What are and where are the bioactive terpenoids metabolites from Dictyotaceae (Phaeophyceae)

Revista Brasileira de Farmacognosia

Volumn 21, Issue 2, 2011, Pages 216-228

  de Paula, Joel Campos ^a   Vallim, Magui A ^b   Teixeira, Valéria Laneuville ^b  

^a FEDERAL UNIVERSITY OF THE STATE OF RIO DE JANEIRO   (Brazil)

^b FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

Bioactivities; Biogeography; Dictyotaceae; Secondary metabolites; Terpenes

Indexed keywords

ANTIBIOTIC AGENT; DITERPENE; DOLABELLANE; DOLASTANE; GUAIANE; NATURAL PRODUCT; PROTEIN TYROSINE KINASE INHIBITOR; SECO DOLASTANE; SPATANE; TERPENOID; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DICTYOTACEAE; ENZYME INHIBITION; GEOGRAPHIC DISTRIBUTION; HERBIVORE; INSECTICIDAL ACTIVITY; METABOLITE; NONHUMAN;

EID: 79958817934     PISSN: 0102695X     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0102-695X2011005000079     Document Type: Article

References (75)

1. Abatis D, Vagias C, Galanakis D, Norris JN, Moreau D, Roussakis C, Roussis V 2005. Atomarianones A and B: two cytotoxic meroditerpenes from the brown alga Taonia atomaria. Tetrahedron Lett 46: 8525-8529.
2. Ali MS, Pervez MK 2003a. Seco-dolastanes from the marine brown alga Dictyota dichotoma (Huds.) Lamour. ZNaturforschung 58b: 438-442.
3. Ali M S, Pervez MK 2003b. Ring-A hydroxylated dolastanes from the marine brown alga Dictyota dichotoma (Huds.) Lamour. Nat Prod Res 17: 281-283.
4. Ali MS, Pervez MK, Saleem M, Ahmed F 2003. Dichotenone-A and -B: two new enones from the marine brown alga Dictyota dichotoma (Hudson) Lamour. Nat Prod Res 17: 301-306.
5. Ali M S, Pervez M K, Ahmed F, Saleem M 2004. Dichotenol-A, B and C: the C-16 oxidized secodolastanes from the marine brown alga Dictyota dichotoma (Huds.) Lamour. Nat Prod Res 18: 543-549.
6. Amico V, Oriente G, Piattelli M, Ruberto G, Tringali C 1982a. 2 novel phenolic-compounds from the brown alga Cystoseira caespitosa. J Chem Res 9: 262-263.
7. Amico V, Oriente G, Piattelli M, Ruberto G, Tringali C 1982b. A quinone-hydroquinone couple from the Brown alga Cystoseira stricta. Phytochemistry 21: 421-424.
8. Areche C, San-Martín A, Rovirosa J, Soto-Delgado J, Contreras R 2009. An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods. Phytochemistry 70: 1315-1320.
9. Awad NE, Selim MA, Metawe HM, Matloub AA 2008. Cytotoxic xenicane diterpenes from the brown alga Padina pavonia (L.) Gaill. Phytother Res 22: 1610-1613.
10. Banaigs B, Francisco C, Gonzalez E, Codomier L, Fenical W 1982. Hydroxylated diterpenoid-hydroquinones from cystoseira elegans: significant products or artifacts? Tetrahedron Lett 23: 3271-3272.
11. Banaigs B, Francisco C, Gonzalez E, Fenical W 1983. Diterpenoid metabolites from the marine alga Cystoseira elegans. Tetrahedron 39: 629-638.
12. Barbosa JP, Pereira, RC, Abrantes JL, Cirne-Santos CC, Rebello MA, Frugulhetti ICPP, Teixeira, VL 2004a. In vitro antiviral diterpenes from Brazilian brown alga Dictyota pfaffii. Planta Med 70: 856-860.
13. Barbosa JP, Teixeira, VL, Pereira, RC 2004b. A dolabellane diterpene from the brown alga Dictyota pfaffii as chemical defense against herbivores. Bot Mar 47: 147-151.
14. Blunt JW, Copp BR, Munro MHG, Northcotec PT, Prinsep MR 2010. Marine natural products. Nat Prod Rep 27: 165-237.
15. Blunt JW, Copp BR, Munro Murray HG, Northcotec PT, Prinsep MR 2011. Marine natural products. Nat Prod Rep 28: on line published.
