Effect of secochiliolide acid isolated from the Patagonian shrub Nardophyllum bryoides as active component in antifouling paints

International Biodeterioration and Biodegradation

Volumn 89, Issue , 2014, Pages 37-44

  Pérez, Miriam ^a,b   García, Mónica ^a   Sánchez, Marianela ^c   Stupak, Mirta ^a   Mazzuca, Marcia ^d   Palermo, Jorge A ^c   Blustein, Guillermo ^a,b  

^a Centro de Investigacion y Desarrollo En Tecnologia de Pinturas   (Argentina)

^b UNIVERSIDAD NACIONAL DE LA PLATA   (Argentina)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^d UNIVERSIDAD NACIONAL DE LA PATAGONIA SAN JUAN BOSCO   (Argentina)

Author keywords

Nardophyllum bryoides; Secochiliolide acid; Soluble matrix antifouling paints; Terpenoids

Indexed keywords

ACTIVE COMPONENTS; ANTIFOULING PERFORMANCE; ENVIRONMENTAL CONCERNS; ETHANOLIC EXTRACTS; NARDOPHYLLUM BRYOIDES; SECONDARY METABOLITES; TERPENOIDS; TERRESTRIAL PLANTS;

MARINE BIOLOGY;

ANTIFOULING PAINT;

ANTIFOULING; BIOFOULING; BIOTECHNOLOGY; BRYOZOAN; COATING; COLONY; ORGANIC ACID; SECONDARY METABOLITE; SHRUB; SUSTAINABILITY; TERPENE;

ARGENTINA; BUENOS AIRES [ARGENTINA]; MAR DEL PLATA HARBOR;

EID: 84893470139     PISSN: 09648305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibiod.2014.01.009     Document Type: Article

References (84)

