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Biofouling
The Journal of Bioadhesion and Biofilm Research
Volume 30, 2014 - Issue 4
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Articles

Nontoxic piperamides and their synthetic analogues as novel antifouling reagents

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Pages 473-481 | Received 25 Sep 2013, Accepted 27 Jan 2014, Published online: 25 Mar 2014

References

  • Al-Adhroey AH, Nor ZM, Al-Mekhlafi HM, Mahmud R. 2010. Ethnobotanical study on some Malaysian anti-malarial plants: a community based survey. J Ethnopharmacol. 132:362–364.
  • ASTM. 1993. Practice for determination of hydrolysis rate constants of organic chemicals in aqueous solutions. ASTM standards on aquatic toxicology and hazard evaluation, E895–E889. Philadelphia (PA): ASTM STP 634; p. 336–340.
  • Carpizo-Ituarte E, Hadfield MG. 1998. Stimulation of metamorphosis in the polychaete Hydroides elegans Haswell (Serpulidae). Biol Bull. 194:14–24.
  • Chandramouli KH, Dash S, Zhang Y, Ravasi T, Qian PY. 2013. Proteomic and metabolic profiles of marine Vibrio sp. 010 in response to an antifoulant challenge. Biofouling. 29:789–802.
  • Dobretsov S, Dahms HU, Qian PY. 2006. Inhibition of biofouling by marine microorganisms and their metabolites. Biofouling. 22:43–54.
  • Dobretsov S, Xiong HR, Xu Y, Levin LA, Qian PY. 2007. Novel antifoulants: inhibition of larval attachment by proteases. Mar Biotechnol. 9:388–397.
  • Fitridge I, Dempster T, Guenther J, DeNys R. 2012. The impact and control of biofouling in marine aquaculture: a review. Biofouling. 28:649–669.
  • Fusetani N. 2004. Biofouling and antifouling. Nat Prod Rep. 21:94–104.
  • Ghosh K, Bhattacharya TK. 2005. Chemical constituents of Piper betle Linn. (Piperaceae) roots. Molecules. 10:798–802.
  • Guha P. 2006. Betel leaf: the neglected green gold of India. J Hum Ecol. 19:87–93.
  • Harder TN, Thiyagarajan V, Qian PY. 2001. Effect of cyprid age on the settlement of Balanus amphitrite Darwin in response to natural biofilms. Biofouling. 17:211–219.
  • Jorge P, Louranco A, Pereira O. 2012. New trends in peptide-based anti-biofilm strategies: a review of recent developments and bioinformatic approaches. Biofouling. 28:1033–1061.
  • Kimmel CB, Ballard WW, Kimmel SR, Ullmann B, Schilling TF. 1995. Stages of embryonic development of the zebrafish. Dev Dynamics. 203:253–310.
  • Kiuchi F, Nakamura N, Tsuda Y, Kondo K, Yoshimura H. 1988. Studies on crude drugs effective on visceral larvae migrans. IV, isolation and identification of larvicidal principles in pepper. Chem Pharm Bull. 36:2452–2465.
  • Kiuchi F, Nishizawa S, Kawanishi H, Kinoshita S, Ohsima H, Uchitani A, Sekino N, Ishida M, Kondo K, Tsuda Y. 1992. Nematocidal activity of long alkyl chain amides, amines, and their derivatives on dog roundworm larvae. Chem Pharm Bull. 40:3234–3244.
  • Kiuchi F, Nakamura N, Saitoh M, Komagome K, Hiramatsu H, Takimoto N, Akao N, Kondo K, Tsuda Y. 1997. Synthesis and nematocidal activity of aralkyl- and aralkenylamides related to piperamide on second-stage larvae of Toxocara canis. Chem Pharm Bull. 45:685–696.
  • Konstantinou IK, Albanis TA. 2004. Worldwide occurrence and effects of antifouling paint booster biocides in the aquatic environment. Environ Int. 30:235–248.
  • Kumar N, Misra P, Dube A, Bhattacharya S, Dikshit M, Ranade S. 2010. Piper betle Linn. a maligned Pan-Asiatic plant with an array of pharmacological activities and prospects for drug discovery. Curr Sci. 99:922–932.
