• Bulletin of the Korean Chemical Society
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• 제16권6호
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• pp.528-533
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• 1995

Metallic iridium and rhodium powders prepared from the reactions of [M(COD)(PhCN)2]ClO4 (M=Ir(1), Rh(2); COD=1,5-cyclooctadiene) with hydrogen at room temperature in methylene chloride show catalytic activities for hydrogenation of arenes at room temperature under atmospheric pressure of hydrogen. Most substituents (CH3, COOH, NO2, CH2OH, CHO, OPh, OCH3, C=C, halogens and CH2Cl) on aromatic ring suppress the rate of the hydrogenation of the aromatic ring while the aromatic ring hydrogenation of phenol and 1,4-dihydroxobenzene is faster than that of benzene over these metallic powders. Hydrogenation of benzoic acid occurs only at the aromatic ring leaving the COOH group intact over iridium metal powders while benzoic acid is not hydrogenated at all over rhodium metal powders. Carbonyl, nitro, acetylenic and olefinic groups on an aromatic ring are hydrogenated prior to the aromatic ring hydrogenation. Hydrogenolysis of OH groups of phenol, benzyl alcohol and 1,4-dihydroxobenzene, and hydrodehalogenation of halobenzenes, benzyl halides and cinnamyl chloride also occur along with the hydrogenation of aromatic ring.

• Food Science and Biotechnology
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• 제16권2호
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• pp.218-222
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• 2007

The anticoagulant properties of Cinnamomum cassia bark-derived materials were evaluated against platelet aggregation induced by arachidonic acid (AA), collagen, platelet activating factor (PAF), or thrombin, and these effects were then compared to those of three commercially available compounds (cinnamic acid, cinnamyl alcohol, and aspirin). The active constituent obtained from C. cassia barks was isolated by silica gel column chromatography and high pressure liquid chromatography (HPLC), and was characterized as trans-cinnamaldehyde by MS, $^1H-NMR$, $^{13}C-NMR$, and IR spectroscopy. With regard to 50% inhibitory concentration ($IC_{50}$) values, cinnamaldehyde was found to effectively inhibit platelet aggregation induced by AA ($IC_{50},\;43.2\;{\mu}M$) and collagen ($IC_{50},\;3.1\;{\mu}M$). By way of comparison, cinnamaldehyde proved to be a significantly more potent platelet inhibitor against platelet aggregation induced by collagen than aspirin. The effect exerted by cinnamaldehyde against platelet aggregation induced by AA was 1.2 times less than that of aspirin. These results indicate that cinnamaldehyde may prove useful as a lead compound for the inhibition of platelet aggregation induced by AA and collagen.

• 생약학회지
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• 제38권4호
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• pp.403-408
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• 2007

xBrassicoraphanus is an intergenic breed crossed between Brassica campetris L. ssp. pekinensis and Raphanus sativus L. that have been daily consumed. xBrassicoraphanus was known to have good tastes and biological activities. Nevertheless, its constituetnts were not elucidated yet. Thus, in the present study, to indirectly evaluate the biological activity of xBrassicoraphanus, 12 compounds were isolated from leaves and roots of xBrassicoraphanus. On the basis of spectroscopic evidences, the structures of these compounds isolated from leaves of xBrassicoraphanus. were identified as ${\beta}-sitosterol$, indole-3-acetonitrile, ferulic acid, methyl ferulate, linolenic acid methyl ester, linolenic acid and coniferyl alcohol, while the chemical structures of compounds isolated from the roots of were xBrassicoraphanus were characterized as ${\beta}-sitosterol$, indole-3-acetonitrile, ferulic acid, methyl ferulate, linolenic acid methyl ester, 1-methoxyindole-3-acetonitrile, goitrin, 4-hydroxycinnamyl alcohol, coniferyl alcohol, palmitic acid and daucosterol. These can be classified as three steroids, two indole cyanides, two cinnamic acid derivatives, one cinnamyl alcohol derivative, three fatty acid derivatives one isothiocyanate. These results suggest that the compounds isolated from xBrassicoraphanus were almost identical with known components of Brassica campetris L. ssp pekinensis or Raphanus sativus L. However, it is necessary to investigate more about the difference of amounts of constituents according to harvest time and variant species amounts.

