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Four new resin glycosides, murasakimasarins I–IV, from the tuber of Ipomoea batatas

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Abstract

Four new resin glycosides having macrolactone structures (jalapins), murasakimasarins I–IV, were isolated from the tubers of Ipomoea batatas (L.) Lam. (‘Murasakimasari’, Convolvulaceae), along with three known glycosides. Their structures were determined on the basis of spectroscopic data as well as chemical evidence. Murasakimasarin III is the first representative of a resin glycoside with 10-methylundecanoic acid as the component organic acid.

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References

  1. Shellard EJ (1961) The chemistry of some convolvulaceous resins part 1. Vera cruz jalap. Plant Med 9:102–116

    Article  CAS  Google Scholar 

  2. Pereda-Miranda R, Rosas-Ramírez D, Castańeda-Gómez J (2010) Resin glycosides from morning glory family. In: Kinghorn AD, Falk H, Kobayashi J (eds) Progress in the chemistry of organic natural products. Springer, Berlin, pp 77–153 (92)

    Google Scholar 

  3. Yoshikawa K, Yagi C, Hama H, Tanaka M, Arihara S, Hashimoto T (2010) Ipomotaosides A-D, resin glycosides from the aerial parts of Ipomoea batatas and their inhibitory activity against COX-1 and COX-2. J Nat Prod 73:1763–1766

    Article  CAS  Google Scholar 

  4. Figueroa-González G, Jacobo-Herrera N, Zentella-Dehesa A, Pereda-Miranda R (2012) Reversal of multidrug resistance by morning glory resin glycosides in human breast cancer cells. J Nat Prod 75:93–97

    Article  Google Scholar 

  5. Ono M, Takigawa A, Kanemaru Y, Kawakami G, Kabata K, Okawa M, Kinjo J, Yokomizo K, Yoshimitsu H, Nohara T (2014) Calysolins V–IX, resin glycosides from Calystegia soldanella and their antiviral activity toward herpes. Chem Pharm Bull 62:97–105

    Article  CAS  Google Scholar 

  6. Noda N, Yoda S, Kawasaki T, Miyahara K (1992) Simonins I–V, ether-soluble resin glycosides (jalapins) from the roots of Ipomoea batatas (cv. Simon). Chem Pharm Bull 40:3163–3168

    Article  CAS  Google Scholar 

  7. Escalante-Sánchez E, Pereda-Miranda R (2007) Batatins I and II, ether-type dimers of acylated pentasaccharides from the resin glycosides of sweet potato. J Nat Prod 70:1029–1034

    Article  Google Scholar 

  8. Yin Y-Q, Kong L-Y (2008) Ether-soluble resin glycosides from the roots of Ipomoea batatas. J Asian Nat Prod Res 10:233–238

    Article  CAS  Google Scholar 

  9. Yin Y, Li Y, Kong L (2008) Pentasaccharide glycosides from the tubers of sweet potato (Ipomoea batatas). J Agric Food Chem 56:2363–2368

    Article  CAS  Google Scholar 

  10. Escalante-Sánchez E, Rosas-Rameírez D, Linares E, Bye R, Pereda-Miranda R (2008) Batatinosides II–VI, acylated lipooligosaccharides from the resin glycosides of sweet potatao. J Agric Food Chem 56:9423–9428

    Article  Google Scholar 

  11. Noda N, Horiuchi Y (2008) The resin glycosides from the sweet potato (Ipomoea batatas L. Lam.). Chem Pharm Bull 56:1607–1610

    Article  CAS  Google Scholar 

  12. Yin Y, Huang X, Kong L, Niwa M (2008) Three new pentasaccharide resin glycosides from the roots of sweet potato (Ipomoea batatas). Chem Pharm Bull 56:1670–1674

    Article  CAS  Google Scholar 

  13. Rosas-Ramírez D, Escalante-Sánchez E, Pereda-Miranda R (2011) Batatins III–VI, glycolipid ester-type dimers from Ipomoea batatas. Phytochemistry 72:773–780

    Article  Google Scholar 

  14. Rosas-Ramírez D, Pereda-Miranda R (2013) Resin glycosides from the yellow-skinned variety of sweet potato (Ipomoea batatas). J Agric Food Chem 61:9488–9494

    Article  Google Scholar 

  15. Rosas-Ramírez D, Pereda-Miranda R (2015) Batatins VIII–XI, glycolipid ester-type dimers from Ipomoea babatas. J Nat Prod 78:26–33

    Article  Google Scholar 

  16. Ono M, Oda S, Yasuda S, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T, Miyahara K (2017) Acylated glycosidic acid methyl esters generated from the convolvulin fraction of Rhizoma Jalapae Braziliensis by treatment with indium(III) chloride in methanol. Chem Pharm Bull 65:107–111

    Article  CAS  Google Scholar 

  17. Takigawa A, Setoguchi H, Okawa M, Kinjo J, Miyashita H, Yokomizo K, Yoshimitsu H, Nohara T, Ono M (2011) Identification and characterization of component organic and glycosidic acids of crude resin glycoside fraction from Calystegia soldanella. Chem Pharm Bull 59:1163–1168

    Article  CAS  Google Scholar 

  18. Ono M, Kawasaki T, Miyahara K (1989) Resin glycosides. V. identification and characterization of the component organic and glycosidic acids of the ether-soluble crude resin glycosides (“jalapin”) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 37:3209–3213

    Article  CAS  Google Scholar 

  19. Ono M (2017) Resin glycosides from convolvulaceae plants. J Nat Med 71:591–604

    Article  CAS  Google Scholar 

  20. Ono M, Nishi M, Kawasaki T, Miyahara K (1990) Resin glycosides. IX. operculins I, II, V, VII and VIII, new ether-soluble resin glycosides of Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 38:2986–2991

    Article  CAS  Google Scholar 

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Acknowledgements

We express our appreciation to Mr. H. Harazono of Fukuoka University for the measurement of the FAB-MS. This research was supported in part by a Grant-in-Aid for Scientific Research (C) (JPS KAKENHI Grant Number JP16K08306) and by the Research and Study Program/Project of Tokai University Educational System General Research Organization (Kanagawa, Japan).

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Authors and Affiliations

  1. School of Agriculture, Tokai University, 9-1-1 Toroku, Higashi-ku, Kumamoto, 862–8652, Japan

    Masateru Ono, Sena Teramoto, Saori Naito, Asuka Takahashi, Akito Yoneda, Masato Shinkai, Naoki Taga & Sin Yasuda

  2. Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka, 814-0180, Japan

    Ryota Tsuchihasi, Masafumi Okawa & Junei Kinjo

  3. Faculty of Pharmaceutical Sciences, Sojo University, 4-22-2 Ikeda, Nishi-ku, Kumamoto, 860-0082, Japan

    Hitoshi Yoshimitsu & Toshihiro Nohara

Authors
  1. Masateru Ono
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  2. Sena Teramoto
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  3. Saori Naito
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  4. Asuka Takahashi
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  5. Akito Yoneda
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  6. Masato Shinkai
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  7. Naoki Taga
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  8. Sin Yasuda
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  10. Masafumi Okawa
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  11. Junei Kinjo
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  12. Hitoshi Yoshimitsu
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  13. Toshihiro Nohara
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Correspondence to Masateru Ono.

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Ono, M., Teramoto, S., Naito, S. et al. Four new resin glycosides, murasakimasarins I–IV, from the tuber of Ipomoea batatas. J Nat Med 72, 784–792 (2018). https://doi.org/10.1007/s11418-018-1197-7

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  • DOI: https://doi.org/10.1007/s11418-018-1197-7

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