Influence of isolation techniques on the composition of glucosinolate breakdown products, their antiproliferative activity and gastrointestinal stability of allyl isothiocyanate

Vrca, Ivana; Šćurla, Josipa; Kević, Nives; Burčul, Franko; Čulić, Vedrana Čikeš; Bočina, Ivana; Blažević, Ivica; Bratanić, Andre; Bilušić, Tea

doi:10.1007/s00217-021-03903-x

Cited by 4 publications

(7 citation statements)

References 40 publications

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“…The essential oil and extract of T. majus were isolated by MAD and MHG extraction techniques, respectively, using an ETHOS X device (Milestone, Italy) and applying microwave power of 500 W as desribed by Vrca et al . ( 1 , 9 ). The essential oil was extracted from the seeds (50 g).…”

Section: Methodsmentioning

confidence: 99%

“…Solvent-free extraction methods such as microwave-assisted distillation (MAD), and microwave hydrodifussion and gravity (MHG) are excellent replacements to conventional extraction methods in order to obtain isolates rich in volatile compounds (9). These new extraction methods are much faster, easier, enviromentally friendly and enable extraction of biologically active compounds with decreased energy (9). ITCs can potentially be used to prevent various cancers such as lung, liver, breast and, colon cancers (11).…”

Section: Introductionmentioning

confidence: 99%

“…Intact GSLs are not biologically active compared to their breakdown products, especially isothiocyanates (ITCs), which are reported to be very active against a wide range of organisms ( 7 ), including microrganisms such as bacteria. GSLs are hydrolyzed by enzyme myrosinase contributing to the formation of various degradation products (ITCs, thiocyanates and nitriles) that depend on physiological conditions such as pH and the presence of certain cofactors like epithiospecifier protein (ESP) ( 8 , 9 ). ITCs are formed at neutral pH, while at acidic pH nitriles are dominant products ( 10 ).…”

Section: Introductionmentioning

confidence: 99%

“…Solvent-free extraction methods such as microwave-assisted distillation (MAD), and microwave hydrodifussion and gravity (MHG) are excellent replacements for conventional extraction methods in order to obtain isolates rich in volatile compounds ( 9 ). These new extraction methods are much faster, easier, enviromentally friendly and they enable the extraction of biologically active compounds with reduced energy ( 9 ). ITCs can potentially be used to prevent various cancers such as lung, liver, breast and colon cancers ( 11 ).…”

Section: Introductionmentioning

confidence: 99%

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Chemical Composition and Biological Activity of Essential Oil and Extract from the Seeds of Tropaeolum majus L. var. altum

Vrca

Ramić

Fredotović

et al. 2022

Food Technol. Biotechnol. (Online)

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Research background. Plant Tropaeolum majus L. belongs to the family Tropaeolaceae, and contains benzyl glucosinolate. The breakdown product of benzyl glucosinolate, benzyl isothiocyanate (BITC), exhibits various biological activities such as antiproliferative, antibacterial, and antiinflammatory activities. In order to optimize the content of biologically active volatile compounds in plant extract and essential oil, the use of appropriate extraction technique has a crucial role. Experimental approach. The current study investigated the effect of two modern extraction methods (microwave-assisted distillation (MAD) and microwave hydrodiffusion and gravity (MHG)) on the chemical composition of volatile components present in essential oil and extract of T. majus L. var. altum seeds. The biological activity of samples (essential oil, extract and pure compounds) was focused on the antiproliferative effect against different cancer cell lines: cervical cancer cell line (HeLa), human colon cancer cell line (HCT116), and human osteosarcoma cell line (U2OS), and the antibacterial activity which was evaluated against growth and adhesion to polystyrene surface of Staphylococcus aureus and Escherichia coli. Results and conclusions. Essential oil and extract of T. majus seeds were isolated by two extraction techniques: MAD and MHG. BITC and benzyl cyanide (BCN) present in extract were identified by GC-MS. Essential oil of T. majus showed higher antiproliferative activity (IC50<5 µg/mL) than T. majus extract (IC50<27 µg/mL) against three cancer cell lines: HeLa, HCT116, and U2OS. BITC showed much higher inhibitory effect on all tested cells in contrast to BCN. Essential oil and extract of T. majus showed strong antimicrobial activity against S. aureus and E. coli. Novelty and scientific contribution. This work represents the first comparative report on the antiproliferative activity of essential oil and extract of T. majus seeds, BITC and BCN against HeLa, HCT116, and U2OS cells as well as their antimicrobial activity against S. aureus and E. coli. This study demonstrated that essential oil of T. majus seeds exhibits stronger antiproliferative and antimicrobial activity than plant extract.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemical Composition and Biological Activity of Essential Oil and Extract from the Seeds of Tropaeolum majus L. var. altum

