Diterpenes content of the brown alga Dictyota ciliolata (Dictyotales, Phaeophyceae) and recognition of a Brazilian haplotype based on psbA sequences

References

• Allender BM, Kraft GT. 1983. The marine algae of Lord Howe Island (New South Wales): The Dictyotales and Cutleriales (Phaeophyta). Brunonia. 6:73–130. doi: 10.1071/BRU9830073
   Google Scholar
• Araujo JM, Tappin MRR, Fortes RR, Lopes-Filho EAP, Salgueiro F, De Paula JC. 2018. Chemodiversity of the brown algae Canistrocarpus cervicornis (Dictyotaceae, Phaeophyceae) in tropical and subtropical populations along the southwestern Atlantic coast of Brazil. J Appl Phycol. 30:611–618. doi: 10.1007/s10811-017-1249-5
   Web of Science ®Google Scholar
• Bandelt H-J, Forster P, Röhl A. 1999. Median-joining networks for inferring intraspecific phylogenies. Mol Biol Evol. 16:37–48. doi: 10.1093/oxfordjournals.molbev.a026036
   PubMed Web of Science ®Google Scholar
• Barbosa JP, Fleury BG, 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. doi: 10.1016/j.bse.2007.01.010
   Web of Science ®Google Scholar
• Barbosa JP, Teixeira VL, Pereira RC. 2004. A dolabellane diterpene from the brown alga Dictyota pfaffii as chemical defense against herbivores. Bot Mar. 47:147–151. doi: 10.1515/BOT.2004.015
   Web of Science ®Google Scholar
• Barbosa JP, Teixeira VL, Villaça R, Pereira RC, Abrantes JL, Frugulhetti ICPP. 2003. A dolabellane diterpene from the Brazilian brown alga Dictyota pfaffii. Biochem Syst Ecol. 31:1451–1453. doi: 10.1016/S0305-1978(03)00120-0
   Web of Science ®Google Scholar
• Bowen BW, Rocha LA, Toonen RJ, Karl SA, ToBo Laboratory. 2013. The origins of tropical marine biodiversity. Trends Ecol Evol. 28(6):359–366. doi: 10.1016/j.tree.2013.01.018
   PubMed Web of Science ®Google Scholar
• Caamal-Fuentes E, Chale-Dzul J, Moo-Puc R, Freile-Pelegrin Y, Robledo D. 2014a. Bioprospecting of brown seaweed (Ochrophyta) from the Yucatan Peninsula: cytotoxic, antiproliferative, and antiprotozoal activities. J Appl Phycol. 26:1009–1017. doi: 10.1007/s10811-013-0129-x
   Web of Science ®Google Scholar
• Caamal-Fuentes E, Moo-Puc R, Freile-Pelegrin Y, Robledo D. 2014b. Cytotoxic and antiproliferative constituents from Dictyota ciliolata, Padina sanctae-crucis and Turbinaria tricostata. Pharmaceutical Biology. 52(10):1244–1248. doi: 10.3109/13880209.2014.886273
   PubMed Web of Science ®Google Scholar
• Cavalcanti DN, Gomes MAV, Pino AC, Rezende CM, Pereira RC, Teixeira VL. 2008. Effects of storage and solvent type in a lipophylic chemical profile of the seaweed Dictyota menstrualis. Braz J Oceanogr. 56:51–57. doi: 10.1590/S1679-87592008000100005
   Web of Science ®Google Scholar
• Cavalcanti DN, Oliveira MAR, De-Paula JC, Barbosa LS, Fogel T, Pinto MA, Paixão ICNP, Teixeira VL. 2011. Variability of a diterpene with potential anti-HIV activity isolated from the Brazilian brown alga Dictyota menstrualis. J Appl Phycol. 23:873–876. doi: 10.1007/s10811-010-9601-z
   Web of Science ®Google Scholar
• Cavalcanti DN, Rezende CM, Pinto AC, Teixeira VL. 2006. Diterpenoid constituents from the brown alga Dictyota menstrualis. Nat Prod Commun. 1:609–611.
