• Title/Summary/Keyword: isothiocyanates

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Evaluation of the Potential of Cancer Chemopreventive Activity Mediated by Inhibition of 12-O-tetradecanoly Phorbol 13-acetate-induced Ornithine Decarboxylase Activity

  • Lee, Sang-Kook;Pezzuto, John-M.
    • Archives of Pharmacal Research
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    • v.22 no.6
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    • pp.559-564
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    • 1999
  • In order to discover new cancer chemopreventive agents from natural or synthetic products, a structurally diverse class of chemopreventive agents was evaluated using in vitro biomarker of inhibition of 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity in cultured mouse epidermal 308 (ME)308 cells. As a results, apigenin, benzylisothiocyanate, curcumin, diallyl disulfide, N-(4-hydroxyphenyl)retinamide (4-HPR), menadione, miconazole, nordihydroguaiaretic acid (NDGA) and phenethyl isothiocyanate showed potent inhibitory effects in this process. A chemically diverse group of compounds was included in the evaluation, such as flavonoids, retinoids, isothiocyanates, sulfur-containing compounds and phenolic antioxidant compounds. These data are suggestive to understand the cancer chemopreventive potential mediated by these substances.

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GC-MS Analysis of the Extracts from Korean Cabbage (Brassica campestris L. ssp. pekinensis ) and Its Seed

  • Hong, Eunyoung;Kim, Gun-Hee
    • Preventive Nutrition and Food Science
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    • v.18 no.3
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    • pp.218-221
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    • 2013
  • Korean cabbage, a member of the Brassicaceae family which also includes cauliflower, mustard, radish, and turnip plants, is a crucial leafy vegetable crop. Korean cabbage is harvested after completion of the leaf heading process and is often prepared for use in "baechu kimchi", a traditional Korean food. Many of the components in Korean cabbage are essential for proper human nutrition; these components can be divided into two groups: primary metabolites, which include carbohydrates, amino acids, fatty acids, and organic acids, and secondary metabolites such as flavonoids, carotenoids, sterols, phenolic acids, alkaloids, and glucosinolates (GSLs). Using gas chromatography-mass spectrometry, this study examined the variety of volatile compounds (including isothiocyanates) contained in Korean cabbage and its seed, which resulted in the identification of 16 and 12 volatile compounds, respectively. The primary volatile compound found in the cabbage was ethyl linoleolate (~23%), while 4,5-epithiovaleronitrile (~46%) was the primary volatile component in the seed.

High Optical Anisotropy Nematic Single Compounds and Mixtures

  • Gauza, Sebastian;Kula, Przemyslaw;Dabrowski, Roman;Sasnouski, Genadz;Lapanik, Valeri
    • Transactions on Electrical and Electronic Materials
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    • v.13 no.1
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    • pp.2-5
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    • 2012
  • We have designed, synthesized, and evaluated the physical properties of some high birefringence (${\Delta}n$) isothiocyanato biphenyl-bistolane liquid crystals. These compounds exhibit ${\Delta}n^-$ 0.4-0.7 at room temperature and wavelength $\lambda$=633 nm. Laterally substituted short alkyl chains and fluorine atom eliminate smectic phase and lower the melting temperature. The moderate melting temperature and very high clearing temperature make those compounds attractive for eutectic mixture formulation. Several mixtures based on those compounds were formulated and its physical properties evaluated.

Synthesis and Cytotoxlcity of Thioureido MAPP Derivatives (치오우레이도 MAPP 유도체의 합성과 세포독성)

  • 전상철;김연숙;김미영;임채욱;임철부
    • YAKHAK HOEJI
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    • v.48 no.5
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    • pp.272-277
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    • 2004
  • The 2-amino-l-phenylpropanols 4∼7 were reacted with isothiocyanates to afford the 20 thioureido MAPP derivatives 8a∼11e, which were tested their cytotoxic activity by MTT assay. The cytotoxicity of alkylthioureido compounds were increased and decreased by alkyl chain length from $C_{8}$ to $C_{14}$ and of phenylthioureido compounds showed poor activity. The compounds (8b, 8c, 9b, 9c, l0b, 10c, 11b, 11c) with $C_{10}$ and $C_{12}$ alkyl chains gave stronger activity than reference compound B13. The $IC_{50}$/ of compound 8c was 1.05$\mu$M and 3 times stronger activity than B13. The stereochemistry of synthesized compounds affected very little to cytotoxic activity.

