• Asian Pacific Journal of Cancer Prevention
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• v.17 no.9
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• pp.4507-4510
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• 2016

Isothiocyanates are naturally occurring small molecules that are formed from glucosinolate precursors of cruciferous vegetables. Many isothiocyanates, both natural and synthetic, display anti-carcinogenic activity because they reduce activation of carcinogens and increase their detoxification. This minireview summarizes the current knowledge on isothiocyanates and focuses on their role as potential anti-cancer agents.

• Journal of the Korean Society of Food Culture
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• v.8 no.2
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• pp.147-151
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• 1993

The composition of isothiocyanates in Dolsan leaf mustard was investigated. Five major volatile isothiocyanates detected in leaf mustard were sec-butyl isothiocyanate, allyl isothiocyanate, 3-butenyl isothiocyanate, n-hexyl isothiocyanate and ${\beta}-phenylethyl$ isothiocyanate. In both leaf and leaf stalk allyl isothiocyanate and 3-butenyl isothiocyanate were the most abundant. The compositional difference of isothiocyanates between leaf and leaf stalk was that n-hexyl and ${\beta}-phenylethyl$ isothiocyanates were present more in leaf than leaf stalk.

• Journal of the Korean Society of Food Science and Nutrition
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• v.32 no.3
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• pp.315-319
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• 2003

Bioactive organosulfur phytochemicals were isolated from fresh broccoli using methlylene chloride as an extract solvent and identified by GC/MSD analyses. Major organosulfur phytochemicals of broccoli extract were found to be isothiocyanates, which constitute 40.42% of total phytochemicals. The isothiocyanates from broccoli extract were identified to be 3-butenyl, 4-methyl thiobutyl, 4-methylthio-3-butenyl, 5-methylthiopentyl, 2-phenylethyl, 3-methyl sulfinyl propyl, and 4-methylsulfinylbutyl isothiocyanates, of which major isothio cyanates were 3 butenyl isothiocyanate and 4-methylsulfinylbutyl isothiocyanate, constituting about 38.55% of total isothiocyanates present in the solvent extract. Also, nitrites, corresponding to products from enzymatic hydrolysis of glucosinolates were identified as 4-methylthiobutyl, 5-methyl thiopentyl, 2-phenylethyl and 4-methylsulfinylbutyl nitrile. In addition, three sulfides were identified as dimethyl disulfide, dimethyl trisulfide and dimethyl tetrasulfide.

• Journal of Microbiology and Biotechnology
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• v.26 no.12
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• pp.2036-2042
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• 2016

We evaluated the potentials of 10 isothiocyanates (ITCs) from cruciferous vegetables and radish root hydrolysate for inhibiting the growth of oral pathogens, with an emphasis on assessing any structure-function relationship. Structural differences in ITCs impacted their antimicrobial activities against oral pathogens differently. The indolyl ITC (indol-3-carbinol) was the most potent inhibitor of the growth of oral pathogens, followed by aromatic ITCs (benzyl ITC (BITC) and phenylethyl ITC (PEITC)) and aliphatic ITCs (erucin, iberin, and sulforaphene). Sulforaphene, which is similar in structure, but has one double bond, showed higher antimicrobial activity than sulforaphane. Erucin, which has a thiol group, showed higher antimicrobial activity than sulforaphane, which has a sulfinyl group. BITC and iberin with a short chain exhibited higher antimicrobial potential than PEITC and sulforaphane with a longer chain, respectively. ITCs have strong antimicrobial activities and may be useful in the prevention and management of dental caries.

• Korean Journal of Fisheries and Aquatic Sciences
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• v.52 no.4
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• pp.349-357
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• 2019

The effect of entrapping isothiocyanates extracted from horseradish root by microencapsulation on the shelf life of Myeongran jeotgal was evaluated. The total viable cell count of Myeongran jeotgal reached $10^7CFU/g$ (initial decomposition level) on days 43 and 45 of treatment with 1.0% and 2.0% microcapsules (4.0 mg/mL), respectively, compared with day 21 of storage at $5^{\circ}C$ as the control treatment. The proteolytic bacterial counts of Myeongran jeotgal treated with 1.0% and 2.0% microcapsules were $2.0{\times}10^5$ and $9.5{\times}10^4CFU/g$, respectively, with 2 and 3 log reductions compared with the control count ($1.1{\times}10^7CFU/g$) on day 33 of storage at $5^{\circ}C$. The total volatile basic nitrogen (TVB-N) level reached 30.0 mg% (initial decomposition level) on days 47 and 48 of treatment with 1.0% and 2.0% microcapsules, respectively, compared with day 33 of storage at $5^{\circ}C$ as the control. Based on the sensory evaluation, the freshness of Myeongran jeotgal treated with 1.0% microcapsules was best compared with the other treatments. Based on the total viable cell count, TVB-N and sensory evaluation, the shelf life of Myeongran jeotgal treated with 1.0% microcapsules was extended by 22, 16 and 15 days, respectively, compared with the control at $5^{\circ}C$.

