• 제목/요약/키워드: isothiocyanates

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Cruciferous Vegetables: Dietary Phytochemicals for Cancer Prevention

  • Abdull Razis, Ahmad Faizal;Noor, Noramaliza Mohd
    • Asian Pacific Journal of Cancer Prevention
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    • 제14권3호
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    • pp.1565-1570
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    • 2013
  • Relationships between diet and health have attracted attention for centuries; but links between diet and cancer have been a focus only in recent decades. The consumption of diet-containing carcinogens, including polycyclic aromatic hydrocarbons and heterocyclic amines is most closely correlated with increasing cancer risk. Epidemiological evidence strongly suggests that consumption of dietary phytochemicals found in vegetables and fruit can decrease cancer incidence. Among the various vegetables, broccoli and other cruciferous species appear most closely associated with reduced cancer risk in organs such as the colorectum, lung, prostate and breast. The protecting effects against cancer risk have been attributed, at least partly, due to their comparatively high amounts of glucosinolates, which differentiate them from other vegetables. Glucosinolates, a class of sulphur-containing glycosides, present at substantial amounts in cruciferous vegetables, and their breakdown products such as the isothiocyanates, are believed to be responsible for their health benefits. However, the underlying mechanisms responsible for the chemopreventive effect of these compounds are likely to be manifold, possibly concerning very complex interactions, and thus difficult to fully understand. Therefore, this article provides a brief overview about the mechanism of such compounds involved in modulation of carcinogen metabolising enzyme systems.

Alyssin and Iberin in Cruciferous Vegetables Exert Anticancer Activity in HepG2 by Increasing Intracellular Reactive Oxygen Species and Tubulin Depolymerization

  • Pocasap, Piman;Weerapreeyakul, Natthida;Thumanu, Kanjana
    • Biomolecules & Therapeutics
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    • 제27권6호
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    • pp.540-552
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    • 2019
  • To determine the chemopreventive potential of alyssin and iberin, the in vitro anticancer activities and molecular targets of isothiocyanates (ITCs) were measured and compared to sulforaphane in hepatocellular carcinoma cell HepG2. The SR-FTIR spectra observed a similar pattern vis-a-vis the biomolecular alteration amongst the ITCs-treated cells suggesting a similar mode of action. All of the ITCs in this study cause cancer cell death through both apoptosis and necrosis in concentration dependent manner ($20-80{\mu}M$). We found no interactions of any of the ITCs studied with DNA. Notwithstanding, all of the ITCs studied increased intracellular reactive oxygen species (ROS) and suppressed tubulin polymerization, which led to cell-cycle arrest in the S and $G_2/M$ phase. Alyssin possessed the most potent anticancer ability; possibly due to its ability to increase intracellular ROS rather than tubulin depolymerization. Nevertheless, the structural influence of alkyl chain length on anticancer capabilities of ITCs remains inconclusive. The results of this study indicate an optional, potent ITC (viz., alyssin) because of its underlying mechanisms against hepatic cancer. As a consequence, further selection and development of effective chemotherapeutic ITCs is recommended.

한국산(韓國産) Horseradish 뿌리의 휘발성 풍미 성분 (Volatile Compounds Characterizing the Flavor of Korean Horseradish Roots)

  • 김인숙;이미순
    • Journal of Nutrition and Health
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    • 제18권4호
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    • pp.293-300
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    • 1985
  • Volatile components of Korean horseradish roots harvested at different dates were prepared by steam distillation. Samples were examined by gas chromatography (GC) and combined gas chromatography-mass spectrometry (GC-MS). The major pungent constituent, allyl isothiocyanate was confirmed add tended to increase with delayed harvest time. Pungent principles also included allyl thiocyanate, 2-phenethyl, 2-butyl, 4- pentenyl, benzyl and 3-methylthiopropyl isothiocyanates. Infrared (IR) spectroscopy study showed that allyl isothiocyanate - thiocyanate interconversion did not occur under the condition of this study.

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Reactions with Heterocyclic Amidines $(Vl)^1$: Synthesis of some new sym. and assym. pyrazolotriazines and pyrazolo[4,5-e]pyrimidine derivatives

  • Ali Elagamey, Abdel Ghani
    • Archives of Pharmacal Research
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    • 제10권3호
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    • pp.173-178
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    • 1987
  • Several new pyrazolo [1, 5-a]-S-triazine, pyrazolo [4, 5, -elpyrimidine, pyrazolo [1, 5-a] pyrimidine derivatives were synthesized via condensation of 3-antipyrinyl-5-amino-pyrazole (2) with $\beta$$-bifunctional reagents. The azo analogues of pyrazolo [1, 5-a] pyrimidines ; i. e. pyrazolo [5, 1, c]-as-triazine and pyrazolo[5, 1, -c]-as-benzotriazine were synthesized by coupling of diazotized 2-with agents containing active hydrogen.

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Synthetic Applications of Di-2-pyridyl Thionocarbonate As a Dehydration, a Dehydrosulfuriation, and a Thiocarbonyl Transfer Reagent

  • Kim, Sung-Gak;Yi, Kyu-Yang
    • Bulletin of the Korean Chemical Society
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    • 제8권6호
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    • pp.466-470
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    • 1987
  • Di-2-pyridyl thionocarbonate, prepared from thiophosgene and 2-hydroxypyridine in the presence of triethylamine in dichloromethane, was found to be very effective for dehydration, dehydrosulfurization, and thiocarbonyl transfer reactions. Di-2-pyridyl thionocarbonate was successfully for the esterification of carboxylic acids, dehydration of aldoximes into nitriles, preparation of isothiocyanates from amines, and preparation of cyclic thionocarbonates from 1,2- and 1,3-diols.