   Web of Science ®Google Scholar
• Cheng S, Zhao M, Sun Z, Yuan W, Zhang S, Xiang Z, Cai Y, Dong J, Huang K, Yan P. 2014. Diterpenes from a Chinese collection of the brown alga Dictyota plectens. J Nat Prod. 77:2685–2693. doi: 10.1021/np5006955
   PubMed Web of Science ®Google Scholar
• Cronin G, Hay ME. 1996. Chemical defenses, protein content, and susceptibility to herbivory of diploid vs. haploid stages of the isomorphic brown alga Dictyota ciliolata (Phaeophyta). Bot Mar. 39:395–399. doi: 10.1515/botm.1996.39.1-6.395
   Web of Science ®Google Scholar
• Cronin G, Lindquist N, Hay ME, Fenical W. 1995. Effects of storage and extraction procedures on yields of lipophilic metabolites from the brown seaweeds Dictyota ciliolata and D. menstrualis. Mar Ecol Prog Ser. 119:265–273. doi: 10.3354/meps119265
   Web of Science ®Google Scholar
• De Clerck O, Leliaert F, Verbruggen H, Lane CE, De Paula JC, Payo DA, Coppejans E. 2006. A revised classification of the Dictyoteae (Dictyotales, Phaeophyceae) based on rbcL and 26S ribosomal DNA sequence analyses. J Phycol. 42:1271–1288. doi: 10.1111/j.1529-8817.2006.00279.x
   Web of Science ®Google Scholar
• De-Paula JC, Bueno LB, Cavalcanti DN, Yoneshigue-Valentin Y, Teixeira VL. 2008. Diterpenes from the brown alga Dictyota crenulata. Molecules. 13:1253–1262. doi: 10.3390/molecules13061253
   PubMed Web of Science ®Google Scholar
• De Paula JC, Bueno LB, Frugulhetti ICPP, Yoneshigue-Valentin Y, Teixeira VL. 2007a. Dictyota dolabellana sp. nov. (Dictyotaceae, Phaeophyceae) based on morphological and chemical data. Bot Mar. 50:288–293.
   Web of Science ®Google Scholar
• De-Paula JC, Cassano V, Yoneshigue-Valentin Y, Teixeira VL. 2007b. Diterpenes from the Brazilian brown alga Dictyota crispata (Dictyotaceae, Phaeophyta). Nat Prod Commun. 2:135–137.
   Web of Science ®Google Scholar
• De-Paula JC, Cavalcanti DN, Yoneshigue-Valentin Y, Teixeira VL. 2012. Diterpenes from marine brown alga Dictyota guineenses. Braz J Pharmacog. 22(4):736–740. doi: 10.1590/S0102-695X2012005000071
   Google Scholar
• De-Paula JC, Pedrini AG, Pinheiro MD, Pereira RC, Teixeira VL. 2001. Chemical similarity between the brown algae Dictyota cervicornis and D. pardalis (Dictyotales, Phaeophyta). Biochem Syst Ecol. 29:425–427. doi: 10.1016/S0305-1978(00)00066-1
   PubMed Web of Science ®Google Scholar
• De Paula JC, Vallim MA, Teixeira VL. 2011. What are and where are the bioactive terpenoids metabolites from Dictyotaceae (Phaeophyceae)? Braz J Pharmacog. 21(2):216–228. doi: 10.1590/S0102-695X2011005000079
   Google Scholar
• Elshamy AIP, Mohamed TA, Marzouk MM, Hussien TA, Umeyama E, Hegazy MEF, Effert M. 2018. Phytochemical constituents and chemosystematic significance of Pulicaria jaubertii E. Gamal-Eldin (Asteraceae). Phytochem Lett. 24:105–109. doi: 10.1016/j.phytol.2018.01.021
   Web of Science ®Google Scholar
• Fernandes DRP, Oliveira VP, Valentin YY. 2014. Seaweed biotechnology in Brazil: Six decades of studies on natural products and their antibiotic and other biological activities. J Appl Phycol. 26:1923–1937. doi: 10.1007/s10811-014-0287-5
   Web of Science ®Google Scholar
• Freitas OSP, Oliveira AS, De-Paula JC, Pereira RC, Cavalcanti DN, Teixeira VL. 2007. Chemical variation in the diterpenes from the Brazilian brown alga Dictyota mertensii (Dictyotaceae, Phaeophyta). Nat Prod Commun. 2:13–15.
