Volatiles of Black Pepper Fruits (Piper nigrum L.)

Dosoky, Noura S.; Satyal, Prabodh; Barata, Luccas M; Silva, Joyce Kelly R. da; Setzer, William N.

doi:10.3390/molecules24234244

Cited by 64 publications

(40 citation statements)

References 27 publications

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“…Caryophyllane sesquiterpenes are natural phytochemicals widely occurring in terrestrial plants and plant-associated fungal species [32][33][34][35][36][37], and are present in marine environments as secondary metabolites from the resident living organisms and microbes [38][39][40][41].…”

Section: Discussionmentioning

confidence: 99%

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Sotto

Irannejad

Eufemi

et al. 2020

IJMS

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Doxorubicin represents a valuable choice for different cancers, although the severe side effects occurring at the high effective dose limits its clinical use. In the present study, potential strategies to potentiate low-dose doxorubicin efficacy, including a metronomic schedule, characterized by a short and repeated exposure to the anticancer drug, and the combination with the natural chemosensitizing sesquiterpenes β-caryophyllene and β-caryophyllene oxide, were assessed in human hepatoma HepG2 cells. The involvement of P-glycoprotein (P-gp) in the HepG2-chemosensitization to doxorubicin was evaluated. Also, the direct interaction of caryophyllene sesquiterpenes with P-gp was characterized by molecular docking and dynamic simulation studies. A metronomic schedule allowed us to enhance the low-dose doxorubicin cytotoxicity and the combination with caryophyllane sesquiterpenes further potentiated this effect. Also, an increased intracellular accumulation of doxorubicin and rhodamine 123 induced by caryophyllane sesquiterpenes was found, thus suggesting their interference with P-gp function. A lowered expression of P-gp induced by the combinations, with respect to doxorubicin alone, was observed too. Docking studies found that the binding site of caryophyllane sesquiterpene was next to the ATP binding domain of P-gp and that β-caryophyllene possessed the stronger binding affinity and higher inhibition potential calculated by MM-PBSA. Present findings strengthen our hypothesis about the potential chemosensitizing power of caryophyllane sesquiterpenes and suggest that combining a chemosensitizer and a metronomic schedule can represent a suitable strategy to overcome drawbacks of doxorubicin chemotherapy while exploiting its powerful activity.Int. J. Mol. Sci. 2020, 21, 633 2 of 28 Int. J. Mol. Sci. 2020, 21, 633 5 of 28 oxide were selected for the combination experiments. Under our experimental conditions, both the sesquiterpenes were able to potentiate the effect of doxorubicin in different experimental conditions, although with different profiles. Particularly, after 24 h exposure, the lower chemosensitizing concentration (50 µM) of β-caryophyllene significantly enhanced the doxorubicin-cytotoxicity starting from the concentration of 10 µM, achieving almost the maximum potentiation of about 32% at concentration of 20 µM (Figure 2a).

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Section: Discussionmentioning

confidence: 99%

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Sotto

Irannejad

Eufemi

et al. 2020

IJMS

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“…India, Brazil, Indonesia, Malaysia, Vietnam, China, and Sri Lanka are the largest producers of black pepper [ 18 , 19 , 20 ]. In Brazil, their economic value started increasing at the end of World War II [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Secondary Metabolic Profile as a Tool for Distinction and Characterization of Cultivars of Black Pepper (Piper nigrum L.) Cultivated in Pará State, Brazil

Barata

Andrade

Ramos

et al. 2021

IJMS

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This study evaluated the chemical compositions of the leaves and fruits of eight black pepper cultivars cultivated in Pará State (Amazon, Brazil). Hydrodistillation and gas chromatography–mass spectrometry were employed to extract and analyze the volatile compounds, respectively. Sesquiterpene hydrocarbons were predominant (58.5–90.9%) in the cultivars “Cingapura”, “Equador”, “Guajarina”, “Iaçará”, and “Kottanadan”, and “Bragantina”, “Clonada”, and “Uthirankota” displayed oxygenated sesquiterpenoids (50.6–75.0%). The multivariate statistical analysis applied using volatile composition grouped the samples into four groups: γ-Elemene, curzerene, and δ-elemene (“Equador”/“Guajarina”, I); δ-elemene (“Iaçará”/“Kottanadan”/“Cingapura”, II); elemol (“Clonada”/“Uthirankota”, III) and α-muurolol, bicyclogermacrene, and cubebol (“Bragantina”, IV). The major compounds in all fruit samples were monoterpene hydrocarbons such as α-pinene, β-pinene, and limonene. Among the cultivar leaves, phenolics content (44.75–140.53 mg GAE·g−1 FW), the enzymatic activity of phenylalanine-ammonia lyase (20.19–57.22 µU·mL−1), and carotenoids (0.21–2.31 µg·mL−1) displayed significant variations. Due to black pepper’s susceptibility to Fusarium infection, a molecular docking analysis was carried out on Fusarium protein targets using each cultivar’s volatile components. F. oxysporum endoglucanase was identified as the preferential protein target of the compounds. These results can be used to identify chemical markers related to the susceptibility degree of black pepper cultivars to plant diseases prevalent in Pará State.

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“…Also, garlic proved effective veterinary medicines (Viegi et al, 2003;Peachey et al, 2015). Black pepper (Piper nigrum L.) is historically one of the most important spices and herbal medicines, and is now cultivated worldwide (Dosoky et al, 2019). Also, metronidazole, amprolium and piperazine are known anti-parasitic chemical drugs (Tojo and Santamarina, 1998) This study aimed to evaluate the effect of garlic & black pepper in treating pigeons natural infected coccidiosis and capillariasis as compared with Meterindazole ® , Amprolium ® and Piperazine ® .…”

Section: Introductionmentioning

confidence: 99%

Effect of Medicinal Plants Against Intestinal Coccidiosis and Capillariasis Infecting Pigeons

Mahmoud

HASSAN

Hafez

2021

Journal of the Egyptian Society of Parasitology

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Volatiles of Black Pepper Fruits (Piper nigrum L.)

Cited by 64 publications

References 27 publications

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Secondary Metabolic Profile as a Tool for Distinction and Characterization of Cultivars of Black Pepper (Piper nigrum L.) Cultivated in Pará State, Brazil

Effect of Medicinal Plants Against Intestinal Coccidiosis and Capillariasis Infecting Pigeons

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