- 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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- PROCESS FOR THE SYNTHESIS OF ISOTHIOCYANATES AND DERIVATIVES THEREOF AND USES OF SAME
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A method for synthesizing an isothiocyanate of general formula (I) [in-line-formulae]SCN—R1—R4—R2??(I)[/in-line-formulae] wherein R1 and R2 represent independently of each other an alkyl-aryl or aryl group, R4 represents a carbonyl, sulfinyl, sulfonyl group or a sulfide group and of its derivatives comprising a step for reacting an alkylalkylamine having the general formula (II) [in-line-formulae]NH2—R1—R4—R2??(II)[/in-line-formulae] wherein R1 and R2 represent independently of each other an alkyl, aryl or alkylaryl group, R4 represents a carbonyl, sulfinyl, sulfonyl or sulfide group, in the presence of carbon sulfide and of di-tert-butyl dicarbonate with formation of the corresponding aforesaid isothiocyanate, compounds obtained by this method as well as their uses.
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- Analysis and anti- helicobacter activity of sulforaphane and related compounds present in Broccoli (Brassica oleracea L.) sprouts
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A crude methanol extract prepared from fresh broccoli sprouts was extracted with hexane, chloroform, ethyl acetate, and butanol sequentially. Residual water fraction was obtained from the residual aqueous layer. The greatest inhibition zones (>5 cm) were noted for Helicobacter pylori strain by the chloroform extract, followed by the hexane extract (5.03 cm), the ethyl acetate extract (4.90 cm), the butanol extract (3.10 cm), and the crude methanol extract (2.80 cm), whereas the residual water fraction did not show any inhibition zone. Including sulforaphane, five sulforaphane-related compounds were positively identified in the chloroform extract, of which 5- methylsulfinylpentylnitrile was found in the greatest concentration (475.7 mg/kg of fresh sprouts), followed by sulforaphane (222.6 mg/kg) and 4-methylsulfinylbutylnitrile (63.0 mg/kg). Among 18 sulforaphane and related compounds synthesized (6 amines, 6 isothiocyanates, and 6 nitriles), 2 amines, 6 isothiocyanates, and 1 nitrile exhibited >5 cm inhibitory zones for H. pylori strain. The results indicate that broccoli sprouts can be an excellent food source for medicinal substances.
- Moon, Joon-Kwan,Kim, Jun-Ran,Ahn, Young-Joon,Shibamoto, Takayuki
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p. 6672 - 6677
(2011/08/06)
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- Stabilized sulforaphane
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A method of stabilizing sulforaphane is provided. The method includes contacting sulforaphane, or an analog thereof, and a cyclodextrin to form a complex between the sulforaphane, or analog thereof, and the cyclodextrin.
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Page/Page column 8
(2008/12/07)
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- Cancer chemopreventive activity of sulforamate derivatives
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Chemoprevention can be defined as an intervention in the carcinogenic process by use of natural or synthetic substances. Induction of Phase II enzyme is an important mechanism of chemoprevention. In the present studies we have synthesized several derivati
- Moriarty, Robert M.,Naithani, Rajesh,Kosmeder, Jerome,Prakash, Om
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p. 121 - 124
(2007/10/03)
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- A facile and efficient synthesis of 14C-labelled sulforaphane
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Isothiocyanates have gained considerable attention for their role as potent chemopreventive agents. Sulforaphane, 1a (SFN), a naturally occurring isothiocyanate, was isotopically labelled in five steps starting from 3-(methylthio)-1-propanol (2). Reacting 2 with tosyl chloride in the presence of Et3N yielded the tosylate 3. Gently refluxing 3 with K 14CN in DMF gave the nitrile 4b. Reduction to the amine 5b was achieved using BH3-THF. Oxidation with 30% hydrogen peroxide followed by treatment with thiophosgene yielded (±)[1-14C]SFN, 1b. The overall radiochemical yield was 4.4% based on the starting K 14CN. Copyright
- D'Souza, Christopher A.,Amin, Shantu,Desai, Dhimant
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p. 851 - 859
(2007/10/03)
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