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Hirtionosides A–C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta

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Abstract

From the 1-BuOH-soluble fraction of a MeOH extract of Euphorbia hirta, collected in the Okinawa islands, three new megastigmane glucoside gallates, named hirtionosides A–C, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside were isolated along with 15 known compounds. The structures of the new compounds were elucidated by detailed analysis of physical data, including one- and two-dimensional NMR spectra, and those of known compounds were determined by comparison of physico-chemical data with those reported in the literature. The absolute structures of the megastigmanes were determined by comparison of NMR data and Cotton effects in the CD spectra. The modified Mosher’s method was applied to determine the absolute structure of the chiral center in 3-hydroxyoctanoic acid. The DPPH radical-scavenging properties of megastigmane glucoside gallates were assayed and, as expected, they showed moderate activity.

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References

  1. Cai W-H, Matsunami K, Otsuka H (2009) Supinaionosides A and B: megastigmane glucosides and supinanitrilosides A–F: hydroxynitrile glucosides from the whole plants of Euphorbia supine Rafinesque. Chem Pharm Bull 57:840–845

    Article  PubMed  CAS  Google Scholar 

  2. Mizutani K, Yuda M, Tanaka O, Saruwatari Y-I, Fuwa T, Jia M-R, Ling Y-K, Pu X-F (1988) Chemical studies on Chinese traditional medicine, dangshen. I. Isolation of (Z)-3- and (E)-2-hexenyl-β-d-glucosides. Chem Pharm Bull 36:2689–2690

    Article  PubMed  CAS  Google Scholar 

  3. Sawabe A, Obata T, Kochika Y, Morita M, Yamashita N, Matsubusa Y, Okamoto T (1998) Glycosides in African dietary leaves, Hibiscus sabdariffa. J Jpn Oil Chem Soc 47:25–30

    Article  CAS  Google Scholar 

  4. De Marino S, Festa C, Zollo F, Iorizzi M (2009) Phenolic glycosides from Cucumis melo var. inodorus seeds. Phytochem Lett 2:130–133

    Article  Google Scholar 

  5. De Tommasi N, Rastrelli L, Cumanda J, Speranza G, Pizza C (1996) Aryl and triterpenic glycosides from Margyricarpus setosus. Phytochemistry 42:163–167

    Article  PubMed  CAS  Google Scholar 

  6. De Rosa S, De Giulio A, Tommonaro G (1996) Aliphatic and aromatic glycosides from the cell cultures of Lycopersicon esculentum. Phytochemistry 42:1031–1034

    Article  PubMed  Google Scholar 

  7. Trifunovic S, Vajs V, Macura S, Juranic N, Djarmati Z, Jankov R, Milosavljevic S (1998) Oxidation products of hyperforin from Hypericum perforatum. Phytochemistry 49:1299–1304

    Article  Google Scholar 

  8. Ninomiya M, Itoh T, Ishikawa S, Saiki M, Narumiya K, Yasuda M, Koshikawa K, Nozawa Y, Koketsu M (2010) Phenolic constituents isolated from Fragaria ananassa Duch. inhibits antigen-stimulated degranulation through direct inhibition of spleen tyrosine kinase activation. Bioorg Med Chem 18:5932–5937

    Article  PubMed  CAS  Google Scholar 

  9. Matsunami K, Otsuka H, Takeda Y (2010) Structural revisions of blumenol C glucoside and byzantionoside B. Chem Pharm Bull 58:438–441

    Article  PubMed  CAS  Google Scholar 

  10. Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kageyama C (1988) Studies on the constituents of leaves of Citrus unshiu MARCOV. Chem Pharm Bull 36:5004–5008

    Article  CAS  Google Scholar 

  11. Yoshikawa M, Shimada H, Saka M, Yoshizumi S, Yamahara J, Matsuda H (1997) Medicinal food stuffs. V. Moroheiya. (1): absolute stereostructures of corchoionosides A, B and C, histamine release inhibitors from the leaves of Vietnamese Corchorus olitorius L. (Tiliaceae). Chem Pharm Bull 45:464–469

    Article  PubMed  CAS  Google Scholar 

  12. Akgul Y, Ferreira D, Abourashed EA, Khan IA (2004) Lotaustralin from Rhodiola rosea roots. Fitoterapia 75:612–614

    Article  PubMed  CAS  Google Scholar 

  13. Otsuka H, Yu Q, Matsunami K (2010) Bumaldosoides A, B and C from the leaves of Staphylea bumalda. Heterocycles 80:339–348

