Evaluation of the in vivo therapeutic properties of (−)-cubebin and (−)-hinokinin against Trypanosoma cruzi

Esperandim, Viviane Rodrigues; Ferreira, Daniele da Silva; Rezende, Karen Cristina Souza; Cunha, Wilson Roberto; Saraiva, Juliana; Bastos, Jairo Kenupp; Silva, Márcio Luís Andrade e; Albuquerque, Sérgio de

doi:10.1016/j.exppara.2012.12.005

Cited by 26 publications

(26 citation statements)

References 37 publications

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“…The animals with acute parasitaemia were investigated by morphometric tissue analysis. There was a significant parasitaemia reduction in animals treated with cubebin compared to the negative control …”

Section: (−)‐Cubebinmentioning

confidence: 89%

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Medicinal Attributes of Lignans Extracted from Piper Cubeba: Current Developments

Lima

Barros

Laurentiz³

2018

ChemistryOpen

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Lignans are a large class of natural products that have been isolated from many plants. They reveal diverse biological activities, especially antiviral and antitumor properties. From Piper cubeba, lignans of several classes can be isolated from the roots, rhizomes, stems, leaves, seeds, and fruits. Among its various chemical constituents, (−)‐cubebin and (−)‐hinokinin are found in significant quantities. Although they have been known for some time, during the last few decades their biological properties have been studied by several research groups. The cubebins have been identified as a lactol monomer and dimers as a mixture of diastereoisomers. Recently, their structural characterization and the synthesis of the possible structures have led to the correction of some earlier structural proposals. This review describes the more recent developments in the study of the medicinal attributes of cubebin and hinokinin extracted from Piper cubeba and the synthesis and biological testing of some analogues.

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Section: (−)‐Cubebinmentioning

confidence: 89%

“…reported studies on infections by Trypanosoma cruzi . This study has already been referenced in Section 3.2.3. for the lignan (−)‐cubebin . The authors described a study criterion in which animals with acute parasitemia were investigated by tissue morphometric analysis.…”

Section: Hinokininmentioning

confidence: 99%

Medicinal Attributes of Lignans Extracted from Piper Cubeba: Current Developments

Lima

Barros

Laurentiz³

2018

ChemistryOpen

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“…As recentes pesquisas com (-)-cubebina tem como foco a descoberta de novas propriedades biológicas dessa lignana e, além disso, a obtenção de derivados semisintéticos, obtidos por modificações estruturais, com a finalidade de potencializar propriedades farmacológicas. 3,[6][7][8][9][10][11][12][13][14][15][16] A (-)-cubebina está presente em várias espécies de plantas, tais como Zanthoxylum narangillo, 17 Alistorolochia odoratissima L., 18 Piper nigrum L., mas em quantidades consideráveis na Piper cubeba que é atualmente a principal fonte de extração.…”

Section: 5unclassified

“…7, 16,23 Em ensaios tripanossomicidas a (-)-cubebina e seus derivados atuaram como inibidores da atividade da NADH oxidase mitocondrial do complexo I do T. cruzi, sendo esta uma constatação da relevância devido ao potencial deste tipo de composto em um contexto farmacológico. Além disso, os resultados indicam potenciais grupos de ligação em CI-B8, especificamente R89 e S96, cuja interação via ligação de hidrogênio pode opor-se à ligação do NADH ao seu sítio de interação e / ou evitar a sua oxidação.…”

Section: Tripanossomicidaunclassified

“…Além disso, os resultados indicam potenciais grupos de ligação em CI-B8, especificamente R89 e S96, cuja interação via ligação de hidrogênio pode opor-se à ligação do NADH ao seu sítio de interação e / ou evitar a sua oxidação. 23 Esperandim et al, 16 avaliaram o efeito da (-)-cubebina em concentrações de 20 mg/kg e 50 mg/kg em animais (ratos machos BALB/c ) infectados com aproximadamente 2×10 …”

Section: Tripanossomicidaunclassified

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Cubebin: A Small Molecule with Great Potential

Pissurno

Laurentiz²

2017

Rev. Virtual Quim.

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Abstract:The (-)-cubebin is a lignan dibenzylbutyrolactolic of occurrence in various species of plants, especially in the genus Piper. Although it has been known for over 150 years, the last few decades the biological properties of this molecule has attracted the attention of several research groups. Recent publications obtained from Scopus bases, SciFinder and PubMed database have highlighted the numerous biological activities attributed to cubebin, as trypanocidal activity, shistomicida, cytotoxicity on cancer lines, vasodilator, antihistaminic, and anti-inflammatory. These studies demonstrate the pharmacological potential of cubebin and its importance as starting material to obtain even more potent derivatives.

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Evaluation of Lignans from Piper cubeba against Schistosoma mansoni Adult Worms: A Combined Experimental and Theoretical Study

Parreira

Costa

Heleno

et al. 2018

Chemistry & Biodiversity

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Six dibenzylbutyrolactonic lignans ((−)‐hinokinin (1), (−)‐cubebin (2), (−)‐yatein (3), (−)‐5‐methoxyyatein (4), dihydrocubebin (5) and dihydroclusin (6)) were isolated from Piper cubeba seed extract and evaluated against Schistosoma mansoni. All lignans, except 5, were able to separate the adult worm pairs and reduce the egg numbers during 24 h of incubation. Lignans 1, 3 and 4 (containing a lactone ring) were the most efficient concerning antiparasitary activity. Comparing structures 3 and 4, the presence of the methoxy group at position 5 appears to be important for this activity. Considering 1 and 3, it is possible to see that the substitution pattern change (methylenedioxy or methoxy groups) in positions 3′ and 4′ alter the biological response, with 1 being the second most active compound. Computational calculations suggest that the activity of compound 4 can be correlated with the largest lipophilicity value.

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Evaluation of the in vivo therapeutic properties of (−)-cubebin and (−)-hinokinin against Trypanosoma cruzi

Cited by 26 publications

References 37 publications

Medicinal Attributes of Lignans Extracted from Piper Cubeba: Current Developments

Medicinal Attributes of Lignans Extracted from Piper Cubeba: Current Developments

Cubebin: A Small Molecule with Great Potential

Evaluation of Lignans from Piper cubeba against Schistosoma mansoni Adult Worms: A Combined Experimental and Theoretical Study

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