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New maltol glycosides from Flos Sophorae

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Abstract

Three new maltol glycosides, designated soyamalosides A (1), B (2), and C (3), together with eight known compounds (411), were obtained from a 70 % EtOH extract of Flos Sophorae. Their structures were elucidated by chemical and spectroscopic methods. Of the known compounds, this is the first report of 46, 9, and 11 in the Sophora genus. Compounds 2, 3, and 10 showed significant protective effects against antimycin A-induced L6 cell injury.

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References

  1. China Pharmacopoeia Committee (2009) Pharmacopoeia of the People’s Republic of China, the First Division of 2010 Edition, China Chemical Industry Press, Beijing, p 83

  2. de Lemos ML (2001) Effects of soy phytoestrogens genistein and daidzein on breast cancer growth. Ann Pharmacother 35:1118–1121

    Article  PubMed  Google Scholar 

  3. Han RM, Tian YX, Liu Y, Chen CH, Ai XC, Zhang JP, Skibsted LH (2009) Comparison of flavonoids and isoflavonoids as antioxidants. J Agric Food Chem 57:3780–3785

    Article  CAS  PubMed  Google Scholar 

  4. Kite GC, Stoneham CA, Veitch NC (2007) Flavonol tetraglycosides and other constituents from leaves of Styphnolobium japonicum (Leguminosae) and related taxa. Phytochemistry 68:1407–1416

    Article  CAS  PubMed  Google Scholar 

  5. Liu L, Li X, Chen Y, Sun J, Liu E, Zhang Y (2014) Study on phenolic acids from Flos Sophorae. Tianjin Zhongyiyao Daxue Xuebao 33:39–41

    Google Scholar 

  6. Liu L, Wang T, Li X, Shi P, Liu E, Zhang Y (2014) Isolation and identification of chemical constituents from Flos Sophorae II. Liaoning Zhongyiyao Daxue Xuebao 16:51–1653

    Google Scholar 

  7. Liu L, Li X, Chen Y, Shi P, Qu L, Zhang Y (2014) Isolation and identification of chemical constituents from Flos Sophorae I. Tianjin Zhongyiyao Daxue Xuebao 33:230–233

    Google Scholar 

  8. Djimtombaye BJ, Alankuş-Çalışkan Ö, Gülcemal D, Khan IA, Anıl H, Bedir E (2013) Unusual secondary metabolites from Astragalus halicacabus Lam. Chem Biodivers 10:1328–1334

    Article  CAS  PubMed  Google Scholar 

  9. Niwa T, Doi U, Osawa T (2003) Inhibitory activity of corn-derived bisamide compounds against α-glucosidase. J Agric Food Chem 51:90–94

    Article  CAS  PubMed  Google Scholar 

  10. Lu J, Sun JH, Tan Y, Kano Y, Yuan D (2013) New triterpenoid saponins from the flowers of Pueraria thomsonii. J Asian Nat Prod Res 15:1065–1072

    Article  PubMed  Google Scholar 

  11. Kitagawa I, Taniyama T, Wang H, Hori K, Yoshikawa M (1988) Saponin and sapogenol. XLV. Structures of kaikasaponins I, II, and III from sophorae flos, the buds of Sophora japonica L. Yakugaku Zasshi 108:538–546

    CAS  Google Scholar 

  12. Wen J, Shi H, Tu P (2006) Chemical constituents of Abrus mollis. Chin Tradit Herb Drug 37:658–660

    CAS  Google Scholar 

  13. Miyao H, Sakai Y, Takeshita T, Kinjo J, Nohara T (1996) Triterpene saponins from Abrus cantoniensis (Leguminosae). I. Isolation and characterization of four new saponins and a new sapogenol. Chem Pharm Bull 46:1222–1227

    Article  Google Scholar 

  14. Morikawa T, Zhang Y, Nakamura S, Matsuda H, Muraoka O, Yoshikawa M (2007) Bioactive constituents from Chinese natural medicines. XXII. Absolute structures of new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, from Sedum sarmentosum (Crassulaceae). Chem Pharm Bull 55:435–441

    Article  CAS  PubMed  Google Scholar 

  15. Yoshikawa M, Morikawa T, Zhang Y, Nakamura S, Muraoka O, Matsuda H (2007) Megastigmanes and their glucosides from the whole plant of Sedum sarmentosum. J Nat Prod 70:575–583

    Article  CAS  PubMed  Google Scholar 

  16. Liu Q, Liu YL (1989) Studies on chemical constituents Glycyrrhiza eurycarpa P. C. LI. Acta Pharm Sin 24:525–531

    CAS  Google Scholar 

  17. Piskernik C, Haindl S, Behling T, Gerald Z, Kehrer I, Redl H, Kozlov AV (2008) Antimycin A and lipopolysaccharide cause the leakage of superoxide radicals from rat liver mitochondria. Biochim Biophys Acta 1782:280–285

    Article  CAS  PubMed  Google Scholar 

  18. Zhang Y, Han LF, Sakah KJ, Wu ZZ, Liu LL, Agyemang K, Gao XM, Wang T (2013) Bioactive protopanaxatriol type saponins isolated from the roots of Panax notoginseng (Burk.) F. H Chen Mol 18:10352–10366

    CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by Program for National Natural Science Foundation of China (NSFC81202995), New Century Excellent Talents in University (NCET-12-1069), and Program for Tianjin Innovative Research Team in University (TD12-5033).

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Correspondence to Tao Wang.

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Zhang, Y., Qu, L., Liu, L. et al. New maltol glycosides from Flos Sophorae. J Nat Med 69, 249–254 (2015). https://doi.org/10.1007/s11418-014-0877-1

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  • DOI: https://doi.org/10.1007/s11418-014-0877-1

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