• Journal of the Korean Wood Science and Technology
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• 제49권1호
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• pp.23-43
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• 2021

본 연구에서는 국내 자생식물 7종의 정유 중 우수한 항산화 효과가 있는 온주밀감, 육계나무 정유 2종을 선별하였고, 피부염을 유발하는 Candida albicans에 대한 항미생물 활성 평가를 통해 식물정유의 항미생물 활성성분을 구명하고자 하였다. 1,1-diphenyl-2-picrylhydrazyl (DPPH) 라디칼 소거활성 측정 결과 SC50값이 온주밀감 정유 0.010 mg/mL, 육계나무 정유 0.09 mg/mL을 나타냈으며, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) 라디칼 소거활성 측정 결과 온주밀감 정유 0.09 mg/mL, 육계나무 정유 0.06 mg/mL로 높은 항산화 활성을 나타냈다. Minimum Inhibitory Concentration는 육계나무 정유 1.25 mg/mL, 온주밀감 정유 5 mg/mL 값으로 육계나무 정유에서 뛰어난 항미생물 활성이 나타났다. Thin layer chromatography (TLC) bioassay를 통해 2종 정유의 성분 분획에 따른 C. albicans에 대한 항미생물 활성을 평가하였고, preparative TLC (prep. TLC)를 통해 활성분획을 획득하고, 동일 Rf값을 가지는 성분들에 대해서 GC/MS 분석을 수행하여 항미생물 활성성분을 구명하였다. 그 결과 항산화 및 항미생물 활성을 나타내는 주성분은 각각 육계나무 정유의 경우 cinnamyl acetate, eucalyptol, linalool, citral 온주밀감 정유의 경우 linalool이었다. 2종 정유에 공통적으로 항산화 및 항미생물 활성을 나타낸 분획부 성분분석 결과 linalool은 항산화, cinnamyl acetate, eucalyptol, citral, geranyl acetate은 항산화와 항미생물 능력이 있다고 사료된다.

• 한국식품과학회지
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• 제41권5호
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• pp.503-508
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• 2009

전주의 음식점 12곳에서 판매되는 모주를 수집하여 제조방법과 알코올 함량, pH, 산도, 고형분 함량, 환원당, 자외부흡수, 유기산 및 유리당 등의 이화학적 특성, 색도, 점도 등의 물리적 특성 그리고 휘발성 화합물 성분을 비교 분석하였다. 원주 막걸리 이외에 감초, 인삼, 당귀, 계피 등의 한약재와 설탕 등을 첨가하여 40분-6시간 끓여 제조한 자가 모주의 알코올 함량은 2.1%이하로 나타났고 pH는 3.85-4.38의 수준을 보였고 총산, 고형분 함량 그리고 자외부 흡수는 모주 제조 시 첨가하는 부재료에 따라 각각 다른 값을 나타내었으며 환원당은 일반 탁주에 비하여 월등히 높은 함량을 보였다. 유기산 중 malic acid와 lactic acid는 다른 4종의 유기산에 비하여 높게 나타났으며 유리당은 maltose>glucose>fructose의 순으로 나타났다. 색도는 전체적으로 명도값이 낮고 황색도 값이 높아 탁하고 황색을 많이 띄는 것을 알 수 있었으며 제조 시 가열 공정을 거쳐 일반 탁주에 비하여 걸쭉한 상태를 나타내었다. GC와 GC/MSD를 사용한 휘발성 화합물 성분 분석 결과 검출된 30개의 휘발성 향기 성분 중 alcohol은 3종, ester는 12종, hydrocarbon은 7종 그리고 aldehyde는 4종이 동정되었다. Alcohol 중 isoamyl alcohol에 비하여 benzeneethanol의 면적 비율이 높았으며, 원주인 막걸리로부터 기인한 것으로 사료되는 ester 중 ethyl caprate, ethyl palmitate 그리고 ethyl linoleate도 높은 면적 비율을 나타내었다. 동정된 7개의 hydrocarbon 중 모주의 종류에 관계없이 (E)-cinnamaldehyde가 가장 높게 나타났는데 검출된 (E)-cinnamyl acetate와 함께 자가 모주 제조 공통적으로 첨가하는 계피에서 기인한 것으로 사료된다.

