Abstract
A scalable procedure was developed for the extraction and purification of pachydictyol A, the main diterpenoid isolated from the brown alga Dictyota dichotoma. The organic extract of this species is a complex mixture of a large variety of diterpenes, and in this work, the protocol was employed successfully for the purification of gram quantities of this compound from Patagonian D. dichotoma collected from algal wash. Pachydictyol A, together with other minor diterpenoids, was tested for antifouling activity against the invading freshwater mussel Limnoperna fortunei, using a byssal thread formation assay. The results obtained in the study showed a potent antifouling activity for pachydictyol A at 4.7 μg cm−2 disk load. As for the other diterpenoids, dictyoxide was also considerably active, while dictyol C and dictyotadiol had a considerably lower activity. Taking into account the large biomass of algal wash and the abundance of D. dichotoma, together with the effectiveness of the purification protocol, these results show that pachydictyol A and dictyoxide have a good chance to become natural, non-toxic, and ecologically friendly additives in antifouling paints for the protection of submersed structures against L. fortunei.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Barbosa JP, Fleury BG, Da Gama BAP, Teixeira VL, Pereira RC (2007) Natural products as antifoulants in the Brazilian brown alga Dictyota pfaffii (Phaeophyta, Dictyotales). Biochem Syst Ecol 35:549–553
Becherucci M, Benavides H (2016) Composición florística de arribazones de algas marinas en playas del sudeste de la provincia de Buenos Aires, Argentina. Iheringia, Série Botânica 71:22–26
Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR (2016) Marine natural products. Nat Prod Rep 33:382–431 and previous reviews
Boltovskoy D, Correa N, Cataldo D, Sylvester F (2006) Dispersion and ecological impact of the invasive freshwater bivalve Limnoperna fortunei in the Rio de la Plata watershed and beyond. Biol Invasions 8:947–963
Boltovskoy D (ed) (2015) Limnoperna fortunei. The ecology, distribution and control of a swiftly spreading invading fouling mussel. Springer International, Cham
Boltovskoy D, Correa N (2015) Ecosystem impacts of the invasive bivalve Limnoperna fortunei (golden mussel) in South America. Hydrobiologia 746:81–95
Claudi R, Oliveira M (2015) Chemical strategies for the control of the golden mussel ( Limnoperna fortunei) in industrial facilities. In: Boltovskoy D (ed) Limnoperna fortunei. The ecology, distribution and control of a swiftly spreading invasive fouling mussel. Springer International, Cham, pp 417–441
Da Gama BAP, Pereira RC, Soares AR, Teixeira VL, Yoneshigue-Valentin Y (2003) Is the mussel test a good indicator of antifouling activity? A comparison between laboratory and field assays. Biofouling 19:161–169
Darrigran GA, Pastorino G (2004) Distribution of the golden mussel Limnoperna fortunei (Dunker 1857), (Bivalvia: Mytilidae) after 10 years invading America. J Conchol 3:95–101
Hay M, Duffy E, Pfister C, Fenical W (1987a) Chemical defense against different marine herbivores. Are amphipods insect equivalents? Ecology 68:1567–1580
Hay M, Fenical W, Gustafson K (1987b) Chemical defense against diverse coral-reef herbivores. Ecology 68:1581–1591
Helbling W, Villafañe V, Häder D (2010) Ultraviolet radiation effects on macroalgae from Patagonia, Argentina. In: Israel A, Einav R, Seckbach J (eds) Seaweeds and their role in globally changing environments. Springer, Dordrecht, pp 199–124
