Disease relevance of Protocatechualdehyde

• Circular dichroism studies have been carried out on both apo- and holoprotocatechuate 3,4-dioxygenase from Pseudomonas aeruginosa, in the absence and presence of competitive inhibitors, protocatechualdehyde and 4-nitrocatechol [1].
• Protocatechualdehyde, a competitive deadend inhibitor, binds Pseudomonas PCD more effectively than Acinetobacter PCD. p-Hydroxymercuribenzoate, specific for free-SH groups, inhibits only Acinetobacter PCD and shows no effect on Pseudomonas PCD [2].
• The apo-form of the soluble methane monooxygenase hydroxylase from Methylococcus capsulatus (Bath) was prepared via chelation of iron(III) with 3,4-dihydroxybenzaldehyde [3].
• 3,4-Dihydroxy, 5-methoxybenzaldehyde and protocatechuic aldehyde were the best in vitro substrates for OMT activity in extracts from developing alfalfa stems, and these compounds were preferred over lignin pathway intermediates for 3-O-methylation by recombinant alfalfa COMT expressed in Escherichia coli [4].
• Among them, protocatechualdehyde (7) was found to be the most potent RLAR inhibitor (IC50=0.7 microg/ml), and may be useful for the prevention and/or treatment of diabetic complications [5].

High impact information on Protocatechualdehyde

• Re-examination of this new activity of tyrosinase has demonstrated that the product of the enzyme action is the o-quinone, which, owing to its instability, evolves to the final product, 3,4-dihydroxybenzaldehyde, by a chemical reaction of oxidative decarboxylation [6].
• The incubation of vanillin, isovanillin, and protocatechuic aldehyde with either guinea pig liver aldehyde oxidase, bovine milk xanthine oxidase, or guinea pig liver aldehyde dehydrogenase demonstrated that the three aldehyde oxidizing enzymes had a complementary substrate specificity [7].
• Oxidation and decarboxylation of the latter yields 3,4-dihydroxybenzaldehyde [8].
• Pseudomonas putida F6 was found to metabolize p-hydroxyphenylacetic acid through 3,4-dihydroxyphenylacetic acid, 3,4-dihydroxymandelic acid, and 3,4-dihydroxybenzaldehyde [8].
• 3,4-Dihydroxyphenyllactic acid, salvianolic acid B and protocatechualdehyde were purified from 100mg water extracted crude sample of Salvia miltiorrhiza Bunge at purity of 97.6%, 94.2% and 98.2% and at yield of 98.6%, 73.6% and 90.2% [9].

Biological context of Protocatechualdehyde

• In addition, we found that treatment with ASODNs, fibronectin antibody, and PA did not affect HepG2.2.15 cell viability [10].
• Furthermore, protocatechuic aldehyde (0.15, 0.45, and 1.35 mM) notably inhibited TNF-alpha-induced upregulation of U937 cell adhesion to HUVECs to 83.7%, 60.9%, and 40.8%, respectively [11].
• Induction of apoptosis in CTLL-2 cells by protocatechualdehyde [12].
• A chemical model of catechol-O-methyltransferase. Methylation of 3,4-dihydroxybenzaldehyde in aqueous solution [13].
• When the cells at phases other than S were blocked with protocatechualdehyde for 14 hr, elongation of the next S phase occurred after removal of protocatechualdehyde [14].

Anatomical context of Protocatechualdehyde

• The current studies examined the effect of a potent water-soluble antioxidant, protocatechuic aldehyde (derived from the Chinese herb, Salvia miltiorrhiza), on the expression of adhesion molecules in human umbilical vein endothelial cells (HUVECs) stimulated with tumor necrosis factor-alpha (TNF-alpha) [11].
• Protocatechuic aldehyde suppresses TNF-alpha-induced ICAM-1 and VCAM-1 expression in human umbilical vein endothelial cells [11].
• Patch-clamp techniques were used to study the effects of three carbonyl compounds, 3,4-dihydroxybenzaldehyde, 2,3-dihydroxybenzaldehyde, and 2,4-dihydroxyacetophenone, on the adenosine-5'-triphosphate(ATP)-sensitive K+ channel current (IK.ATP) in guinea-pig ventricular myocytes [15].

Associations of Protocatechualdehyde with other chemical compounds

• One-step separation and purification of 3,4-dihydroxyphenyllactic acid, salvianolic acid B and protocatechualdehyde from Salvia miltiorrhiza Bunge by high-speed counter-current chromatography [9].
• METHODS: Vanillin, isovanillin or protocatechuic aldehyde was incubated with liver slices in the presence/absence of specific inhibitors of each enzyme, followed by HPLC [16].
• Separation and determination of protocatechuic aldehyde and protocatechuic acid in Salivia miltorrhrza by capillary electrophoresis with amperometric detection [17].
• The redox mediators were, potassium hexacyanoferrate (II), Meldola's Blue (MB), dichlorophenolindophenol (DCPIP), p-benzoquinone (p-BQ), o-phenylenediamine (o-PDA) and 3,4-dihydroxybenzaldehyde (3,4-DHB) [18].
• It uses 3,4-dihydroxymandelic acid (DOMA) as the substrate of tyrosinase and measures the final product, 3,4-dihydroxybenzaldehyde (DOBA) [19].

Gene context of Protocatechualdehyde

• Collectively, these results indicate that protocatechuic aldehyde inhibits TNF-alpha-stimulated VCAM-1 and ICAM-1expression in HUVECs through a mechanism that involves NF-kappaB and AP-1 [11].
• Modulation of ornithine decarboxylase activity and mitogen-activated protein kinases in protocatechualdehyde-induced apoptosis of CTLL-2 cells [20].
• A simple and sensitive high-performance liquid chromatography method is developed for the simultaneous determination of (3,4-dihydroxyphenyl)-lactic acid (Dhpl) and protocatechuic aldehyde (Pal) in rat serum after oral administration of Radix Salviae miltiorrhizae extract [21].

Analytical, diagnostic and therapeutic context of Protocatechualdehyde

• This compound was identified to be 3,4-dihydroxybenzaldehyde based on its HPLC elution profile, cochromatography with authentic sample and UV spectral properties [22].
• By using fibronectin antisense oligonucleotide (ASODN), fibronectin antibody, and Protocatechuic aldehyde (PA), we were able to show that HBV productions in HepG2.2.15 cell culture were reduced in a dose-dependent manner by fibronectin inhibition [10].
• Attempted crystallization in the presence of air was observed to result in formation of the [Co(bpy)2(BACat)]+ (H2BACat, 3,4-dihydroxybenzaldehyde) cation by aerobic oxidation [23].
• Simultaneous determination and pharmacokinetic studies on (3,4-Dihydroxyphenyl)-lactic acid and protocatechuic aldehyde in rat serum after oral administration of Radix Salviae miltiorrhizae extract [21].

References