• Title/Summary/Keyword: 3-butenyl isothiocyanate

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Purification of 4-Methylthio-3-butenyl isothiocyanate the Pungent Principle in Radish Roots by RP-HPLC (RP-HPLC법에 의한 무우의 매운 성분인 4-methylthio-3-butenyl isothiocyanate의 분리 및 정제)

  • Kim, Mee-Ree;Rhee, Hei-Soo
    • Korean journal of food and cookery science
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    • v.2 no.2
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    • pp.16-20
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    • 1986
  • The major pungent component from Korean radish roots was purified by reverse phase high performance liquid chromatography (RPHPLC), and characterized as 4-methylthio-3-butenyl isothiocyanate on the basis of the sensory test (pungency), UV spectrum and mass spectrum analysis. The purified isothiocyanate moved as a single peak(retention time, 5.2 min) in RP-HPLC analysis, and as a single spot(Rf, 0.9) in TLC analysis.

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Volatile Sulfur Components from Fresh Radishes of Korean Origin (한국산 무우의 휘발성 함유황화합물에 관하여)

  • Kim, Mee-Ree;Rhee, Hei-Soo
    • Korean journal of food and cookery science
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    • v.1 no.1
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    • pp.33-39
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    • 1985
  • The volatile sulfur components from two varieties of radishes ('Taeback' and 'Altali'), obtained by steam distillation and solvent ($CCl_4$) extraction, were isolated and charac-terized by GC/MS analysis. The GC profile of the volatile sulfur com-pounds in the steam distillates from two types of radishes was quite similar. 4-Me-thylpentyl, 3-methylthiopropyl, 4-methylthio-3-butenyl, 4-methylthiobutyl and 5-methyl-thiopentyl isothiocyanates, 5-methylthio-4-pentenenitrile, 1-methylthio-3-pentanone, and dimethyl sulfides were commonly identified. In the $CCl_4$ extract, 4-methylsulfinyl-3-bu-tenyl isothiocyanate was obtained as another major constituent. Whereas 4-methylthiobutyl isothiocyanate was found to be a predominent component in the steam distillate, 4-methylthio-3-butenyl isothiocyananate was a major one in the $C1_4$ extract.

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Changes in 3-Butenyl Isothiocyanate and Total Glucosinolates of Seeds and Young Seedlings during Growth of Korean Chinese Cabbages (배추 종자 및 어린 싹의 성장 시기에 따른 3-butenyl isothiocyanate 및 total glucosinolates 함량 변화)

  • 김연경;김건희
    • Food Science and Preservation
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    • v.10 no.3
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    • pp.365-369
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    • 2003
  • The main objective of this study was to investigate the pattern of glucosinolates, in terms of 3-butenyl isothiocyanate, and total glucosinolates, in different parts of young seedlings and seeds in Korean Chinese cabbages. For determination of glucosinolates, 55 days and Winter pride cultivars of Korean Chinese cabbages seeds and different parts of 1, 3, 5, and 7-day-old seedlings were used for analytical sample preparation provided with an anion exchanges column, and measured by GC and UV-visible Spectrophotometer. The concentration of 3-butenyl ITC was higher in the cotyledon and the hypocotyl parts of 55 days cultivar seedling than those of Winter Pride cultivar. In the cotyledon parts of Winter pride cultivar seedling, 3-butenyl ITC amount was increase to 3-day-old seedling and then reduced. The cotyledon of 55 days cultivar contained the highest concentration of total glucosinolates while those were increased in the hypocotyl and decreased in the root. The level of total glucosinolates was increased to 5-day-old seedling and then decreased in the cotyledon and the hypocotyl parts of seedling in Winter pride cultivar. There was no significant difference of total glucosinolates in the root part. In the seeds, 55 days cultivar concentration was higher than Winter pride cultivar both of 3-butenyl ITC and total glucosinolates. In our study, the levels of 3-butenyl ITC and total glucosinolates depended on cultivars, growth stages, and parts in Korean Chinese cabbage.

Isolation and Identification of Bioactive Organosulfur Phytochemicals from Solvent Extract of Broccoli (브로콜리 용매추출물의 Bioactive Organosulfur 화합물의 분리 및 동정)

  • 석대은;김진희;김미리
    • 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.

Determination of 3-Butenyl Isothiocyanate in Different Parts and Cultivars of Chinese Cabbages

  • Kim, Youn-Kyung;Kim, Gun-Hee
    • Food Science and Biotechnology
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    • v.14 no.4
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    • pp.466-469
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    • 2005
  • Chinese cabbage (Brassica campestris L. Pekinensis) is Brassica vegetable that contains high amounts of glucosinolates. Glucosinolates and their breakdown products are thought to contribute to health promotion by preventing some cancers. Chinese cabbage is the most commonly consumed vegetable in Asian countries including Korea. In this study, qualitative and quantitative analyses of 3-butenyl glucosinolate (Gluconapin) from different cultivars and different parts of the cabbage were performed. Gluconapin of Chinese cabbage was extracted by hot ethanol ($80^{\circ}C$), isolated by an anion exchange column and identified by GC/MS and LC/MS. The levels of glucosinolates in Chinese cabbage varied according to the different parts, cultivars, and blanching time. In general, the concentrations of 3-butenyl isothiocyanate (ITC) were higher in the leaf than in the midribs parts. The cultivar 'Bulam no. 3' had a much greater content of 3-butenyl ITC than the cultivar 'Garak no. 1,' and the levels of butenyl ITC were highest after two weeks of storage. Blanching treatment decreased the concentration of 3-butenyl ITC. The ITC concentration varied extensively among different crops of the same species, and according to the different parts on the cabbage, the storage duration and the boiling time.