1. Alam M., Lee D. Cytotoxic and antimicrobial properties of furoflavones and furochalcones. J.Korean Soc. Appl. Biol. Chem. 2011, 54:725-730.
2. Angarano M., McMahon R., Hawkins D., Schetz J. Exploration of structure-antifouling relationships of capsaicin-like compounds that inhibit zebra mussel (Dreissena polymorpha) macrofouling. Biofouling 2007, 23:295-305.
3. Barboza G., Cantero J., Núñez C., Pacciaroni A., Ariza L. Medicinal plants: a general review and a phytochemical and ethnopharmacological screening of the native Argentine flora. Kurtziana 2009, 34:7-365.
4. Blihoghe D., Manzo E., Villela A., Cutignano A., Picariello G., Faimali M., Fontana A. Evaluation of the antifouling properties of 3-alyklpyridine compounds. Biofouling 2011, 27:99-109.
5. Blustein G., Pérez M., García M., Stupak M., Cerruti C. Reversible effect of potassium sorbate on Balanus amphitrite larvae. Potential use as antifoulant. Biofouling 2009, 25:573-580.
6. Bonifacino J. Nardophyllum cabrerae (Asteraceae: Astereae), a new species from Argentina and new taxonomic changes involving Nardophyllum Hook. Et. Arn. Taxon. 2005, 54:688-692.
7. Brango Vanegas J. Búsqueda de compuestos inhibidores de Quorum Sensing (IQS) a partir de extractos de origen natural 2011, Primera Fase. Tesis, Universidad Nacional de Colombia, Bogotá, Colombia, Facultad de Ciencias, Departamento de Química.
8. Casero C., Estévez-Braun A., Ravelo A., Demo M., Méndez-Álvarez S., Machín F. Achyrofuran is an antibacterial agent capable of killing methicillin- resistant vancomycin-intermediate Staphylococcus aureus in the nanomolar range. Phytomedicine 2013, 20:133-138.
9. Chen J., Feng D., Yang Z., Wang Z., Qiu Y., Lin Y. Antifouling metabolites from the mangrove plant Ceriops tagal. Molecules 2008, 13:212-219.
10. Chiruvella K., Mohammed A., Dampuri G., Ghanta R., Raghavan S. Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-o-glucoside isolated from callus cultures of Soymida febrifuga. Int. J. Biol. Sci. 2007, 3:269-278.
11. Clare A. Marine natural product antifoulants: status and potential. Biofouling 1996, 9:211-229.
12. Clare A. Towards nontoxic antifouling. J.Mar. Biotechnol. 1998, 6:3-6.
13. Clare A., Rittschof D., Hooper I., Bonaventura J. Antisettlement and narcotic action of analogues of diterpene marine natural product antifoulants from octocorals. Mar. Biotechnol. 1999, 1:427-436.
14. Da Gama B., Pereira R., Carvalho A., Coutinho R., Yoneshigue-Valentin Y. The effects of seaweed secondary metabolites on biofouling. Biofouling 2002, 18:13-20.
15. de Nys R., Givskov M., Kumar N., Kjelleberg S., Steinberg P. Furanones. Prog. Mol. Subcell. Biol. 2006, 42:55-86.
16. DellaGreca M., Florentino A., Isidoro M., Monaco P., Temussi M., Zarrelli A. Antialgal furano-diterpenes from Potamogeton natans L. Phytochemistry 2001, 58:299-304.
17. Dobretsov S., Dahms H.-U., YiLi H., Wahl M., Qian P. The effect of quorum-sensing blockers on the formation of marine microbial communities and larval attachment. FEMS Microbiol. Ecol. 2007, 60:177-188.
18. D'Almeida R., Zampini I., Isla M. Phytochemical and biological study of Nardophyllum armatum Wedd. extracts. Boletín Latinoam. del Caribe Plantas Med. Aromáticas 2007, 5:242-243.
19. D'Almeida R., Alberto M., Zampini I., Ordoñez R., Isla M. Actividad de extractos alcohólicos de Nardophyllum armatum (Wedd.) Reiche (Asteraceae) de dos áreas geográficas de la Puna argentina sobre microorganismos fitopatógenos. Lilloa 2011, 48:17-25.
20. Etoh H., Kondoh T., Noda R., Singh I., Sekiwa Y., Morimitsu K., Kubota K. Shogaols from Zingiber officinale as promising antifouling agents. Biosci. Biotechnol. Biochem. 2002, 66:1748-1750.
21. Evans S. TBT or not TBT?. That is the question. Biofouling 1999, 14:117-129.
