• 한국균학회지
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• 제26권4호통권87호
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• pp.525-530
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• 1998

Cinnamaldehyde 유도체의 항진균활성을 조사한 결과 ${\alpha}-chlorocinnamadehyde$가 가장 항균활성이 우수한 것으로 평가되었다. ${\alpha}-Chlorocinnamaldehyde$는 피부진균증의 원인균주인 Tricophyton mentagrophytes, Microsporium gypseum, Epidermophyton floccosum, Cryptococcus neoformans, Aspergillus niger, Candida albicans와 Penicillium avellaneum에 대해 $9.8{\sim}19.5\;{\mu}g/ml$의 최소저지농도를 보였으나 시판중인 항진균제 clotrimzole보다는 역가가 낮은 것으로 나타났다. ${\alpha}-Chlorocinnamaldehyde$를 제외한 나머지 관련 유도체를 비교한 결과 phenyl기 주위의 유도체 화합물에서는 우수한 항균활성이 관찰되지 않았으며, acrolein기가 항균활성에 중요한 관능기로 작용하는 것으로 나타났다.

• 약학회지
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• 제45권5호
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• pp.431-436
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• 2001

Antifungal activities of trans-cinnamaldehyde (CA) derivatives including commercial CA derivatives as well as synthesized CA derivatives against various human pathogenic fungi were investigated. Among the derivatives tested, -chlorocinnamaldehyde, $\alpha$-bromocinnamaldehyde and 7-phenyl-2,4,6-heptatrienal were more potent than CA in antifungal activity, $\alpha$-Bromocinnamaldehyde was the most effective in inhibiting the growth of representative fungi of dermatomycosis with minimum inhibitory cocentration(MIC) of 0.61~9.76$\mu\textrm{g}$/ml . In the structure-activity relationship, introduction of the chlorine and bromine group into the C-2 of CA resulted in the decrease of MIC. Derivative with more double bonds exhibited the increase of antifungal activity against various pathogenic fungi.

• Archives of Pharmacal Research
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• 제15권3호
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• pp.239-241
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• 1992

The methanol extract of Cinnamoni Cortex showed antibacterial action against cariogenic bacterium, Streptococcus mutans OMZ 176. The active principle of the extract was identified to be trans-cinnamaldehyde, which was bactericidal in the minimal inhibitory concentration (MIC) of $100\;\mu$g/ml against the strain. From the results of antibacterial activity of cinnamaldehyde and its derivatives, the acrolein group in the cinnamaldehyde was elucidated to be an essential element for the activity.

• Biomolecules & Therapeutics
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• 제25권3호
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• pp.279-287
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• 2017

The chemical property of cinnamaldehyde is unstable in vivo, although early experiments have shown its obvious therapeutic effects on viral myocarditis (VMC). To overcome this problem, we used cinnamaldehyde as a leading compound to synthesize derivatives. Five derivatives of cinnamaldehyde were synthesized: 4-methylcinnamaldehyde (1), 4-chlorocinnamaldehyde (2), 4-methoxycinnamaldehyde (3), ${\alpha}$-bromo-4-methylcinnamaldehyde (4), and ${\alpha}$-bromo-4-chlorocinnamaldehyde (5). Neonatal rat cardiomyocytes and HeLa cells infected by coxsackievirus B3 (CVB3) were used to evaluate their antiviral and cytotoxic effects. In vivo BALB/c mice were infected with CVB3 for establishing VMC models. Among the derivatives, compound 4 and 5 inhibited the CVB3 in HeLa cells with the half-maximal inhibitory concentrations values of $11.38{\pm}2.22{\mu}M$ and $2.12{\pm}0.37{\mu}M$, respectively. The 50% toxic concentrations of compound 4 and 5-treated cells were 39-fold and 87-fold higher than in the cinnamaldehyde group. Compound 4 and 5 effectively reduced the viral titers and cardiac pathological changes in a dose-dependent manner. In addition, compound 4 and 5 significantly inhibited the secretion, mRNA and protein expressions of inflammatory cytokines TNF-${\alpha}$, IL-$1{\beta}$ and IL-6 in CVB3-infected cardiomyocytes, indicating that brominated cinnamaldehyde not only improved the anti-vital activities for VMC, but also had potent anti-inflammatory effects in cardiomyocytes induced by CVB3.

• Applied Biological Chemistry
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• 제41권4호
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• pp.218-221
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• 1998

Various cinnamaldehyde derivatives were synthesized and their inhibition activity $(pI_{50})$ of farnesyl protein transferase (FPTase) was measured to examine the structure-activity relationships (SAR) on the basis that FPTase was inhibited by ortho-hydroxycinnamaldehyde derived from extracts of the bark of Cinnamomum cassia Blume. The ortho-substituents on the phenyl backbone of cinnamaldehyde showed higher activity than those with meta- and para-substituents, and the side chain required unsaturated aldehyde. In particular, 2-chlorocinnamaldehyde, 5 showed the highest inhibition activity on the FPTase among them and its inhibition activity $(pI_{50})$ value was 4.45.

