Research Portal

Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

Research output: Contribution to journal › Article › peer-review

Standard Standard

Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. / Santos, M.F.; Harper, P.M.; Williams, D.E. et al.
In: Journal of natural products, Vol. 78, No. 5, 29.04.2015, p. 1101-1112.

Research output: Contribution to journal › Article › peer-review

HarvardHarvard

Santos, MF, Harper, PM, Williams, DE, Mesquita, JT, Pinto, EG, da Costa-Villa, TA, Hajdu, E, Ferreira, AG, Santos, RA, Murphy, PJ, Anderson, RJ, Tempone, AG & Berlinck, RG 2015, 'Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula', Journal of natural products, vol. 78, no. 5, pp. 1101-1112. https://doi.org/10.1021/acs.jnatprod.5b00070

APA

Santos, M. F., Harper, P. M., Williams, D. E., Mesquita, J. T., Pinto, E. G., da Costa-Villa, T. A., Hajdu, E., Ferreira, A. G., Santos, R. A., Murphy, P. J., Anderson, R. J., Tempone, A. G., & Berlinck, R. G. (2015). Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. Journal of natural products, 78(5), 1101-1112. https://doi.org/10.1021/acs.jnatprod.5b00070

CBE

Santos MF, Harper PM, Williams DE, Mesquita JT, Pinto EG, da Costa-Villa TA, Hajdu E, Ferreira AG, Santos RA, Murphy PJ, et al. 2015. Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. Journal of natural products. 78(5):1101-1112. https://doi.org/10.1021/acs.jnatprod.5b00070

MLA

Santos, M.F. et al. "Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula". Journal of natural products. 2015, 78(5). 1101-1112. https://doi.org/10.1021/acs.jnatprod.5b00070

VancouverVancouver

Santos MF, Harper PM, Williams DE, Mesquita JT, Pinto EG, da Costa-Villa TA et al. Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. Journal of natural products. 2015 Apr 29;78(5):1101-1112. doi: 10.1021/acs.jnatprod.5b00070

Author

Santos, M.F. ; Harper, P.M. ; Williams, D.E. et al. / Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. In: Journal of natural products. 2015 ; Vol. 78, No. 5. pp. 1101-1112.

RIS

TY - JOUR

T1 - Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

AU - Santos, M.F.

AU - Harper, P.M.

AU - Williams, D.E.

AU - Mesquita, J.T.

AU - Pinto, E.G.

AU - da Costa-Villa, T.A.

AU - Hajdu, E.

AU - Ferreira, A.G.

AU - Santos, R.A.

AU - Murphy, P.J.

AU - Anderson, R.J.

AU - Tempone, A.G.

AU - Berlinck, R.G.

PY - 2015/4/29

Y1 - 2015/4/29

N2 - HPLC-UV-ELSD-MS-guided fractionation of the anti-parasitic extract obtained from the marine sponge Monanchora arbuscula, collected off the southeastern coast of Brazil, led to the isolation of a series of guanidine and pyrimidine alkaloids. The pyrimidines monalidine A (1) and arbusculidine A (7), as well as the guanidine alkaloids batzellamide A (8) and hemibatzelladines 9–11, represent new minor constituents that were identified by analysis of spectroscopic data. The total synthesis of monalidine A confirmed its structure. Arbusculidine A (7), related to the ptilocaulin/mirabilin/netamine family of tricyclic guanidine alkaloids, is the first in this family to possess a benzene ring. Batzellamide A (8) and hemibatzelladines 9–11 represent new carbon skeletons that are related to the batzelladines. Evaluation of the anti-parasitic activity of the major known metabolites, batzelladines D (12), F (13), L (14), and nor-L (15), as well as of synthetic monalidine A (1), against Trypanosoma cruzi and Leishmania infantum is also reported, along with a detailed investigation of parasite cell-death pathways promoted by batzelladine L (14) and norbatzelladine L (15).

AB - HPLC-UV-ELSD-MS-guided fractionation of the anti-parasitic extract obtained from the marine sponge Monanchora arbuscula, collected off the southeastern coast of Brazil, led to the isolation of a series of guanidine and pyrimidine alkaloids. The pyrimidines monalidine A (1) and arbusculidine A (7), as well as the guanidine alkaloids batzellamide A (8) and hemibatzelladines 9–11, represent new minor constituents that were identified by analysis of spectroscopic data. The total synthesis of monalidine A confirmed its structure. Arbusculidine A (7), related to the ptilocaulin/mirabilin/netamine family of tricyclic guanidine alkaloids, is the first in this family to possess a benzene ring. Batzellamide A (8) and hemibatzelladines 9–11 represent new carbon skeletons that are related to the batzelladines. Evaluation of the anti-parasitic activity of the major known metabolites, batzelladines D (12), F (13), L (14), and nor-L (15), as well as of synthetic monalidine A (1), against Trypanosoma cruzi and Leishmania infantum is also reported, along with a detailed investigation of parasite cell-death pathways promoted by batzelladine L (14) and norbatzelladine L (15).

U2 - 10.1021/acs.jnatprod.5b00070

DO - 10.1021/acs.jnatprod.5b00070

M3 - Article

VL - 78

SP - 1101

EP - 1112

JO - Journal of natural products

JF - Journal of natural products

SN - 0163-3864

IS - 5

ER -