A Review of the Potency of Plant Extracts and Compounds from Key Families as an Alternative to Synthetic Nematicides: History, Efficacy, and Current Developments

  • Mwamula, Abraham Okki;Kabir, Md. Faisal;Lee, DongWoon
    • The Plant Pathology Journal
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    • v.38 no.2
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    • pp.53-77
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    • 2022
  • The global nematicides market is expected to continue growing. With an increasing demand for synthetic chemical-free organic foods, botanical nematicides are taking the lead as replacements. Consequently, in the recent years, there have been vigorous efforts towards identification of the active secondary metabolites from various plants. These include mostly glucosinolates and their hydrolysis products such as isothiocyanates; flavonoids, alkaloids, limonoids, quassinoids, saponins, and the more recently probed essential oils, among others. And despite their overwhelming potential, variabilities in quality, efficacy, potency and composition continue to persist, and commercialization of new botanical nematicides is still lagging. Herein, we have reviewed the history of botanical nematicides and regional progresses, the potency of the identified phytochemicals from the key important plant families, and deciphered some of the impediments involved in standardization of the active compounds in addition to the concerns over the safety of the purified compounds to non-target microbial communities.

Glucosinolate and isothiocyabate contents according to processing of Kimchi cabbage (Brassica rapa L. ssp. pekinensis) (배추의 가공에 따른 glucosinolates 및 isothiocyanates 함량 변화)

  • Jang, Miran;Kim, Gun-Hee
    • Food Science and Preservation
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    • v.24 no.3
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    • pp.367-373
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    • 2017
  • This study examined the total glucosinolate (GSL) and isothiocyanate (ITC) contents according to different processing conditions; fresh Kimchi cabbage (Brassica rapa L. ssp. pekinensis), salted Kimchi cabbage and kimchi (storage temperature $4^{\circ}C$ and $20^{\circ}C$) using two different cultivars (Bomatnorang and Chunkwang). Four GSL peaks representing gluconapin, glucobrassicanapin, glucobrassicin and 4-methoxyglucobrassicin were detected in Kimchi cabbage by HPLC and HPLC/MS analysis. The total GSL contents of fresh Kimchi cabbage of Bomatnorang and Chunkwang were $21.37{\pm}1.06{\mu}g/g$ dry weight (DW) and $20.96{\pm}3.33{\mu}g/g$ DW, respectively. After salting, the total GSL contents of salted Kimchi cabbage decreased by 39% and 52% in Bomatnorang and Chunkwang, respectively. Finally, the total GSL contents of kimchi after storage at $20^{\circ}C$ decreased by 83% and 56% in Bomatnorang and Chunkwang, respectively. The extracted ITC contents were analyzed by GC/MS. Three ITC peaks were detected in Kimchi cabbage representing 2-phenylethyl ITC, 3-butenyl ITC and 4-pentenyl ITC. The 2-phenylethyl ITC levels increased during the salting process but this generally fell during storage at $20^{\circ}C$ as kimchi. The 3-butenyl ITC levels of Kimchi cabbage according to processing decreased rapidly due to salting and then decreased slowly during storage as kimchi. The 4-pentenyl ITC of Kimchi cabbage was lost during the salting process. The results for the change in GSL and ITC contents during the kimchi making process will be used in the food industry.