16. Bouaicha N, Pesando D, Puel D, Tringali C 1993. Cytotoxic diterpenoids from the brown alga Dilophus ligulatus. J Nat Prod 56: 1747-1752.
17. Cortés M, Valderrama JA, Cuellar M, Armstrong V, Preite M 2001. Synthesis of (+)-cyclozonarone and the absolute configuration of naturally occurring (-)-cyclozonarone. J Nat Prod 64: 348-349.
18. Dave M-N, Kusumi T, Ishitsuka M, Iwashita T, Kakisawa H 1984. A piscicidal chromanol and a chromenol from the brown alga Dictyopteris undulata. Heterocycles 22: 2301-2307.
19. 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.
20. 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.
21. De Paula JC, Bueno LB, Frugulhetti ICPP, Yoneshigue-Valentin Y, Teixeira VL 2007. Dictyota dolabellana sp. nov. (Dictyotaceae, Phaeophyceae) based on morphological and chemical data. Bot Mar 50: 288-293.
22. De Rosa S, De Giulio A, Iodice C, Zavodink N 1994. Sesquiterpenes from the brown alga Taonia atomaria. Phytochemistry 37: 1327-1330.
23. De Rosa S, De Stefano S, Macura S, Trivellone E, Zavodnik N 1984. Chemical studies of north adriatic seaweeds-I. New dolabellane diterpenes from the brown alga Dilophus fasciola. Tetrahedron 40: 4991-4995.
24. De Silva SSM, Gamage SKT, Kumar NS, Balasubramaniam S 1982. Anti-bacterial activity of extracts from the Brown seaweed stoechospermum marginatum. Phytochemistry 21: 944-945.
25. Dewick PM 2002. The biosynthesis of C5-C25 terpenoid compounds. Nat Prod Rep 19: 181-222.
26. Dorta E, Cueto M, Bito I, Darias J 2002. New terpenoids from the brown alga Stypopodium zonale. J Nat Prod 65: 1727-1730.
27. Durán R, Zubía E, Ortega MJ, Salvá J 1997. New diterpenoids from the alga Dictyota dichotoma. Tetrahedron 53: 8675-8688.
28. Faulkner JD 1984. Marine natural products: metabolites of marine algae and herbivorous marine molluscs. Nat Prod Rep 1: 251-280.
29. Fenical W, Sims JJ, Squatrito D, Wing RM, Radlick P 1973. Zonarol and isozonarol, fungitoxic hydroquinones from the brown seaweed Dictyopteris zonarioides. J Org Chem 38: 2383-2386.
30. 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.
31. Garcia DG, Bianco EM, Santos MCB, Pereira RC, Faria MVC, Teixeira VL, Burth P 2009. Inhibition of mammal Na+K+-ATPase by diterpenes extracted from the Brazilian brown alga Dictyota cervicornis. Phytother Res 23: 943-947.
32. Gerwick WH, Fenical W, Fritsch N, Clardy J 1979. Stypotriol and stypoldione - ichthyotoxins of mixed biogenesis from the marine alga Stypopodium zonale. Tetrahedron Lett 2: 145-148.
33. Gerwick WH, Fenical W 1981. Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss. J Org Chem 46: 22-27.
34. Gerwick WH, Fenical W 1982. Phenolic lipids from related marine algae of the order Dictyotales. Phytochemistry 21: 633-637.
35. Gerwick WH, Fenical W 1983. Spatane diterpenoids from the tropical marine algae Spatoglossum schmittii and Spatoglossum howleii (Dictyotaceae). J Org Chem 48: 3325-3329.
36. Gerwick WH, Fenical W, Engen DV, Clardy J 1983. Isolation and structure of spatol, a potent inhibitor of cell replication from the brown seaweed Spatoglossum schmittii. J Am Chem Soc 102: 7991-7993.
37. Guiry, MD, Guiry GM 2011. Algae Base. World-wide electronic publication, National University of Ireland, Galway. http://www.algaebase.org.
