Cytotoxicity potential of chemical constituents isolated and derivatised from Rhinella marina venom.
| Autor: | Filho EDSM; Laboratory of Natural Products, Department of Chemistry, Federal University of Piauí, Teresina, Piauí, Brazil., Chaves MH; Laboratory of Natural Products, Department of Chemistry, Federal University of Piauí, Teresina, Piauí, Brazil., Ferreira PMP; Laboratory of Experimental Cancerology, Department of Biophysics and Physiology, Federal University of Piauí, Teresina, Piauí, Brazil., Pessoa C; Department of Physiology and Pharmacology, Faculty of Medicine, Federal University of Ceará, Fortaleza, Ceará, Brazil., Lima DJB; Department of Physiology and Pharmacology, Faculty of Medicine, Federal University of Ceará, Fortaleza, Ceará, Brazil., Maranhão SSA; Department of Physiology and Pharmacology, Faculty of Medicine, Federal University of Ceará, Fortaleza, Ceará, Brazil., de Jesus Rodrigues D; Institute of Natural, Humanities and Social Sciences, Federal University of Mato Grosso, Sinop, Mato Grosso, Brazil., Vieira Júnior GM; Laboratory of Natural Products, Department of Chemistry, Federal University of Piauí, Teresina, Piauí, Brazil. Electronic address: magela@ufpi.edu.br. |
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| Jazyk: | angličtina |
| Zdroj: | Toxicon : official journal of the International Society on Toxinology [Toxicon] 2021 Apr 30; Vol. 194, pp. 37-43. Date of Electronic Publication: 2021 Feb 19. |
| DOI: | 10.1016/j.toxicon.2021.02.006 |
| Abstrakt: | Chemical compounds from skin secretions from toads of Bufonidae family have been long-studied. In the search for new molecules with pharmacological action, the 3β-OH groups of bufadienolides are commonly derivatised using acetyl groups. This work described the isolation and/or structural elucidation of isolated and derivatised compounds from the venom of the Brazilian anuran Rhinella marina, and their evaluation in in vitro assays. In the methanolic extract of the R. marina venom, compound cholesterol (1) was isolated from the CRV-52 fraction by classic column chromatography, dehydrobufotenine (2) by Sephadex LH-20 from the CRV-28 fraction, and a mix of suberoyl arginine (3) and compound 2 was obtained from the CRV-6-33 fraction. The compounds marinobufagin (4), telocionbufagin (5) and bufalin (6) were isolated by classic column chromatography, followed by separation via HPLC in the CRV-70 fraction, and the compound marinobufotoxin (9) was isolated by classic column chromatography in the CRV-6 fraction, here being isolated for the first time in R. marina specimens. Compounds 4 and 5 were submitted for acetylation with acetic anhydride, in the presence of pyridine and 4-dimethyilaminopiridine (DMAP), in order to obtain the compounds 3-acetyl-marinobufagin (7) and 3-acetyl-telocinobufogin (8). The isolated and derivatised compounds were identified by 1 H and 13 C NMR, and their molecular mass confirmed by mass spectrometry. All compounds (except 1 and 3) were tested in cytotoxic assays by the MTT method and presented cytotoxic potential against human cancer cell lines, as well as against non-tumoral human embryonic kidney HEK-293 cells. With the exception of compound 2, all molecules presented IC (Copyright © 2021 Elsevier Ltd. All rights reserved.) |
| Databáze: | MEDLINE |
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