Structure Elucidation, Antimicrobial and Cytotoxic Activities of a Halimane Isolated from Vellozia kolbekii Alves (Velloziaceae)

Carmelita G Silva; Helvécio M Santos Júnior; Jussara P Barbosa; Gisela L Costa; Felipe A R Rodrigues; Denilson F Oliveira; Letícia V Costa-Lotufo; Ruy J V Alves; Elis C A Eleutherio; Claudia M Rezende

doi:10.1002/cbdv.201500071

Structure Elucidation, Antimicrobial and Cytotoxic Activities of a Halimane Isolated from Vellozia kolbekii Alves (Velloziaceae)

Chem Biodivers. 2015 Dec;12(12):1891-901. doi: 10.1002/cbdv.201500071.

Affiliations

¹ Institute of Chemistry, Federal University of Rio de Janeiro, Rio de Janeiro, 21941-909, Brazil, (phone: +55 21 39387121; fax: +55 21 39387735).
² Laboratório de Taxonomia, Bioquímica e Bioprospecção em Fungos FIOCRUZ, Rio de Janeiro 21045-900, Brazil.
³ Department of Physiology and Pharmacology, School of Medicine, Federal University of Ceará, Ceará 60430-270, Brazil.
⁴ Departament of Chemistry, Federal University of Lavras, Minas Gerais 37200-000, Brazil.
⁵ Museu Nacional, Federal University of Rio de Janeiro, Rio de Janeiro 20940-040, Brazil.
⁶ Institute of Chemistry, Federal University of Rio de Janeiro, Rio de Janeiro, 21941-909, Brazil, (phone: +55 21 39387121; fax: +55 21 39387735). claudia.rezendeufrj@gmail.com.

PMID: 26663842
DOI: 10.1002/cbdv.201500071

Abstract

A new halimane diterpene was isolated from Vellozia kolbekii Alves (Velloziaceae) and identified as (5R,8R,9S,13R)-halim-1,10-ene-15,16-diol (1). It showed cytotoxicity against three human cancer cell lines, SF-295 (glioblastoma), MDA-MB-435 (melanoma), and HCT-8 (colon adenocarcinoma). In the mechanism of cytotoxic action, halimane 1 interferes in two major phases of the cell cycle: in S phase, in which DNA synthesis occurs and where it is very sensitive to damage, and G2M phase which is the phase of preparation for mitosis and mitosis itself, showing apoptosis-inducing properties. Antimicrobial activity towards Gram-positive and Gram-negative bacteria was studied and, against Bacillus cereus, B. subtilis, Escherichia coli, and Pseudomonas aeruginosa, a MIC value of 0.025 μM was observed for halimane 1, which is more active than the positive control chloramphenicol.

Keywords: (5R,8R,9S,13R)-Halim-1,10-ene-15,16-diol; Antimicrobial activity; Cytotoxicity; Vellozia kolbekii.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Infective Agents* / chemistry
Anti-Infective Agents* / pharmacology
Bacteria / drug effects*
Cell Cycle / drug effects
Cell Line, Tumor
Cell Survival / drug effects*
Circular Dichroism
Cytotoxins* / chemistry
Cytotoxins* / pharmacology
Diterpenes / chemistry*
Humans
Inhibitory Concentration 50
Magnoliopsida / chemistry*
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*

Substances

Anti-Infective Agents
Cytotoxins
Diterpenes
Plant Extracts
halimane