Chemical Composition and Antioxidant Activity of Essential Oil Obtained from Bitter Orange Peel (Citrus aurantium L.) Using Two Methods

In this study, it was shown that the chemical composition of the essential oil obtained from bitter orange peel (Aurantii amari flavedo, Citrus aurantium L., from Croatia) depends on the method of isolation. The peel essential oil was obtained by hydrodistillation and cold press method, and their chemical compositions were analyzed by gas chromatography-mass spectrometry (GC-MS). Twenty two components were characterized by mass spectra and linear retention indices. Limonene was found as dominant compound in both hydrodistillation and cold press essential oil with 91.1 % and 51.3 %, respectively. When comparing the chemical composition of two oils, a significant difference in percentage composition of three major compounds, limonene, linalool and hexadecanoic acid was observed. The antioxidant activity of the oils was tested using 2,2-diphenyl-1-picrylhydrazyl radical scavenging method (DPPH). Both oils showed very poor antioxidant activity. This work is licensed under a Creative Commons Attribution 4.0 International License

Comparison of gastrointestinal stability of isothiocyanates from Tropaeolum Majus L. Altum using in vitro and ex vivo digestion methods

Tropaeolum majus L. is an annual herbaceous plant and a member of the Tropaeolaceae family, which belongs to the Brassicales order. It is an excellent source of flavonoids, carotenoids, phenolic acids, vitamin C, and it is a plant that contains the glucosinolate glucotropaeolin. The major degradation product of glucotropaeolin is benzyl isothiocyanate which is known for its various biological activities. In this study, an essential oil was isolated from the seeds of the Tropaeolum majus L. altum plant by microwave-assisted distillation and analysed using the GC-MS technique. Two compounds were identified, benzyl isothiocyanate as the major one (97.81%), and 2-phenylacetonitrile as a minor one (0.80%). Tropaeolum majus L. altum essential oil and pure benzyl isothiocyanate were then submitted to the two-phase in vitro and ex vivo digestion simulations. The analysis performed by the GC-MS/MS technique showed greater stability of benzyl isothiocyanate from essential oil after in vitro (97.57%), and ex vivo (73.47%) gastric phases of the simulated digestion methods, compared to its stability after in vitro (71.17%) and ex vivo (54.90%) intestinal phases. A similar trend was shown for pure benzyl isothiocyanate

The Garden Candytuft (Iberis umbellata L.): At the Crossroad of Copper Accumulation and Glucosinolates

The copper accumulation ability and its impact on the glucosinolate content of the garden candytuft were studied. Different copper sources (adsorbents or solution) were used. Generally, the seedlings copper uptake from the adsorbents was in the amount needed for its growth and development with the beneficial or no impact on the glucosinolate content. The lowest copper concentration was detected in the total seedlings biomass which grew in the humus with the addition of Cu-exchanged zeolite NaX (27.88 μg g−1 DW) having glucosinolate content of 9757.81 µg g−1 DW (23.86 µmol g−1 DW). The highest copper concentration among all the garden candytuft samples was detected in the seedlings watered with CuSO4∙5H2O solution (514.63 μg g−1 DW) with a sharp decrease of the glucosinolate content 3103.33 µg g−1 DW (7.59 µmol g−1 DW). Based on the results obtained, the garden candytuft can be considered as a copper accumulator plant

Glucosinolates and Cytotoxic Activity of Collard Volatiles Obtained Using Microwave-Assisted Extraction

Glucosinolates (GSLs) in Brassica oleracea L. convar. acephala var. viridis (collard) flower, leaf, stem, and root were analyzed qualitatively and quantitatively via their desulfo-counterparts using UHPLC-DAD-MS/MS. Twelve GSLs were identified, including Met-derived GSLs (sinigrin, glucoibervirin, glucoerucin, glucoiberin, glucoraphanin, progoitrin), Trp-derived GSLs (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrassicin), and Phe-derived GSLs (glucotropaeolin and gluconasturtiin). Total GSL content was highest in the root, having 63.40 μmol/g dried weight (DW), with gluconasturtiin (34.02 μmol/g DW) as the major GSL, followed by sinigrin and glucoibervirin (12.43 and 7.65 μmol/g DW, respectively). Total GSL contents in the flower, leaf, and stem were lower than in root, having 6.27, 2.64, and 1.84 μmol/g DW, respectively, with Trp and/or Met-derived GSLs as the predominant ones. GSL breakdown products were obtained via microwave hydrodiffusion and gravity (MHG) and volatile breakdown products were analyzed using GC-MS techniques. Volatile isolates were tested for their cytotoxic activity using MTT assay. MHG volatile extract from the root demonstrated the best cytotoxic activity against human bladder cancer cell line T24 and breast cancer cell line MDA-MB-231 during an incubation time of 72 h (IC50 21.58, and 11.62 μg/mL, respectively). The activity of the root extract can be attributed to its major volatile, 2-phenylethyl isothiocyanate (gluconasturtiin breakdown product)

Glucosinolates and Cytotoxic Activity of Collard Volatiles Obtained Using Microwave-Assisted Extraction

