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A glycerol α-d-glucuronide and a megastigmane glycoside from the leaves of Guettarda speciosa L.

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Abstract

From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Guettarda speciosa L., two new compounds (1, 2) were isolated together with six known compounds. Spectroscopic analysis of 1 and 2 established their structures to be derivatives of a glycerol α-glucuronide and a megastigmane glycoside, respectively. HPLC analysis of the hydrolyzate of 1 confirmed the presence of d-glucuronic acid in the structure, and the modified Mosher’s method established the absolute structure of 2.

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References

  1. Hatusima S (1975) Flora of the Ryukyus. Added and Corrected. The Biological Society of Okinawa, Naha, p 569

    Google Scholar 

  2. Montagnac A, Litaudon M, Pais M (1997) Quinine- and quinicine-derived alkaloids from Guettarda noumeana. Phytochemistry 46:973–975

    Article  CAS  Google Scholar 

  3. Kan-Fan C, Brillanceau MH, Husson HP (1986) Plants of New Caledonia. Part 107. 3-Epi-antirhine, a new alkaloid from Guettarda heterosepala. J Nat Prod 49:1130–1132

    Article  CAS  Google Scholar 

  4. Aquino R, de Simone F, Pizza C, de Mello JF (1989) Further quinovic glycosides from Guettarda platypoda. Phytochemistry 28:199–201

    Article  CAS  Google Scholar 

  5. Aquino R, De Simone F, Pizza C, Cerri R, De Mello JF (1988) Further quinovic acid glycosides from Guettarda platypoda. Phytochemistry 27:2927–2930

    Article  CAS  Google Scholar 

  6. Matos MEO, Sousa MP, Machado MIL, Braz Filho R (1986) Quinovic acid glycosides from Guettarda angelica. Phytochemistry 25:1419–1422

    Article  CAS  Google Scholar 

  7. Yaga S, Kinjo K (1985) On the termite-resistance of Okinawan timbers. IX. Termiticidal substance from the wood of Guettarda speciosa L. Mokuzai Gakkaishi 31:684–687

    CAS  Google Scholar 

  8. Boros CA, Stermitz FR (1991) Iridoids. An updated review, part II. J Nat Prod 54:1173–1246

    Article  CAS  Google Scholar 

  9. Otsuka H, Kijima (nee Yuasa) K (2001) An iridoid gentiobioside, a benzophenone glucoside and acylated flavone C-glycosides from Tripterospermum japonicum (Sieb. et Zucc.) Maxim. Chem Pharm Bull 49:699–702

    Article  PubMed  CAS  Google Scholar 

  10. Píš J, Buděšínský M, Vokáč K, Laudová V, Harmatha J (1994) Ecdysteroids from the roots of Leuzea carthamoides. Phytochemistry 37:707–711

    Article  Google Scholar 

  11. Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H (1987) Studies on the glycosides of Epimedium grandiflorum Morr. var. thunbergianum (Miq.) Nakai II. Chem Pharm Bull 35:3713–3719

    CAS  Google Scholar 

  12. Handa SS, Borris RP, Cordell GA, Phillipson JD (1983) NMR spectral analysis of cadambine from Anthocephalus chinensis. J Nat Prod 46:325–330

    Article  CAS  Google Scholar 

  13. Maggi A, Taskova K, Gotfredsen CH, Bianco A, Jensen SR (2009) Chemical markers in Veronica sect. Hebe. III. Biochem Syst Ecol 37:731–736

    Article  CAS  Google Scholar 

  14. Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I (2007) Facile discrimination of aldose enatiomers by reversed-phase HPLC. Chem Pharm Bull 55:899–901

    Article  PubMed  CAS  Google Scholar 

  15. Morikawa T, Wang L-B, Ninomiya K, Nakamura S, Matsuda H, Muraoka O, Wu L-J, Yoshikawa M (2009) Medicinal flowers XXX. Eight new glycosides, everlastosides F–M, from the flowers of Helichrysum arenarium. Chem Pharm Bull 57:853–859

    Article  PubMed  CAS  Google Scholar 

  16. Tommasi ND, Piacente S, Simone FD, Pizza C (1996) Constituents of Cydonia vulgaris. Isolation and structure elucidation of four new flavonol glycosides and nine new α-ionol-derived glycosides. J Agric Food Chem 44:1676–1681

    Article  Google Scholar 

  17. Galbraith MN, Horn DHS (1972) Structures of the natural products blumenols A, B, and C. J Chem Soc Chem Commun 113–114

  18. 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 

  19. 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 

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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, the Japan Society for the Promotion of Science, and the Ministry of Health, Labour and Welfare. Thanks are also due to the Research Foundation for Pharmaceutical Sciences and the Takeda Science Foundation for their financial support.

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Correspondence to Hideaki Otsuka.

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Cai, WH., Matsunami, K., Otsuka, H. et al. A glycerol α-d-glucuronide and a megastigmane glycoside from the leaves of Guettarda speciosa L.. J Nat Med 65, 364–369 (2011). https://doi.org/10.1007/s11418-010-0484-8

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  • DOI: https://doi.org/10.1007/s11418-010-0484-8

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