   Web of Science ®Google Scholar
• Guella G, Pietra F. 1993. Photochemical conversion of xenicane into the crenulatane skeleton with diterpenoids of the brown seaweed Dictyota sp. from the coasts of Senegal. J Chem Soc Chem Comm. 20:1539. doi: 10.1039/c39930001539
   Google Scholar
• Guiry MD, Guiry GM. 2018. AlgaeBase. World-wide Electronic Publication. Galway: National University of Ireland; [searched 2018 February 19]. http://www.algaebase.org.
   Google Scholar
• John DM, Prud’homme van Reine WF, Lawson GW, Kostermans TB, Price JH. 2004. A taxonomic and geographical catalogue of the seaweeds of the Western Coast of Africa and adjacent islands. Nova Hedwigia. 127:4–139.
   Google Scholar
• Kelecom A, Teixeira VL. 1986. Diterpenes of marine brown algae of the family Dictyotaceae: their possible role as defense compounds and their use in chemotaxonomy. Sci Total Environ. 58:109–115. doi: 10.1016/0048-9697(86)90081-1
   PubMed Web of Science ®Google Scholar
• Kelecom A, Teixeira VL. 1988. Dolastane diterpenes from the marine brown alga Dictyota cervicornis. Phytochemistry. 27:2907–2909. doi: 10.1016/0031-9422(88)80686-1
   Web of Science ®Google Scholar
• Kelecom A, Teixeira VL, Pitombo LF. 1991. Quimiotaxonomia de Dictyotales (Phaeophyta). 6. Da sinonímia entre as algas pardas Dictyota dentata e D. mertensii. Ann. Acad Bras Quim. 40:67–70.
   Google Scholar
• Kraft GT. 2009. Algae of Australia. Marine benthic algae of Lord Howe Island and the southern Great Barrier Reef, 2. Brown algae. Australian. Canberra and Melbourne: Australian Biological Resources Study and CSIRO Publishing.
   Google Scholar
• Kumar S, Stecher G, Tamura K. 2016. MEGA7: molecular evolutionary genetics analysis version 7.0 for bigger datasets. Mol Biol Evol. 33:1870–1874. doi: 10.1093/molbev/msw054
   PubMed Web of Science ®Google Scholar
• Lara-Isassi G, Alvarez-Herández S, Collado-Vides L. 2000. Ichtyotoxic activity of extracts from Mexican marine macroalgae. J Appl Phycol. 12:45–52. doi: 10.1023/A:1008103609841
   Web of Science ®Google Scholar
• Leite PM, Castilho RO. 2017. Chemosystematics of Brassicales. Biochem Syst Ecol. 71:205–211. doi: 10.1016/j.bse.2017.02.011
   Web of Science ®Google Scholar
• Lira MLF, Lopes R, Gomes AP, Barcellos G, Verícimo M, Osako K, Ortiz-Ramirez FA, Ramos CJB, Cavalcanti DN, Teixeira VL, Amaral V. 2016. Anti-leishmanial activity of Brazilian green, brown, and red algae. J Appl Phycol. 28:591–598. doi: 10.1007/s10811-015-0538-0
   Web of Science ®Google Scholar
• Lopes-Filho EAP, Salgueiro F, Nascimento SM, Gauna MC, Parodi ER, De Paula JC. 2017. Molecular evidence of the presence of Dictyota dichotoma (Dictyotales: Phaeophyceae) in Argentina based on sequences from mtDNA and cpDNA and a discussion of its possible origin. New Zeal J Bot. 55(3):293–305. doi: 10.1080/0028825X.2017.1326387
   Web of Science ®Google Scholar
• Lozano-Orozco JG, Sentíes A, Díaz-Larrea J, Pedroche FF, De Clerck O. 2014. The occurrence of Dictyota canariensis (Dictyotales, Phaeophyceae) in the Gulf of Mexico. Bot Mar. 57:359–365. doi: 10.1515/bot-2013-0111
   Web of Science ®Google Scholar
• Lozano-Orozco JG, Sentíes A, Pedroche FF, Díaz-Larrea J. 2016. Dictyota chalchicueyecanensis sp. nov. (Dictyotales, Phaeophyceae) en el Golfo de México: Evidencias moleculares y morfológicas. Hidrobiológica. 26(2):225–231.
