2′-Hydroxycinnamaldehyde from Stem Bark of<i>Cinnamomum cassia</i>

Kwon, Byoung‐Mog; Cho, Young Kwon; Lee, Seung Ho; Nam, Jiyoun; Bok, Song Hae; Chun, Soo-Kyoung; Kim, Jeong Ah; Lee, Ihn-Rhan

doi:10.1055/s-2006-957851

Cited by 65 publications

(27 citation statements)

References 2 publications

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“…2′-Benzoyloxycinnamaldehyde (BCA; Figure 1), currently under preclinical development as an antitumour agent, was originally synthesized as a derivative of 2′-hydroxycinnamaldehyde (HCA; Figure 1) (Kwon et al 1997), a natural product isolated from the stem bark of Cinnamomum cassia Blume (Lauraceae) (Kwon et al 1996). BCA has also been isolated recently from the aerial parts of Pleuropterus ciliinervis Nakai (Polygonaceae) (Kang et al 2007).…”

Section: Introductionmentioning

confidence: 99%

“…The authors' studies further demonstrated that their anti-proliferative activity against tumour cells was mediated by induction of apoptosis via reactive oxygen species (ROS) (Han et al 2004) and inhibition of proteasome (Hong et al 2007). In addition, HCA was reported to have various other pharmacological activities including farnesyl protein transferase inhibition (Kwon et al 1996), anti-inflammatory activity (Lee et al 2005), immunomodulation (Koh et al 1998), and antifungal activity (Kang et al 2007). …”

Section: Introductionmentioning

confidence: 99%

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Plasma pharmacokinetics and metabolism of the antitumour drug candidate 2′-benzoyloxycinnamaldehyde in rats

et al. 2009

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The pharmacokinetics and metabolism of 2'-benzoyloxycinnamaldehyde (BCA) was characterized in male Sprague-Dawley rats as part of the preclinical evaluations for developing this compound as an antitumour agent. BCA was not detected in the plasma following either intravenous or oral dose, whereas its putative metabolites 2'-hydroxycinnamaldehyde (HCA) and o-coumaric acid were present at considerable levels. In separate pharmacokinetics studies, HCA exhibited a high systemic clearance and a large volume of distribution, whereas both pharmacokinetic parameters were much lower for o-coumaric acid. The terminal half-life of both metabolites was approximately 2 h. BCA was converted rapidly to HCA in rat serum, liver microsomes and cytosol in vitro; HCA was subsequently converted to o-coumaric acid in a quantitative manner only in the liver cytosol. In addition, the formation of o-coumaric acid was inhibited significantly by menadione, a specific inhibitor for aldehyde oxidase. Taken collectively, the results suggest that the rapid systemic clearance of HCA is likely due mainly to hepatic clearance occurring from aldehyde oxidase-catalysed biotransformation to o- coumaric acid. In conclusion, the present work demonstrates that the anticancer drug candidate BCA is highly likely to work as its active metabolite HCA in the body.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Plasma pharmacokinetics and metabolism of the antitumour drug candidate 2′-benzoyloxycinnamaldehyde in rats

et al. 2009

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“…Cinnamaldehyde compounds have found wide applications in food, cosmetic [1,2] or agrochemical [3][4][5][6] and pharmaceutical industries. [7][8][9][10][11][12] Some cinnamaldehyde derivatives exhibit non-linear optical properties. [13][14][15][16][17][18][19][20] Several methods based on the Perkin and Claisen condensations of aromatic aldehydes have been reported for the synthesis of cinnamaldehyde derivatives on the industrial scale.…”

Section: Introductionmentioning

confidence: 99%

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

et al. 2007

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) 4 ]/NaY} catalyst was applied successfully to the Heck arylation of acrolein diethyl acetal using a large variety of aryl and heteroaryl bromides. Depending on the reaction conditions (Heck versus Cacchi) good to high selectivities toward the 3-arylpropionic esters or to the cinnamaldehydes were achieved, respectively. Under classical Heck conditions, while the catalyst was found to be stable over the two first runs, it showed significant loss of activity from the third cycle. Under Cacchi conditions, the catalyst could not be reused as it led to high dehalogenation rates. All results indicate that the reactions proceed through dissolved palladium species in the bulk solution (leaching). As observed by transmission electronic microscopic (TEM) analyses, while these species can be trapped and stabilised by the zeolite framework under the Heck conditions, they tend to form large palladium(0) aggregates under the Cacchi conditions leading to dehalogenation rather than to the expected Heck coupling.

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“…2Ј-Hydroxycinnamaldehyde (HCA), 1 isolated from the stem bark of Cinnamomum cassia, was reported to have an inhibitory effect on farnesyl protein transferase activity in vitro (1). The cinnamaldehydes have also been shown to have various activities such as anti-angiogenic activity (2) and to be immunomodulators (3), CDK4/cyclinD1 kinase (4), and the proliferation of several human cancer cell lines including breast, leukemia, ovarian, lung, and colon tumor cells (5).…”

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2′-Benzoyloxycinnamaldehyde Induces Apoptosis in Human Carcinoma via Reactive Oxygen Species

Han

Lee

Shin

et al. 2004

Journal of Biological Chemistry

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2 -Hydroxycinnamaldehyde (HCA) has been shown to have inhibitory effects on farnesyl protein transferase in vitro, angiogenesis, and tumor cell growth. However, mechanism for these inhibitions remains unknown. As a derivative of HCA, BCA (2 -benzoyl-oxycinnamaldehyde) was synthesized by replacing hydroxyl group with benzoyl-oxyl group. When p53-mutated cancer cell lines (MDA-MB-231 breast cancer cell and SW620 colon cancer cell) were treated with 10 M HCA or BCA, it induced growth arrest and apoptosis of tumor cells. Markers of apoptosis such as degradations of chromosomal DNA and poly(ADP-ribose) polymerase and activation of caspase-3 were detected after HCA or BCA treatment. BCA-induced apoptosis was blocked by pretreatment of cells with anti-oxidants, glutathione, or N-acetyl-cysteine. In addition, BCA-induced activation of caspase-3 and degradation of poly(ADP-ribose) polymerase were abolished by pretreatment of cells with the anti-oxidants. These results suggest that reactive oxygen species are major regulator of BCA-induced apoptosis. HCA or BCA-induced accumulation of reactive oxygen species was detected by using DCF-DA, an intracellular probe of oxidative stress. Furthermore, when BCA (100 mg/kg) was administrated intraperitoneally or orally into a nude mouse, it inhibited >88 or 41% of tumor growth, respectively, without any detectable weight change. These results suggest that BCA is a good drug candidate for cancer therapy.

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2′-Hydroxycinnamaldehyde from Stem Bark ofCinnamomum cassia

Cited by 65 publications

References 2 publications

Plasma pharmacokinetics and metabolism of the antitumour drug candidate 2′-benzoyloxycinnamaldehyde in rats

Plasma pharmacokinetics and metabolism of the antitumour drug candidate 2′-benzoyloxycinnamaldehyde in rats

Efficient Heterogeneously Palladium‐Catalysed Heck Arylation of Acrolein Diethyl Acetal. Selective Synthesis of Cinnamaldehydes or 3‐Arylpropionic Esters

2′-Benzoyloxycinnamaldehyde Induces Apoptosis in Human Carcinoma via Reactive Oxygen Species

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