Sesquiterpene lactones from Vernonia scorpioides and their in vitro cytotoxicity.
Fresh leaves of Vernonia scorpioides are widely used in Brazil to treat a variety of skin disorders. Previous in vivo studies with extracts of this species had also demonstrated a high antitumor potential. This paper reports isolation of four sesquiterpene lactones (hirsutinolides and glaucolides), together with diacetylpiptocarphol, 8-acetyl-13-etoxypiptocarphol, luteolin, apigenin, and ethyl caffeate from fresh leaves and flowers of Vernonia scorpioides. The hypothesis that hirsutinolide 3 is formed during extraction was verified theoretically using Density Functional Theory. The effects of isolated compounds on in vitro tumor cells were investigated, as well as their genotoxicity by means of an in vitro comet assay. The results indicate that glaucolide 2 and hirsutinolide 4 are toxic to HeLa cells. These compounds were genotoxic in vitro, a property that appears to be related to the presence of their epoxy groups, which has been a more reliable indication of toxicity than substitution on C-13 or the presence of alpha,beta-unsaturated keto-groups. These results need to be replicated in vivo in order to ascertain their toxicity.
Buskuhl
Humberto
H
Curso de Farmácia, Centro de Ciências da Saúde, Universidade do Vale do Itajaí (UNIVALI), Itajaí, SC, Brazil.
de Oliveira
Fabio L
FL
Blind
Luise Z
LZ
de Freitas
Rilton A
RA
Barison
Andersson
A
Campos
Francinete R
FR
Corilo
Yuri E
YE
Eberlin
Marcos N
MN
Caramori
Giovanni F
GF
Biavatti
Maique W
MW
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000633:toxicity; D045744:Cell Line, Tumor; D000431:Ethanol / Q000737:chemistry; D035264:Flowers / Q000737:chemistry; D006801:Humans; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D009152:Mutagenicity Tests; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000633:toxicity; D035741:Vernonia / Q000737:chemistry*
D000970:Antineoplastic Agents; D007783:Lactones; D010936:Plant Extracts; D012717:Sesquiterpenes; D000431:Ethanol