Ent-labdane type diterpene with antifungal activity from Gymnosperma glutinosum (Spreng.) Less. (Asteraceae)

Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 01/2009;
Source: DOAJ


The aim of this work was to isolate and identify the antifungal compounds present in the hexanic extract of the aerial parts of Gymnosperma glutinosum. The antifungal activity against six pathogenic fungi was determined in accordance with the inhibition of radial growth method. Four of those fungi Aspergillus niger, Candida albicans, Fusarium sporotrichum and Trichophyton mentagrophytes are of clinical importance and two fungi Fusarium moniliforme and Rhyzoctonia solani are of agricultural importance. The bioassay-guide purification of the methanolic partition (from hexanic extract) resulted in the isolation and identification of three antifungal compounds an ent-labdane type diterpene and two methoxylated flavones, as the metabolites responsible for activity.

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Available from: Carlos L Cespedes, Oct 06, 2015
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    ABSTRACT: The antitumor potential of Gymnosperma glutinosum was previously reported using the in vitro and in vivo L5178Y-R lymphoma murine model. The present study was carried out to isolate and identify the cytotoxic compounds present in the Gymnosperma glutinosum leaf hexane extract. Gymnosperma glutinosum was collected in the semi-arid region of Escobedo, State of Nuevo León, México, but it is commonly found in northeastern Mexico; it is traditionally used as a treatment for diarrhea, ulcers and rheumatism. G. glutinosum leaves were extracted with hexane and further fractioned and subfractioned over silica gel by gradient elution with hexane, chloroform, ethyl acetate and methanol. The cytotoxicity of fractions and subfractions was assessed in vitro against L5178Y-R lymphoma cells. Structure elucidation of the active compounds was determined by spectroscopic methods. Fractions and subfractions showed significant (p < 0.05) and concentration-dependent 20% to 56% cytotoxicity against L5178Y-R cells at concentrations ranging from 7.8 µg/mL to 500 µg/mL. The bioassay-guided fractionation of the hexane extract resulted in the isolation and identification of the alkane hentriacontane and the diterpene ent-labd-7-en-13S,14R,15-triol as the metabolites responsible for the activity. Copyright © 2012 John Wiley & Sons, Ltd.
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    ABSTRACT: Bioassay-guided fractionation of hexane extracts of Gymnosperma glutinosum (Asteraceae) leaves, collected in North Mexico, afforded the known compounds hentriacontane ( 1 ) and (+)-13 S ,14 R ,15-trihydroxy- ent -labd-7-ene ( 2 ), as well as the new ent -labdane diterpene (-)-13 S ,14 R ,15-trihydroxy-7-oxo- ent -labd-8(9)-ene ( 3 ). In addition, D-glycero-D-galactoheptitol ( 4 ) was isolated from the methanolic extract of this plant. Their structures were established on the basis of high-field 1D- and 2D NMR methods supported by HR-MS data. The cytotoxic activity was determined by using the in vitro L5178Y-R lymphoma murine model. Hentriacontane ( 1 ) and the new ent -labdane 3 showed weak cytotoxicity, whereas the ent -labdane 2 showed significant ( p < 0.05) and concentration dependent cytotoxicity (up to 78%) against L5178Y-R cells at concentrations ranging from 7.8 to 250 µg/mL.
    Molecules 12/2012; 17(9):11229-41. DOI:10.3390/molecules170911229 · 2.42 Impact Factor