청갓 김치의 휘발성 성분과 발효 숙성시의 변화 (Volatile Compounds of Mustard Leaf (Brassica juncea) Kimchi and Their Changes during Fermentation)

  • 표영희;김정수;한영숙
    • 한국식품과학회지
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    • 제32권1호
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    • pp.56-61
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    • 2000
  • 청갓으로 만든 갓김치의 휘발성 화합물의 종류를 GC/FID와 GC/MSD를 사용하여 분리 동정하고, 발효 숙성 중 isothiocyanates와 그 유도체함량의 변화를 측정하였다. 청갓 김치의 수증기 증류물로부터 14종의 휘발성화합물을 분리, 동정하였으며 그 중 hexadecanoic acid를 비롯한 acid와 nitromethane등의 hydrocarbons류가 전체의 63%이상을 차지하였다. 갓의 특징적인 자극성 성분으로 알려진 isothiocyanates와 유도체들의 함량은 전체화합물의 30%로, 2-phenylethyl isothiocyanate가 주요성분이었고, 그밖에 benzothiazole 2-methylbenzothiazole, 2-(3H)-benzothiazolone 등이 동정되었다. 청갓 김치의 발효숙성 중 isothiocyanates와 그 유도체들의 상대적 함량 변화는 저장4일 이후부터 뚜렷하게 감소되었으며, 그 중 2-phenylethyl isothiocyanate경우 저장 7일째에 50%이상, 저장 14일째에는 80%이상 소실되는 것으로 나타났다.

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용매의 분획에 따른 겨자 물추출물의 항균성 (Antimicrobial Activities in the Water Extract of Mustard Seed Fractionated by Solvents)

  • 서권일;김홍출;심기환
    • 한국식품저장유통학회지
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    • 제4권3호
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    • pp.295-300
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    • 1997
  • The water extract of mustard seed was fractionated by solvents with an increase of polarity, and antimicrobial activities of each extracts were examined, and volatile compounds of each extract were identified by GC-MS. When the water extract was fractionated with solvents, the antimicrobial activities were high in the order of chloroform, ethylacetate, hexane, butanol and aqueous layer. In chloroform fraction, 16 volatile compounds, including 2 isothiocyanates such as 3-isothiocyanato- 1-propene and 4-isothiocyanato- 1-butane, 1 nitrile and 4 acids were identified, their contents were higher than other fractions. Twelve, 10, 4 and 7 volatile compounds were identified in ethylaceate, hexane, butanol and water fractions, respectively. The volatile compounds were considerably less in the fractions of butanol and water than others.

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EFFECTS OF AMMONIATION, IODINATION AND SUPPLEMENTATION OF AVOPARCIN ON THE NUTRITIONAL VALUE OF RAPESEED MEALS

  • Paik, I.K.;Chung, J.S.;An, M.S.;Um, J.S.;Namkung, H.
    • Asian-Australasian Journal of Animal Sciences
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    • 제4권1호
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    • pp.47-57
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    • 1991
  • Supplementation of iodine at the level of 3.5mg/kg reduced weight gain of the rats fed rapeseed oil meal (ROM) diets. Treatment of ROM with ammonia at the level of 2 or 4% tended to increase metabolizable energy value and availability of dry matter, crude protein and crude ash of ROM in the chicken. Potential goitrin level of ROM was reduced by ammoniation at 6% level, while the level of potential isothiocyanates was increased by ammoniation. Treatment of ROM with ammonia at the level of 3% and above reduced weight gain of the chickens fed treated ROMs. Weight of thyroid glands of the birds increased as the level of ammoniation of ROM increased. Supplementation of Avoparcin to the diets containing ROM improved weight gain and dressing percentage of the broiler chickens.

채소류의 기능성 (Bioactive Compounds in Vegetables: Their Role in the Prevention of Disease)

  • 이영은
    • 한국식품조리과학회지
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    • 제21권3호
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    • pp.380-398
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    • 2005
  • There are various bioactive compounds in vegetables which are called 'phytochemicals' They are extranutritional constituents that typically occur in small quantities. They are being intensively studied to evaluate their effects on health. These biologically active compounds vary widely in chemical structure and function and are grouped accordingly, carotenoids, flavonoids, isothiocyanates, allyl compounds, indoles, isoflavones and saponins, etc. Traditionally used vegetables are defined, and their trivial names, biological functions and traditional and oriental medicinal effects are investigated in this study. Much scientific research needs to be conducted before we can begin to make science-based dietary recommendations. Despite this, there is sufficient evidence to recommend consuming vegetables rich in bioactive compounds, especially for the prevention of cancer.

Thiocarbamyl Enoxacin 유도체의 합성 및 항균작용 (Synthesis and Antimicrobial Activities of Thiocarbamyl Enoxacin Derivatives)

  • 신화우;고무수;정동훈;최광식;임철부
    • 약학회지
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    • 제35권5호
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    • pp.353-359
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    • 1991
  • Treatment of 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(l-piperazinyl)-I, 8- naphthyridine-3-ca rboxylic acid (Enoxacin) with alkyl(or aryl) isothiocyanates which obtained from alkyl(or aryl) amines afforded six 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(1-alkylthiocarbamylpiperazinyl)-1, 8- naphthyridine-3-carboxylic acids and five 1-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(l-arylthiocarbamyl piperazinyl)-1, 8-naphthyridine-3-carboxylic acids. The compounds synthesized were evaluated for their antimicrobial activities, in vitro, against Escherichia coli 6-PE-4, Bacillus subtilis 74-51, Proteus vulgaris 78645, Klebsiella pneumoniae JYA-78314, Staphylococcus aureus 79110 and Pseudomonas aeruginosa 8765-1 P$_{2}$.

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