Abstract
Piper glabratum and P. acutifolium were analyzed for their content of main secondary constituents, affording nine new benzoic acid derivatives (1, 2, 4, 5, 7, and 10-13), in addition to four known compounds (3, 6, 8, and 9). Their structures were elucidated on the basis of spectroscopic data. Riguera ester reactions and optical rotation measurements established the new compounds as racemates. In the search for antiparasitic agents, the compounds were evaluated in vitro against the promastigote forms of Leishmania spp., Trypanosoma cruzi, and Plasmodium falciparum. Among the evaluated compounds, methyl 3,4-dihydroxy-5-(3'-methyl-2'-butenyl)benzoate (7) exhibited leishmanicidal effect (IC50 13.8-18.5 microg/mL) against the three Leishmania strains used, and methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbutenyl)benzoate (1), methyl 4-hydroxy-3-(2-hydroxy-3-methyl-3-butenyl)benzoate (3), and methyl 3,4-dihydroxy-5-(3-methyl-2-butenyl) benzoate (7) showed significant trypanocidal activity, with IC50 values of 16.4, 15.6, and 18.5 microg/mL, respectively.
References
Aug 20, 1976·Science·W Trager, J B Jensen
Dec 1, 1993·Planta medica·J OrjalaO Sticher
Mar 1, 1997·Journal of Natural Products·R Pereda-MirandaL San Román
Mar 10, 1998·Planta medica·B ChataingA Usubillaga
Jan 5, 2002·Advances in Parasitology·S Tagboto, S Townson
Aug 21, 2003·Bioorganic & Medicinal Chemistry·Alicia HermosoBasilio Valladares
Sep 3, 2005·Nature Reviews. Drug Discovery·Richard PinkMary Bendig
Feb 16, 2006·Current Medicinal Chemistry·Guadalupe E García LiñaresJuan B Rodriguez
Oct 4, 2006·Biological & Pharmaceutical Bulletin·Patrícia Shima LuizeCelso Vataru Nakamura
Mar 14, 2007·Planta medica·Ninoska FloresIsabel L Bazzocchi
Apr 3, 2007·Phytochemistry·Bénédicte PortetClaude Moulis
Sep 22, 2007·Current Opinion in Chemical Biology·Alan L Harvey
Citations
Dec 18, 2013·Fitoterapia·Xu-Jie QinXiao-Dong Luo
Aug 25, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ronan BatistaAlaíde Braga de Oliveira
May 28, 2014·Fitoterapia·Camilla R Dal PicoloJoão Henrique G Lago
Apr 11, 2013·Phytochemistry·Shuai HuangJie Weng
Jun 11, 2009·Journal of Ethnopharmacology·Céline ValadeauGeneviève Bourdy
Aug 8, 2014·Journal of Basic Microbiology·Peihong ShenBo Wu
Apr 17, 2016·Fitoterapia·Dayany da Silva A MacielJoão Henrique G Lago
Aug 8, 2014·Evidence-based Complementary and Alternative Medicine : ECAM·Thiago Bruno Lima PrandoArquimedes Gasparotto Junior
Oct 6, 2016·Phytotherapy Research : PTR·Nazif UllahMuhammad Hamayun
Nov 5, 2016·Parasitology International·Carlos Luan Alves PassosElvira Maria Saraiva
Jan 23, 2017·Journal of Ethnopharmacology·Lidiane Schultz BranquinhoArielle Cristina Arena
Apr 19, 2017·Pharmaceutical Biology·Keline Medeiros de Araújo-VilgesSelma Aparecida Souza Kuckelhaus
Feb 8, 2013·International Journal of Molecular Sciences·Dieudonné NdjonkaCarsten Wrenger
Feb 15, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dominique F Moura do CarmoJefferson Rocha de Andrade Silva
Jul 22, 2010·Pharmaceutical Biology·Angela I CalderónMahabir P Gupta
Jan 26, 2021·Journal of Natural Products·Fu-Cai RenJun Zhou
Aug 10, 2021·Chemistry & Biodiversity·Yu-Xi ChenChuan-Rui Zhang
Sep 26, 2014·Chemical Reviews·Hidayat HussainSimon Gibbons