• 한국수산과학회지
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• 제46권1호
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• pp.53-58
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• 2013

The active antifouling compounds coumarin and its derivatives were isolated from the cinnamon tree Cinnamomum loureiroi. The antifouling activities were determined using representative soft fouling organisms: the seaweed Ulvapertusa and diatom Navicula annexa. The chemical constituents with antifouling activities were identified as coumarin, hydroxylcoumarin, coumaric acid, and cinnamaldehyde by interpreting nuclear magnetic resonance, and high-resolution mass spectroscopy data. These compounds were isolated from 1.09 g of crude Cinnamomum sp. methanol extract, yielding approximately 18.4, 6.3, 9.8, and 14.7 mg of coumarin, hydroxylcoumarin, coumaric acid, and cinnamaldehyde, respectively. The compounds inhibited U. pertusa zoospores with $EC_{50}$ values of $0.13-0.25{\mu}g/mL$, and the diatom N. annexa with $EC_{50}$ of $0.21-0.81{\mu}g/mL$.

• 농약과학회지
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• 제20권3호
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• pp.197-202
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• 2016

계피 추출물의 지표성분으로 알려진 cinnamaldehyde와 cinnamyl alcohol, 데리스 추출물의 지표성분인 deguelin과 rotenone을 대상으로 유기농업자재 제품 중 안정성을 평가하였다. 시험은 $4^{\circ}C$, $23^{\circ}C$, $35^{\circ}C$, $45^{\circ}C$, $54^{\circ}C$에서 각각 진행하였으며, 계피 추출물을 주성분으로 하는 유기농업자재 중 고상제품(Biopesticide A, B)의 유효성분 반감기가 15.1-46.2 days로 액상제품(Biopesticide C, D)에 비해 보관 중 안정성이 높게 나타났다. 또한, 동일 제품 내에서는 cinnamaldehyde의 안정성이 cinnamyl alcohol보다 높은 것으로 나타났다. 데리스 추출물을 사용한 제품(Biopesticide E, F, G)의 rotenoid계 유효성분 반감기는 1.5-173 days로 제품별 보관온도에 따른 지표성분 안정성이 큰 차이를 나타내었으며, 동일 제품에서 deguelin과 rotenone의 안정성은 큰 차이를 나타내지 않았다.

• 약학회지
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• 제37권3호
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• pp.247-253
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• 1993

Eight new derivatives of allylamine which are related to naftifine and expected to have antifungal activity were synthesized. Schiff base 2a-2d and 2'e-2'h were obtained by conventional methods using trans-cinnamylamine or trans-cinnamaldehyde. The reduction of azomethine linkage with NaBH$_{4}$ yielded secondary amine 3a-3h, which were then methylated by means of HCHO and excess NaBH$_{4}$ or HCOOH to give 4a-4h.

• Bulletin of the Korean Chemical Society
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• 제11권1호
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• pp.22-25
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• 1990

The condensation of 1-amino-1,2-dihydro-3,6-pyridazinedione (1) and 2-amino-2,3-dihydro-1,4-phthalazinedione (2) with mesityl oxide or 3-penten-2-one in acetic acid-ethanol (1:1) gave 3,4,6,9-tetrahydro-6,9-dioxopyridazino[1,2-a][1,2, 3]triazines (9,11) and 3,4,6,11-tetrahydro-6,11-dioxo[1,2,3]triazino[1,2- b]phthalazines (10,12), respectively. The condensation of 1 and 2 with crotonaldehyde, cinnamaldehyde or acrylaldehyde under the same reaction condition gave only N-alkylidene derivatlives (3-8). When the N-alkylidene derivatives isolated from the reaction of 1 and 2 with crotonaldehyde and cinnamaldehyde (3-6) were refluxed in acetic acid, the corresponding heterocyclic compounds (13-16) were obtained.

• 한국응용과학기술학회지
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• 제8권1호
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• pp.1-7
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• 1991

The kinetic of hydrolysis for cinnamylidene aniline derivatives has been investigated by ultraviolet spectrophotometry in 20% (v/v) dioxane - $H_2O$ at $25^{\circ}C$. A rate equation which can be applied over wide pH range was obtained. The substituent effects on cinnamylidene aniline derivatives were studied and the hydrolysis was facilitated by electron attracting group. Final products of the hydrolysis were cinnamaldehyde and aniline. From the rate equation, substituent effect and final products, the hydrolysis of cinnamylidene aniline derivatives was initiated by the neutral molecule of $H_2O$ which does not dissociate at below pH 9.0${\sim}$12.0, but proceeded by the hydrogen ion at above pH 5.0${\sim}$9.0.