Abstract
We characterized the biological functions of protocatechualdehyde (PA) isolated from the butanol extract of culture supernatant from Streptomyces lincolnensis M-20. Following butanol extraction, it was purified by silica gel and Sephadex LH-20 column chromatography. PA was analyzed by Furier Transform Infrared Spectroscopy (FT-IR), Gas chromatograph-Mass Spectrometer (GC-MS), and Nuclear Magnetic Resonance (NMR). PA had potent antioxidant activity, as measured by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. Antitumor activity against MCF-7 human breast cancer cells was evaluated by the 3-(4,5-dimethylthazol-2-yl)-2,5-diphenyl tetrazolium-bromide (MTT) assay. PA treatment (0∼150 μM) dose-dependently blocked apoptosis, as shown by improved cell viability and inter-nucleosomal DNA fragmentation. Our findings suggest that Streptomyces lincolnensis M-20, a lincomycin producer, also produces protocatechualdehyde.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abe, N., Murata, T., and Hirota, A., 1.1-Diphenyl-2-picrylhydrazyl-radical scavengers, bisorbicillin and demethyltrichodimerol, from a fungus. Biosci. Biotechnol. Biochem. 62, 661–662 (1998).
Adelson, R., Saul, R. L., and Ames, B. N., Oxidative damage to DNA: Relation to species metabolic and life span. Proc. Natl. Acad. sci. USA. 85, 2706–2708 (1988).
Benzie, I.F.F. and Strain, J. J., The ferric reducing ability of plasma (FRAP) as a measure of antioxidant power: The FRAP assay. Anal. Biochem., 239, 70–76 (1996).
Berlett, B. S., Levine, R. L., Chock, P. B., Chevion, M., and Stadtman, E. R., Antioxidant activity of Ferrozine-ironamino acid complexes. Proc Natl Acad Sci USA., 98, 451–456 (2001).
Bisby, R. H. and Paker, A. W., Radiation-induced free radical reactions, in Poli, G., E. Albano and M. U. Dianzani (ed), Free radicals: From basic science to medicine, Birkhauser Verlag, Basel, Switzerland, pp. 31–37 (1993).
Blois, M. S., Antioxidant determination by the use of a stable free radical. Nature, 181, 1199–1200 (1985).
Britigan, B. E., Miller, R. A., Hassett, D. J., Pfaller, M. A., McCormick, M. L., and Rasmussen, G. T., Antioxidant enzyme expression in clinical isolates of pseudomonas aeruginosa: Identification of an atypical form of manganese superoxide dismutase. Infect Immun., 69, 7396–7401 (2001).
Cheeseman, M., Lipid peroxidation. An overview, In Poli, G., E. Albano and M. U. Dianzani (ed.), Free radicals: From basic science to medicine, Birkhuser Verlag, Basel, Switzerland. pp. 66–77 (1993).
Cynshi, O., Kawabe, Y., Suzuki, T., Takashima, Y., Kaise, H., Nakamura, M., Ohba, Y., Kato, Y., Tamura, K., Hayasaka, A. Higashida, A., Sakaguchi, H. Takeya, M., Takahashi, K., Inoue, K., Noguchi, N., Niki, E., and Kodama, T., Antiatherogenic effects of the antioxidant BO-653 in three different animal models. Proc Natl Acad Sci U S A. 95, 10123–10131 (1998).
Factor, V. M., Laskowska, D., Jensen, M. R., Woitach, J. T., Popescu, N. C., and Thorgeirsson, S. S., Vitamin E reduces chromosomal damage and inhibits hepatic tumor formation in a transgenic mouse model. Proc Natl Acad Sci USA. 97,2196–2201 (2000).
Garewal, H. S. and Meyskens, F. L., Chemoprevention of cancer. Hematol Oncol Clin North Am., 5, 69–77 (1991).
Hengartner, M. O., The biochemistry of apoptosis, Nature, 407, 770–776 (2000).
Kim, K. J., Yang, Y. J., and Kim, J. K., Purification and characterization of chitinase from Streptomyces sp. M-20. J. Biochem. Mol. Biol., 36, 185–189. (2003).
Klings, E. S. and Farber, H. W., Role of free radicals in the pathogenesis of acute chest syndrome in sickle cell disease. Respir. Res., 2, 280–285 (2001).
Malins, D. C., Hellström, K. E., Anderson, K. M., Johnson, P. M., and Vinson, M. A., Antioxidant-induced changes in oxidized DNA. Proc Natl. Acad. Sci, USA. 99, 5937–5941(2002).