22. Faimali M., Falugi F., Gallus L., Piazza V., Tagliafierro G. Involvement of ACh in settlement process of Balanus amphitrite. Biofouling 2003, 19:213-220.
23. Feng D., Ke C., Lu C., Li S. Herbal plants as a promising source of natural antifoulants: evidence from barnacle settlement inhibition. Biofouling 2009, 25:181-190.
24. Floerl O., Pool T., Inglis G. Positive interactions between nonindigenous species facilitate transport by human vectors. Ecol. Appl. 2004, 14:1724-1736.
25. Floerl O., Inglis G., Marsh H. Selectivity in vector management: an investigation of the effectiveness of measures used to prevent transport of nonindigenous species. Biol. Invasions 2005, 7:459-475.
26. Foster M., Harrold C., Hardin D. Points versus photo quadrat estimates of the cover of sessile marine organisms. J.Exp. Mar. Biol. Ecol. 1991, 146:193-203.
27. Gavin N., Durako M. Localization and antioxidant capacity of flavonoids from intertidal and subtidal Halophila johnsonii and Halophila decipiens. Aquat. Bot. 2011, 95:242-247.
28. Göransson U., Sjogren M., Svangard E., Claeson P., Bohlin L. Reversible antifouling effect of the cyclotide cycloviolacin O2 against barnacles. J.Nat. Prod. 2004, 67:1287-1290.
29. Harada A., Sakata K., Ina H. Isolation and identification of xanthatin as an anti-attaching repellent against blue mussel. Agric. Biol. Chem. 1985, 49:1887-1888.
30. Hellio C., Bremer G., Pons A., Le Gal Y., Bourbougnon N. Inhibition of the development of microorganisms (bacteria and fungi) by extracts of marine algae from Brittany (France). Appl. Microbiol. Biotechnol. 2000, 54:543-549.
31. Hellio C., Tsoukatou M., Maréchal J., Aldred N., Beaupoil C., Clare A., Vagias C., Roussis V. Inhibitory effects of Mediterranean sponge extracts and metabolites on larval settlement of the barnacle Balanus amphitrite. Mar. Biotechnol. 2005, 7:297-305.
32. Hyodo S., Etoh H., Yamashita N., Sakata K., Ina K. Structure of resinosides from Eucalyptus resinifera as repellents against the blue mussel, Mytilus edulis. Biosci. Biotechnol. Biochem. 1992, 56:138.
33. Iyapparaj P., Ramasubburayan R., Raman T., Das N., Kumar P., Palavesam A., Immanuel G. Evidence for the antifouling potentials of marine macroalgae Sargassum wightii. Adv. Nat. Appl. Sci. 2012, 6:153-162.
34. Jakupovic J., Banerjee S., Bohlmann F., King R., Robinson H. New diterpenes from Chiliotrichium rosmarinifolium and Nardophyllum lanatum. Tetrahedron 1986, 42:1305-1313.
35. Kamal M., Shakya A., Jawaid T. Benzofurans: a new profile of biological activities. Int. J. Med. Pharm. Sci. 2011, 3:1-5.
36. Keifer P., Reinhart L., Hooper I. Renillafoulings, antifouling diterpenes from the sea pansy Renilla reniformis (Octocorallia). J.Org. Chem. 1986, 51:4450-4454.
37. Leer-Andersen M., Larsson L. An experimental/numerical approach for evaluating skin friction on fullscale ships with surface roughness. J.Mar. Sci. Technol. 2003, 8:26-36.
38. Lejars M., Margaillan A., Bressy C. Fouling release coatings: a nontoxic alternative to biocidal antifouling coatings. Chem. Rev. 2012, 112:4347-4390.
39. Lewthwaite J., Molland A., Thomas K. An investigation into the variation of ship skin frictional resistance with fouling. Transact. Royal Inst. Nav. Archit. 1985, 127:269-284.
40. Li Y., Wu H., Xu Y., Shao C., Wang C., Qian P. Antifouling activity of secondary metabolites isolated from Chinese Marine organisms. Mar. Biotechnol. 2013, 10.1007/s10126-013-9502-7.
41. Lin W., Lu C., Ye Y. Toxicity of crude extracts from several terrestrial plants to barnacle larvae on mangrove seedlings. Ecol. Eng. 2009, 35:502-510.
42. Lowery C., Abe T., Park J., Eubanks L., Sawada D., Kaufmann G., Janda K. Revisiting AI-2 quorum sensing inhibitors: direct comparison of alkyl-DPD analogues and a natural product fimbrolide. J.Am. Chem. Soc. 2009, 131:15584-15585.
