Biological activity of terpene compounds produced by biotechnological methods

Paduch, Roman; Trytek, Mariusz; Król, Sylwia; Kud, Joanna; Frant, Maciej; Kandefer‐Szerszeń, Martyna; Fiedurek, J.

doi:10.3109/13880209.2015.1103753

Cited by 47 publications

(16 citation statements)

References 28 publications

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“…After 24 h, the cells were incubated with the NR reagent for 3 h, fixed with the NR fixative solution (1% CaCl 2 in 0.5% formalin) for 3 min at room temperature, and solubilized in 1% acetic acid in 50% ethanol under shaking for 20 min. Absorbance was measured at 550 nm using an Emax Miocroplate Reader [23].…”

Section: Methodsmentioning

confidence: 99%

“…The activity of each extract was determined by comparing its absorbance with that of a control solution (reagents without extract) and standards. The capability to scavenge DPPH radical was calculated by the following formula: DPPH scavenging effect (%) = [(Xcontrol − Xextract/Xcontrol) × 100] where Xcontrol is the absorbance of the control and Xextract is the absorbance in the presence of extracts [23].…”

Section: Cell Cycle Progression -Propidium Iodide Stainingmentioning

confidence: 99%

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Evaluation of anticancer activity of water and juice extracts of young <i>Hordeum vulgare</i> in human cancer cell lines HT-29 and A549

Czerwonka¹,

Kawka²,

Cykier³

et al. 2017

Ann Agric Environ Med.

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Introduction and objective. Barley (Hordeum vulgare L.) is known as a rich source of different bioactive compounds. At present, considerable attention of researchers is focused on young barley grass. It can be a good source of dietary minerals, vitamins, carbohydrates, amino acids, phenolic compounds and proteins. It is possible that the composition of chemical ingredients beneficial for health may induce an anticancer potential of young barley in human colon adenocarcinoma (HT-29) and human lung adenocarcinoma (A549) cell lines. Materials and method. Hordeum vulgare water extract (HWE) and Hordeum vulgare juice extract (HJE) were prepared. Cell proliferation and viability were examined with the use of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) and NR (neutral red) methods. Induction of necrosis was assessed by propidium iodide/Hoechst staining. Progress of the cell cycle involved in cell proliferation, apoptosis, and regulation of transcription was estimated using flow cytometry analysis. Additionally, the capability of free radical scavenging was evaluated with the DPPH assay. Results. The study revealed that extracts inhibited the proliferation of cancer cells. The NR study confirmed the low cytotoxic activity of the tested extracts to normal human colon epithelial cells (CCD 841 CoTr) and human skin fibroblasts (HSF). Furthermore, a dose-dependent cytotoxicity against HT-29 cells, but not A549 cells, has been reported. The free radical scavenging activity was observed in the case of the HWE but not the HJE. Conclusions. The obtained results indicate a cancer chemopreventive potential of young barley as a safe dietary agent in colon carcinoma.

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Section: Methodsmentioning

confidence: 99%

Section: Cell Cycle Progression -Propidium Iodide Stainingmentioning

confidence: 99%

Evaluation of anticancer activity of water and juice extracts of young <i>Hordeum vulgare</i> in human cancer cell lines HT-29 and A549

Czerwonka¹,

Kawka²,

Cykier³

et al. 2017

Ann Agric Environ Med.

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“…In the only study in which the terpenoids were evaluated for those effects, Rufino and co‐workers found that they were less effective, or even completely inactive, as opposed to their hydrocarbon counterpart, pinene . Our own earlier finding, however, was that some monoterpene derivatives exerted a considerably higher bioactivity against human colon tumour cells in comparison with their precursor …”

Section: Discussionmentioning

confidence: 92%

“…In our previous study, we showed that certain biotransformation products of pinene ( trans ‐verbenol and verbenone) exerted stronger biological inhibitory effects against human colon tumour cells than their precursors . One serious obstacle to the wide‐scale use of these compounds in the treatment of cancer, however, was their high price.…”

Section: Introductionmentioning

confidence: 99%

Biological activity of oxygenated pinene derivatives on human colon normal and carcinoma cells