• 식품기술
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• 제12권4호
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• pp.28-35
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• 1999

밀원식물을 달리하여 채집된 두 종류의 국내산 propolis의 향기성분을 Aroma Scan과 GC/MS로 분석하였다. Aroma Scan으로 아까시나무와 밤나무 유래의 두 propolis는 서로 다른 향기를 지닌것을 확인하였다. GC/MS로 분석한 propolis의 향기 성분은 아까시나무 유래 propolis의 44종과 밤나무 유래 propolis의 47종을 포함한 총 55종이 검출되었다. Aldehydes 5종, alcohols 8종, ketones 5종, esters 3종, fatty acid 1종을 비롯하여 27종의 hydrocarbons과 2종의 terpenes 및 4종의 phenolic derivatives가 검출되었다. Benzaldehyde, cinnamyl alcohol, dudesmol 및 benzylbenzoate 등을 포함한 36종의 화합물은 두시료에서 공통적으로 검출되었고, geraniol과 n-undecane을 포함한 8종의 성분은 아까시나무 유래의 propolis에서만 확인되었으며, piperitenone과 valencene을 포함한 11종의 화합물은 밤나무 유래의 propolis에서만 검출되어 밀원식물에 따라 향기성분에 차이가 있는 것으로 나타났다.

• Journal of Microbiology and Biotechnology
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• 제14권6호
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• pp.1176-1181
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• 2004

The cytotoxic activities of Cinnamomum cassia (Blume) bark-derived materials toward six human HeLa epithelioid cervix, A549 lung, SK-OV-3 ovarian, SK-MEL-2 melanoma, XF-498 central nerve system, and HCT-15 colon tumor cell lines were evaluated by using sulforhodamine B assay and compared to those of the anticancer agents, cisplatin and mitomycin C. The biologically active constituent of the Cinnamomum bark was characterized as trans­cinnamaldehyde by spectroscopic analysis. The cytotoxic activity of cinnamaldehyde against HeLa, SK-MEL-2, and HCT -15 cell lines was comparable to that of cisplatin and mitomycin C. The compound showed lower activity against A549, SK-OV-3, and XF-498 cell lines than the anticancer agents. Eugenol exhibited moderate activity against SK-OV­3, XF-498, and HCT-15 tumor cells, and trans-cinnamic acid, cinnamyl alcohol, $\alpha-pinene,\;and\;\beta-pinene$ showed little or no activity against model tumor cells. Cinnamaldehyde was not mutagenic against four strains (TA 98, TA 100, TA 1535, and TA 1537) of Salmonella typhimurium (Castel and Chalm). These results indicate at least one pharmacological action of C. cassia.

• Archives of Pharmacal Research
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• 제21권2호
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• pp.147-152
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• 1998

Cinnamaldehydes and related compounds were synthesized from various cinnamic acids based on the $2^{I}$-hydroxycinnamaidehyde isolated from the bark of Cinnamomum cassia Blume. The cytotoxicity to human solid tumor cells such as A549, SK-OV-3, SK-MEL-2, XF498 and HCT15 were measured. Cinnamic acid, cinnamates and cinnamyl alcohols did not show any cytotoxicity against the human tumor cells. Cinnamaldehydes and realted compounds were resistant to A549 cell line up to 15 .mu.g/ml. In contrast, HCT15 and SK-MEL-2 cells were much sensitive to these cinnamaidehyde analogues which showed $ED{50} values 0.63-8.1{\mu}g/ml.$Cytotoxicity of the saturated aldehydes was much weak compared to their unsaturated aldehydes. From these studies, it was found that the key functional group of the cinnamaldehyde-related compounds in the antitumor activity is the propenal group.p.

