Ethyl 4-methoxycinnamate

Oriental Journal of Chemistry, 2016, 32(5): 2731-4.

Cytotoxicity Activity of Biotransformed Ethyl p-methoxycinnamate by Aspergillus niger.[Reference: WebLink]

METHODS AND RESULTS:
The extraction of Kaempferiagalanga rhizome using steam distillation and supercritical fluid extraction (SFE) carried out. After fractionation, the major compound of the K. galanga, ethyl p-methoxycinnamate (EPMC) was Aspergillus ethyl p-hydroxycinnamate (Ethyl 4-methoxycinnamate,EPHC). The biological activity of EPMC and its biotransformed product (EPHC) established by activity on human breast cancer (MCF-7) cell line using MTT assay. Ethyl p-hydroxycinnamate (EPHC) was most cytotoxic at 1000 μg/mL percentage cell viability was 9.87% IC50 was 340μg/mL. showed slight cytotoxicity activity compared to EPMC.
CONCLUSIONS:
that the biotransformation process was able to produce metabolite (EPHC) higher cytotoxicity activity compared to its parent compound (EPMC).

Phytother Res. 2014 Feb;28(2):274-9.

Hypopigmentary effects of ethyl P-methoxycinnamate isolated from Kaempferia galanga.[Pubmed: 23610003 ]

We isolated crystals from the chloroform fraction of an ethanol extract of Kaempferia galanga and identified it as ethyl p-methoxycinnamate(Ethyl 4-methoxycinnamate)through nuclear magnetic resonance analysis.
METHODS AND RESULTS:
In the present study, we found that ethyl p-methoxycinnamate significantly decreased melanin synthesis in B16F10 murine melanoma cells stimulated with α-melanocyte stimulating hormone (α-MSH). In a cell-free system, however, ethyl p-methoxycinnamate did not directly inhibit tyrosinase, the rate-limiting enzyme of melanogenesis. Instead, it inhibited tyrosinase activity in B16F10 cells in a dose-dependent manner. Furthermore, Western blot analysis showed that ethyl p-methoxycinnamate decreased microphthalmia-associated transcription factor and tyrosinase levels in α-MSH-stimulated B16F10 cells.
CONCLUSIONS:
These results indicate that the pigment-inhibitory effect of ethyl p-methoxycinnamate results from downregulation of tyrosinase. Ethyl p-methoxycinnamate isolated from K. galanga could be developed as a skin whitening agent to treat hyperpigmentary disorders.

Lloydia. 1976 Jul-Aug;39(4):218-22.

Isolation of Ethyl p-methoxycinnamate, the major antifungal principle of Curcumba zedoaria.[Pubmed: 785141]

An antifungal principle of the dried rhizomes of Curcuma zedoaria was extracted with hot ethanol.
METHODS AND RESULTS:
By successive chromatography on neutral alumina and silica gel, three antibiotic compounds A, B, and C, all active against Trichophyton rubrum, Aspergillus niger and Saccharomyces cerevisiae, were obtained in chemically pure form. By uv, ir, pmr and ms analysis, the structure of the most abundant one of these compounds (C, 69.8%; H, 6,8%; and 0.23.4%) was assigned as ethyl p-methoxycinnamate (Ethyl 4-methoxycinnamate,EPMC). The proposed structure was confirmed by synthesis and comparison of the chemical and biological properties of the natural and synthetic products. EPMC inhibits the growth of Trichophyton rubrum, Aspergillus niger, Saccharomyces cerevisiae and Epidermophyton floccosum at a concentration less than 10 mug/ml; A. fumigatus, Penicillium purpurogenum, Trignoposis variabilis, Microsporum gypseum, Sclerotium rolifsii, Geotricular candiade, Fusarium oxysporum and Helminthosporium oryzale at a concentration less than 25 mug/ml; and Candida krusei and T. mentagrophytes At a concentration less than 50 mug/ml. The spores of T. rubrum Lose viability or ability to germinate when wxposed to its ethanolic solution (30 mug/ml) for 2 hours.

Int. J. Pharm. Pharm.Sci., 2012, 4:528-32.