• Proceedings of the Korean Society of Food Science and Nutrition Conference
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• 2004.11a
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• pp.150-157
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• 2004

Cruciferous vegetables are rich in organosulfur compounds such as isothiocyanates and sulfides. While the isothiocyanates, corresponding to pungent principle, are generated from myrosinase-catalyzed hydrolysis of glucosinolates, the sulfides can be generated non-enzymatically. Recent studies provide evidences that some sulfur compounds in these vegetables show a chemopreventive action against carcinogenesis; while isothiocyanates such as sulforaphane induce phase 2 enzymes (glutathione S-transferase/quinone reductase), disulfides tends to elevate the level of phase 1 and 2 enzymes. Especially, sulforaphane rich in Cruciferae vegetables has been reported to express anticarcinogenic effect in some organs such as liver, kidney or intestine. When the level of sulfur compounds in Cruciferous and Alliaceous vegetables was determined by GC/MS (SIM), the richest in sulforaphane is broccoli followed by turnip, cabbage, radish, kale, cauliflower and Chinese cabbage. Meanwhile, the sulfides are predominant in Alliaceous vegetables such as onion. In related study, the administration of vegetable extract elevated the GST level by 1.5 fold for broccoli, 1.4 fold for radish, and 1.3 for onion. Thus, the vegetables frequently used in Korean dish contain relatively high amount of anticarcinogenic sulfur compounds. Moreover, the combination of broccoli and radish extracts elevated the GST induction up to 1.84 folds of control. In addition, the Kakdugi, fermented radish Kimchi was observed to show a comparable GST induction despite the decomposition of methylthio-3-butenylisothiocyanate (MTBI). Therefore, the combination of vegetables including broccoli, and fermented radish Kimchi would be useful as a functional food for chemoprevention.

• Toxicological Research
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• v.30 no.2
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• pp.109-116
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• 2014

Glucosinolates (GLSs) are abundant in cruciferous vegetables and reported to have anti thyroidal effects. Four GLSs (sinigrin, progoitrin, glucoerucin, and glucotropaeolin) were administered orally to rats, and the breakdown products of GLSs (GLS-BPs: thiocyanate ions, cyanide ions, organic isothiocyanates, organic nitriles, and organic thiocyanates) were measured in serum. Thiocyanate ions were measured by colorimetric method, and cyanide ions were measured with CI-GC-MS. Organic isothiocyanates and their metabolites were measured with the cyclocondensation assay. Organic nitriles and organic thiocyanates were measured with EI-GC-MS. In all treatment groups except for progoitrin, thiocyanate ions were the highest among the five GLS-BPs. In the progoitrin treated group, a high concentration of organic isothiocyanates (goitrin) was detected. In the glucoerucin treated group, a relatively low amount of goitrogenic substances was observed. The metabolism to thiocyanate ions happened within five hours of the administration, and the distribution of GLSs varied with the side chain. GLSs with side chains that can form stable carbocation seemed to facilitate the degradation reaction and produce a large amount of goitrogenic thiocyanate ions. Because goitrogenic metabolites can be formed without myrosinase, the inactivation of myrosinase during cooking would have no effect on the anti-nutritional effect of GLSs in cruciferous vegetables.

• Bulletin of the Korean Chemical Society
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• v.33 no.1
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• pp.55-59
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• 2012

Treatments of organic isothiocyanates (R-NCS) with $NaN_3$ in the presence of pyridine in water at room temperature gave corresponding various organic tetrazole-thiones, [$S=CN_4(R)$] (R = alkyl or aryl). Isolated products are obtained as white or yellow solids in good yields (76-97%). The molecular structure by X-ray diffraction study for one of products shows the proposed formation. In addition, one-pot synthesis of 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles has been demonstrated. Addition of alkyl or aryl halides into the mixture of organic isothiocyanates, $NaN_3$, and pyridine in water at room temperature exclusively formed 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles (S-derivatives) in high yields.

• YAKHAK HOEJI
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• v.26 no.2
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• pp.91-96
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• 1982

In an attempt to design prodrugs for the Derivatives of the Isothiocyanates R-N=C=S were synthesized eleven novel bis-dithiocarbamates. The best way of preparing the dithiocarbamates was the formation of the dithiocarbonates followed by the reaction of the dithiocarbonates with amines. Thus, the treatment of the diols with carbon disulfide in the presense of potassium hydroxide afforded the potassium salts of the ditniocarbonic acids. The potassium salts were then reacted with alkyl halides to give the dithiocarbonates, which upon treatment with amines produces the dithiocarbamates. In case of vicinal diol (n=o in the above formula), only one of the hydroxy groups was reacted to give the mono-dithiocarbonate. The dithiocarbonates failed to react with amides and aromatic amines. Dithiocarbonates of the different types were obtained when the active double bonds, such as $CH_{2}=CH-Z$ , (Z are electron withdrawing groups), were allowed to react with the free dithiocarbonic acids produced in situ by carefully neutralizing the Potassium salts of the corresponding acids. These compounds are considered to be of some value as prodrugs for the active double bonds.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.231.2-231.2
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• 2003

One of the possible mechanisms of multi-drug resistance found in cancer cells is the over-expression of P-glycoprotein (P-gp). Studies have shown that compounds found in plants including vegetables and fruits not only have anticancer activities but may also modulate P-gp activity. The effect of flavonoids and organic isothiocyanates on P-gp activity was studied in human uterine sarcoma cell lines, MES-Sa (sensitive) and MES-SD/DX5 (resistant). The accumulation of daunomycin (DNM), a P-gp substrate, was approximately 10 times greater in the sensitive cell as compared to the resistant cells over the entire time course (up to 2 hrs). (omitted)