• BMB Reports
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• 제55권8호
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• pp.407-412
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• 2022

A well-controlled inflammatory response is crucial for the recovery from injury and maintenance of tissue homeostasis. The anti-inflammatory response of 2-methoxycinnamaldehyde (2-MCA), a natural compound derived from cinnamon, has been studied; however, the underlying mechanism on macrophage has not been fully elucidated. In this study, LPS-stimulated production of TNF-α and NO was reduced by 2-MCA in macrophages. 2-MCA significantly activated the NRF2 pathway, and expression levels of autophagy-associated proteins in macrophages, including LC3 and P62, were enhanced via NRF2 activation regardless of LPS treatment, suggesting the occurrence of 2-MCA-mediated autophagy. Moreover, evaluation of autophagy flux using luciferase-conjugated LC3 revealed that incremental LC3 and P62 levels are coupled to enhanced autophagy flux. Finally, reduced expression levels of TNF-α and NOS2 by 2-MCA were reversed by autophagy inhibitors, such as bafilomycin A1 and NH4Cl, in LPS-stimulated macrophages. In conclusion, 2-MCA enhances autophagy flux in macrophages via NRF2 activation and consequently reduces LPS-induced inflammation.

• 약학회지
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• 제57권4호
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• pp.235-240
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• 2013

For the quality control of traditional herbal medicine, Cinnamomi Ramulus, simultaneous determination of cinnamic acid, cinnamaldehyde, and 2-methoxycinnamaldehyde was established by using a high performance liquid chromatographic (HPLC) method with diode array detector. To separate three constituents, Eclipse XDB C18 ($5{\mu}m$, $4.6{\times}250mm$) was used with 0.1% acetic acid and acetonitrile. Validation of the chromatography method was evaluated by linearity, recovery, and precision test. Calibration curve of standard components showed excellent linearity ($R^2$ >0.9999). A simple and efficient method by HPLC was developed to evaluate the quality of traditional herbal medicines made from Cinnami Ramulus. Three major bioactive ingredients in 30 samples that are from China(8) and Vietnam(22) were separated and quantified.

• Applied Biological Chemistry
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• 제48권3호
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• pp.267-272
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• 2005

계피(계지, Cinnanmomum cassia)의 주요성분인, trans-cinnamaldehyde를 $^1H-NMR$ 분광법을 이용하여 정량분석하였다. 핵자기 공명법을 이용한 정량분석의 응용가능성을 확인하기 위하여, t-cinnamaldehyde의 $^1H-NMR$ 스펙트럼에서 시료의 농도와 측정온도를 변화시킴에 따라 chemical shift의 변화와 적분값의 변화를 관찰하였다. t-Cinnamaldehyde(7.1429 mg/ml)를 19, 25, 30, 40 및 $50^{\circ}C$ 하에서 $^1H-NMR$ 측정한 결과, aldehyde methine signal(doublet)의 chemical shift가 9.7202, 9.7184, 9.7169, 9.7142 및 9.7124 ppm에서 관측되었다. 이는 측정온도는 signal의 chemical shift의 변화에 중요한 변수가 되지 않는다는 것을 의미하였다. 또한, aldehyde signal의 적분값이 $1.37(19^{\circ}C),\;1.37(25^{\circ}C),\;1.37(30^{\circ}C),\;1.37(40^{\circ}C)$ 및 $1.37(50^{\circ}C)$로써, 측정온도가 signal의 적분값에는 전혀 영향을 미치지 않는 것으로 나타났다. 동일한 온도 $25^{\circ}C$에서 0.4464, 0.8929, 1.7857, 3.5714, 7.1429 및 14.286 mg/ml의 농도의 시료에 대한 $^1H-NMR$ 측정 결과, aldehyde기의 chemical shifts는 각각 9.7206, 9.7201, 9.7196, 9.7192, 9.7185 및 9.7174 ppm에서 나타났다. 이는 각 시료의 농도가 증가함에 따라서 aldehyde의 signal이 고자장으로 약간 이동하는 것으로 나타났다. Aldehyde기의 doublet methine signal의 적분값과 각 시료의 농도에 따른 calibration curve는 직선으로 나타났으며, 매우 높은 회귀율($r^2=1.0000$)을 보였다. t-Cinnamaldehyde와 aldehyde기를 갖는 물질로써, C. cassia의 또 다른 구성성분인 t-2-methoxycinnamaldehyde($7.1429\;mg/ml\;CDCl_3,\;25^{\circ}C$)에 대해서, $^1H-NMR$ 스펙트럼을 측정한 결과, t-cinnamaldehyde는 ${\delta}_H$ 9.7174(9.7078, 9.7270)서 관측되었다. t-2-Methoxycinnamaldehyde는 ${\delta}_H$ 9.6936(9.6839, 9.7032)에서 관측되었다. 따라서, 두 화합물의 chemical shift의 차이는 resolution 값이 0.45 Hz인 NMR 스펙트럼 상에서 충분히 구분할 수 있을 정도로 나타났다. 위의 방법을 이용하여, 추출용매에 따른 C. cassia 내의 t-cinnamaldehyde의 함량을 분석한 결과, n-hexane, $CHCl_3$ 및 EtOAc로 추출하였을 때에, 각각 94.2 mg/g(0.94%), 137.6 mg/g(1.38%), 140.1 mg/g(1.40%)으로 결정되었다.

• 농약과학회지
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• 제18권4호
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• pp.439-442
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• 2014

신나밀계 화합물은 다양한 생물에 넓게 분포하는 생물 2차대사산물로 잘 알려져 있으며, 여러 생리활성이 규명되었다. 하지만, 작물의 생장조절기능성 연구결과는 잘 알려져 있지 않아, 본 연구에서는 신나밀기를 갖는 acid, amide, alcohol, aldehyde, ester등 46종의 유도체를 대상으로 발아와 유근생장억제능을 비교평가 하였다. 시험 결과, cinnamyl group을 기본 골격으로 하는 화합물의 경우 carboxylic acid group보다는 ester, amide, aldehyde와 같은 functional group에서 유근생장 억제능이 쉽게 관찰되는 것으로 확인되었다. 또한, EWG는 meta-position에 위치할 때 가장 효과가 높은 것으로 확인되었으며, cinnamamide, 3-chlorocinnamic acid와 4-methoxycinnamaldehyde는 100 mg/L 미만의 처리농도에서 배추에 대한 발아억제를 일으키지 않으며, 유근생장 생장억제기능성이 높아 작물 생장억제제로 사용가능한 cinnamyl 유도체임을 확인하였다.

• 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.