43. Maréchal J., Hellio C. Challenges for the development of new non-toxic antifouling solutions. Int. J. Mol. Sci. 2009, 10:4623-4637.
44. Minchin D., Gollasch S. Fouling and ships' hulls: how changing circumstances and spawning events may result in the spread of toxic species. Biofouling 2003, 19:111-122.
45. Nguyen X., Longeon A., Pham V., Urvois F., Bressy C., Trinh T., Nguyen H., Phan V., Chau V., Briand J., Bourguet-Kondracki M. Antifouling 26,27-cyclosterols from the Vietnamese marine sponge Xestospongia testudinaria. J.Nat. Prod. 2013, 76:1313-1318.
46. Ovesen R., Brandt K., Göransson U., Nilesen J., Hansen H., Cedergreen N. Biomedicine in the environment: cyclotides constitute potent natural toxins in plants and soil bacteria. Environ. Toxicol. Chem. 2011, 30:1190-1196.
47. Pérez M., García M., Blustein G., Stupak M. Tannin and tannate from the quebracho tree: an eco-friendly alternative for controlling marine biofouling. Biofouling 2007, 23:151-159.
48. Pinori E., Berglin M., Brive L., Hulander M., Dahlström M., Elwing H. Multi-seasonal barnacle (Balanus improvisus) protection achieved by trace amounts of a macrocyclic lactone (ivermectin) included in rosin-based coatings. Biofouling 2011, 27:941-953.
49. Qian P.-Y., Xu S. Antifouling activity of marine natural products. Handbook of Marine Natural Products 2012, 749-816. Springer Science+Business Media B.V, Dordrecht, Netherlands. E. Fattorusso, W. Gerwick, O. Taglialatela-Scafati (Eds.).
50. Raveendran T., Limna Mol V. Natural product antifoulants. Curr. Sci. 2009, 97:509-520.
51. Rittschof D. Natural product antifoulants and coatings development. Marine Chemical Ecology 2001, 543-566. CRC Press, Boca Raton. J.B. McClintock, B.J. Baker (Eds.).
52. Samir A., Abdelgaleil Okamura H., Iwagawa T., Sato A. Antifeedants from Khaya senegalensis. Tetrahedron 2001, 57:119-126.
53. Sánchez M., Mazzuca M., Veloso M., Fernández L., Siless G., Puricelli L., Palermo J. Cytotoxic terpenoids from Nardophyllum bryoides. Phytochemistry 2010, 71:1395-1399.
54. Sardari S., Nishibe S., Daneshtalab M. Coumarins, the bioactive structures with antifungal property. Stud. Nat. Prod. Chem. 2000, 23:335-393.
55. Sawant S., Wagh A. Studies on the antifouling properties of some natural products from Goa. Recent Developments in Biofouling Control 1994, 275-282. Oxford and IBH Publishing Company, New Delhi. M. Thompson, R. Nagabhushanam, R. Sarojini, M. Fingerman (Eds.).
56. Sawant S., Wagh A. Terrestrial plants: a potential source for isolation of eco-friendly antifouling compounds. Proceedings of Emerging Nonmetallic Materials for the Marine Environment, Honolulu, HI, USA 1997.
57. Sawant S., Sonak S., Garg A. Growth inhibition of fouling bacteria and diatoms by extracts of terrestrial plant, Derris scandens (Dicotyledonae: Leguminocae). Indian J. Mar. Sci. 1995, 24:229-230.
58. Schultz M. Effects of coating roughness and biofouling on ship resistance and powering. Biofouling 2007, 23:331-341.
59. Schultz M., Bendick J., Holm E., Hertel W. Economic impact of biofouling on a naval surface ship. Biofouling 2011, 27:87-98.
60. Shao C., Wu H., Wang C., Liu Q., Xu Y., Wei M., Qian P., Gu Y., Zheng C., She Z., Lin Y. Potent antifouling resorcylic acid lactones from the gorgonian-derived fungus Cochliobolus lunatus. J.Nat. Prod. 2011, 74:629-633.
61. Shapiro S., Wilk M. An analysis of variance test for normality (complete samples). Biometrika 1965, 52:591-611.
62. Siless E., Lozano E., Sánchez M., Mazzuca M., Sosa A., Palermo A. Preparation and antitrypanosomal activity of secochiliolide acid derivatives. Bioorganic Med. Chem. Lett. 2013, 23:4964-4967.
63. Singh I., Takahashi K., Etoh H. Potent attachment-inhibiting and -promoting substances for the blue mussel, Mytilus edulis galloprovincialis, from two species of Eucalyptus. Biosci. Biotechnol. Biochem. 1996, 60:1522-1523.