Hirschfeld DR, Fenical W, Lin G, Wing RM, Radlick P, Sims JJ (1973) Marine natural products. VIII. Pachydictyol A, an exceptional diterpene alcohol from the brown alga, Pachydictyon coriaceum. J Am Chem Soc 95:4049–4050
Ina K, Takasawa R, Yagi A, Yamashita N, Etoh H (1989) An improved assay method for antifouling substances using the blue mussel Mytilus edulis. Agric Biol Chem 53:3319–3321
Matsui Y, Nagaya K, Funahashi G, Goto Y, Yuasa A, Yamamoto H, Ohkawa K, Magara Y (2002) Effectiveness of antifouling coatings and water flow in controlling attachment of the nuisance mussel Limnoperna fortunei. Biofouling 18:137–148
Moura LA, De Almeida AM, Domingos TFS, Ortiz-Ramirez F, Cavalcanti DN, Teixeira VL, Lopes Fuly A (2014) Antiplatelet and anticoagulant effects of diterpenes isolated from the marine alga Dictyota menstrualis. Mar Drugs 12:2471–2484
Ohkawa K, Nishida A, Honma R, Matsui Y, Nagaya K, Yuasa A, Yamamoto H (1999) Studies on fouling by the freshwater mussel Limnoperna fortunei and the antifouling effects of low energy surfaces. Biofouling 13:337–350
Oliveira MD, Hamilton SK, Jacobi CM (2010) Forecasting the expansion of the invasive golden mussel Limnoperna fortunei in Brazilian and North American rivers based on its occurrence in the Paraguay river and Pantanal wetlands of Brazil. Aquat Invasions 5:59–73
Palermo J, Bernardo JJ, Seldes A (1994) Dictyol-D monoacetate and other diterpenoids from the brown alga Dictyota dichotoma. Anales Asoc Quim Arg 82:355–356
Pastorino G, Darrigran GA, Martin SM, Lunaschi L (1993) Limnoperna fortunei (Dunker 1857) (Mytilidae), nuevo bivalvo invasor en aguas del Rio de la Plata. Neotropica 39:101–102
Pereira HS, Leao-Ferreira LR, Moussatché N, Teixeira VL, Cavalcanti DN, Costa LJ, Diaz R, Frugulhetti IC (2004) Antiviral activity of diterpenes isolated from the Brazilian marine alga Dictyota menstrualis against human immunodeficiency virus type 1 (HIV-1). Antivir Res 64:69–76
Perepelizin P, Boltovskoy D (2011) Thermal tolerance of Limnoperna fortunei to gradual temperature increase and its applications for biofouling control in industrial and power plants. Biofouling 27:667–674
Schmitt TM, Lindquist N, Hay M (1998) Seaweed secondary metabolites as antifoulants: effects of Dictyota spp. diterpenes on survivorship, settlement, and development of marine invertebrate larvae. Chemoecology 8:125–131
Siamopoulou P, Bimplakis A, Iliopoulou D, Vagias C, Cos P, Vanden Berghe D, Roussis V (2004) Diterpenes from the brown algae Dictyota dichotoma and Dictyota linearis. Phytochemistry 65:2025–2030
Viano Y, Bonhomme D, Camps- Jardin M, Culioli G (2009) Diterpenoids from the mediterranean brown alga Dictyota sp evaluated as antifouling substances against a marine bacterial biofilm. J Nat Prod 72:1299–1304
Acknowledgements
This work was supported by ANPCyT (Argentina) under Grant PICT-2010-1808, CONICET (Argentina) under Grant 11220090100516, and the University of Buenos Aires under Grant UBACyT 20020100100704. The CIDEPINT group thanks Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Comisión de Investigaciones Científicas de la provincia de Buenos Aires (CIC), and Universidad Nacional de La Plata (Argentina) for their financial support.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
ESM 1
(DOCX 1694 kb)
Rights and permissions
About this article
Cite this article
Siless, G.E., García, M., Pérez, M. et al. Large-scale purification of pachydictyol A from the brown alga Dictyota dichotoma obtained from algal wash and evaluation of its antifouling activity against the freshwater mollusk Limnoperna fortunei . J Appl Phycol 30, 629–636 (2018). https://doi.org/10.1007/s10811-017-1261-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10811-017-1261-9