107

6. REFERNCIAS BIBLIOGRFICAS

AGUILAN, J. T.; BROOM, J. E.; HEMMINGSON, J. A.; DAYRIT, F. M.; MONTAO, M. N. E.; DANCEL, M. C. A.; NIONUEVO, M. R.; FURNEAUX, R. H. Structural analysis of carrageenan from farmed varieties of Philippine seaweed. Bot. Mar., v. 46, p. 179-192, 2003. ALBAN S. Carbohydrates with anticoagulant and antithrombotic properties. In: WITCZAK, Z. J.; NIEFORTH, K. A. Carbohydrates in drug design. M. Dekker, New York, 703 p., 1997. ANDERSON, N. S.; DOLAN, T. C. S.; REES, D. A. Carrageenans. Part VII. Polysaccharides from Eucheuma spinosum and Eucheuma cottoni. The covalent structure of -carrageenan. J. Chem. Soc., v. 19, p. 2182-2187, 1973. AUG C.; NARVOR, C.; LUBINEAU, A. Enzymatic synthesis of oligosaccharides. Carbohydrates in Europe, v. 27, p. 22-32, 1999. BELLION, C.; HAMER, G. K.; YAPHE, W. The degradation of Eucheuma spinosum and Eucheuma cottoni carrageenans by -carrageenases and -carrageenases from marine bacteria. Can. J. Microbiol., v. 28, p. 874-880, 1982. BREITMAIER, E.; VOELTER, W. Carbon-13 nmr spectroscopy. High-resolution methods and applications in organic chemistry and biochemistry, 3a edio. VHC, New York, 515 p., 1987. CHIOVITTI, A.; KRAFT, G. T.; BACIC, A.; CRAIK, D. J.; LIAO, M. Chemistry, properties, and phylogenetic implications of the methylated carrageenans from red algae of the genus Areschougia (Areschougiaceae, Gigartinales, Rhodophyta). J. Phycol., v. 37, p. 1127-1137, 2001. De RUITER, G. A.; RUDOLPH, B. Carrageenan biotechnology. Trends Food Sci. Technol., v. 8, p. 389-395, 1997. DUARTE, M. E. R.; CAUDURO, J. P.; NOSEDA, D. G.; NOSEDA, M. D.; GONALVES, A. G.; PUJOL, C. A.; DAMONTE, E. B.; CEREZO, A. S. The structure of the agaran sulfate from Acanthophora spicifera (Rhodomelaceae, Ceramiales) and its antiviral activity. Relation between structure and antiviral activity in agarans. Carbohydr. Res., v. 339, p. 335-347, 2004. DUARTE, M. E. R. Heteropolissacardeos cidos isolados de Laminaria brasiliensis J. & O.: cido algnico e fucanas. Dissertao (Doutorado em Cincias, Bioqumica) Setor de Cincias Biolgicas, Universidade Federal do Paran, 202 p., 1990.

108

DUBOIS, M; GILLES, K. A; HAMILTON, J. K; REBERS, P. A; SMITH, F.. Colorimetric method for determination of sugars and related substances. Anal. Chem.., v. 28, p. 350-356, 1956. DUFF, R. B.; PERCIVAL, G. V. Carbohydrate sulphuric esters. Part IV. Production of a derivative of 5:6-anhydroglucose by the hydrolysis of a sulphate. J. Chem. Soc., p. 1675-1678, 1947. EKEBERG, D.; KNUTSEN, S. H.; SLETMOEN, M. Negative-ion electrospray ionisation-mass spectrometry (ESI-MS) as a tool for analysing structural heterogeneity in kappa-carrageenan oligosaccharides. Carbohydr. Res., v. 334, p. 49-59, 2001. FERNNDEZ, L. E.; VALIENTE, O. G.; MAINARDI, V.; BELLO, J. L. Isolation and characterization of an antitumor active Agar-type polysaccharide of Gracilaria dominguensis. Carbohydr. Res., v. 190, p. 77-83, 1989. FRANCIS, D.J.; PARISH, C. R.; MCGARRY, M.; SANTIAGO, F. S.; LOWE, H. C.; BROWN, K. J.; BINGLEY, J. A.; HAYWARD, I. P.; COWDEN, W. B.; CAMPBELL, J. H.; CAMPBELL, G. R.; CHESTERMAN, C. N.; KHACHIGIAN, L. M. Blockade of vascular smooth muscle cell proliferation and intimal thickening after balloon injury by the sulfated oligosaccharide PI-88. Circulation Research., v. 92. p. 70-77, 2003. GAREGG, P. J.; JANSSON, P.; LINDBERG, B.; LINDH, F. LNNGREN, J.; KVARNSTRM, I.; NIMMICH, W. Configuration of the acetal carbon atom of pyruvic acid acetals in some bacterial polysaccharides. Carbohydr. Res., v. 78, p. 127-132, 1980. GONALVES, A. G. Oligossacardeos piruvatados e sulfatados obtidos a partir de galactanas de algas vermelhas (Rhodophyta). Dissertao (Mestrado em Cincias, Bioqumica) Setor de Cincias Biolgicas, Universidade Federal do Paran, 102p., 2001. GONALVES, A. G.; DUCATTI, D. R. B.; DUARTE, M. E. R.; NOSEDA, M. D., Sulfated and pyruvylated disaccharide alditols obtained from a red seaweed galactan: ESIMS and NMR approaches. Carbohydr. Res. v. 337, p. 2443-2453, 2002. GORIN, P. A. J.; MAZUREK, M. Further studies on the assignment of signals in 13C magnetic resonance spectra of aldoses and derived methyl glycosides. Can. J. Chem., v. 53, p. 1212-1222, 1975. GREER, C. W.; YAPHE, W. Characterization of hybrid (beta-kapa-gamma) carrageenan from Eucheuma gelatinae J. Agardh (Rhdophyta, Solieriaceae) using carrageenases, infrared and 13C-nuclear magnetic resonance spectroscopy. Bot. Mar., v. 27, p. 473-478, 1984.

