Schistosomicidal and trypanocidal structure–activity relationships for (±)-licarin A and its (−)- and (+)-enantiomers

Pereira, Ana Carolina; Magalhães, Lizandra Guidi; Gonçalves, Ubirajara Oliveira; Luz, Priscilla Paiva; Moraes, Ana C G; Rodrigues, Vanderlei; Guedes, Paulo Marcos da Matta; Filho, Ademar A. Da Silva; Cunha, Wilson Roberto; Bastos, Jairo Kenupp; Nanayakkara, N. P. Dhammika; Silva, M.L.A. e

doi:10.1016/j.phytochem.2011.04.007

Cited by 46 publications

(52 citation statements)

References 43 publications

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“…Animals administered licarin A (5mg/kg for 30 days) showed significant reduction in lung bacilli and pneumonia incidence. The anti-parasitic effect of licarin A was further corroborated against both Schistosoma mansoni and Trypanosoma cruzi (Pereira et al 2011). It is evident that the potential anti-parasitic activity of licarin A is worth further investigation in the hope of future development of effective medications.…”

Section: Pharmacological Evaluation Of Pure Nutmeg Compoundsmentioning

confidence: 82%

Chemical diversity and pharmacological significance of the secondary metabolites of nutmeg (Myristica fragrans Houtt.)

Abourashed

El‐Alfy

2016

Phytochem Rev

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Nutmeg is a valued kitchen spice that has been used for centuries all over the world. In addition to its use in flavoring foods and beverages, nutmeg has been used in traditional remedies for stomach and kidney disorders. The antioxidant, antimicrobial and central nervous system effects of nutmeg have also been reported in literature. Nutmeg is a rich source of fixed and essential oil, triterpenes, and various types of phenolic compounds. Many of the secondary metabolites of nutmeg exhibit biological activities that may support its use in traditional medicine. This article provides an overview of the chemistry of secondary metabolites isolated from nutmeg kernel and mace including common methods for analysis of extracts and pure compounds as well as recent approaches towards total synthesis of some of the major constituents. A summary of the most significant pharmacological investigations of potential drug leads isolated from nutmeg and reported in the last decade is also included.

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Section: Pharmacological Evaluation Of Pure Nutmeg Compoundsmentioning

confidence: 82%

Chemical diversity and pharmacological significance of the secondary metabolites of nutmeg (Myristica fragrans Houtt.)

Abourashed

El‐Alfy

2016

Phytochem Rev

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“…According to IUPAC, one pharmacophore is 'the set of steric and electronic features necessary to ensure optimal supramolecular interactions with a structure of a specific biological target and to trigger (or block) its biological response.' N ND [55] (+)-limonene epoxide Natural products with antischistosomal activity Review around the tubercles. Furthermore, experiments performed using carvacryl acetate at sublethal concentrations (ranging from 1.562 to 6.25 μg/ml) showed an inhibitory effect on the daily egg output of paired adult schistosomes.…”

Section: Monoterpenesmentioning

confidence: 99%

“…Quinones, flavonoids, neolignans and other phenolic derivatives have anthelmintic activities against schistosomes. The phenolic compounds with antischistosomal activity are: plumbagin [64,65], β-lapachone [53,54], quercetin 3-O-β-d-glucoside, quercetin 3-O-β-drhamnoside [37], kaempferol [52], sativan [67], hesperidin [50,51], (±)-licarin A and its enantiomer [55], curcumin [40][41][42][43][44] and some phloroglucinol derivatives such as aspidin, flavaspidic acid, methylene-bis-aspidinol and desaspidin (Figure 3) [35].…”

Section: Phenolicsmentioning

confidence: 99%

“…They have attracted the attention of many researchers over the years as a result of the variety of their chemical structures and their broad range of biological activities [55,99]. The neolignan (±)-licarin A (32) and its enantiomer (-)-enantiomer (33) are active in vitro against Schistosoma mansoni adult worms, whereas (+)-enantiomer (34) did not show activity [55]. The racemic mixture is more active than (-)-enantiomer (33), with LC 50 values of 53.57 and 91.71 μM, respectively.…”

Section: Neolignansmentioning

confidence: 99%

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Natural Products with Antischistosomal Activity

Moraes¹

2015

Future Med. Chem.

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In recent years, natural product groups have been gaining prominence as possible sources of new drugs for schistosomiasis. This review attempts to update the antischistosomal natural compounds, or natural product-derived compounds, from the mid-1980s. Some of the main metabolites obtained from plants (e.g., terpenes, alkaloids, phenolic compounds and peptides) with in vitro and/or in vivo antischistosomal properties are discussed. Less thoroughly, due to scarcity of data in the literature, molecules from animals (e.g., peptides) are also described. Special mention of the anthelmintic activity against different parasitic stages of schistosomes is made; the mechanism of action of most of the metabolites is discussed, and a number of bioassay procedures are listed.

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“…In this context, in continuation of our search for bioactive schistosomicidal compounds [20, 21] and on the basis of their antiparasitic potential, this work describes the in vitro schistosomicidal activity of a series of lipophilic diamines and amino alcohols, as well as glycosylated amino alcohols derivatives against adult worms of Schistosoma mansoni .…”

Section: Introductionmentioning

confidence: 99%

Anthelmintic Effects of Alkylated Diamines and Amino Alcohols againstSchistosoma mansoni

Fernandes

Júnior

Fernandes

et al. 2013

BioMed Research International

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Polyamines are substances involved in many aspects of cell growth, division, and differentiation. Because of the metabolic differences between host cells and parasite cells, polyamine metabolism has been considered as a potential target for the chemotherapy of parasitic diseases. The aim of this work was to evaluate the schistosomicidal activity of different N-alkylated diamines (3a–3h), amino alcohols (4a–4d), and glycosylated amino alcohols (10a–10d). Compounds were prepared by synthetic methods and submitted to in vitro evaluation against adult worms of Schistosoma mansoni. At 100 μM, 3b, 3e, and 3h as well as 4a, 4b, 4d, 10a, 10b, and 10d resulted in 100% mortality of adult schistosomes. Compound 3d (12.5 to 100 μM) caused the death of 100% of both male and female adult schistosomes, while 3f (12.5 to 100 μM) resulted in 100% mortality of only male adult worms, whereas no mortality in female worms was observed. Compounds 3d and 3f were also able to reduce viability and decrease production of developed eggs in comparison with the negative control group. Diamines 3d and 3f may represent useful lead compounds for further optimization in order to develop new schistosomicidal agents.

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Schistosomicidal and trypanocidal structure–activity relationships for (±)-licarin A and its (−)- and (+)-enantiomers

Cited by 46 publications

References 43 publications

Chemical diversity and pharmacological significance of the secondary metabolites of nutmeg (Myristica fragrans Houtt.)

Chemical diversity and pharmacological significance of the secondary metabolites of nutmeg (Myristica fragrans Houtt.)

Natural Products with Antischistosomal Activity

Anthelmintic Effects of Alkylated Diamines and Amino Alcohols againstSchistosoma mansoni

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