3,4-Dihydroxybenzaldehyde

Acta Histochem Cytochem. 2014 Jun 28;47(3):103-12.

3,4-Dihydroxybenzaldehyde Derived from Prunus mume Seed Inhibits Oxidative Stress and Enhances Estradiol Secretion in Human Ovarian Granulosa Tumor Cells.[Pubmed: 25320407]

Granulosa cells form ovarian follicles and play important roles in the growth and maturation of oocytes. The protection of granulosa cells from cellular injury caused by oxidative stress is an effective therapy for female infertility.
METHODS AND RESULTS:
We here investigated an effective bioactive compound derived from Prunus mume seed extract that protects granulosa cells from hydrogen peroxide (H2O2)-induced apoptosis. We detected the bioactive compound, 3,4-Dihydroxybenzaldehyde (3,4-DHBA), via bioactivity-guided isolation and found that it inhibited the H2O2-induced apoptosis of granulosa cells. We also showed that 3,4-DHBA promoted estradiol secretion in granulosa cells and enhanced the mRNA expression levels of steroidogenic factor 1, a promoter of key steroidogenic enzymes.
CONCLUSIONS:
These results suggest that P. mume seed extract may have clinical potential for the prevention and treatment of female infertility.

Phytochemistry, 1969, 8(2):393-5.

3,4-dihydroxybenzaldehyde, a fungistatic substance from green Cavendish bananas.[Reference: WebLink]

A fungistatic substance has been isolated from the outer skin of green Cavendish bananas and identified as 3,4-Dihydroxybenzaldehyde. The compound has been shown to inhibit the growth of Gloeosporium musarum, a fungus which causes ripe fruit rot in the banana.

Molecules . 2016 Jun 9;21(6):754.

Evaluation of the Antibacterial Effects and Mechanism of Action of Protocatechualdehyde against Ralstonia solanacearum[Pubmed: 27294898]

Abstract Protocatechualdehyde (PCA) is an important plant-derived natural product that has been associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging and an anti-inflammatory agent. However, fewer reports concerning its antibacterial effects on plant-pathogenic bacteria exist. Therefore, in this study, protocatechualdehyde was evaluated for its antibacterial activity against plant pathogens along with the mechanism of its antibacterial action. PCA at 40 μg/mL was highly active against R. solanacearum and significantly inhibited its growth. The minimum bactericidal concentration and minimum inhibitory concentration values for PCA were 40 μg/mL and 20 μg/mL, respectively. Further investigation of the mechanism of action of PCA via transmission electron microscopy and biological assays indicated that the destruction of the cell structure, the shapes and the inhibition of biofilm formation were important. In addition, the application of PCA effectively reduced the incidence of bacterial wilt on tobacco under greenhouse conditions, and the control efficiency was as high as 92.01% at nine days after inoculation. Taken together, these findings suggest that PCA exhibits strong antibacterial activity against R. solanacearum and has the potential to be applied as an effective antibacterial agent for controlling bacterial wilt caused by R. solanacearum. Keywords: Ralstonia solanacearum; antibacterial activity; bacterial wilt; biofilm formation; protocatechualdehyde.

Nat Prod Res. 2008;22(16):1441-50.

Apoptotic cell death through inhibition of protein kinase CKII activity by 3,4-dihydroxybenzaldehyde purified from Xanthium strumarium.[Pubmed: 19023807]

