Antibacterial activity of (−)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections

Rezende, Karen Cristina Sousa; Lucarini, Rodrigo; Símaro, Guilherme Venâncio; Pauletti, Patrícia Mendonça; Januário, Ana Helena; Esperandim, Viviane Rodrigues; Martins, Carlos Henrique Gomes; Silva, Mislaine A; Cunha, Wilson Roberto; Bastos, Jairo Kenupp; Silva, Márcio Luís Andrade e

doi:10.1016/j.bjp.2015.12.006

Cited by 14 publications

(8 citation statements)

References 34 publications

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“…The effect of (-)-cubebin on 3T3-L1 cells has been reported by Muhammad et al [26]. Antibacterial activity [27] and analgesic activity [28] by (-)-O-methylcubebin have been reported, but we could not find any reports concerned with the antidiabetic or anti-obesity effects of MC.…”

Section: Discussionmentioning

confidence: 54%

(-)-O-Methylcubebin from Vitex trifolia Enhanced Adipogenesis in 3T3-L1 Cells via the Inhibition of ERK1/2 and p38MAPK Phosphorylation

et al. 2019

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In this study, for the purpose of elucidation for antidiabetic components, we isolated and identified compounds that could become lead compounds for the development of antidiabetic agents from the herbal medicine Vitex trifolia, which is used for liver protection in Myanmar. Three kinds of lignan, (-)-O-methylcubebin (MC), (-)-hinokinin, and (-)-cubebin, were isolated from the ethyl acetate extract of the leaves of V. trifolia, using various chromatography. Among the three isolated compounds, MC showed the strongest effects to increase intracellular lipid accumulation in 3T3-L1 cells. From the results of the elucidation of the MC’s effects on the adipogenesis of 3T3-L1 cells, the downsizing of adipocytes and the promotion of the expression of adipogenesis-related proteins, as well as adiponectin, were observed. On the other hand, since the activity of MC was inhibited by antagonists of PPARγ and improved by inhibitors of the classical mitogen-activated protein kinase (MAPK) pathway and p38MAPK pathway, MC was considered to be an agonist of PPARγ, and furthermore promoted adipogenesis via the inhibition of extracellular signal-regulated kinase 1/2 (ERK1/2) and p38MAPK phosphorylation. Although MC showed similar effects to those of rosiglitazone (RO) used as a positive control, RO promoted the migration of GLUT4 from the cytoplasm to the cell membrane, whereas MC did not show such an effect. From the abovementioned results, it was considered that MC could be a lead compound for the development of antidiabetic drugs that does not show weight gain, which is a side effect of RO.

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Section: Discussionmentioning

confidence: 54%

(-)-O-Methylcubebin from Vitex trifolia Enhanced Adipogenesis in 3T3-L1 Cells via the Inhibition of ERK1/2 and p38MAPK Phosphorylation

et al. 2019

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“…[28] Some interesting biological activities of lignans extracted from P. cubeba have been reported, and these lignans could potentially be developed as new drugs. [1,6,25,29] Thus, the aim of this review is to describe the medicinal attributes and current developments of the structurally similarl ignans hinokinin and cubebin, which possess ab road range of biological activities and are major componentsoft he fruits of P. cubeba. [1]…”

Section: Lignans In Generalmentioning

confidence: 99%

“…Semisynthetic derivatives of (À)-cubebin (1)h ave been obtained by transformationo fn atural compound 1 by using the reagents and conditions indicated in Scheme 2. [2,8,29,30,[34][35][36] In 2005, De Souza et al developed novel therapeutic compounds for the treatment of Chagasd isease and studied their biological activity against the amastigote formso fl ignans 1, 10, 11,a nd 12 (Scheme 2). [35] Of the (À)-cubebind erivatives tested, the most promising was (À)-hinokinin (12).…”

Section: Semisynthetic Derivatives Of (à)-Cubebinmentioning

confidence: 99%

“…In this study, it wasp ossiblet oo btainr elevantd atac oncerning ther elationship betweens tructure anda ntimicrobial activity for( À)cubebina nd otherl ignand erivativesa gainstm icroorganisms that cause root-canal infections.T his study allowed determination of which substituent groups were important to maintain or increaset he antimicrobial activity of these compounds. [29]…”

Section: Antibacterial Activitymentioning

confidence: 99%

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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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“…The pepper is rich with the valuable phytochemical compounds such as alkaloids (piperine and cubebin), amides, flavanones, flavones, lignans, neolignans, terpenes, sesquiterpenes and propenylphenols (Parmar et al, 1997). Scientifically, the antimicrobial effect of P. cubeba berries such as antifungal (Rukayadi et al, 2013), antibacterial (Aneja et al, 2010;Rezende et al, 2016), antiparasitic (Esperandim et al, 2013) and antiviral (Hussein et al, 2000) has been reported in several studies.…”

Section: Introductionmentioning

confidence: 99%

Antifungal activity of Piper cubeba L. extract on spoilage fungi isolated from tomato, grapes and lemon

Fazly-Ann¹,

Nor-Hafizah²,

Rukayadi³

2019

Food Res.

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The berries of Piper cubeba L. or commonly recognized as tailed pepper are traditionally used as flavoring ingredients in various types of food. It has been reported with abundant of phytochemical compounds that contribute to its nutritional and medicinal properties. The antimicrobial effect of the spice including antifungal activity was believed to reduce the potential of fungal spoilage thus minimizing food losses and wastage. This study was aimed to determine the antifungal activity of P. cubeba L. extract against isolated spoilage fungi namely Geotricum candidum (TMa 001), Penicillium citrinum (GRd 001) and Trametes hirsuta (LMd 001) by in vitro and in vivo techniques. Disc diffusion assay, minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) test of the methanolic extract were performed on the selected fungi. The largest inhibition zone, fungistatic and fungicidal effects were detected in T. hirsuta with 18.30±3.00 mm, 0.039 mg/mL and 0.078 mg/mL, respectively. The inhibition of conidial germination assay was performed at 0 × MIC, 0.5 × MIC, 1 × MIC, 2 × MIC, and 4 × MIC, and the result showed G. candidum were completely inhibited at 4 × MIC. The ideal concentration of P. cubeba L. extract on different selected food commodities were 0.50% against G. candidium in tomato, 0.50% to 5.00% against P. citrinum in grapes, and 5.00% against T. hirsuta in lemon. The findings implied that P. cubeba L. extract can be listed as one of the natural antifungal agents in food. The availability of various types of natural antifungal agents will help in reducing the usage of chemical fungicide, which may lead to adverse and deteriorating health effects in the events of prolong consumption.

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Antibacterial activity of (−)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections

Cited by 14 publications

References 34 publications

(-)-O-Methylcubebin from Vitex trifolia Enhanced Adipogenesis in 3T3-L1 Cells via the Inhibition of ERK1/2 and p38MAPK Phosphorylation

(-)-O-Methylcubebin from Vitex trifolia Enhanced Adipogenesis in 3T3-L1 Cells via the Inhibition of ERK1/2 and p38MAPK Phosphorylation

Medicinal Attributes of Lignans Extracted from Piper Cubeba: Current Developments

Antifungal activity of Piper cubeba L. extract on spoilage fungi isolated from tomato, grapes and lemon

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