1. Academic Validation
  2. Antibacterial Labdane Diterpenoids from Vitex vestita

Antibacterial Labdane Diterpenoids from Vitex vestita

  • J Nat Prod. 2015 Jun 26;78(6):1348-56. doi: 10.1021/acs.jnatprod.5b00206.
Nina Corlay 1 Marylin Lecsö-Bornet Erell Leborgne 1 Florent Blanchard 1 Xavier Cachet 1 Jérôme Bignon 1 Fanny Roussi 1 Marie-Jose Butel Khalijah Awang 2 Marc Litaudon 1
Affiliations

Affiliations

  • 1 †Centre de Recherche de Gif, LabEx CEBA, Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, 91198 Gif-sur-Yvette, France.
  • 2 ∥Department of Chemistry, University Malaya, 59100 Kuala Lumpur, Malaysia.
Abstract

A large-scale in vitro screening of tropical Plants using an Antibacterial assay permitted the selection of several species with significant Antibacterial activities. Bioassay-guided purification of the dichloromethane extract of the leaves of the Malaysian species Vitex vestita, led to the isolation of six new labdane-type Diterpenoids, namely, 12-epivitexolide A (2), vitexolides B and C (3 and 4), vitexolide E (8), and vitexolins A and B (5 and 6), along with six known compounds, vitexolides A (1) and D (7), acuminolide (9), 3β-hydroxyanticopalic acid (10), 8α-hydroxyanticopalic acid (11), and 6α-hydroxyanticopalic acid (12). Their structures were elucidated on the basis of 1D and 2D NMR analyses and HRMS experiments. Both variable-temperature NMR spectroscopic studies and chemical modifications were performed to investigate the dynamic epimerization of the γ-hydroxybutenolide moiety of compounds 1-4. Compounds were assayed against a panel of 46 Gram-positive strains. Vitexolide A (1) exhibited the most potent Antibacterial activity with minimal inhibitory concentration values ranging from 6 to 96 μM, whereas compounds 2 and 6-9 showed moderate Antibacterial activity. The presence of a β-hydroxyalkyl-γ-hydroxybutenolide subunit contributed significantly to Antibacterial activity. Compounds 1-4 and 6-9 showed cytotoxic activities against the HCT-116 Cancer cell line (1 < IC50s < 10 μM) and human fetal lung fibroblast MRC5 cell line (1 < IC50s < 10 μM for compounds 1, 2, 7, 8, and 9).

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