38. Hardt IH, Fenical W, Cronin G, Hay ME 1996. Acutilols, potent herbivore feeding deterrents from the tropical brown alga, Dictyota acutiloba. Phytochemistry 43: 71-73.
39. Hirschfeld DR, Fenical W, Lin GHY, 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.
40. Ishitsuka M, Kusumi T, Nomura Y, Konno T, Kakisawa H 1979. New geranylgeranylbenzoquinone derivatives from Sargassum tortile. Chem Lett 10: 1269-1272.
41. Ishitsuka MO, Kusumi T, Ichikawa A, Kakisawa H 1990. Bicyclic diterpenes from two species of brown algae of the Dictyotaceae. Phytochemistry 29: 2605-2610.
42. Jacobs RS, Culver P, Langdon R, O'Brien T, White S 1985. Some pharmacological observations on marine natural products. Tetrahedron 41: 981-984.
43. Ji N-Y, Wen W, Li X-M, Xue Q-Z, Xiao H-L, Wang B-G 2009. Brominated selinane sesquiterpenes from the marine brown alga Dictyopteris divaricata. Mar Drugs 7: 355-360.
44. Kubanek J, Jensen PR, Keifer PA, Sullards MC, Collins DO, Fenical W 2003. Seaweed resistance to microbial attack: a targeted chemical defense against marine fungi. Proc Nat Acad Sci USA 100: 6916-6921.
45. Kurata K, Shiraishi K, Takato T, Taniguchi K, Suzuki MA 1988. New feeding-deterrent diterpenoids from brown alga Dilophus okamurae Dawson. Chem Lett 10: 1629-1632.
46. Kurata K, Taniguchi K, Shiraishi K, Suzuki M 1989. Structures of secospapane-type diterpene with feeding-deterrent activity from the brown alga Dilophus okamurae. Tetrahedron Lett 30: 1567-1570.
47. Kurata K, Taniguchi K, Suzuki M 1996. Cyclozonarone, a sesquiterpene-substituted benzoquinone derivative from the brown alga dictyopteris undulata. Phytochemistry 41: 749-752.
48. Kusumi T, Shibata Y, Ishitsuka M, Kinoshita T, Kakisawa H 1979. Structures of new plastoquinones from the brown alga Sargassum serratifolium. Chem Lett 3: 277-278.
49. Loya S, Bakhanashvili M, Kashman Y, Hizi A 1995. Peyssonols A e B, two novel inhibitors of the reverse transcriptases of human immunodeficiency virus types 1 and 2. Arch Biochem Biophys 316: 789-796.
50. Ochi M, Kotsuki H, Inoue S, Taniguchi M, Tokoroyama T 1979a. Isolation of 2-(3,7,11-trimethyl-2,6,10-dodecatrienyl) hydroquinone from the brown seaweed Dictyopteris undulate. Chem Lett 7: 831-832.
51. Ochi M, Kotsuki H, Muraoka K, Tokoroyama T 1979b. Structure of yahazunol, a new sesquiterpenesubstituted hydroquinone from the brown seaweed Dictyopteris undulata Okamura. Bull Chem Soc Jpn 52: 629-630.
52. Parameswaran PS, Bhat KL, Das B, Kamat SY, Harnos S 1994. Halogenated terpenoids from the brown alga Padina tetrastromatica (Hauck). Indian J Chem Sect B 33: 1006.
53. Parameswaran PS, Naik CG, Das B, Kamat SY, Bose AK, Nair MSR 1996. Constituents of the brown alga Padina tetrastromatica (Hauck). Indian J Chem Sect B 35: 463-467.
54. Pereira RC, Cavalcanti DN, Teixeira VL 2000a. Effect of secondary metabolites from the tropical Brazilian brown alga Dictyota menstrualis on the feeding by amphipod herbivores. Mar Ecol Prog Ser 205: 95-100.
55. Pereira RC, Donato R, Cavalcanti DN, Teixeira VL 2000b. Chemotaxis and chemical defenses in seaweed susceptibility to herbivory. Rev Bras Biol 59: 407-419.
56. Pereira HS, Leão-Ferreira LR, Moussatché N, Teixeira VL, Cavalcanti DN, Costa LJ, Diaz R, Frugulhetti ICPP 2004. Antiviral activity of diterpenes isolated from the Brazilian marine alga Dictyota menstrualis against human immunodeficiency virus type 1 (HIV-1). Antiviral Res 64: 69-76.
