Planta Med 2015; 81 - PM_28
DOI: 10.1055/s-0035-1565405

Pentacyclic triterpenoids from roots of Lantana montevidensis (Spreng.) Briq. cultivated in Egypt

SA Ross 1, 2, NM Mohamed 1, 3, MA Makboul 3, SF Farag 3
  • 1National Center for Natural Products Research, School of Pharmacy, University, United States
  • 2Department of BioMolecular Sciences, School of Pharmacy, The University of Mississippi, University, United States
  • 3Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut, Egypt

Eight pentacyclic triterpenoids have been isolated from the chloroform fraction of the roots of Lantana montevidensis (Spreng.) Briq. cultivated in Egypt. Compound (1), which is a new compound, established as 13β-hydroxy-3-Oxo-Olean-11-en-28-oic acid (1) obtained as white amorphous powder with molecular formula C30H46O4 as determined by the HRESIMS at m/z 453.3370 [M- H2O+H]+. The 1H- and 13C-NMR spectra showed the presence of seven quaternary methyls and two olefinic protons, an oxygen bearing quaternary carbon, one carbonyl group and a carboxylic group. The hydroxyl group at C-13 and the double bond at Δ11(12) were located using HMBC experiment. The known compounds are: oleanonic acid (2), oleanolic acid (3), 3β,25β-dihydroxy-olean-12-en-28-oic acid (4), lantadene A (5), 19α-hydroxy-3-oxo-olean-12-en-28-oic (6), pomolic acid (7), camaric acid (8), together with β-sitosterol (9) and its glycoside (10). The isolated compounds were tested for antimicrobial activity and subjected to cannabinoid and opioid receptor binding assay. Compound 8 showed a good activity in Mu and delta opioid receptor binding assay with % of inhibition 48.8 and 46.0, respectively while it showed mild activity in CB2 cannabinoid receptor binding assay with % of inhibition 32.8. Compound 4 showed mild activity in CB1 and Delta opioid receptor assay with % of inhibition 32.1 and 27.9, respectively. Compound 8 showed potent antibacterial activity against Staphylococcus aureus and methicillin-resistant Staphylococcus with IC50 values of 4.95 and 4.58 µg/mL, respectively, while Compounds 2 and 4 showed moderate antibacterial activity toward methicillin-resistant Staphylococcus with IC50 15.74 and 14.22 µg/mL, respectively (using ciprofloxacin as a positive control with IC50 of 0.12 µg/mL, for both organisms). Compound 3 showed mild activity toward Cryptococcus neoformance with IC50 19.84 µg/mL. (Using amphotericin B as a positive control with IC50 of 0.28 µg/mL).