2,4,5-Trimethoxybenzaldehyde

The rhizoma of Acorus tatarinowii Schott

Asaraldehyde is a natural COX-2 inhibitor, exhibiting 17-fold selectivity over COX-1.

[Chemical constituents from rhizomes of Acorus tatarinowii].[Pubmed:23713285]

Zhongguo Zhong Yao Za Zhi. 2013 Feb;38(4):569-73.

Fifteen compounds were isolated from the rhizomes of Acorus tatarinowii by means of various chromatographic techniques such as silica gel, ODS, Sephadex LH-20 and preparative HPLC, and their structures were elucidated as tatanone A (1), calamusenone (2), acoronene (3), 2-acetyloxyacoronene (4), acorenone (5), alpha-asarone (6), beta-asarone (7), 1,2-dimethoxy-4-(1'Z-propenyl) benzene (8), methyleugenol (9), asarylaldehyde (10), acoramone (11), gamma-asarone (12), 5-hydroxymethyl-2-furaldehyde (13), galgravin (14) and eudesmin (15) on the basis of spectroscopic data analysis. Compound 1 was a new compound, and compounds 3-5 were separated from Acorus species for the first time.

Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata.[Pubmed:17397476]

Lett Appl Microbiol. 2007 Apr;44(4):387-92.

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.

2,4,5-trimethoxybenzaldehyde, a bitter principle in plants, suppresses adipogenesis through the regulation of ERK1.[Pubmed:25222709]

J Agric Food Chem. 2014 Oct 8;62(40):9860-7.

Because of the prevalence of obesity, there is particular interest in finding potential therapeutic targets. In a previous study, we demonstrated that 2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA), a bitter principle in plants and a natural cyclooxygenase II (COX-2) inhibitor, suppressed the differentiation of preadipocyts into adipocytes at the concentration of 0.5 mM. In this current study, we aimed to investigate the stage during adipogenesis that is critically affected by 2,4,5-TMBA and the effects of 2,4,5-TMBA on the time-course expression of signaling molecules MAP kinase kinase (MAPKK, represented by MEK) and extracellular signal-regulated kinase (ERK), transcription factors CCAAT/enhancer binding protein (C/EBP)alpha, beta, and delta and peroxisome proliferator-activated receptor (PPAR)gamma, lipogenic enzymes acetyl-CoA carboxylase (ACC) and fatty acid synthase (FAS), and lipid droplet-coating protein perilipin A. When preadipocytes were co-cultured with 2,4,5-TMBA (0.5 mM) specifically at post-induction days 0-2, 2-4, 4-6, or 6-8 only, relative lipid accumulation was decreased by 67.93, 34.65, 49.56, and 34.32%, respectively. A time-course study showed that treatment of 2,4,5-TMBA suppressed the phosphorylation of ERK1 at the initial stage of adipogenesis but upregulated the phosphorylation at the late stage, which is opposite to the conditions required for the differentiation process. The overall expression of C/EBPalpha, beta, and delta, PPARgamma2, ACC, FAS, and perilipin A in preadipocytes was downregulated by the treatment of 2,4,5-TMBA. Taken together, our findings suggest that 2,4,5-TMBA suppresses adipogenesis through the regulation of ERK1 phosphorylation. Although results from in vitro studies cannot be directly extrapolated into clinical effects, our study will help to elucidate the anti-adipogenic potential of 2,4,5-TMBA.

Asarylaldehyde is a natural COX-2 inhibitor, which isolated from carrot (Daucus carota L.) seeds significantly inhibits cyclooxygenase II (COX-2) activity at IC50 value 100 μg/mL.

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