57. Qiao Y-Y, Ji N-Y, Wen W, Yin X-L, Xue Q-Z 2009. A new epoxy-cadinane sesquiterpene from the marine brown alga Dictyopteris divaricata. Mar Drugs 7: 600-604.
58. Rovirosa J, Sepúlveda M, Quezada E, San-Martín A 1992. Isoepitaondiol, a diterpenoid of Stypopodium flabelliforme and the insecticidal activity of stypotriol, epitaondiol and derivatives. Phytochemistry 31: 2679-2681.
59. Sabry OMM, Andrews S, McPhail KL, Goeger DE, Yokochi A, LePage KT, Murray TF, Gerwick WH 2005. Neurotoxic meroditerpenoids from the tropical marine brown alga Stypopodium flabelliforme. J Nat Prod 68: 1022-1030.
60. Sampli P, Tsitsimpikou C, Vagias C, Harvala C, Roussis V 2000. Schimperiol, a new meroterpenoid from the brown alga Stypopodium schimperi. Nat Prod Lett 14: 365-372.
61. Smit AJ 2004. Medicinal and pharmaceutical uses of seaweed natural products: A review. J Appl Phycol 16: 245-262.
62. Soares AR, Abrantes JL, Souza TML, Fontes CFL, Pereira RC, Frugulhetti ICDP, Teixeira VL 2007. In vitro antiviral effect of meroditerpenes isolated from the Brazilian seaweed Stypopodium zonale (Dictyotales). Planta Med 73: 1221-1224.
63. Song F, Fan X, Xu XL, Zhao JL, Yang Y, Shi JG 2004a. Cadinane sesquiterpenes from the brown alga Dictyopteris divaricata. J Nat Prod 67: 1644-1649.
64. Song FH, Fan X, Xu XL, Zhao JL, Han LJ, Shi JG 2004b. A new sesquiterpene-substituted benzoic acid from the brown alga Dictyopteris divaricata. Chin Chem Lett 15: 316-318.
65. Song F, Xu X, Li S, Wang S, Zhao J, Cao P, Yang Y, Fan X, Shi J, He L, Lü Y 2005. Norsesquiterpenes from the brown alga Dictyopteris divaricata. J Nat Prod 68: 1309-1313.
66. Song F, Xu X, Li S, Wang S, Zhao J, Yang Y, Fan X, Shi J, He L 2006. Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata. J Nat Prod 69: 1261-1266.
67. Teixeira VL, Kelecom, A, Gottlieb OR 1991. Produtos Naturais de algas Marinhas. Quim Nova 14: 83-90.
68. Tringali C, Oriente G, Piattelli M, Geraci C, Nicolosi G, Breitmaier E 1988. Crenuladial, an antimicrobial diterpenoid from the brown alga Dilophus ligulatus. Can J Chem 66: 2799-2802.
69. Tringali C, Oriente G, Piatelli M, Nicolosi G 1984. Structure and conformation of two new dolabellanebased diterpenes from Dictyota sp. J Nat Prod 47: 615-619.
70. Tziveleka L-A, Abatis D, Paulus K, Bauer R, Vagias C, Roussis V 2005. Marine polyprenylated hydroquinones, quinones, and chromenols with inhibitory effects on leukotriene formation. Chem Biodivers 2: 901-909.
71. Vallim MA, De Paula JC, Pereira RC, Teixeira VL 2005. The diterpenes from Dictyotacean marine brown algae in the Tropical Atlantic American region. Biochem System Ecol 33: 1-16.
72. Vallim MA, Teixeira VL, Pereira RC 2007. Feedingdeterrent properties of diterpenes of Dictyota mertensii (Phaeophyceae, Dictyotales). Braz J Ocean 55: 223-229.
73. Vallim MA, Barbosa JE, Cavalcanti DN, De Paula JC, Silva, VAGG, Teixeira VL, Paixão ICNP 2010. In vitro antiviral activity of diterpenes isolated from the Brazilian brown alga Canistrocarpus cervicornis. J Med Plant Res 4: 2379-2382.
74. Wen W, Li F, Ji N-Y, Li X-M, Cui C-M, Li X-D, Zhang L-N, Xue Q-Z, Wang B-G 2009. A new cadinane sesquiterpene from the marine brown alga Dictyopteris divaricata. Molecules 14: 2273-2277.
75. Wessels M, König GM, Wright AD 1999. A new tyrosine kinase inhibitor from the marine brown alga Stypopodium Zonale. J Nat Prod 62: 927-930.