Structure modification of ethyl p-methoxycinnamate and their bioassay as chemopreventive agent against mice's fibrosarcoma[Reference: WebLink]

METHODS AND RESULTS:
In the present study, ethyl p-methoxycinnamate(Ethyl 4-methoxycinnamate) isolated from Kaempferia galanga was used as starting material to produce thiourea derivatives (4a, 4b, 4c) in a good yield. The synthesis products were confirmed by FTIR, 1 H-NMR, 13 Keywords: Kaempferia galanga, cyclooxygenase-2, Ethyl p-methoxycinnamate(Ethyl 4-methoxycinnamate), Thiourea derivatives, Fibrosarcoma C-NMR and HRMS spectroscopic methods. Their activities against fibrosarcoma were tested in vivo using mouse model induced by 0.3% benzo(a)pyrene injected subcutaneously, which was given five times, once every two days.
CONCLUSIONS:
Our results showed that fibrosarcoma can be inhibited by all synthesized compounds. In silico analysis predicted that one of mechanism chemopreventive activity of all synthesized compounds against fibrosarcoma through inhibition of COX-2.

Molecules. 2012 Jul 23;17(7):8720-34.

Bioactivity-guided isolation of ethyl-p-methoxycinnamate, an anti-inflammatory constituent, from Kaempferia galanga L. extracts.[Pubmed: 22825623]

This study evaluated the anti-inflammatory effect of Kaempferia galanga (KG) using an activity-guided approach. KG rhizomes were serially extracted with petroleum ether, chloroform, methanol and water.
METHODS AND RESULTS:
These extracts (2 g/kg each) were tested for their ability to inhibit carrageenan-induced rat paw edema. The chloroform extract was found to exert the highest inhibition (42.9%) compared to control (p < 0.001), hence it was further fractionated by washing serially with hexane, hexane-chloroform (1:1) and chloroform. The chloroform fraction (1 g/kg) showed the highest inhibitory effect (51.9%, (p < 0.001), on carrageenan-induced edema. This chloroform fraction was further fractionated with hexane-chloroform (1:3) and chloroform, and of the two fractions, the hexane-chloroform sub-fraction was the most effective in inhibiting edema (53.7%, p < 0.001). GC-MS analysis of the active sub-fraction identified ethyl-p-methoxycinnamate (Ethyl 4-methoxycinnamate,EPMC) as the major component, which was re-crystallized. EPMC dose-dependently inhibited carrageenan-induced edema with an MIC of 100 mg/kg. Moreover, in an in vitro study, EPMC non-selectively inhibited the activities of cyclooxygenases 1 and 2, with IC₅₀ values of 1.12 μM and 0.83 μM respectively.
CONCLUSIONS:
These results validate the anti-inflammatory activity of KG which may be exerted by the inhibition of cyclooxygenases 1 and 2. EPMC isolated from this plant may be the active anti-inflammatory agent.

J Agric Food Chem. 2012 Nov 14;60(45):11309-17.

Antiangiogenic effects and mechanisms of trans-ethyl p-methoxycinnamate from Kaempferia galanga L.[Pubmed: 23106130]

Kaempferia galanga L. (Zingiberaceae) is an aromatic herb and a popular spice used as a condiment in Asian cuisine.
METHODS AND RESULTS:
The ethanol extract of the dried plant and its successive four subfractions were investigated on zebrafish model by quantitative endogenous alkaline phosphatase assay. Both n-hexane and ethyl acetate fractions had antiangiogenic activity, and two major active components (trans-ethyl p-methoxycinnamate(Ethyl 4-methoxycinnamate) and kaempferol) showed potent antiangiogenic effects on wild-type zebrafish. Because of its much stronger effect and no antiangiogenic activity reported, trans-ethyl p-methoxycinnamate was further investigated for its action mechanism. It dose dependently inhibited vessel formation on both wild- and Tg(fli1a:EGFP)y1-type zebrafish embryos.
CONCLUSIONS:
The semiquantitative reverse transcription polymerase chain reaction assay suggested that trans-ethyl p-methoxycinnamate affects multiple molecular targets related to angiogenesis. In vitro, it specifically inhibited the migration and tube formation of human umbilical vein endothelial cells. In vivo, it could block bFGF-induced vessel formation on Matrigel plug assay.