Milano, J. and Day, B. J., A catalytic antioxidant metalloporphyrin blocks hydrogen peroxide-induced mitochondrial DNA damage. Nucleic Acids Res., 28, 968–973 (2000).
Pecker, L., (ed.). Antioxidant identification, characterization, and assay. In Meth. Enzymol. Vol. 234, Oxygen radicals in biological systems, Academic Press, San Diego, pp. 266–642 (1994).
Sawyer, D. T. and Valentine, J. S., How super is superoxide? Acc. Chem. Res., 14, 393. (1981).
Shaish A, Daugherty, A., O’sullivan, F., Schonfeld, G., and Heinecke, J. W., Beta-carotene inhibits atherosclerosis in hypercholesterolemic rabbits. J. Clin Invest., 96, 2075–2082 (1995).
Singh, A., Chemical and biochemical aspects of activated oxygen: singlet oxygen, superoxide anlon, and related species, In Miquel, J., A. T. Quintanilha, H. Weber (ed.), Handbook of free radicals and antioxidants in biomedicine, Vol. I, CRC Press, Boca Raton, Florida, pp. 17–24 (1989).
Tanaka, Y., Tran, P. O., Harmon, J., and Robertson, R. P., A role for glutathione peroxidase in protecting pancreatic β-cells against oxidative stress in a model of glucose toxicity. Proc Natl Acad Sci USA., 99, 12363–12368 (2002).
Tseng, T. H., Tsheng, Y. M., and Lee, Y. J., Cytotoxicity effects of di- and tri-hydroxybenzaldehydes as a chemopreventive potential agent on tumor cells. Toxicology, 161, 179–187 (2001).
Turley, J. M., Ruscetti, T., Mikovits, J. A., Bertolette, D. C., and Birchenall-Roberts, M. C., Vitamin E succinate induces Fas-mediated apoptosis in estrogen receptor-negative human breast cancer cells. Cancer Res., 57, 881–890 (1997).
Valko, M., Morris, H., Mazur, M., Rapta, P., and Bilton, R. F., Oxygen free radical generating mechanisms in the colon: Do the semiquinones of Vitamin K play a role in the aetiology of colon cancer?, Biochim. Biophys. Acta., 1527, 161–166 (2001).
Valko, M., Izakovic, M., Mazur, M., Rhodes, C. J., and Telser, J., Role of oxygen radicals in DNA damage and cancer incidence, Mol. Cell. Biochem., 266, 37–56 (2004).
Valko, C., Rhodes, J., Moncol, J., Izakovic, M., and Mazur, M., Free radicals, metals and antioxidants in oxidative stress-induced cancer, Chem. Biol. Interact., 160, 1–10(2006).
Wayner, D. D. M., Buton, G. W. Ingold, K. V., Barclay, L. R. C., and Locke, S. L., The relative contribution of vitamin E, urate, ascorbate and proteins to the total peroxy radicaltrapping antioxidant activity of human blood plasma. Biochem. biophy. Acta., 924, 408–419 (1987).
Xu, M., Zhang, Z., Fu, G., Sun, S., Sun, J., Yang, M., Liu, A., Han, J., and Guo, D., Liquid chromatography-tandem mass spectrometry analysis of protocatechuic aldehyde and its phase I and II metabolites in rat, J. Chromatogr. 856, 100–107 (2007).
Zhou, Z., Zhang, Y., Ding, X., Chen, S. H., Yang, J., Wang, X. J., Jia, G. L., Chen, H. S., Bo, X. C., and Wang, S. Q., Protocatechuic aldehyde inhibits hepatitis B virus replication both in vitro and in vivo. Antivir. Res., 74, 59–64 (2007).
Zhou, Z., Liu, Y., Miao, A. D., and Wang, S. Q., Protocatechuic aldehyde suppresses TNF-α-induced ICAM-1 and VCAM-1 expression in human umbilical vein endothelial cells. European Journal of Pharmacology, 513, 1–8 (2005).
Zou, C., Liebert, M., Zou, C. H., Grossman, B., and Lotan, R., Identification of effective retinoids for inhibiting growth and inducing apoptosis in bladder cancer cells, J. Urol., 165, 986–992 (2001).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, KJ., Kim, MA. & Jung, JH. Antitumor and antioxidant activity of protocatechualdehyde produced from Streptomyces lincolnensis M-20. Arch. Pharm. Res. 31, 1572–1577 (2008). https://doi.org/10.1007/s12272-001-2153-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-001-2153-7