  • Li YX, Zhang FY, Xu Y, Matsumura K, Han Z, Liu LL, Lin WH, Jia YX, Qian PY. 2012. Structural optimization and evaluation of butenolides as potent antifouling agents: modification of the side chain affects the biological activities of compounds. Biofouling. 28:857–864.
  • Pei YQ. 1983. A review of pharmacology and clinical use of piperine and its derivatives. Epilepsia. 24:177–182.
  • Qian PY, Pechenik JA. 1998. Effects of larval starvation and delayed metamorphosis on juvenile survival and growth of the tube-dwelling polychaete Hydroides elegans (Haswell). J Exp Mar Biol Ecol. 227:169–185.
  • Qian PY, Xu Y, Fusetani N. 2010. Natural products as antifouling compounds: recent progress and future perspectives. Biofouling. 26:223–234.
  • Qian P-Y, Chen L, Xu Y. 2013. Mini-review: Molecular mechanisms of antifouling compounds. Biofouling. 29:381–400.
  • Rathee JS, Patro BS, Mula S, Gamre S, Chattopadhyay S. 2006. Antioxidant activity of Piper betel leaf extract and its constituents. J Agric Food Chem. 54:9046–9054.
  • Rowa LCM, Hob JC. 2009. The antimicrobial activity, mosquito larvicidal activity, antioxidant property and tyrosinase inhibition of Piper betle. J Chin Chem Soc. 56:653–658.
  • Schultz MP, Bendick JA, Holm ER, Hertel WM. 2011. Economic impact of biofouling on a naval surface ship. Biofouling. 27:87–98.
  • Sievers M, Fitridge I, Dempster T, Keough MJ. 2013. Biofouling leads to reduced shell growth and flesh weight in the cultured mussel Mytilis galloprovincialis. Biofouling. 29:97–107.
  • Singh M, Shakya S, Soni VK, Dangi A, Kumar N, Bhattacharya SM. 2009. The n-hexane and chloroform fractions of Piper betle L. trigger different arms of immune responses in BALB/c mice and exhibit antifilarial activity against human lymphatic filarid Brugia malayi. Int Immunopharmacol. 9:716–728.
  • Strunz GM, Finlay H. 1994. Concise, efficient new synthesis of pipercide, an insecticidal unsaturated amide from Piper nigrum, and related compounds. Tetrahedron. 50:11113–11122.
  • Surrinder K, Jawahir LK, Subhash CT, Kanaya LD, Deshvir SJ, Kuldeep S, Rashmeet KR, Jaswant S. 2000. Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities. Bioorg & Med Chem. 8:251–268.
  • Torsten H. 2007. Capsaicin derivates and the production and use thereof. European Patent. 1670310:B1.
  • Virinder SP, Subhash CJ, Sangita G, Sangeeta T, Vivek KR, Rajesh K, Abul A, Sanjay M, Naresh K, Rajni J, et al. 1998. Polyphenols and alkaloids from Piper species. Phytochemistry. 38:1069–1078.
  • Wang K, Xiao L, Yu XY, Chen ZT, Yu HJ, Gui TJ. 2010. Discussion on the influence of biocides on marine environment. China Coatings. 25:24–30.
  • Westerfield M. 1995. The zebrafish book: a guide for the laboratory use of zebrafish (Danio rerio), 3rd ed. Eugene (OR): University of Oregon Press. Chapter 2, Breeding; p. 2.1–2.10.
  • Zar JH. 1996. Biostatistical analysis, 4th ed. Englewood Cliffs (NJ): Prentice Hall. p. 279.
  • Zhou XJ, Okamura H, Nagata S. 2007. Abiotic degradation of triphenylborane pyridine (TPBP) antifouling agent in water. Chemosphere. 67:1904–1910.
  • Zhou XJ, Zhang Z, Xu Y, Jin CL, He HP, Hao XJ, Qian PY. 2009. Flavone and isoflavone derivatives of terrestrial plants as larval settlement inhibitors of the barnacle Balanus amphitrite. Biofouling. 25:69–76.

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