute configurations of fungal and plant metabolites by chiroptical methods. ORD, ECD, and VCD studies on phyllostin, scytolide, and oxysporone. Journal of Natural Product 76: 588–599.

    Article  CAS  Google Scholar 

  • Miyase, T., A. Ueno, N. Takizawa, H. Kobayashi, and H. Oguchi. 1988. Studies on the glycosides of Epimedium grandiflorum Morr var Tunbergianum (Miq) Nakai. Chemical & Pharmaceutical Bulletin 36: 2475–2488.

    Article  CAS  Google Scholar 

  • Park, H.B., K.H. Lee, K.H. Kim, I.K. Lee, H.J. Noh, S.U. Choi, and K.R. Lee. 2009. Lignans from the Roots of Berberis amurensis. Natural Product Sciences 15: 17–21.

    CAS  Google Scholar 

  • Straubinger, M., B. Bau, S. Eckstein, M. Fink, and P. Winterhalter. 1998. Identification of novel glycosidic arom a precursors in Saffron (Crocus sativus L.). Journal of Agricultural Food Chemistry 46: 3238–3243.

    Article  CAS  Google Scholar 

  • Shi, S.Y., C.X. Zhou, Y. Xu, Q.F. Tao, H. Bai, F.S. Lu, W.Y. Lin, H.Y. Chen, W. Zheng, L.W. Wang, Y.H. Wu, S. Zeng, K.X. Huang, Y. Zhao, X.K. Li, and J. Qu. 2008. Studies on chemical constituents from herbs of Taraxacum mongolicum. China Journal of Chinese Materia Medica 33: 1147–1157.

    CAS  PubMed  Google Scholar 

  • Wu, L.J., T. **ang, B.L. Hou, W. Liang, S. Yin, and X.C. Zhou. 1998. Chemical constituents from fruits of Ligustrum lucidum. Acta Botanica Sinica 40: 83–87.

    CAS  Google Scholar 

  • **ang, T., L.J. Wu, R.H. Lin, J.W. Sun, and X.B. Dai. 1999. Studies on the chemical constituents of Lonicera bournei Hemsl. II. Chinese Journal of medicinal chemistry 1: 48–49.

    Google Scholar 

  • Yu, Y., Z.L. **e, H. Gao, W.W. Ma, Y. Dai, Y. Wang, Y. Zhong, and X.S. Yao. 2009. Bioactive iridoid glucosides from the fruit of Gardenia jasminoides. Journal of Natural Product 72: 1459–1464.

    Article  CAS  Google Scholar 

  • Zhang, H.Q., Y.M. Ding, G.Y. Chen, and Y.F. Dong. 1987. Studies on active constituents of root of Euphorbia ebracteolata hayata (Euphorbiaceae). Journal of Integrative Plant Biology 29: 429–431.

    CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by Shanxi **nghuaCun Fen Wine Group Co., Ltd. (Shanxi Province, China) and National Key Technology R&D Program (2012BAI30B02). We thank the analytical group from Shihezi University and Shenyang Pharmaceutical University for measuring the UV, CD, NMR and MS spectra.

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Authors and Affiliations

  1. School of Traditional Chinese Materia Medica 49#, Shenyang Pharmaceutical University, Wenhua Road 103, Shenyang, 110016, People’s Republic of China

    Hong-Ying Gao, Jian Huang & **-Hui Wang

  2. School of Pharmacy, Shihezi University, Shihezi, 832002, People’s Republic of China

    Guo-Yu Li, Hang-Yu Wang & **-Hui Wang

  3. Shanxi **nghuacun Fen Jiu Group Co., Ltd., Lvliang, 033000, Shanxi, People’s Republic of China

    **ao-Wei Du, Ying Han & Li-Fei Wang

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  1. Hong-Ying Gao
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  2. Guo-Yu Li
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  4. Jian Huang
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  8. **-Hui Wang
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Correspondence to Jian Huang or **-Hui Wang.

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Gao, HY., Li, GY., Wang, HY. et al. Constituents from Zhuyeqing Liquor with hepatoprotective effect on alcohol-induced HepaG 2 toxicity. Arch. Pharm. Res. 38, 683–690 (2015). https://doi.org/10.1007/s12272-014-0414-5

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  • DOI: https://doi.org/10.1007/s12272-014-0414-5

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