Vrca

Ramić

Fredotović

et al. 2022

Food Technol. Biotechnol. (Online)

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“…On the other hand, microwave distillation can sometimes lead to the isolation of few components, as stated in the study of Wu et al [ 3 ]. However, modern techniques such as MAE are much faster, easier to use, and environmentally acceptable and enable extraction of bioactive components with less energy than conventional extraction methods [ 4 , 5 ]. Two types of samples can be obtained using the MAE technique, essential oil (EO), and hydrosol (HY).…”

Section: Introductionmentioning

confidence: 99%

Isolation of Volatile Compounds by Microwave-Assisted Extraction from Six Veronica Species and Testing of Their Antiproliferative and Apoptotic Activities

Vrca,

Čikeš Čulić,

Lozić

et al. 2023

Plants

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This study was conducted to determine the differences in the chemical composition of the essential oils and hydrosols of six different Veronica species (V. agrestis, V. anagalloides, V. austriaca ssp. jacquinii, V. beccabunga, Veronica cymbalaria, and V. officinalis) and to test their antiproliferative and apoptotic activities, according to the authors’ knowledge, because of insufficient research and lack of information. Also, the goal was to determine which obtained samples were better in achieving antiproliferative and apoptotic activities and due to which volatile components. Therefore, essential oils (EOs) and hydrosols (HYs) were isolated from the above-mentioned Veronica species by microwave-assisted extraction (MAE). Phytochemical identification of the free volatile compounds was performed using a GC equipped with a flame ionization detector and a mass spectrometer. Their antiproliferative and apoptotic activities against two human cancer cell lines, breast cancer cell line MDA-MB-231 and bladder cancer cell line T24, were determined. The main compounds identified in the studied Veronica EOs and HYs were terpinen-4-ol (0.34–6.49%), linalool (0.34–6.61%), (E)-caryophyllene (0.97–7.55%), allo-aromadendrene (0.18–2.21%), caryophyllene oxide (1.42–23.83%), benzene acetaldehyde (0.26–13.34%), and β-ionone (1.08–16.53%). In general, HYs of the tested Veronica species showed higher antiproliferative activity (IC50 13.41–42.05%) compared to EOs (IC50 158.1–970.4 µg/mL) on MDA-MB-231 and T24 cancer cell lines after 48 and 72 h. V. agrestis EO showed the best apoptotic effect among the EOs on the MDA-MB-231 cancer cell line (10.47 ± 0.53% and 9.06 ± 0.74% of early/late apoptosis, compared with control 3.61 ± 0.62% and 0.80 ± 0.17% of early/late apoptosis, respectively) and among the HYs V. cymbalaria showed 9.95 ± 1.05% and 3.06 ± 0.28% of early/late apoptosis and V. anagalloides 8.29 ± 1.09% and 1.95 ± 0.36% of early/late apoptosis compared with control (for EO was 7.45 ± 1.01% and 0.54 ± 0.25%, and for HY was 4.91 ± 1.97% and 0.70 ± 0.09% of early/late apoptosis, respectively) on the T24 cancer cell line. Future research will include other Croatian species of the genus Veronica to gain a more complete insight into the biological activity of the volatile products of this genus for potential discovery of drugs based on natural plant extracts.

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Recent advances in the contribution of glucosinolates degradation products to cruciferous foods odor: factors that influence degradation pathways and odor attributes

Jia,

An,

Zhang

et al. 2024

Critical Reviews in Food Science and Nutrition

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Influence of isolation techniques on the composition of glucosinolate breakdown products, their antiproliferative activity and gastrointestinal stability of allyl isothiocyanate

Cited by 4 publications

References 40 publications

Chemical Composition and Biological Activity of Essential Oil and Extract from the Seeds of Tropaeolum majus L. var. altum

Chemical Composition and Biological Activity of Essential Oil and Extract from the Seeds of Tropaeolum majus L. var. altum

Isolation of Volatile Compounds by Microwave-Assisted Extraction from Six Veronica Species and Testing of Their Antiproliferative and Apoptotic Activities

Recent advances in the contribution of glucosinolates degradation products to cruciferous foods odor: factors that influence degradation pathways and odor attributes

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