Caatinga plants: Natural and semi-synthetic compounds potentially active against Trichomonas vaginalis

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• 作者：Patrí ; cia de Brum Vieira^a ; ^{patriciasbrum@yahoo.com.br" class="auth_mail" title="E-mail the corresponding author} ; Ní ; colas Luiz Feijó ; Silva^a ; ^{nicolaslfsilva@gmail.com" class="auth_mail" title="E-mail the corresponding author} ; Gloria Narjara Santos da Silva^b ; ^{narjarags@gmail.com" class="auth_mail" title="E-mail the corresponding author} ; Denise Brentan Silva^c ; ^d ; ^{denise.brentan@ufms.com" class="auth_mail" title="E-mail the corresponding author} ; Norberto Peporine Lopes^d ; ^{npelopes@fcfrp.usp.b" class="auth_mail" title="E-mail the corresponding author} ; Simone Cristina Baggio Gnoatto^b ; ^{simone.gnoatto@ufrgs.br" class="auth_mail" title="E-mail the corresponding author} ; Má ; rcia Vanusa da Silva^e ; ^{Marcia.vanusa@ufpe.br" class="auth_mail" title="E-mail the corresponding author} ; Alexandre José ; Macedo^f ; ^g ; ^{Alexandre.jose.macedo@gmail.com" class="auth_mail" title="E-mail the corresponding author} ; Jaume Bastida^h ; ^{jaumebastida@ub.edu" class="auth_mail" title="E-mail the corresponding author} ; Tiana Tasca^a ; ^g ; ^{tiana.tasca@ufrgs.br" class="auth_mail" title="E-mail the corresponding author}
• 关键词：1H or 13C NMR ; proton or carbon nuclear resonance magnetic ; CDCl3 ; deuterated chloroform ; TMS ; tetramethylsilane ; EI ; electron ionization ; MS ; mass spectroscopy ; GC ; gas chromatography ; RI ; retention index ; IR ; infrared spectra ; IPA ; Instituto Agronô ; mico de Pernambuco ; VLC ; vacuum liquid chromatography ; EtOAc ; ethyl acetate ; MeOH ; methanol ; TLC ; thin liquid chromatography ; DMAP ; 4-dimethylaminopyridine ; (1) ; α-amyrin ; (2) ; β-amyrin ; (3) ; lupeol ; (1a) ; acetate of α-amyrin ; (1b) ; caproate of
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：1 May 2016
• 年：2016
• 卷：26
• 期：9
• 页码：2229-2236
• 全文大小：905 K

文摘

Trichomonas vaginalis causes trichomoniasis; the most common but overlooked non-viral sexually transmitted disease worldwide. The treatment is based at 5′-nitroimidazoles, however, failure are related to resistance of T. vaginalis to chemotherapy. Caatinga is a uniquely Brazilian region representing a biome with type desert vegetation and plants present diverse biological activity, however, with few studies. The aim of this study was to investigate the activity against T. vaginalis of different plants from Caatinga and identify the compounds responsible by the activity. A bioguided fractionation of Manilkara rufula was performed and four major compounds were identified: caproate of α-amyrin (1b), acetate of β-amyrin (2a), caproate of β-amyrin (2b), and acetate of lupeol (3a). In addition, six derivatives of α-amyrin (1), β-amyrin (2) and lupeol (3) were synthesized and tested against the parasite. Ursolic acid (5) reduced about 98% of parasite viability after 2 h of incubation and drastic ultrastructural alterations were observed by scanning electron microscopy. Moreover, 5 presented high cytotoxicity to HMVII and HeLa cell line and low cytotoxicity against Vero line at 50 μM (MIC against the parasite). Metronidazole effect against T. vaginalis resistant isolate was improved when in association with 5.