   Web of Science ®Google Scholar
• Manzo E, Ciavatta ML, Bakkas S, Villani G, Varcamonti M, Zanfardino A, Gavagnin M. 2009. Diterpene content of the alga Dictyota ciliolata from a Moroccan lagoon. Phytochem Lett. 2:211–215. doi: 10.1016/j.phytol.2009.08.003
   Web of Science ®Google Scholar
• McDougal OM, Heenan PB, Perry NB, van Klink JW. 2018. Chemotaxonomy of kōwhai: leaf and seed flavonoids of New Zealand Sophora species. New Zeal J Bot. 56(3):227–236. doi: 10.1080/0028825X.2018.1472107
   Web of Science ®Google Scholar
• Norte M, González AG, Zárraga M, Pérez C, Rodriguez ML, Ruiz-Perez C, Dorta L. 1990. New xenicane diterpenes from the brown algae of Dictyotaceae. Tetrahedron. 46:6125–6132. doi: 10.1016/S0040-4020(01)87934-5
   Web of Science ®Google Scholar
• Oliveira AS, Cavalcanti DN, Bianco EM, De-Paula JC, Pereira RC, Yoneshigue-Valentin Y, Teixeira VL. 2008. Chemical composition of diterpenes from the brown alga Canistrocarpus cervicornis (Dictyotaceae, Phaeophyceae). Nat Prod Commun. 3(9):1469–1472.
   Web of Science ®Google Scholar
• Ortiz-Ramirez FA, Cavalcanti DN, Villaça RC, De-Paula JC, Yoneshigue-Valentin Y, Teixeira VL. 2008. Chemical variation in the diterpenes from the Brazilian brown alga Dictyota menstrualis (Dictyotaceae, Phaeophyceae). Nat Prod Commun. 3:1879–1884.
   Web of Science ®Google Scholar
• Othmani A, Bouzidi N, Viano Y, Alliche Z, Seridi H, Blache Y, Hattab ME, Briand JF, Culioli G. 2014. Anti-microfouling properties of compounds isolated from several Mediterranean Dictyota spp. J Appl Phycol. 26:1573–1584.
   Web of Science ®Google Scholar
• Phang SM, Yeong HY, Ganzon-Fortes ET, Lewmanomont K, Prathep A, Hau LN, Gerung GS, Tan KS. 2016. Marine algae of the South China Sea bordered by Indonesia, Malaysia, Philippines, Singapore, Thailand and Vietnam. Raffles B Zool. 34(Suppl):13–59.
   Google Scholar
• Rozas J, Ferrer-Mata A, Sánchez-DelBarrio JC, Guirao-Rico S, Librado P, Ramos-Onsins SE, Sánchez-Gracia A. 2017. DnaSP 6: DNA sequence polymorphism analysis of large datasets. Mol Biol Evol. 34:3299–3302. doi: 10.1093/molbev/msx248
   PubMed Web of Science ®Google Scholar
• Saunders GW. 1993. Gel purification of red algal genomic DNA: an inexpensive and rapid method for the isolation of polymerase chain reaction-friendly DNA. J Phycol. 29:251–254. doi: 10.1111/j.0022-3646.1993.00251.x
   Web of Science ®Google Scholar
• Silva ANO, Oliveira AFM, Santos DYAC, Silva SI. 2010. An approach to chemotaxonomy to the fatty acid content of some Malvaceae species. Biochem Syst Ecol. 38:1035–1038. doi: 10.1016/j.bse.2010.10.006
   Web of Science ®Google Scholar
• Simas DLR, Kaiser CR, Gestinari LM, Duarte HM, Paula JC, Soares AR. 2014. Diterpenes from the brown seaweed Dictyota caribaea (Dictyotaceae, Phaeophyceae): The ecological and taxonomic significance. Biochem Syst Ecol. 52:33–37. doi: 10.1016/j.bse.2013.11.001
   Web of Science ®Google Scholar
• Tauwhare SEK, Newman RH, Scheele S, Kanawa RTE. 2006. Chemotaxonomy of Phormium based on sugar-residue analyses of the leaf exudates. New Zeal J Bot. 44(2):129–133. doi: 10.1080/0028825X.2006.9513013
   Web of Science ®Google Scholar
• Teixeira VL. 2010. A taxonomia química de algas marinhas bentônicas. In: Pedrini AG, editor. Macroalgas: uma introdução à taxonomia. Série Flora Marinha do Brasil, vol. 1, Rio de Janeiro, cap. 6: Technical Books; p. 83–97.