64. Sjögren M., Dahlström M., Hedner E., Jonsson R., Vik A., Gundersen L.-L., Bohlin L. Antifouling activity of the sponge metabolite agelasine D and synthesized analogs on Balanus improvisus. Biofouling 2008, 24:251-258.
65. Steinberg P., de Nys R. Chemical mediation of colonization of seaweed surfaces. J.Phycol. 2002, 38:621-629.
66. Steinberg P., Schneider R., Kjelleberg S. Chemical defenses of seaweeds against microbial colonization. Biodegradation 1997, 8:211-220.
67. Stupak M., García M., Pérez M. Non-toxic alternative compounds for marine antifouling paints. Int. Biodeterior. Biodegrad. 2003, 52:49-52.
68. Takasawa R., Etoh H., Yagi A., Sakata K., Ina K. Nonylphenols as promising antifouling agents found by a simple bioassay method using the blue mussel, Mytilus edulis. Agric. Biol. Chem. 1990, 54:1607-1610.
69. Tan L., Goh P., Tripathi A., Lim M., Dickinson G., Lee S., Teo S. Natural antifoulants from the marine cyanobacterium Lyngbya majuscula. Biofouling 2010, 26:685-695.
70. Thomas K., Brooks S. The environmental fate and effects of antifouling paint biocides. Biofouling 2010, 26:73-88.
71. Tran T., Nguyen T., Do T., Huynh T., Tran C., Thai K. Synthesis and antibacterial activity of some heterocyclic chalcone analogues alone and in combination with antibiotics. Molecules 2012, 17:6684-6696.
72. Tsoukatou M., Philippe Maréchal J., Hellio C., Novaković I., Tufegdzic S., Sladić D., Gasić M., Clare A., Vagias C., Roussis V. Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms. Molecules 2007, 12:1022-1034.
73. Viju N., Satheesha S., Vincenta S. Antibiofilm activity of coconut (Cocos nucifera Linn.) husk fibre extract. Saudi J. Biol. Sci. 2013, 20:85-91.
74. Villa F., Albanese D., Giussani B., Stewart P., Daffonchio D., Cappitelli F. Hindering biofilm formation with zosteric acid. Biofouling 2010, 26:739-752.
75. Wang Z., Feng D., Ke C. Coumarins from the herb Cnidium monnieri and chemically modified derivatives as antifoulants against Balanus albicostatus and Bugula neritina larvae. Int. J. Mol. Sci. 2013, 14:1197-1206.
76. Waridel P., Wolfender J., Lachavanne Hostettmann K. ent-Labdane diterpenes from the aquatic plant Potamogeton pectinatus. Phytochemistry 2003, 64:1309-1317.
77. Widelski J., Popova M., Graikou K., Glowniak K., Chinou I. Coumarins from Angelica lucida L. Antibacterial activities. Molecules 2009, 14:2729-2734.
78. Xu Q., Barrios C., Cutright T., Newby B. Assessment of antifouling effectiveness of two natural product antifoulants by attachment study with freshwater bacteria. Environ. Sci. Pollut. Res. 2005, 12:278-284.
79. Xu Q., Barrios C., Cutright T., Newby B. Evaluation of toxicity of capsaicin and zosteric acid and their potential application as antifoulants. Environ. Toxicol. 2005, 20:467-474.
80. Xu Y., He H., Schulz S., Liu X., Fusetani N., Xiong H., Xiao X., Qian P. Potent antifouling compounds produced by marine Streptomyces. Bioresour. Technol. 2010, 101:1331-1336.
81. Yamashita N., Etoh H., Sakata K., Ina H., Ina K. New acylated rhaponticin isolated from Eucalyptus rubida as a repellent against the blue mussel Mytilus edulis. Agric. Biol. Chem. 1986, 53:2827-2829.
82. Yamashita N., Etoh H., Sakata K., Yagi A., Ina H., Ina K. An acylated kaempferol glucoside isolated from Quercm dentata as a repellent against the blue mussel Mytilus edulis. Agric. Biol. Chem. 1989, 35:1383-1385.
83. Yoshioka A., Etoh H., Yagi A., Sakata K., Ina K. Isolation of flavonoids and cerebrosides from the bark of Prunus jamasakura as repellents against the blue mussel, Mytilus edulis. Agric. Biol. Chem. 1990, 54:3355-3356.
84. Zhou X., Zhang Z., Xu Y., Jin C., He H., Hao X., Qian P. Flavone and isoflavone derivatives of terrestrial plants as larval settlement inhibitors of the barnacle Balanus amphitrite. Biofouling 2009, 25:69-76.