    Article  CAS  Google Scholar 

  14. Peng J, Fan G, Hong Z, Chai Y, Wu Y (2005) Preparative separation of isovitexin and isoorientin from Patrinia villosa Juss. by High-speed counter-current chromatography. J Chromatogr A 1074:111–115

    Article  PubMed  CAS  Google Scholar 

  15. Chung S-K, Kim Y-C, Takaya Y, Terashima K, Niwa M (2004) Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans and its antioxidant effect. J Agric Food Chem 52:4664–4668

    Article  PubMed  CAS  Google Scholar 

  16. Matsuura H, Yoshihara T, Ichihara A, Kikuta Y, Koda Y (1993) Tuber-forming substance in Jerusalem artichose (Helianthus tuberosus L.). Biosci Biotechnol Biochem 57:1253–1256

    Article  CAS  Google Scholar 

  17. Tsuboi Y, Doi T, Matsunami K, Otsuka H, Shinzato T, Takeda Y (2011) Gallates of isoorientin and (2S)-1,2-propanediol glucoside from the leaves of Schoepfia jasminodora. J Nat Med 65:617–622

    Article  PubMed  CAS  Google Scholar 

  18. Wei K, Li W, Koike K, Liu L, Fu X, Lin L, Chen Y, Nikaido T (2004) Two new galloylglucosides from the leaves of Mallotus fuaretianus. Chem Pharm Bull 52:776–779

    Article  PubMed  CAS  Google Scholar 

  19. Matsunami K, Otsuka H, Kondo K, Shinzato T, Kawahata M, Yamaguchi K, Takeda Y (2009) Absolute configuration of (+)-pinoresinol 4-O-(6″-O-galloyl)-β-d-glucopyranoside, macarangionosides E and F, isolated from the leaves of Macaranga tanarius. Phytochemistry 70:1277–1285

    Article  PubMed  CAS  Google Scholar 

  20. Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J Am Chem Soc 113:4092–4096

    Article  CAS  Google Scholar 

  21. Kasai R, Suzuno M, Asakawa J, Tanaka O (1977) Carbon-13 chemical shifts of isoprenoid-β-d-glycopyranosides and -β-d-mannopyranosides. Stereochemical influences of aglycone alcohols. Tetrahedron Lett 18:175–178

    Google Scholar 

  22. Fiorentino A, D’Abrosca B, Pacifico S, Mastellone C, Piscopo V, Caputo R, Monaco P (2008) Isolation and structure elucidation of antioxidant polyphenols from quince (Cydonia vulgaris) peels. J Agric Food Chem 56:2660–2667

    Article  PubMed  CAS  Google Scholar 

  23. Nakamura S, Zhang Y, Matsuda H, Ninomiya K, Muraoka O, Yoshikawa M (2011) Chemical structures and hepatoprotective effects of constituents from the leaves of Salacia chinensis. Chem Pharm Bull 59:1020–1028

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful for access to the superconducting NMR instrument (JEOL JNM α-400) at the Analytical Center of Molecular Medicine of the Hiroshima University Faculty of Medicine, and an Applied Biosystem QSTAR XL system ESI (Nano Spray)-MS at the Analysis Center of Life Science of the Graduate School of Biomedical Sciences, Hiroshima University. This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and the Japan Society for the Promotion of Science. Thanks are also due to the Research Foundation for Pharmaceutical Sciences and the Takeda Science Foundation for financial support.

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Authors and Affiliations

  1. Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan

    Yuya Nomoto, Sachiko Sugimoto, Katsuyoshi Matsunami & Hideaki Otsuka

  2. Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University, 6-13-1 Yasuhigashi, Asaminami-ku, Hiroshima, 731-0153, Japan

    Hideaki Otsuka

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  1. Yuya Nomoto
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  2. Sachiko Sugimoto
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  3. Katsuyoshi Matsunami
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  4. Hideaki Otsuka
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Correspondence to Hideaki Otsuka.

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Nomoto, Y., Sugimoto, S., Matsunami, K. et al. Hirtionosides A–C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta . J Nat Med 67, 350–358 (2013). https://doi.org/10.1007/s11418-012-0692-5

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  • DOI: https://doi.org/10.1007/s11418-012-0692-5

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