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2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA), a natural inhibitor of cyclooxygenase II activity, is a bitter principle present in plants. In our previous study, 2,4,5-TMBA suppresses differentiation of preadipocytes and enhances lipolysis in mature adipocytes. This study aimed to investigate the absolute bioavailability, tissue distribution, and excretion of 2,4,5-TMBA in Sprague-Dawley rats. After oral administration (po) and intravenous administration (iv) of 100 and 10 mg/kg 2,4,5-TMBA, respectively, the absolute bioavailability was estimated as 62.77% by calculating [(AUCpo × Doseiv)/(AUCiv × Dosepo)] × 100% (AUC: area under curve). Half hour after oral administration, 2,4,5-TMBA reached the highest concentration of 211.661 μg/g in stomach. In one hour, 2,4,5-TMBA reached the highest concentrations in heart, liver, kidney, small intestine, and large intestine. Total amount of unconverted 2,4,5-TMBA eliminated in feces and urine in 24 h is only 0.03% of oral dosage administrated. The data presented provides useful information for the future application of 2,4,5-TMBA as nutraceutical.

2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA), a natural inhibitor of cyclooxygenase II activity, is a bitter principle present in plants. In our previous study, 2,4,5-TMBA suppresses differentiation of preadipocytes and enhances lipolysis in mature adipocytes. This study aimed to investigate the absolute bioavailability, tissue distribution, and excretion of 2,4,5-TMBA in Sprague-Dawley rats. After oral administration (po) and intravenous administration (iv) of 100 and 10 mg/kg 2,4,5-TMBA, respectively, the absolute bioavailability was estimated as 62.77% by calculating [(AUC po × Dose iv )/(AUC iv × Dose po )] × 100% (AUC: area under curve). Half hour after oral administration, 2,4,5-TMBA reached the highest concentration of 211.661 μg/g in stomach. In one hour, 2,4,5-TMBA reached the highest concentrations in heart, liver, kidney, small intestine, and large intestine. Total amount of unconverted 2,4,5-TMBA eliminated in feces and urine in 24 h is only 0.03% of oral dosage administrated. The data presented provides useful information for the future application of 2,4,5-TMBA as nutraceutical. [ABSTRACT FROM AUTHOR]

The title compound, 1-(2,5-dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (3) was synthesized in high yield by an aldol condensation reaction of 3-acetyl-2,5-dimethythiophene and 2,4,5-trimethoxybenzaldehyde in methanolic NaOH at room temperature. Its structure was fully characterized by elemental analysis, IR, 1H NMR, 13C NMR and EI-MS spectral data.

Aims: To investigate the active ingredient in fruiting bodies and to produce it with cultured mycelium in Antrodia camphorata (BCRC 35398). Methods and Results: The volatile components from the fruiting bodies, the liquid cultured broth of A. camphorata and Cinnamomum kanehirae wood were separately isolated by steam distillation–solvent extraction and identified by gas chromatography–mass spectrometry. In the fruiting bodies, a COX-2 inhibitor 2,4,5-trimethoxybenzaldehyde (TMBA) was found to be the most abundant constituent, but was totally absent in its cultured broth and its natural host, C. kanehirae wood. On feeding with the acid-digested sawdust of C. kanehirae wood or vanillin to the broth for culture, TMBA was produced in both cultured broths. Conclusion: The TMBA identified in fruiting bodies was an active ingredient whose functions consisted with the reported experiences of this mushroom. Feeding vanillin to culture broth could produce TMBA containing mycelium product like its fruiting bodies did. Significance and Impact of the Study: This study found an active ingredient in fruiting bodies of A. camphorata and elucidated this compound derived from digested sawdust of C. kanehirae wood. A feasible method was also developed to produce TMBA containing mycelium by feeding vanillin. [ABSTRACT FROM AUTHOR]

Natural products are viable sources for the design of new chemical entities that may have their activities improved by fast/inexpensive synthetic modifications of their substituents. Herein we report the synthesis of six analogs of 2,4,5-trimethoxybenzaldehyde (1), a phenolic derivate isolated from Duguetia furfuracea , their corresponding phytotoxic activities and the predicted affinities concerning the inhibition of the auxin-binding protein (ABP-1). The synthesized compound 4b , methyl 2-(2,4,5-trimethoxyphenoxy)propanoate, showed the same growth-inhibition effect compared to the natural product 1 on the hypocotyl of the dicotyledon model, while 4c and 5a, (2-(2,4,5-trimethoxyphenoxy) acetic acid and 2-(2,4,5-trimethoxyphenoxy propanoic acid, respectively), demonstrated epinastic activities. The potential of interacting with the auxin-binding protein (ABP-1) was investigated by molecular docking and has shown that all the synthesized compounds were able to bind to the ABP-1 active site by similar patters of binding of the reference compound, 1-naphthalene acetic acid by hydrogen bond interactions and hydrophobic contributions. The compounds presented in this study could be highlighted as potential herbicide agents with anti -ABP-1, as well as 2,4,5-trimethoxybenzaldehyde as a good prototype to the development of new herbicides agents to the agrochemical industry. • The synthesized compounds presented interesting growth-inhibition effect. • Compounds 4c and 5a demonstrated epinastic activities. • The synthesized compounds highlighted as potential herbicide agents. • Compound 1 is as a good prototype for the design of potential herbicide agents. • Docking studies revealed a binding pattern to the ABP-1 active site. [ABSTRACT FROM AUTHOR]