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. 2012 Sep 20;17(9):11229-41.
doi: 10.3390/molecules170911229.

Bioassay-guided isolation and identification of cytotoxic compounds from Gymnosperma glutinosum leaves

Ramiro Quintanilla-Licea  1 , Rolando Morado-Castillo, Ricardo Gomez-Flores, Hartmut Laatsch, María Julia Verde-Star, Humberto Hernández-Martínez, Patricia Tamez-Guerra, Reyes Tamez-Guerra, Cristina Rodríguez-Padilla
Affiliations

Bioassay-guided isolation and identification of cytotoxic compounds from Gymnosperma glutinosum leaves

Ramiro Quintanilla-Licea et al. Molecules. .

Abstract

Bioassay-guided fractionation of hexane extracts of Gymnosperma glutinosum (Asteraceae) leaves, collected in North Mexico, afforded the known compounds hentriacontane (1) and (+)-13S,14R,15-trihydroxy-ent-labd-7-ene (2), as well as the new ent-labdane diterpene (-)-13S,14R,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.

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Figures

Figure 1
Figure 1
Structures of compounds 1–4.
Figure 2
Figure 2
Selected H,H COSY (↔) and HMBC (→) correlations of diterpene 3 in CDCl3.
Figure 3
Figure 3
Microbiological transformation of labdane 5 into 6 [33].
Figure 4
Figure 4
Conformations and hydrogen bridges of labdane 6 (left partial structure) and ent-labdane 3 (right fragment) according to DFT calculations with SPARTAN®. The carbon shifts were calculated for solutions in CH2Cl2.
Figure 5
Figure 5
Cytotoxicity of extracts and fractions SC1 to SC4 from hexane extract of Gymnosperma glutinosum against L5178Y-R cells in vitro, as compared with untreated control (culture medium). Data represent means ± SD of triplicate determinations from 3 independent experiments. Optical density at 540 nm for untreated cells was 0.53 ± 0.06.
Figure 6
Figure 6
Cytotoxicity of pure compound 2 from Gymnosperma glutinosum against L5178Y-R cells in vitro, as compared with untreated control (culture medium). Data represent means ± SD of triplicate determinations from three independent experiments. Optical density at 540 nm for untreated cells was 0.53 ± 0.06.
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