Algicidal activity of stilbene analogues

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 19, 2008, Pages 9140-9145

  Mizuno, Cassia S ^a   Schrader, Kevin K ^a   Rimando, Agnes M ^a  

^a NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

Author keywords

Algicide; Cyanobacteria; Off flavor; Pterostilbene; Resveratrol; Stllbenes

Indexed keywords

2 METHYLISOBORNEOL; 2-METHYLISOBORNEOL; BORNANE DERIVATIVE; STILBENE DERIVATIVE;

ANIMAL; ARTICLE; CATFISH; DRUG EFFECT; METABOLISM; OSCILLATORIA; SYNTHESIS; TASTE;

ANIMALS; BORNANES; ICTALURIDAE; OSCILLATORIA; STILBENES; TASTE;

CYANOBACTERIA; OSCILLATORIA PERORNATA;

EID: 54349098071     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf801988p     Document Type: Article

References (33)

1. Schrader, K. K.; Nanayakkara, N. P. D.; Tucker, C. S.; Rimando, A. M.; Ganzere, M.; Schaneberg, B. T. Novel derivatives of 9,10-anthraquinone are selective algicides against the musty-odor cyanobacterium Oscillatoria perornata. Appl. Environ. Microbiol. 2003, 69, 5319-5327.
2. Zimba, P. V.; Grimm, C. C. A synoptic survey of musty/muddy odor metabolites and microcystin toxin occurrence and concentration in southeastern USA channel catfish (Ictalurus punctatus Ralfinesque) production ponds. Aquaculture 2003, 218, 81-87.
3. Paerl, H. W.; Tucker, C. S. Ecology of blue-green algae in aquaculture ponds. J. World Aquacult. Soc. 1995, 26, 109-131.
4. Howgate, P. Tainting of farmed fish by geosmin and 2-methyl-iso-borneol: A review of sensory aspects and of uptake/depuration. Aquaculture 2004, 234, 155-181.
5. Tucker, C. S. Off-flavor problems in aquaculture. Rev. Fish. Sci. 2000, 8, 45-88.
6. Martin, J. F.; Izaguirre, G.; Waterstrat, P. A planktonic Oscillatoria species from Mississippi catfish ponds that produces the off-flavor compound 2-methylisoborneol. Water Res. 1991, 25, 1447-1451.
7. Stivala, L. A.; Savio, M.; Carafoli, F.; Perucca, P.; Bianchi, L.; Maga, G.; Forti, L.; Pagnoni, U. M.; Albini, A.; Prosperi, E.; Vannini, V. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. J. Biol. Chem. 2001, 276, 22586-22594.
8. Kimura, Y.; Okuda, H.; Arichi, S. Effects of stilbenes on arachidonate metabolism in leukocytes. Biochim. Biophys. Acta 1985, 834, 275-278.
9. Mannila, E.; Talvitie, A.; Kolehmainen, E. Antileukemic compounds derived from stilbenes in Picea abies bark. Phytochemistry 1993, 33, 813-816.
10. Mahady, G. B.; Pendland, S. L.; Chadwick, L. R. Resveratrol and red wine extracts inhibit the growth of CagA+ strains of Helicobacter pylori in vitro. Am. J. Gastroenterol. 2003, 98, 1440-1441.
11. Creasy, L. L.; Coffee, M. Phytoalexin production potential of grape berries. J. Am. Soc. Hortic. Sci. 1988, 113, 230-234.
12. Chung, M. I.; Teng, C. M.; Cheng, K. L.; Ko, F. N.; Lin, C. N. An antiplatelet principle of Veratrum formosanum. Planta Med. 1992, 58, 274-276.
13. Inamori, Y.; Kubo, M.; Tsujibo, H.; Ogawa, M.; Saito, Y.; Miki, Y.; Takemura, S. The ichthyotoxicity and coronary vasodilator action of 3,3′-dihydroxy-alpha,beta-diethylstilbene. Chem. Pharm. Bull. (Tokyo) 1987, 35, 887-890.
14. Schneider, Y.; Duranton, B.; Gosse, F.; Schleiffer, R.; Seiler, N.; Raul, F. Resveratrol inhibits intestinal tumorigenesis and modulates host-defense-related gene expression in an animal model of human familial adenomatous polyposis. Nutr. Cancer 2001, 39, 102-107.
15. Arlt, H. G., Jr.; Conroy, N. E. Algicidal 2,2′- methylenebis(trans-3,5-dihydroxystilbene). U.S. Patent 3,531,533, 1970.
