Curso de Farmácia, Centro de Ciências da Saúde, Universidade do Vale do Itajaí (UNIVALI), Itajaí, SC, Brazil.
Phytochemistry. 2010 Sep;71(13):1539-44. doi: 10.1016/j.phytochem.2010.06.007. Epub 2010 Jul 3.
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.
新鲜的斑鸠菊属蝎子草叶子在巴西被广泛用于治疗各种皮肤疾病。此前，该物种提取物的体内研究也表现出了很高的抗肿瘤潜力。本文报道了从新鲜的斑鸠菊属蝎子草叶子和花中分离出的四种倍半萜内酯（hirsutinolides 和 glaucolides），以及二乙酰 piptocarphol、8-乙酰-13-乙氧基 piptocarphol、木犀草素、芹菜素和咖啡酸乙酯。使用密度泛函理论从理论上验证了 hirsutinolide 3 在提取过程中形成的假设。研究了分离得到的化合物对体外肿瘤细胞的影响，以及通过体外彗星试验研究它们的遗传毒性。结果表明，glaucolide 2 和 hirsutinolide 4 对 HeLa 细胞有毒性。这些化合物在体外具有遗传毒性，这一特性似乎与其环氧基团的存在有关，与 C-13 上的取代或α,β-不饱和酮基团的存在相比，环氧基团是更可靠的毒性指示物。这些结果需要在体内进行复制，以确定它们的毒性。
