Protocatechuic acid

Protocatechuic acid
IUPAC name

3,4-Dihydroxybenzoic acid
Other names

3,4-Dihydroxybenzoic acid, PCA
Identifiers
CAS number 99-50-3 Y
PubChem 72
ChemSpider 71 N
DrugBank DB03946
ChEBI CHEBI:36062 N
ChEMBL CHEMBL37537 N
Jmol-3D images Image 1
Properties
Molecular formula C7H6O4
Molar mass 154.12 g/mol
Exact mass 154.026608 u
Acidity (pKa) 4.48 [1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.[2]

Contents

Biological effects

PCA has been reported to induce apoptosis of human leukemia cells, as well as malignant HSG1 cells taken from human oral cavities,[3] but PCA was found to have mixed effects on TPA-induced mouse skin tumours. Depending on the amount of PCA and the time before application, PCA could reduce or enhance tumour growth.[4] Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells.[5] In an in vitro model using HL-60 leukemia cells, protocatechuic acid showed an antigenotoxic effect and tumoricidal activity.[6]

Occurrence in nature

Açaí oil, obtained from the fruit of the açaí Palm (Euterpe oleracea), is rich in protocatechuic acid (630 +/- 36 mg/kg).[7], Protocatechuic acid also exists in the skins of some strains of onion as an antifungal mechanism, increasing endogenous resistance against smudge fungus. It is also found in Allium cepa (17,540 ppm).[8]

Protocatechuic acid is also found in Agaricus bisporus[9]

Metabolism

Protocatechuic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.[10]

Enzymes

Biosynthesis enzymes
Degradation enzymes

The enzyme protocatechuate decarboxylase uses 3,4-dihydroxybenzoate to produce catechol and CO2.
The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate.

See also

References

  1. ^ Dawson, R. M. C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  2. ^ Lin HH, Chen JH, Huang CC, Wang CJ. (June 2007). "Apoptotic effect of 3,4-dihydroxybenzoic acid on human gastric carcinoma cells involving JNK/p38 MAPK signaling activation.". Int J Cancer. 120 (11): 2306–2316. doi:10.1002/ijc.22571. PMID 17304508. 
  3. ^ Babich H, Sedletcaia A, Kenigsberg B (November 2002). "In vitro cytotoxicity of protocatechuic acid to cultured human cells from oral tissue: involvement in oxidative stress". Pharmacol. Toxicol. 91 (5): 245–253. doi:10.1034/j.1600-0773.2002.910505.x. PMID 12570031. http://www.blackwell-synergy.com/openurl?genre=article&sid=nlm:pubmed&issn=0901-9928&date=2002&volume=91&issue=5&spage=245. 
  4. ^ Nakamura Y, Torikai K, Ohto Y, Murakami A, Tanaka T, Ohigashi H (October 2000). "A simple phenolic antioxidant protocatechuic acid enhances tumor promotion and oxidative stress in female ICR mouse skin: dose-and timing-dependent enhancement and involvement of bioactivation by tyrosinase". Carcinogenesis 21 (10): 1899–1907. doi:10.1093/carcin/21.10.1899. PMID 11023549. http://carcin.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11023549. 
  5. ^ Guan S, Ge D, Liu TQ, Ma XH, Cui ZF (March 2009). "Protocatechuic acid promotes cell proliferation and reduces basal apoptosis in cultured neural stem cells". Toxicology in vitro : an international journal published in association with BIBRA 23 (2): 201–208. doi:10.1016/j.tiv.2008.11.008. PMID 19095056. 
  6. ^ Anter J, Romero-Jiménez M, Fernández-Bedmar Z, Villatoro-Pulido M, Analla M, Alonso-Moraga A, Muñoz-Serrano A.,"Antigenotoxicity, cytotoxicity, and apoptosis induction by apigenin, bisabolol, and protocatechuic acid." J Med Food. 2011 Mar;14(3):276-83
  7. ^ Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.)". J Agric Food Chem 56 (12): 4631–6. doi:10.1021/jf800161u. PMID 18522407. 
  8. ^ http://www.ars-grin.gov/cgi-bin/duke/highchem.pl
  9. ^ Delsignore, A; Romeo, F; Giaccio, M (1997). "Content of phenolic substances in basidiomycetes". Mycological Research 101: 552–6. doi:10.1017/S0953756296003206. 
  10. ^ Catechin metabolites after intake of green tea infusions. P. G. Pietta, P. Simonetti, C. Gardana, A. Brusamolino, P. Morazzoni and E. Bombardelli, BioFactors, 1998, Volume 8, Issue 1-2, pp. 111–118,doi:10.1002/biof.5520080119
Monohydroxybenzoic acids
Dihydroxybenzoic acids
Trihydroxybenzoic acids