Glucosinolates (GSLs) in Brassica oleracea L. convar. acephala var. viridis (collard) flower, leaf, stem, and root were analyzed qualitatively and quantitatively via their desulfo-counterparts using UHPLC-DAD-MS/MS. Twelve GSLs were identified, including Met-derived GSLs (sinigrin, glucoibervirin, glucoerucin, glucoiberin, glucoraphanin, progoitrin), Trp-derived GSLs (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrassicin), and Phe-derived GSLs (glucotropaeolin and gluconasturtiin). Total GSL content was highest in the root, having 63.40 μmol/g dried weight (DW), with gluconasturtiin (34.02 μmol/g DW) as the major GSL, followed by sinigrin and glucoibervirin (12.43 and 7.65 μmol/g DW, respectively). Total GSL contents in the flower, leaf, and stem were lower than in root, having 6.27, 2.64, and 1.84 μmol/g DW, respectively, with Trp and/or Met-derived GSLs as the predominant ones. GSL breakdown products were obtained via microwave hydrodiffusion and gravity (MHG) and volatile breakdown products were analyzed using GC-MS techniques. Volatile isolates were tested for their cytotoxic activity using MTT assay. MHG volatile extract from the root demonstrated the best cytotoxic activity against human bladder cancer cell line T24 and breast cancer cell line MDA-MB-231 during an incubation time of 72 h (IC50 21.58, and 11.62 μg/mL, respectively). The activity of the root extract can be attributed to its major volatile, 2-phenylethyl isothiocyanate (gluconasturtiin breakdown product)

Isothiocyanates: cholinesterase inhibiting, antioxidant, and anti-inflammatory activity

Finding a new type of cholinesterase inhibitor that would overcome the brain availability and pharmacokinetic parameters or hepatotoxic liability has been a focus of investigations dealing with the treatment of Alzheimer’s disease. Isothiocyanates have not been previously investigated as potential cholinesterase inhibitors. These compounds can be naturally produced from their glucosinolate precursors, secondary metabolites widely distributed in our daily Brassica vegetables. Among 11 tested compounds, phenyl isothiocyanate and its derivatives showed the most promising inhibitory activity. 2-Methoxyphenyl ITC showed best inhibition on acetylcholinesterase with IC50 of 0.57 mM, while 3-methoxyphenyl ITC showed the best inhibition on butyrylcholinesterase having 49.2% at 1.14 mM. Assessment of the antioxidant efficacy using different methods led to a similar conclusion. The anti-inflammatory activity was also tested using human COX-2 enzyme, ranking phenyl isothiocyanate, and 3-methoxyphenyl isothiocyanate as most active, with ∼99% inhibition at 50 μM

Antiphytoviral Activity of Sesquiterpene-Rich Essential Oils from Four Croatian Teucrium Species

The purpose of this study was to compare the essential oil profiles of four Croatian Teucrium species (Lamiaceae), as determined by GC and GC/MS, with their antiphytoviral efficiency. A phytochemical analysis showed that T. polium, T. flavum, T. montanum and T. chamaedrys are characterized by similar essential oil compositions. The investigated oils are characterized by a high proportion of the sesquiterpene hydrocarbons β-caryophyllene (7.1–52.0%) and germacrene D (8.7–17.0%). Other important components were β-pinene from T. montanum and α-pinene from T. flavum. The investigated essential oils were proved to reduce lesion number in the local host Chenopodium quinoa Willd. infected with Cucumber Mosaic Virus (CMV), with reductions of 41.4%, 22.9%, 44.3% and 25.7%, respectively

Biological Effects of Glucosinolate Degradation Products from Horseradish: A Horse that Wins the Race

Horseradish degradation products, mainly isothiocyanates (ITC) and nitriles, along with their precursors glucosinolates, were characterized by GC-MS and UHPLC-MS/MS, respectively. Volatiles from horseradish leaves and roots were isolated using microwave assisted-distillation (MAD), microwave hydrodiffusion and gravity (MHG) and hydrodistillation (HD). Allyl ITC was predominant in the leaves regardless of the isolation method while MAD, MHG, and HD of the roots resulted in different yields of allyl ITC, 2-phenylethyl ITC, and their nitriles. The antimicrobial potential of roots volatiles and their main compounds was assessed against sixteen emerging food spoilage and opportunistic pathogens. The MHG isolate was the most active, inhibiting bacteria at minimal inhibitory concentrations (MICs) from only 3.75 to 30 µg/mL, and fungi at MIC50 between <0.12 and 0.47 µg/mL. Cytotoxic activity of volatile isolates and their main compounds were tested against two human cancer cell lines using MTT assay after 72 h. The roots volatiles showed best cytotoxic activity (HD; IC50 = 2.62 μg/mL) against human lung A549 and human bladder T24 cancer cell lines (HD; IC50 = 0.57 μg/mL). Generally, 2-phenylethyl ITC, which was tested for its antimicrobial and cytotoxic activities along with two other major components allyl ITC and 3-phenylpropanenitrile, showed the best biological activities