   Google Scholar
• Teixeira VL, Cavalcanti DN, Pereira RC. 2001. Chemotaxonomic study of the diterpenes from the brown alga Dictyota menstrualis. Biochem Syst Ecol. 29:313–316. doi: 10.1016/S0305-1978(00)00055-7
   PubMed Web of Science ®Google Scholar
• Teixeira VL, Kelecom A. 1988. A chemotaxonomic study of diterpenes from marine brown algae of the genus Dictyota. Sci Total Environ. 75(2–3):271–283. doi: 10.1016/0048-9697(88)90040-X
   Web of Science ®Google Scholar
• Teixeira VL, Kelecom A. 1989. Chemotaxonomy of Dictyotales. 2. The Dictyota group. Ínsula. 19(Suppl):249–270.
   Google Scholar
• Tronholm A, Carrillo JA, Sansón M, Leliaert F, García CF, De Clerck O. 2013. Taxonomy of the Dictyota ciliolata – crenulata complex (Dictyotales, Phaeophyceae). Phycologia. 52(2):171–181. doi: 10.2216/12-005.1
   Web of Science ®Google Scholar
• Tronholm A, Leliaert F, Sansón M, Afonso-Carrillo J, Tyberghein L, Verbruggen H, De Clerck O. 2012. Contrasting geographical distributions as a result of thermal tolerance and long-distance dispersal in two allegedly widespread tropical brown algae. Plos One. 7:E30813. doi: 10.1371/journal.pone.0030813
   PubMed Web of Science ®Google Scholar
• Tronholm A, Steen F, Tyberghein L, Leliaert F, Verbruggen H, Siguan MAR, De Clerck O. 2010. Species delimitation, taxonomy and biogeography of Dictyota in Europe (Dictyotales, Phaeophyceae). J Phycol. 46:1301–1321. doi: 10.1111/j.1529-8817.2010.00908.x
   Web of Science ®Google Scholar
• Vallim MA, De-Paula JC, Pereira RC, Teixeira VL. 2005. The diterpenes from Dictyotacean marine brown algae in the Tropical Atlantic American region. Biochem Syst Ecol. 33:1–16. doi: 10.1016/j.bse.2004.06.002
   Web of Science ®Google Scholar
• Vallim MA, Teixeira VL, Pereira RC. 2007. Feeding-deterrent properties of diterpenes of Dictyota mertensii (Phaeophyceae, Dictyotales). Braz J Oceanogr. 55(3):223–229.
   Google Scholar
• Vázquez JT, Chang M, Nakanishi K, Manta E, Perez C, Martin JD. 1988. Structure of hydroazulenoid diterpenes from a marine alga and their absolute configuration based on circular dichroism. J Org Chem. 53:4797–4800. doi: 10.1021/jo00255a025
   Web of Science ®Google Scholar
• Zarraga M, Arroyo P, Norte M. 1998. New crenulides from brown algae of the Dictyotaceae family. Bol Soc Chil Quim. 43(1):73–79.
   Google Scholar
• Zhao M, Cheng S, Yuan W, Dong J, Huang K, Sun Z, Yan P. 2015. Further New Xenicanes from a Chinese collection of the brown alga Dictyota plectens. Chem Pharm Bull. 63:1081–1086. doi: 10.1248/cpb.c15-00556
   PubMed Web of Science ®Google Scholar
• Zidorn C, Stuppner H. 2001. Chemosystematics of taxa from the Leontodon section Oporinia. Biochem Syst Ecol. 29:827–837. doi: 10.1016/S0305-1978(01)00019-9
   PubMed Web of Science ®Google Scholar
• Zubia M, Robledo D, Freile-Pelegrin Y. 2017. Antioxidant activities in tropical marine macroalgae from the Yucatan Peninsula, Mexico. J Appl Phycol. 19:449–458. doi: 10.1007/s10811-006-9152-5
   Google Scholar