15β-Senecioyl-oxy-ent-kaur-16-en-19-oic Acid, a Diterpene Isolated from Baccharis lateralis, as Promising Oral Compound for the Treatment of Schistosomiasis.

Praziquantel is the only available drug to treat schistosomiasis, and therefore, urgent studies must be performed to identify new anthelmintic agents. This study reports the anthelmintic evaluation of two related ent-kaurane diterpenes isolated from aerial parts of Baccharis lateralis (Asteraceae), ent-kaur-16-en-19-oic acid (1) and 15β-senecioyl-oxy-ent-kaur-16-en-19-oic acid (2) against Schistosoma mansoni in vitro and in a murine model of schistosomiasis. Both compounds exhibited in vitro activity with lethal concentration 50% (LC50) values of 26.1 μM (1) and 11.6 μM (2) as well as reduced toxicity against human cell lines, revealing a good selectivity profile, mainly with compound 2 (selectivity index > 10). Compound 2 also decreased egg production and caused morphological alterations in the parasite reproductive system. In mice infected with S. mansoni, oral treatment with compound 2 at 400 mg/kg, the standard dose used in this model of schistosomiasis, caused a significant reduction in a total worm burden of 61.9% (P < 0.01). S. mansoni egg production, a key mechanism for both transmission and pathogenesis, was also markedly reduced. In addition, compound 2 achieved a significant reduction in hepatosplenomegaly. Therefore, the diterpene 15β-senecioyl-oxy-ent-kaur-16-en-19-oic acid (2) has an acceptable cytotoxicity profile and is orally active in a murine schistosomiasis model.

[1]  L. Magalhães,et al.  Schistosomicidal activity of kaurane, labdane and clerodane-type diterpenes obtained by fungal transformation , 2020 .

[2]  J. de Moraes,et al.  Brazilian red propolis exhibits antiparasitic properties in vitro and reduces worm burden and egg production in an mouse model harboring either early or chronic Schistosoma mansoni infection. , 2020, Journal of ethnopharmacology.

[3]  Leonardo L. G. Ferreira,et al.  H1-antihistamines as antischistosomal drugs: in vitro and in vivo studies , 2020, Parasites & Vectors.

[4]  J. de Moraes,et al.  Schiff bases of 4-Phenyl-2-Aminothiazoles as hits to new antischistosomals: Synthesis, in vitro, in vivo and in silico studies. , 2020, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[5]  J. de Moraes,et al.  Antiparasitic activity of piplartine (piperlongumine) in a mouse model of schistosomiasis. , 2020, Acta tropica.

[6]  Leonardo L. G. Ferreira,et al.  Phenotypic screening of nonsteroidal anti-inflammatory drugs identified mefenamic acid as a drug for the treatment of schistosomiasis , 2019, EBioMedicine.

[7]  J. Moraes,et al.  Vanillin-Related N-Acylhydrazones: Synthesis, Antischistosomal Properties and Target Fishing Studies. , 2019, Current topics in medicinal chemistry.

[8]  K. Hoffmann,et al.  An Abies procera-derived tetracyclic triterpene containing a steroid-like nucleus core and a lactone side chain attenuates in vitro survival of both Fasciola hepatica and Schistosoma mansoni , 2018, International journal for parasitology. Drugs and drug resistance.

[9]  J. Utzinger,et al.  Schistosomiasis , 2018, Nature Reviews Disease Primers.

[10]  J. de Moraes,et al.  Antiparasitic, structural, pharmacokinetic, and toxicological properties of riparin derivatives. , 2018, Toxicology in vitro : an international journal published in association with BIBRA.

[11]  M. Chimbari,et al.  Efficacy of praziquantel treatment regimens in pre-school and school aged children infected with schistosomiasis in sub-Saharan Africa: a systematic review , 2018, Infectious Diseases of Poverty.

[12]  G. Antar,et al.  Antitrypanosomal activity and evaluation of the mechanism of action of diterpenes from aerial parts of Baccharis retusa (Asteraceae). , 2018, Fitoterapia.

[13]  J. de Moraes,et al.  Antischistosomal agents: state of art and perspectives. , 2018, Future medicinal chemistry.

[14]  J. de Moraes,et al.  Cyclohexene-fused 1,3-oxazines with selective antibacterial and antiparasitic action and low cytotoxic effects. , 2017, Toxicology in vitro : an international journal published in association with BIBRA.

[15]  J. de Moraes,et al.  Antiparasitic activity of nerolidol in a mouse model of schistosomiasis. , 2017, International journal of antimicrobial agents.

[16]  M. Catauro,et al.  Synthesis of Bioactive Chlorogenic Acid-Silica Hybrid Materials via the Sol–Gel Route and Evaluation of Their Biocompatibility , 2017, Materials.

[17]  J. de Moraes,et al.  Synergistic effects of in vitro combinations of piplartine, epiisopiloturine and praziquantel against Schistosoma mansoni. , 2017, Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.

[18]  Leonardo G Ferreira,et al.  Discovery of Novel Antischistosomal Agents by Molecular Modeling Approaches. , 2016, Trends in parasitology.

[19]  H. Bourobou Bourobou,et al.  Ethnobotanical survey of medicinal plants used as anthelmintic remedies in Gabon. , 2016, Journal of ethnopharmacology.

[20]  Luis Alexandre Muehlmann,et al.  Synthesis and evaluation of novel 1,2,3-triazole-based acetylcholinesterase inhibitors with neuroprotective activity. , 2016, Bioorganic & medicinal chemistry letters.

[21]  Tatiana Zuccolotto,et al.  Baccharis (Asteraceae): Chemical Constituents and Biological Activities , 2016, Chemistry & biodiversity.

[22]  J. de Moraes,et al.  Effect of neem (Azadirachta indica A. Juss) leaf extract on resistant Staphylococcus aureus biofilm formation and Schistosoma mansoni worms. , 2015, Journal of ethnopharmacology.

[23]  A. P. Silva,et al.  Garcinielliptone FC: antiparasitic activity without cytotoxicity to mammalian cells. , 2015, Toxicology in vitro : an international journal published in association with BIBRA.

[24]  J. Moraes Natural products with antischistosomal activity. , 2015 .

[25]  J. de Moraes,et al.  Anthelmintic Activity In Vivo of Epiisopiloturine against Juvenile and Adult Worms of Schistosoma mansoni , 2015, PLoS neglected tropical diseases.

[26]  J. de Moraes,et al.  Antischistosomal Activity of the Terpene Nerolidol , 2014, Molecules.

[27]  J. de Moraes,et al.  Phytol, a Diterpene Alcohol from Chlorophyll, as a Drug against Neglected Tropical Disease Schistosomiasis Mansoni , 2014, PLoS neglected tropical diseases.

[28]  E. Nakano,et al.  Anthelmintic activity of carvacryl acetate against Schistosoma mansoni , 2012, Parasitology Research.

[29]  J. Amaro-Luis An ent-kaurenolide from Stevia lucida , 1993 .

[30]  M. Hutchison,et al.  Carbon-13 nuclear magnetic resonance spectra of eighteen derivatives of ent-kaur-16-en-19-oic acid , 1985 .