Trytek

Paduch

Pięt

et al. 2018

Flavour & Fragrance J

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The antitumour activity of the oxygenated derivatives of pinene is still poorly understood. We hypothesized that the derivatives of pinene, (−)‐myrtenol, (−)‐myrtanol, and (−)‐myrtenal, would express different effects on human colon tumour cells and normal intestinal cells in vitro. For cytotoxic and nitric oxide (NOx) assays, human colon tumour (HT29) and human normal colon epithelial cells (CCD 841 CoTr) were incubated for 24 h with 0.1–5.0 mM of the terpenoids. The NOx level was determined in cells pre‐incubated or not with lipopolysaccharide (LPS). All three terpenoids decreased the activity of succinate dehydrogenase in tumour and normal cells, with a mixture (1 : 1 : 1) of the pinene derivatives having the strongest effect (with half‐maximal inhibitory concentrations, IC50, of 2.56 and 1.05 mM, respectively). The cytotoxic effect of the terpenes on tumour cells was observed at concentrations higher than 2 mM, with (–)‐myrtenal exerting the strongest activity (IC50 = 5.3 mM). Normal cells were more sensitive to the activity of the terpenes, especially when administered as a mixture (IC50 = 0.08 mM). The terpenoids synergistically stimulated tumour cells for NOx release and acted antagonistically in the case of normal cells. Tumour cells released the highest (1.111 μM) and normal cells released the lowest (0.146 μM) quantities of NOx after incubation with 1 mM terpenoid mixture. LPS‐induced tumour cells produced higher quantities of NOx than the unstimulated culture. An opposite effect was observed for normal intestinal cells. The investigated pinene derivatives inhibit the activity of human colon tumour cells in vitro by affecting mitochondrial enzyme activity, NOx release, and membrane stability. Differences in the bioactivity of the individual compounds can be determined on the basis of their structure and degree of oxidation.

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“…21 α-Pinene (1) is a monoterpene found also in P. hispidum essential oil 8a and other Piperaceae species 9 and was described as insecticidal repellent 22 and cytotoxic selectively against tumor cells. 23 The linalool (15) was the major substance of inflorescences essential oil and was found in high concentration in inflorescence hydrolate but was absent or in low concentrations in the other samples, so may be thought of as a chemical marker for quality control of inflorescences. This compound shows the importance of chemical composition studies of different plant organs.…”

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confidence: 99%

Chemical Analysis of Essential Oil and Hydrolates of Leaves, Inflorescences and Stems of Piper chimonanthifolium Kunth

Macedo

2017

Rev. Virtual Quim.

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Resumo: Plantas do gênero Piper são frequentemente utilizadas comercialmente. A espécie Piper chimonanthifolium Kunth. apresenta poucos estudos em literatura quanto a sua composição química e atividades biológicas. Óleos essenciais de outras espécies deste gênero apresentam boas atividades biológicas, principalmente contra microrganismos. Este trabalho apresenta uma comparação da composição química de óleos essenciais e hidrolatos de folhas, inflorescências e caules desta espécie. As amostras foram obtidas por co-destilação e analisadas por cromatografia com fase gasosa acoplada à espectrometria de massas (CG-EM). As amostras mostraram presença de monoterpenos e sesquiterpenos, com predominância de monoterpenos. A piperitona, um monoterpeno com atividades biológicas anteriormente relatadas na literatura, foi a substância com maior destaque. Além desta substância, destacaram-se: L-linalol, cis-β-ocimeno, trans-β-cimeno, 1-felandreno, α-pineno, limoneno e espatulenol. Algumas dessas substâncias podem exibir variação na composição de acordo com fatores ambientais e podem ser agentes de controle biológico, demonstrando importância ecológica. As análises por CG-EM evidenciaram diferenças na composição química entre folhas, inflorescências e caules, além de demonstrarem potencial biológico para esta espécie. Palavras-chave:Atividade biológica; Óleo essencial; Monoterpeno; Piperaceae; Piperitona. AbstractPlants of the genus Piper are widely used commercially. Piper chimonanthifolium Kunth. is a species with few studies on chemistry and biological activities. Essential oils of other species of this genus show good biological activities, especially against microorganisms. This work presents a comparative analysis of chemical composition of essential oils and hydrolates of leaves, inflorescences and stems of this specie. Samples were obtained by co-distillation and analyzed by gas chromatography-mass spectrometry (GC-MS). The samples were composed of monoterpenes and sesquiterpenes, with predominance of monoterpenes. Piperitone, a monoterpene with important biological activities, was the most important substance and in addition to this compound, L-linalool, cis-β-ocimene, trans-β-ocimene, 1-phellandrene, α-pinene, limonene, and spathulenol stood out. Some of these substances can exhibit a variation in the composition according to environmental factors or may be biological control agents, demonstrating ecological importance. The chemical characterization showed chemical differences between leaves, stems and inflorescences and demonstrated biological potential for this species.

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Biological activity of terpene compounds produced by biotechnological methods

Cited by 47 publications

References 28 publications

Evaluation of anticancer activity of water and juice extracts of young <i>Hordeum vulgare</i> in human cancer cell lines HT-29 and A549

Evaluation of anticancer activity of water and juice extracts of young <i>Hordeum vulgare</i> in human cancer cell lines HT-29 and A549

Biological activity of oxygenated pinene derivatives on human colon normal and carcinoma cells

Chemical Analysis of Essential Oil and Hydrolates of Leaves, Inflorescences and Stems of Piper chimonanthifolium Kunth

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