Korean Journal of Chemical Engineering, Vol.26, No.2, 433-437, March, 2009
Molecular design of anti-biofouling materials from natural phenolic compounds
E-mail:
Many natural phenolic compounds found in plants are well known for their antibiotic and antioxidant activities. It has been hypothesized that these activities of natural phenols could be used for developing permanent antibiofouling coatings. In this study, two phenolic components, anacardic acid and cardanol, were extracted from cashew nut shell liquid, and tested for their antibiotic and anti-biofouling activities against Pseudomonas fluorescens. Both compounds killed all the cells within 18 hours (anacardic acid) and 30 hours (cardanol) after the addition to the culture media at a concentration of 800 μg/ml. To form a stable permanent coating of these compounds, first they were polymerized by enzymatic polymerization, and the polymers were cross-linked on a glass slide. P. fluorescens were cultured on the coated and uncoated glasses for two weeks, and the images of the cells grown on the surfaces were taken by SEM. The coated surfaces clearly demonstrated anti-biofouling activities, showing not only fewer numbers of cells but also less exopolymer than the uncoated surfaces. Based on these results, a phenolic compound with a similar structure of anacardic acid was synthesized by using propylene diamine and fluorocarboxylic acid with cardanol. The synthesized phenolic compound was polymerized and cross-linked on a glass slide to test the anti-biofouling activity. The SEM images of the cells on the coated surface showed considerable decreases in the number of adhered cells and the amount of exopolymers even more than the anacardic acid and cardanol coatings. It is thought that the natural phenolic compounds with active functional groups can be used for anti-biofouling agents.
- Davidson PM, in Antimicrobials in foods, Branen AL, Davidson PM Eds., Marcel Dekker, New York (1983)
- Kozubek A, Zarnowski R, Stasiuk M, Gubernator J, Cell Mol. Biol. Lett., 6, 351 (2001)
- Krinsky NI, Proc. Soc. Exp. Biol. Med., 200, 248 (1992)
- Chen L, Lu Q, Go VL, Heber D, Ma L, J. Clin. Mcrobiol., 43, 3574 (2005)
- Heim KE, Tagliaferro AR, Bobilya DJ, J. Nutr. Biochem., 13, 572 (2002)
- Harborne JB, Williams CA, Phytochem., 55, 481 (2000)
- Regelson W, Formica JV, Fd. Chem. Toxic., 33, 1061 (1995)
- Kalus JS, Piotrowski AA, Fortier CR, Liu X, Kluger J, White CM, Ann. Pharmacother., 37, 345 (2003)
- Balasubashini MS, Rukkumani R, Viswanathan P, Menon VP, Phytother. Res., 18, 310 (2004)
- Kubo J, Lee JR, Kubo I, J. Agric. Food Chem., 47, 533 (1999)
- Himejima M, Kubo I, J. Agric. Food Chem., 39, 418 (1991)
- Fiuza SM, Gomes C, Teixeira LJ, Girao da Cruz MT, Cordeiro MNDS, Milhazes N, Borges F, Marques MPM, Bioorg. Med. Chem., 12, 3581 (2004)
- Kubo I, Ochi M, Vieira PC, Komatsu S, J. Agric. Food Chem., 41, 1012 (1993)
- Kubo I, Chen QX, Nihei KI, Food Chem., 81, 241 (2003)
- Paramashivappa R, Phani KP, Vithayathil PJ, Rao AS, J. Agric. Food Chem., 49, 2548 (2001)
- Lebert I, Begot C, Lebert A, Int. J. Food Microbiol., 39, 53 (1998)
- Kim YH, An ES, Song BK, Kim DS, Chelikani R, Biotechnol. Lett., 25(18), 1521 (2003)
- Chelikani R, Kim YH, Yoon DY, Kim DS, Appl. Biochem. Biotechnol. In press.
- Rozee KR, Cooper D, Lam K, Costerton JW, Appl. Environ. Microbiol., 43, 1451 (1982)
- Santos M, Roy BC, Goicoechea C, Campiglia AD, Mallik S, J. Am. Chem. Soc., 126(34), 10738 (2004)
- Green TW, Wuts PGM, Protective groups in organic synthesis, 2nd ed., Wiley, New York (1999)
- Bergbreiter DE, Hughes R, Besinaiz J, Li CM, Osburn PL, J. Am. Chem. Soc., 125(27), 8244 (2003)
- Ikeda R, Tanaka H, Uyama H, Kobayashi S, Macromol. Rapid Commun., 21(8), 496 (2000)
- Lee HJ, Han DG, Lee SH, Yoo JW, Baek SH, Lee EK, Korean J. Chem. Eng., 15(1), 71 (1998)