16. Sheers, E. H. trans-3,5-Dihydroxystilbene as algicide. U.S. Patent 3,577,230, 1971.
17. Mizuno, C. S.; Ma, G.; Khan, S.; Patny, A.; Avery, M. A.; Rimando, A. M. Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPAR alpha. Bioorg. Med. Chem. 2008, 16, 3800-3808.
18. Orsini, F.; Pelizzoni, F.; Bellini, B.; Miglierini, G. Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series). Carbohydr. Res. 1997, 301, 95-109.
19. De Medina, P.; Casper, R.; Savouret, J.-F.; Poirot, M. Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators. J. Med. Chem. 2005, 48, 287-291.
20. Zhang, J.-T.; Dai, W.; Harvey, R. G. Synthesis of higher oxidized metabolites of dibenz[a,j]anthracene implicated in the mechanism of carcinogenesis. J. Org. Chem. 1998, 63, 8125-8132.
21. Pettit, G. R.; Grealish, M. P.; Jung, M. K.; Hamel, E.; Pettit, R. K.; Chapuis, J. C.; Schmidt, J. M. Antineoplastic agents. 465. Structural modification of resveratrol: Sodium resverastatin phosphate. J. Med. Chem. 2002, 45, 2534-2542.
22. Conner, S. E.; Mantlo, N. B.; Zhu, G.; Herr, R. J. Preparation of bicyclic derivatives as PPAR modulators. WO 2005/066136 A1.
23. Hasegawa, J.-Y.; Hamada, M.; Miyamoto, T.; Nishide, K.; Kajimoto, T.; Uenishi, J.-I.; Node, M. The application of phenylmethanethiol and benzenethiol derivatives as odorless organo-sulfur reagents in the synthesis of thio-sugars and thioglycosides. Carbohydr. Res. 2005, 340, 2360-2368.
24. Boyd, C. E.; Tucker, C. S. Pond Aquaculture Water Quality Management; Boyd, C. E., Tucker, C. S., Eds.; Kluwer Academic Publishers: Massachusetts, 1998; 700 pp.
25. Schrader, K. K.; de Regt, M. Q.; Tidwell, P. D.; Tucker, C. S.; Duke, S. O. Compounds with selective toxicity towards the off-flavor metabolite-producing cyanobacterium Oscillatoria cf. chalybea. Aquaculture 1998, 163, 85-99.
26. Langcake, P. Disease resistance of Vitis spp. and the production of the stress metabolites resveratrol, e-viniferin a-viniferin and pterostilbene. Physiol. Plant Pathol. 1981, 18, 213-226.
27. Alessandro, M.; Di Marco, S.; Osti, F.; Cesari, A. Bioassays on the activity of resveratrol, pterostilbene and phosphorous acid towards fungi associated with esca of grapevine. Phytopathol. Mediterr. 2000, 39, 357-365.
28. Jung, H. J.; Seu, Y. B.; Lee, D. G. Candicidal action of resveratrol isolated from grapes on human pathogenic yeast C. albicans. J. Microbiol. Biotechnol. 2007, 17, 1324-1329.
29. Kukric, Z. Z.; Topalic-Trivunovic, L. N. Antibacterial activity of cis- and trans-resveratrol isolated from Polygonum cuspidatum rhizome. Acta Period. Technol. 2006, 37, 131-136.
30. Lu, C.-C.; Lai, H.-C.; Hsieh, S.-C.; Chen, J.-K. Resveratrol ameliorates Serratia marcescens-induced acute pneumonia in rats. J. Leukocyte Biol. 2008, 83, 1028-1037.
31. Jung, H. J.; Hwang, I. A.; Sung, W. S.; Kang, H.; Kang, B. S.; Seu, Y. B.; Lee, D. G. Fungicidal effect of resveratrol on human infectious fungi. Arch. Pharmacal Res. 2005, 28, 557-560.
32. Kedzierski, L.; Curtis, J. M.; Kaminska, M.; Jodynis-Liebert, J.; Murias, M. In vitro antileishmanial activity of resveratrol and its hydroxylated analogues against Leishmania major promastigotes and amastigotes. Parasitol. Res. 2007, 102, 91-97.
33. Crowell, J. A.; Korytko, P. J.; Morrissey, R. L.; Booth, T. D.; Levine, B. S. Resveratrol-associated renal toxicity. Toxicol. Sci. 2004, 82, 614-619.