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Open AccessArticle

Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû)

1
Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Campus Lircay, Talca 3460000, Chile
2
Departamento de Ciencias Básicas Biomédicas, Facultad de Ciencias de la Salud, Universidad de Talca, Campus Lircay, Talca 3460000, Chile
3
Laboratorio de Cultivo Celular, Facultad de Ciencias de la Salud, Universidad de Talca, Campus Lircay, Talca 3460000, Chile
4
Centro de Estudios Rurales Interdisciplinarios, Oliva 1019, Edificio Lider V, Piso 17, oficina 172, Asunción 01421, Paraguay
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(1), 180; https://doi.org/10.3390/molecules25010180
Received: 5 December 2019 / Revised: 19 December 2019 / Accepted: 27 December 2019 / Published: 1 January 2020
(This article belongs to the Section Natural Products Chemistry)
The crude drug ysypó hû (Adenocalymma marginatum DC., Bignoniaceae) is used traditionally by the Guarani of Eastern Paraguayan as a male sexual enhancer. The aim of the present study was to identify the main constituents of the crude drug and to evaluate the in vitro inhibitory activity towards the enzyme phosphodiesterase-5 (PDE-5). The main compounds were isolated by counter-current chromatography (CCC). The metabolites were identified by spectroscopic and spectrometric means. The chemical profiling of the extracts was assessed by high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS/MS). The crude extract and main isolated compounds were tested for their PDE-5 inhibitory activity using commercial kits. The iridoid theviridoside and 4-hydroxy-1-methylproline were isolated as the main constituent of the crude drug. Four chlortheviridoside hexoside derivatives were detected for the first time as natural products. Chemical profiling by HPLC-MS/MS led to the tentative identification of nine iridoids, six phenolics, and five amino acids. The crude extracts and main compounds were inactive towards PDE-5 at concentrations up to 500 µg/mL. Iridoids and amino acid derivatives were the main compounds occurring in the Paraguayan crude drug. The potential of ysypó hû as a male sexual enhancer cannot be discarded, since other mechanisms may be involved. View Full-Text
Keywords: Adenocalymma marginatum; Bignoniaceae; counter-current chromatography; iridoids; amino acid derivatives; Guarani medicine; Paraguayan crude drug Adenocalymma marginatum; Bignoniaceae; counter-current chromatography; iridoids; amino acid derivatives; Guarani medicine; Paraguayan crude drug
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MDPI and ACS Style

Schmeda-Hirschmann, G.; Burgos-Edwards, A.; Jiménez-Aspee, F.; Mieres-Castro, D.; Theoduloz, C.; Pormetter, L.; Fogel, R.; Céspedes, C.; Soria, N.; Valdez, S. Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû). Molecules 2020, 25, 180. https://doi.org/10.3390/molecules25010180

AMA Style

Schmeda-Hirschmann G, Burgos-Edwards A, Jiménez-Aspee F, Mieres-Castro D, Theoduloz C, Pormetter L, Fogel R, Céspedes C, Soria N, Valdez S. Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû). Molecules. 2020; 25(1):180. https://doi.org/10.3390/molecules25010180

Chicago/Turabian Style

Schmeda-Hirschmann, Guillermo; Burgos-Edwards, Alberto; Jiménez-Aspee, Felipe; Mieres-Castro, Daniel; Theoduloz, Cristina; Pormetter, Lisa; Fogel, Ramon; Céspedes, Claudia; Soria, Nelida; Valdez, Sintya. 2020. "Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó hû)" Molecules 25, no. 1: 180. https://doi.org/10.3390/molecules25010180

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