METHODS AND RESULTS:
The CKII inhibitory compound was purified from the fruit of Xanthium strumarium by organic solvent extraction and silica gel chromatography. The inhibitory compound was identified as 3,4-Dihydroxybenzaldehyde by analysis with FT-IR, FAB-Mass, EI-Mass, (1)H-NMR and (13)C-NMR. 3,4-Dihydroxybenzaldehyde inhibited the phosphotransferase activity of CKII with IC(50) of about 783 microM. Steady-state studies revealed that the inhibitor acts as a competitive inhibitor with respect to the substrate ATP. A value of 138.6 microM was obtained for the apparent K(i). Concentration of 300 microM 3,4-Dihydroxybenzaldehyde caused 50% growth inhibition of human cancer cell U937. 3,4-Dihydroxybenzaldehyde-induced cell death was characterised with the cleavage of poly(ADP-ribose) polymerase and procaspase-3. Furthermore, the inhibitor induced the fragmentation of DNA into multiples of 180 bp, indicating that it triggered apoptosis. This induction of apoptosis by 3,4-Dihydroxybenzaldehyde was also confirmed by using flow cytometry analysis.
CONCLUSIONS:
Since CKII is involved in cell proliferation and oncogenesis, these results suggest that 3,4-Dihydroxybenzaldehyde may function by inhibiting oncogenic disease, at least in part, through the inhibition of CKII activity.

Phytomedicine. 2009 Jan;16(1):85-94.

3,4-dihydroxybenzaldehyde purified from the barley seeds (Hordeum vulgare) inhibits oxidative DNA damage and apoptosis via its antioxidant activity.[Pubmed: 19022639]

Barley is a major crop worldwide. It has been reported that barley seeds have an effect on scavenging ROS. However, little has been known about the functional role of the barley on the inhibition of DNA damage and apoptosis by ROS.
METHODS AND RESULTS:
In this study, we purified 3,4-Dihydroxybenzaldehyde from the barley with silica gel column chromatography and HPLC and then identified it by GC/MS. And we firstly investigated the inhibitory effects of 3,4-Dihydroxybenzaldehyde purified from the barley on oxidative DNA damage and apoptosis induced by H(2)O(2), the major mediator of oxidative stress and a potent mutagen. In antioxidant activity assay such as DPPH radical and hydroxyl radical scavenging assay, Fe(2+) chelating assay, and intracellular ROS scavenging assay by DCF-DA, 3,4-Dihydroxybenzaldehyde was found to scavenge DPPH radical, hydroxyl radical and intracellular ROS. Also it chelated Fe(2+). In in vitro oxidative DNA damage assay and the expression level of phospho-H2A.X, it inhibited oxidative DNA damage and its treatment decreased the expression level of phospho-H2A.X. And in oxidative cell death and apoptosis assay via MTT assay and Hoechst 33342 staining, respectively, the treatment of 3,4-Dihydroxybenzaldehyde attenuated H(2)O(2)-induced cell death and apoptosis.
CONCLUSIONS:
These results suggest that the barley may exert the inhibitory effect on H(2)O(2)-induced tumor development by blocking H(2)O(2)-induced oxidative DNA damage, cell death and apoptosis.

The Korea Jounnal of Herbology, 2006, 21(2):1-7.

Tyronase Inhibitory Effect of 3,4-Dihydroxybenzaldehyde Isolated from Pinellia ternata.[Reference: WebLink]

The purpose of this study is to isolate tyrosinase inhibitory material from Pinellia ternata and characterize its own structure and activity.
METHODS AND RESULTS:
Pinellia ternata (600g) was extracted with 95% methanol (1L) at for 4 days, with shaking at 250rpm. The extract was further solvent-fractionated with n-hexane, chloroform, ethylacetate and water. The active fraction was subjected to JAI recycling prep-HPLC JAIGEL GS-320 column. The structure was identified for the active peak with NMR and GC. Results : Tyrosinase was potently inhibited by 95% methanol extracts from Pinellia ternata. The IC(50) value of the extracts was estimated to be 0.05mg/ml. The extracts was divided into four solvent-fractions, and the most potent tyrosinase inhibition was found in ethylacetate layer. IC(50) value of ethylacetate fraction was 0.001mg/ml. This fraction was further purified with JAI Recycling Preparative HPLC (Model: LC 9104). The isolated compound showing inhibitory activity was characterized on its chemical structure by NMR and the compound was identified as 3,4-Dihydroxybenzaldehyde. IC(50) was found to be 7.74 which is much lower than that of kojic acid .
CONCLUSIONS:
The data suggest that 3,4-Dihydroxybenzaldehyde isolated and identified from Pinellia ternata is very strong inhibitor to melanin biosynthesis.