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X-ray structure of O-methyl-acrocol and anti-cancer, anti-parasitic, anti-bacterial and anti-Zika virus evaluations of the Brazilian palm tree Acrocomia totai

Souza, Gredson Keiff, Albrecht Schuquel, Ivania Teresinha, Moura, Vagner Marques, Belloto, Andrezza Correia, Rovigatti Chiavelli, Lucas Ulisses, Ruiz, Ana Lúcia Tasca Gois, Shiozawa, Larissa, de Carvalho, João Ernesto, Garcia, Francielle Pelegrin, Kaplum, Vanessa, da Silva Rodrigues, Jean Henrique, Scariot, Débora Botura, Delvecchio, Rodrigo, Machado-Ferreira, Erik, Santana, Renato, Gomes Soares, Carlos Augusto, Nakamura, Celso Vataru, de Oliveira Santin, Silvana Maria, Pomini, Armando Mateus
Industrial crops and products 2017 v.109 pp. 483-492
Acrocomia aculeata, Staphylococcus aureus, Trypanosoma cruzi, X-radiation, X-ray diffraction, Zika virus, antibacterial properties, bioassays, biodiesel, breast neoplasms, cervix, chemical constituents of plants, crystals, ethyl acetate, fuel production, inhibitory concentration 50, leishmaniasis, lung neoplasms, mass spectrometry, median effective concentration, methanol, neoplasm cells, nuclear magnetic resonance spectroscopy, nuts, oils, plant spines, spectral analysis, steroids, toxicity, triterpenoids, viruses, Brazil
Acrocomia totai Mart (“macaúba”) is a palm tree native from Brazil, whose potential for biodiesel production has been widely explored. In spite of the industrial interest in the oil from the nuts, little is known about the potential applications of other parts of the plant, especially in the pharmacological area. A phytochemical study of the plant thorns led to the identification of a new compound 3-(R)-methoxy-21-(R)-H-hop-22(29)-en-30-ol 1, two known triterpenes 2–3, four steroids 4–7 and a stilbene, piceatannol 8. The structures were elucidated by spectroscopic analyses, including 1D and 2D NMR and low and high resolution mass spectrometry. Compound 1 was purified as crystals, which allowed the determination of the absolute configuration of the asymmetric carbons by analysis of the X-ray diffraction spectrum. Biological tests were performed with crude extract (CE), fractions and isolated compound. The assays showed activity for CE against lung carcinoma (GI50 59.2μgmL−1). The ethyl acetate fraction (EAF) showed efficacy against many tumor cell lines, and the tests showed the most prominent activity for breast cancer (GI50 10.4μgmL−1), glioma (GI50 77.3μgmL−1), uterine cervix (SiHa) HPV 16 (IC50 39.8μgmL−1), (HeLa) HPV 18 (IC50 12.0μgmL−1) and Caco-2 (IC50 40.0μgmL−1) and showed bacteriostatic action against Staphylococcus aureus (MIC 50μgmL−1). Piceatannol 8 isolated from EAF showed activity against the protozoan which causes leishmaniosis (IC50 58.4μgmL−1). For Trypanosoma cruzi, the methanol fraction (EC50 15.5μgmL−1), CE (20.5μgmL−1), and HEF (43.8μgmL−1) were the most active, being highly selective for the protozoan and less toxic against Vero cells. The compound 8 was further tested against Zika virus MR 766 strain on MOI 2, however the assays showed no inhibition against virus infection.