Analysis of Isothiocyanates in Dolsan Leaf Mustard(Brassica juncea) (돌산갓의 Isothiocyanate류의 분석)

  • Cho, Young-Sook;Park, Seok-Kyu;Chun, Soon-Sil;Park, Jeong-Ro
    • 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.

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Glucosinolates (3-Butenyl Isothiocyanate, Total Glucosinolates) Change in Seeds and Young Seedlings on Chinese Cabbages

  • Kim, Youn-Kyung;Hong, Eun-Young;Kim, Gun-Hee
    • Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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    • 2003.04a
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    • pp.97.2-98
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    • 2003
  • The main objective of this study was to investigate the patterns of glucosinolates (3-butenyl isothiocyanate, total glucosinolates) in different parts of young seedling and seeds on Korean Chinese cabbages 55 days and Winter pride cultivars. For determination of glucosinolates, two cultivars of Chinese cabbages seeds and different parts of 1-day-old, 3-day-old, 5-day-old, and 7-day-old seedlings were used for analytical sample preparation provided with an anion exchanges column, and measured by GC and UV-Visible Spectrophotometer. 3-Butenyl ITC concentration was the highest in the cotyledon and the hypocotyl parts of 55 days cultivar seedling. In the cotyledon part of Winter pride cultivar seedling, 3-butenyl ITC amount was increase to 3-day-old seedling and then reduced. The cotyledon of 55 days cultivar contained the highest concentration of total glucosinolates while those were increased in the hypocotyl and decreased by degrees in the root. Total glucosinolates amounts were increased to 5-day-old seedling and then decreased in the cotyledon and the hypocotyl parts of seedling on Winter pride cultivar. There was no significant difference in the root part. In the seeds, both of 3-butenyl ITC and total glucosinolates, 55 days cultivar concentration was higher than Winter pride cultivar. The study has shown the variability in 3-butenyl ITC and total glucosinolates concentrations among cultivars, growth stages, and parts.

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Quantitative Determination of 4-methylthio-3-butenyl isothiocyanate in Radish Root by RP-HPLC (RP-HPLC법에 의한 무우의 4-methylthio-3-butenyl isothiocyanate의 정량)

  • Kim, Mee-Ree;Rhee, Hei-Soo
    • Korean Journal of Food Science and Technology
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    • v.18 no.6
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    • pp.475-478
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    • 1986
  • RP-HPLC (Reverse phase-high performance liquid chromatography) assay which was introduced to measure quantitatively the amount of 4-methylthio-3-butenyl isothiocyanate in the radish root, proved to be convenient, accurate and reproducible, showing a good linearity between 10 n moles/ml and 120 n moles/ml (r=0.9997). The results of this assay showed that while the isohtiocyanate was hydrolyzed slowly in the basic medium, it decomposed rapidly in the acidic aqueous medium. On the other hand, the isothiocyanate was relatively stable in the organic solvent (65% acetonitrile). Also, it was found that intact root of Korean radish contain 210-420 ${\mu}moles/100g$, based on the measurement with radish homogenate (pH 8.5, 1 min).

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Mitochondria-mediated Apoptosis in Human Lung Cancer A549 Cells by 4-Methylsulfinyl-3-butenyl Isothiocyanate from Radish Seeds

  • Wang, Nan;Wang, Wei;Huo, Po;Liu, Cai-Qin;Jin, Jian-Chang;Shen, Lian-Qing
    • Asian Pacific Journal of Cancer Prevention
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    • v.15 no.5
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    • pp.2133-2139
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    • 2014
  • 4-Methylsulfinyl-3-butenyl isothiocyanate (MTBITC) found in the radish (Raphanus sativus L.), is a wellknown anticancer agent. In this study, the mechanisms of the MTBITC induction of cell apoptosis in human A549 lung cancer cells were investigated. Our PI staining results showed that MTBITC treatment significantly increased the apoptotic sub-G1 fraction in a dose-dependent manner. The mechanism of apoptosis induced by MTBITC was investigated by testing the change of mitochondrial membrane potential (${\Delta}{\Psi}m$), the expression of mRNAs of apoptosis-related genes by RT-PCR, and the activities of caspase-3 and -9 by caspase colorimetric assay. MTBITC treatment decreased mitochondrial membrane potential by down-regulating the rate of Bcl-2/Bax and Bcl-xL/Bax, and activation of caspase-3 and -9. Therefore, mitochondrial pathway and Bcl-2 gene family could be involved in the mechanisms of A549 cell apoptosis induced by MTBITC.

Changes in the Factors Associated with Decrease of Pungency in ‘Kagdugi’ during Fermentation (깍두기 숙성중 매운맛 감소에 관련된 인자들의 변화)

  • Kim, Mee-Ree;Rhee, Hei-Soo
    • Korean Journal of Food Science and Technology
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    • v.24 no.4
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    • pp.361-366
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    • 1992
  • Studies were carried out on the factors responsible for the change of pungency in 'Kagdugi'. During fermentation, the pH in 'Kagdugi' decreased to around to 4, while acidity increased continuously. In accordance with the decrease of pungency, the content of 4-methylthio-3-butenyl isothiocyanate (MTB-NCS) in the homogenate of 'Kagdugi' decreased gradually and on 3rd day, the optimum period for good flavor, below 5% of that in the homogenate of fresh radish. The decrease of MTB-NCS formation was accompanied by the gradual loss of 4-methylthio-3-butenyl glucosinolate (MTB-glucosinolate), which was found to disappear more rapidly than total glucosinolate. Also, the ascorbic acid-dependent myrosinase activity was observed to decline gradually with the fermentation time, although the ascorbic acid content varied above the concentration required for maximal enzyme activity. Thus, it was suggested that the decline of MTB-NCS may be related to the gradual losses of MTB-glucosinolate content and myrosinase activity which are both susceptible to the effect of acidic pH.

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