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Resin glycosides from Ipomoea tyrianthina and their sedative and vasorelaxant effects

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Abstract

The methanol-soluble extract from the root of Ipomoea tyrianthina was studied in order to isolate compounds with activity on the central nervous system and vasorelaxant effects. Chromatographic methods were used to isolate and purify seven new glycolipids (2–8). The structures of compounds 1–8 were elucidated by a combination of NMR spectroscopy and mass spectrometry. Tyrianthinoic acid (1) is a glycosidic acid composed of a linear pentasaccharide core bonded to a 11-hydroxyhexadecanoic acid. The structure of tyrianthinic acids III (2), IV (3), and V (4) consists of a partially acylated tyrianthinoic acid. Tyrianthinic acid VI (8) is a tetrasaccharide core bonded to a jalapinolic acid, acylated by a 2-methyl-3-hydroxybutanoic acid. Tyrianthins C (5), D (6), and E (7) are ester-type heterodimers of scammonic acid A with different acylating residues in the two monomeric units. The macrolactonization site was located at C-3 of the rhamnose unit. The position of the ester linkage for monomeric unit B on the macrocyclic unit A was established at C-4 of the terminal quinovose. Compounds 5–7 increased the sleeping time induced by pentobarbital and the release of gamma-aminobutyric acid in brain cortex. In addition, compounds 5–7 showed significant in vitro relaxant effects on aortic rat rings, in endothelium- and concentration-dependent manners.

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Acknowledgments

This research was supported by CONACyT (Grants 90268 and CB2011-168569). J. M. Castro is grateful to CONACyT for a graduate student scholarship (43923). We thank LANEM (CIQ) for recording the NMR spectra. We also thank V. Labastida (CIQ, UAEM) for recording the FABMS, and M. Medina (CIQ, UAEM) for recording the GC–MS and IR spectra.

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Authors and Affiliations

  1. Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209, Cuernavaca, Morelos, Mexico

    Ismael León-Rivera & Gabriela Vargas

  2. Centro de Investigación en Biotecnología, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209, Cuernavaca, Morelos, Mexico

    José Manuel Castro & María del Carmen Gutiérrez

  3. Facultad de Química, Universidad Autónoma de Yucatán, Calle 41 por 26 y 28, Col. Industrial, Mérida, Yucatán, Mexico

    Gumersindo Mirón-López

  4. Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Coyoacán, Distrito Federal, Mexico

    Federico del Río-Portilla, Raúl G. Enríquez & Angeles Mendoza

  5. Department of Chemistry, University of Toronto, Toronto, ON, M5S 3H6, Canada

    William F. Reynolds

  6. Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209, Cuernavaca, Morelos, Mexico

    Samuel Estrada-Soto & Priscilla Rendón-Vallejo

  7. Centro de Investigación Biomédica del Sur, IMSS, Argentina 1, Col. Centro, 62790, Xochitepec, Morelos, Mexico

    Maribel Herrera-Ruiz

Authors
  1. Ismael León-Rivera
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  2. José Manuel Castro
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  3. Gumersindo Mirón-López
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  4. Federico del Río-Portilla
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  5. Raúl G. Enríquez
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  6. William F. Reynolds
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  7. Samuel Estrada-Soto
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  8. Priscilla Rendón-Vallejo
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  9. María del Carmen Gutiérrez
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  10. Maribel Herrera-Ruiz
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  11. Angeles Mendoza
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  12. Gabriela Vargas
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Corresponding author

Correspondence to Ismael León-Rivera.

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León-Rivera, I., Castro, J.M., Mirón-López, G. et al. Resin glycosides from Ipomoea tyrianthina and their sedative and vasorelaxant effects. J Nat Med 68, 655–667 (2014). https://doi.org/10.1007/s11418-014-0844-x

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  • DOI: https://doi.org/10.1007/s11418-014-0844-x

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