- Antioxidant activity of two edible isothiocyanates: Sulforaphane and erucin is due to their thermal decomposition to sulfenic acids and methylsulfinyl radicals
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Sulforaphane (SFN) and erucin (ERN) are isothiocyanates (ITCs) bearing, respectively, methylsulfinyl and methylsulfanyl groups. Their chemopreventive and anticancer activity is attributed to ability to modulate cellular redox status due to induction of Phase 2 cytoprotective enzymes (indirect antioxidant action) but many attempts to connect the bioactivity of ITCs with their radical trapping activity failed. Both ITCs are evolved from their glucosinolates during food processing of Cruciferous vegetables, therefore, we studied antioxidant behaviour of SFN/ERN at elevated temperature in two lipid systems. Neither ERN nor SFN inhibit the oxidation of bulk linolenic acid (below 100 °C) but both ITCs increase oxidative stability of soy lecithin (above 150 °C). On the basis of GC-MS analysis we verified our preliminary hypothesis (Antioxidants 2020, 9, 1090) about participation of sulfenic acids and methylsulfinyl radicals as radical trapping agents responsible for the antioxidant effect of edible ITCs during thermal oxidation of lipids at elevated temperatures (above 140 °C).
- Cedrowski, Jakub,D?browa, Kajetan,Przybylski, Pawe?,Krogul-Sobczak, Agnieszka,Litwinienko, Grzegorz
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- Sulforaphane stabilization
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A stable galenic composition of a compound of general formula (I) wherein R1 and R2 both represent independently of each other an alkyl, aryl, arylalkyl group, optionally substituted with one or more linear or branched groups, optionally bearing one or more heteroatoms, comprising said compound of formula I in an amount ranging from 0.01 to 15% by weight based on the total weight of the final composition; at least one anhydrous ester, the main chain and/or optionally the branched chains of which are free from free and/or reactive groups or functions, in an amount ranging from 0.1 to 99.9% by weight based on the total weight of the cosmetically and pharmaceutically acceptable composition; and optionally a cosmetically and pharmaceutically acceptable excipient for completing the 100% of the total weight of the composition.
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Page/Page column 2
(2016/03/07)
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- Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard
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Allyl isothiocyanate (ITC) (4) is the main pungent component in wasabi, and it generates an acrid sensation by activating TRPA1. The flavor and pungency of ITCs vary depending on the compound. However, the differences in activity to activate TRPA1 between ITCs are not known except for a few compounds. To investigate the effect of carbon chain length and substituents of ITCs, the TRPA1-activiting ability of 16 ITCs was measured. Since most of the ITCs showed nearly equal TRPA1-activiting potency, the ITC moiety is likely the predominant contributor to their TRPA1-activating abilities, and contributions of other functional groups to their activities to activate TRPA1 are comparatively small. (Figure Presented).
- Terada, Yuko,Masuda, Hideki,Watanabe, Tatsuo
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p. 1937 - 1941
(2015/09/08)
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- Synthesis of isothiocyanate-derived mercapturic acids
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Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables.
- Vermeulen, Martijn,Zwanenburg, Binne,Chittenden, Gordon J.F.,Verhagen, Hans
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p. 729 - 737
(2007/10/03)
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- THE INTRAMOLECULAR FORMATION OF EPITHIOALKANENITRILES FROM ALKENYLGLUCOSINOLATES BY CRAMBE ABYSSINICA SED FLOUR
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Enzymatic degradations of mixtures of potassium 3-butenylglucosinolate and allylglucosinolate by aqueous suspensions of Crambe abyssinica seed flour led to the formation of 4,5-epithiopentanenitrile and essentially unlabelled 3,4-epithiobutanenitrile.The formation of epithioalkanenitriles from alkenylglucosinolates is, therefore deduced to be an intramolecular process. -- Key Word Index - Crambe abyssinica; Cruciferae; allylglucosinolate; 3-butenylglucosinolate; 3,4-epithiobutanenitrile; 4,5-epithiopentanenitrile; sinigrin; episulphide; thiirane; biosynthesis.
- Brocker, Erich R.,Benn, M. H.
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p. 770 - 772
(2007/10/02)
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