• Bulletin of the Korean Chemical Society
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• 제18권3호
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• pp.274-280
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• 1997

The rates and stoichiometry of the reaction of gallane-trimethylamine with selected organic compounds containing representative functional groups were examined in tetrahydrofuran solution under standardized conditions (THF, 0 ℃). And its reducing characteristics were compared with those of aluminum hydride-triethylamine(AHTEA). The rate of hydrogen evolution from active hydrogen compounds varied considerably with the nature of the functional group and the structure of the hydrocarbon moiety. Alcohols, phenol, amines, thiols evolved hydrogen rapidly and quantitatively. Aldehydes and ketones were reduced moderately to the corresponding alcohols. Cinnamaldehyde was reduced to cinnamyl alcohol, which means that the conjugated double bond was not attacked by gallane-trimethylamine. Carboxylic acids, esters, and lactones were stable to the reagent under standard conditions. Acid chlorides also were rapidly reduced to the corresponding alcohols. Epoxides and halides were inert to the reagent. Caproamide and nitrile were stable to the reagent, whereas benzamide was rapidly reduced to benzylamine. Nitropropane, nitrobenzene and azoxybenzene were stable to the reagent, whereas azobenzene was reduced to 1,2-diphenylhydrazine. Oximes and pyridine N-oxide were reduced rapidly. Di-n-butyl disulfide and dimethyl sulfoxide were reduced only slowly, but diphenyl disulfide was reduced rapidly. Finally, sulfones and sulfonic acids were inert to the reagent under the reaction.

• Bulletin of the Korean Chemical Society
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• 제13권5호
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• pp.531-537
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• 1992

The approximate rates and stoichiometry of the reaction of excess potassium 2-thexyl-1,3,2-dioxaborinane hydride(KTDBNH) with 55 selected compounds containing representative functional groups under standardized conditions (tetrahydrofuran, TEX>$0^{\circ}C$, reagent : compound=4 : 1) was examined in order to define the characteristics of the reagent for selective reductions. Benzyl alcohol and phenol evolve hydrogen immediately. However, primary, secondary and tertiary alcohols evolve hydrogen slowly, and the rate of hydrogen evolution is in order of $1^{\circ}$> $2^{\circ}$> $3^{\circ}$. n-Hexylamine is inert toward the reagent, whereas the thiols examined evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to give the corresponding alcohols. Cinnamaldehyde is rapidly reduced to cinnamyl alcohol, and further reduction is slow under these conditions. The reaction with p-benzoquinone dose not show a clean reduction, but anthraquinone is cleanly reduced to 9,10-dihydro-9,10-anthracenediol. Carboxylic acids liberate hydrogen immediately, further reduction is very slow. Cyclic anhydrides slowly consume 2 equiv of hydride, corresponding to reduction to the caboxylic acid and alcohol stages. Acid chlorides, esters, and lactones are rapidly and quantitatively reduced to the corresponding carbinols. Epoxides consume 1 equiv hydride slowly. Primary amides evolve 1 equiv of hydrogen readily, but further reduction is slow. Tertiary amides are also reduced slowly. Both aliphatic and aromatic nitriles consume 1 equiv of hydride rapidly, but further hydride uptake is slow. Analysis of the reaction mixture with 2,4-dinitrophenylhydrazine yields 64% of caproaldehyde and 87% of benzaldehyde, respectively. 1-Nitropropane utilizes 2 equiv of hydride, one for hydrogen evolution and the other for reduction. Other nitrogen compounds examined are also reduced slowly. Cyclohexanone oxime undergoes slow reduction to N-cyclohexylhydroxyamine. Pyridine ring is slowly attacked. Disulfides examined are reduced readily to the correponding thiols with rapid evolution of 1 equiv hydrogen. Dimethyl sulfoxide is reduced slowly to dimethyl sulfide, whereas the reduction of diphenyl sulfone is very slow. Sulfonic acids only liberate hydrogen quantitatively without any reduction. Finally, cyclohexyl tosylate is inert to this reagent. Consequently, potassium 2-thexyl-1,3,2-dioxaborinane hydride, a monoalkyldialkoxyborohydride, shows a unique reducing characteristics. The reducing power of this reagent exists somewhere between trialkylborohydrides and trialkoxyborohydride. Therefore, the reagent should find a useful application in organic synthesis, especially in the field of selective reduction.