Chemical Properties
white to light yellow crystal powder
Uses
3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).
Uses
A phenolic acid antioxidant and chemopreventive agent
Definition
ChEBI: A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.
Biosynthesis
Protocatechuic acid is synthesized from the intermediates of the shikimate pathway. In this case, 3-dehydroshikimate is converted to protocatechuic acid as shown in Fig.11.2. Activity measurements from mung bean seedlings, on the other hand, indicate that 3-dehydroshikimate can be converted to protocatechuic acid (Widhalm and Dudareva 2015). Protocatechuic acid (11.12) upon hydroxylation produces gal- lic acid. The enzyme catalyzing this reaction is not well understood (Muir et al.2011).
Biosynthesis of Protocatechuic Acid
General Description
Protocatechuic acid belongs to the class of polyphenolic compounds, which can be generally isolated from the dried flower of roselle. It can serve as a potential candidate possessing anticancer property, which can be involved in suppressing the growth of human promyelocytic leukemia HL-60 cells.
Biological Activity
Protocatechuic acid (PCA) is a dihydroxybenzoic acid phenolic compound found in many edible and medicinal plants. It is a major metabolite of antioxidant polyphenols found in green tea and demonstrates free radical scavenging capability in a 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity assay (IC50 = 16.3 μM). It is thought to possess anti-inflammatory, antihyperglycemic, neuroprotective, and anticancer activities. Dietary administration of PCA dose dependently inhibits in vitro chemical carcinogenesis and exerts pro-apoptotic and anti-proliferative effects in different tissues. In studies of tumor cell migration and invasion using mouse melanoma B16/F10 cells, PCA at 0.1-2 mM down-regulated the Ras/Akt/NF-κB pathway by targeting RhoB activation, leading to a reduction of MMP-mediated activity.
Biochem/physiol Actions
Chemopreventive in several animal models of carcinogenesis. Blocks cell proliferation in the post-initiation phase.
Source
Protocatechuic acid, in free or bound form, is found in the leaves, fruits, wood, barks, flowers of many angiosperms. Free protocatechuic acid is found in the scales of onion (Allium cepa L.), star anise fruits (Illicium L.) and leaves of grapevines (Vitis L.). It is part of the tannins from leaves of apple trees, bark of oak, bark and flowers of acacia (Acacia L). The 3,4-dimethyl ether of protocatechuic acid, the socalled veratric acid, is widely distributed.
