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Identification and characterization of a compound from Cuminum cyminum essential oil with antifibrilation and cytotoxic effect.

ABSTRACT: Amyloid pathology is associated with fibril aggregation of different proteins which results in the progressive damage of affected organs. It is strongly believed that specific small molecules interfere with fibrillation by interacting with the amyloidogenic proteins. We had previously reported the strong and long-term inhibition of fibrillation of hen egg white lysozyme (HEWL) by Cuminum cyminum oil. Herein, it was intended to rationally identify the active anti-amyloidogenic compounds of the oil. After fractionation, the highest inhibitory effect was observed in the toluene-ethyl acetate part of the oil. Gas chromatography-mass spectrometry (GC-MS) analysis of this fraction indicated that eight compounds were predominantly present in the fraction. Unexpectedly, two compounds including terpinolene and limonene, having very similar chemical structures, inhibited and induced fibrillation, respectively. PC12 cells (derived from a transplantable rat pheochromocytoma) were affected by HEWL fibrils, whereas the inhibited forms of fibrils in the presence of terpinolene led to higher levels of viability, as shown by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT), lactate dehydrogenase (LDH) and flow cytometry assays. Molecular local docking analysis suggested a site of interaction for terpinolene in the flexible cleft of the protein. This interaction site is close to tryptophan -62 and -63 and two other hydrophobic residues in the hot spot regions of the protein. Seemingly, these interactions interrupt protein self-assembly and therefore, fibril formation. Despite previously reported small anti-amyloid molecules which have aromatic flat rings, terpinolene ring is not flat. This functionally durable small molecule may aid us toward developing new anti-amyloidogenic compounds with extended activity.

SUBMITTER: Morshedi D

PROVIDER: S-EPMC4326981 | biostudies-literature | 2014 Nov-Dec

REPOSITORIES: biostudies-literature

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Identification and characterization of a compound from Cuminum cyminum essential oil with antifibrilation and cytotoxic effect.

Morshedi D D Kesejini T Salmani TS Aliakbari F F Karami-Osboo R R Shakibaei M M Marvian A Tayaranian AT Khalifeh M M Soroosh M M

Research in pharmaceutical sciences 20141101 6

Amyloid pathology is associated with fibril aggregation of different proteins which results in the progressive damage of affected organs. It is strongly believed that specific small molecules interfere with fibrillation by interacting with the amyloidogenic proteins. We had previously reported the strong and long-term inhibition of fibrillation of hen egg white lysozyme (HEWL) by Cuminum cyminum oil. Herein, it was intended to rationally identify the active anti-amyloidogenic compounds of the oi ...[more]

PMID: 26339258

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Project description:IntroductionThe aims of this study were i) to define the chemical constituents of Cuminum cyminum (cumin) essential oil, ii) to compare the antimicrobial activity of this oil to that of chlorhexidine (CHX) and co-trimoxazole on planktonic and biofilm forms of bacteria isolated from the teeth with persistent endodontic infection and iii ) to compare the cytotoxicity of these medicaments on L929 fibroblasts.Methods and materialsThree groups of microorganisms [aerobic bacterial mixture, anaerobic bacterial mixture and Enterococcus faecalis (E .faecalis)] were isolated from the teeth with persistent apical periodontitis. Zone of inhibition (ZOI), minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), minimum biofilm inhibitory concentration (MBIC) and time-kill tests were performed to assess the antimicrobial efficacy of the medicaments. Further, a cytocompatibility analysis of the medicaments was performed on L929 fibroblasts. The results obtained from disc diffusion test and mean cell viability values of the experimental medicaments were analyzed using two-way and one-way analysis of variance (ANOVA).ResultsSeventeen constituents were recognized in cumin oil (predominantly cumin aldehyde and γ-terpinene). Co-trimoxazole showed the greatest ZOI followed by cumin and CHX. The smallest MIC and MBC belonged to co-trimoxazole followed by cumin and CHX for all groups of bacteria except for E. faecalis for which the MBC of cumin was smaller than co-trimoxazole. The results of time-kill assay revealed that all medicaments totally inhibited the bacterial growth in all groups after 24 h. CHX was the most cytotoxic solution while there were no significant differences between the cytocompatibility of different concentrations of cumin essential oil and co-trimoxazole.ConclusionCumin exhibited a strong antimicrobial efficiency against the microbial flora of the teeth with failed endodontic treatments and it was biocompatible for L929 mouse fibroblasts.

Project description:IntroductionEarly-life osteosarcoma is associated with severe morbidity and mortality, particularly affecting young children and adults. The present cancer treatment regimen is exceedingly costly, and medications like ifosfamide, doxorubicin, and cisplatin have unneeded negative effects on the body. With the introduction of hyphenated technology to create medications based on plant molecules, the application of ayurvedic medicine as a new dimension (formulation, active ingredients, and nanoparticles) in the modern period is rapidly growing. The primary source of lead compounds for the development of medications for avariety of ailments is plants and their products. Traditionally, Cuminum cyminum (cumin) has been used as medication to treat a variety of illnesses and conditions.MethodsThe cumin seed was successfully extracted with solvents Hexane, Chloroform, Methanol, Ethanol and Acetone. Following the solvent extraction, the extract residue was assayed in MG63 cells for their anti-proliferative properties.ResultsFirst, we used the [3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide] (MTT) assay to test the extracted residue's cytotoxicity. The results show that hexane extract Half-maximal inhibitory concentration (IC50 86 µG/mL) effciently inhibits cells by causing programmed cell death. Furthermore, using the Acridine orange/ethidium bromide (AO/EB) staining method, the lactate dehydrogenase assay, and the reactive oxygen species assay using the Dichloro-dihydro-fluorescein diacetate (DCHFDA) staining method, we have demonstrated that the hexane extract causes apoptosis in MG63 cells. Furthermore, flow cytometry research revealed that the hexane extract stops the cell cycle in the S phase. In addition, the hexane extract limits colony formation and the migration potential as shown by the scratch wound healing assay. Furthermore, the extract from cumin seeds exhibits remarkable bactericidal properties against infections that are resistant to drugs. Gas chromatography analysis was used to quantitatively determine the hexane and methanolic extract based on the experimental data. The primary chemical components of the extract are revealed by the study, and these help the malignant cells heal. The present study finds that there is scientific validity in using cumin seeds as a novel method of anticancer therapy after undergoing both intrinsic and extrinsic research.

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Identification and characterization of a compound from Cuminum cyminum essential oil with antifibrilation and cytotoxic effect.

Publications

Identification and characterization of a compound from Cuminum cyminum essential oil with antifibrilation and cytotoxic effect.

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