Changes in Isothiocyanate Levels in Korean Chinese Cabbage Leaves during Kimchi Storage

  • Hong, Eun-Young;Kim, Gun-Hee
    • Food Science and Biotechnology
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    • v.15 no.5
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    • pp.688-693
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    • 2006
  • Glucosinolates are hydrolyzed by the enzyme myrosinase and are mainly found in cruciferous vegetables such as Chinese cabbage (Brassica campestris L. ssp. pekinensis). lsothiocyanates (ITCs) are glucosinolate degradation products with reported anticarcinogenic properties. Korean Chinese cabbage in the form of 'kimchi' is a staple part of the Korean diet. In this study, we examined the effects of storage temperature and duration on glucosinolate, ITC, soluble sugar, and organic acid levels in kimchi. Changes in pH and the impact of various parts of the Korean Chinese cabbage being used during the preparation of the dish were also assessed. Extracted ITC levels, analyzed via gas chromatography (GC) and GC/mass spectrometry (GC/MS), were higher in the midrib parts than in the cabbage leaves after storage at both 4 and $20^{\circ}C$. During storage, organic acid levels increased while soluble sugars were depleted. The pH initially increased (after 1 day at $20^{\circ}C$, and 1 week at $4^{\circ}C$), but subsequently decreased over time at both temperatures. Glucosinolate and ITC levels increased in the beginning of storage but then generally fell during further storage. Our data suggest that acidity-related reduction in myrosinase activity during storage may decrease glucosinolate and ITC levels. The changes in these levels depended on the storage conditions and the Korean Chinese cabbage parts used for the kimchi preparation.

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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Effects of Isothiocyanates on Antioxidant Response Element-mediated Gene Expression and Apoptosis

  • Hong Sung-Jae;Kim Sung-Min;Kim Young-Sook;Hu Rong;Kong A.N. Tony;Kim Bok-Ryang
    • Proceedings of the Korean Society of Food Science and Nutrition Conference
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    • 2004.11a
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    • pp.53-60
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    • 2004
  • The pro-apoptotic effect of phenethyl isothiocyanate (PEITC) and the role of glutathione (GSH) in sulforaphane (SFN)-induced antioxidant response element-dependent gene expression were investigated. The caspase-3 and caspase-9 activities were stimulated by PEITC. The release of cytochrome c was time- and dose- dependent. SP600125 suppressed apoptosis induced by PEITC. Similarly, this JNK inhibitor attenuated both cytochrome c release and caspase-3 activation induced by PEITC. SFN is converted to the glutathione conjugate by glutathione S-transferases (GSTs). It was accumulated in mammalian cells by up to several hundred-fold over the extracellular concentration, by conjugation with intracellular GSH. The induction of ARE by SFN was 8.6-fold higher than by SFN-NAC. The decrease in ARE expression at higher concentrations of SFN and SFN-NAC was correlated with the accelerated apoptotic cell death, with a dose-dependent activation of caspase 3 activity by SFN. Upon addition of extracellular GSH within 6 hr of treatment with SFN, the effect on ARE expression was blocked almost completely.

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Synthesis and Reactivity of Dinuclear Ni(II) Azido Complexes Containing Bithienylene or Terthienylene Bridging Ligands

  • Kim, Yong-Joo;Lee, Hyuck-Hee;Zheng, Zhen Nu;Lee, Soon-W.
    • Bulletin of the Korean Chemical Society
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    • v.32 no.9
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    • pp.3239-3244
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    • 2011
  • Dinuclear Ni(II)-thiophene halides, which contain linear bridging thienylenes, trans,trans-[$(PR_3)_2$(X)Ni-Y-Ni(X)$(PR_3)_2$] {X = Cl, Br; $H_2Y$ = 5,5'-dichloro-2,2'-bithiophene ($H_2bth$); $H_2tth$ = 5,5"-dichloro-2,2':5',2''-terthiophene ($H_2tth$)} were prepared by the oxidative addition of dihalobithiophene ($H_2bth$) or dihaloterthiophene ($H_2tth$) to [$Ni(COD)_2$] in the presence of tertiary phosphines. Subsequent reactions of $NaN_3$ with the dinuclear Ni(II)-thiophene chlorides gave the corresponding Ni(II)-azido complexes, trans,trans-[$(PR_3)_2(N_3)$Ni-Y-Ni$(N_3)(PR_3)_2$], whose reactivity toward trimethylsilyl pseudohalides such as trimethylsilyl isothiocyanates and cyanides was investigated. In addition, the reaction of trans-[$BrNi(PEt_3)_2-C_4H_2S-C_4H_2S$-CHO], a thienyl Ni(II) complex containing a terminal aldehyde group, with phosphonium ylide was examined.