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

sexta-feira, julho 05, 2019

Authors: Gredson KeiffSouza; Ivania Teresinha Albrecht Schuquel; Vagner Marques Moura; Andrezza Correia Belloto; Lucas Ulisses Rovigatti Chiavelli; Ana Lúcia Tasca Gois Ruiz; Larissa Shiozawa; João Ernesto de Carvalho; Francielle Pelegrin Garcia; Vanessa Kaplum; Jean Henriqueda Silva Rodrigues; Débora Botura Scariot; Rodrigo Delvecchioe Erik Machado-Ferreira; Renato Santana; Carlos Augusto Gomes Soares; Celso Vataru Nakamura; Silvana Maria de Oliveira Santin; Armando Mateus Pomini

Abstract: 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 59.2 μg mL−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 10.4 μg mL−1), glioma (GI50 77.3 μg mL−1), uterine cervix (SiHa) HPV 16 (IC50 39.8 μg mL−1), (HeLa) HPV 18 (IC50 12.0 μg mL−1) and Caco-2 (IC50 40.0 μg mL−1) and showed bacteriostatic action against Staphylococcus aureus (MIC 50 μg mL−1). Piceatannol 8 isolated from EAF showed activity against the protozoan which causes leishmaniosis (IC50 58.4 μg mL−1).

For Trypanosoma cruzi, the methanol fraction (EC50 15.5 μg mL−1), CE (20.5 μg mL−1), and HEF (43.8 μg mL−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.

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Page: Science Direct