109

GUIMARES, M. Aspectos fisiolgicos de Gracilaria domingensis (Gracilariales, Rhodophyta): subsdios para a compreenso da manuteno do polimorfismo pigmentar. Dissertao (Doutorado em Cincias, Botnica) Instituto de Biocincias, Universidade de So Paulo, 98p., 2000. GVEN, K. C.; ZSOY, Y.; ULUTIN, O. N. Anticoagulant, fibrinolytic and antiaggregant activity of carrageenans and alginic acid. Bot. Mar., v. 34, p. 429-432, 1991. KANDLER, O.; HOPF, H. Occurrence, metabolism and function of oligosaccharides. In: STUMPF, P.K.; CONN, E.E. (eds.). The biochemistry of plants: a comprehensive treatise Carbohydrates: structure and function, New York: Academic Press, v. 3, p. 221-226, 1980. KSBAUER, C. W.; PAPER, D. H.; FRANZ, G. Sulfated -(14)-galactooligosaccharides and their effect on angiogenesis. Carbohydr. Res., v. 330, p. 427430, 2001. KATSURAYA, H.; NAKASHIMA, H.; YAMAMOTO, N.; URYU, T. Synthesis of sulfated oligosaccharide glycosides having high anti-HIV activity and the relationship between activity and chemical structure. Carbohydr. Res., v. 315, p. 234-242, 1999. KNUTSEN, S. H.; GRASDALEN, H. Characterization of water-extractable polysaccharides from norwegian Furcellaria lumbricalis (Huds.) Lamour. (Gigartinales, Rhodophyceae) by IR and NMR spectroscopy. Bot. Mar., v. 30, p. 497505, 1987. KNUTSEN, S. H.; MYSLABODSKI, D. E.; LARSEN, B.; USOV, A. I. A modified system of nomenclature for red algal galactans. Bot. Mar., v. 37, p. 163-169, 1994. KNUTSEN, S. H.; GRASDALEN, H. The use of neocarrabiose oligosaccharides with different length and sulphate substitution as model compounds for 1H-NMR spectroscopy. Carbohydr. Res., v. 229, p. 233-244, 1992. KNUTSEN, S. H.; SLETMOEN, M.; KRISTENSEN, T.; BARBEYRON, T.; KLOAREG, B.; POTIN, P. A rapid method for the separation and analysis of carrageenan oligosaccharide released by iota- and kappa-carrageenase. Carbohydr. Res., v. 331, p. 101-106, 2001. LAHAYE, M.; YAPHE, W.; VIET, M. T. P.; ROCHAS, C. 13C-nmr spectroscopic investigation of methylated and charged agarose oligosaccharides and polysaccharides. Carbohydr. Res., v. 190, p. 249-265, 1989.

110

LINHARDT, R. J.; TOIDA, T. Heparin oligosaccharides: New analogues development and applications. In: WITCZAK, Z. J.; NIEFORTH, K. A. Carbohydrates in drug design. M. Dekker, New York, 703p., 1997. LIU, J.; SHRIVER, Z.; POPE, R. M.; THORP, S. C.; DUNCAN, M. B.; COPELAND, R. J.; RASKA, C. S.; YOSHIDA, K.; EISENBERG, R. J.; COHEN, G.; LINHARDT, R. J.; SASISEKHRARAN, R. Characterization of a heparan sulfate octasaccharide that binds to herpes simplex virus type 1 glycoprotein D. J. Biol. Chem., v. 277, p. 3345633467, 2002. MAZUMDER, S.; GHOSAL, P. K.; PUJOL, C. A.; CARLUCCI, M. J.; DAMONTE, E. B.; RAY, B. Isolation, chemical investigation and antiviral activity of polysaccharides from Gracilaria corticata (Gracilariaceae, Rhodophyta). Int. J. Biol. Macromol., v. 31, p. 87-95, 2002. NOMURA, K.; NAITOH, Y.; MURAMATSU, S.; YOSHIZAWA, Y.; TSUNEHIRO, J.; FUKUI, F.; ITOH, M. New sulfated oligosaccharide produced by Pseudomonas agarase from Gracilaria verrucosa polysaccharide. Biosci. Biotechnol. Biochem., v. 62, p. 1190-1195, 1998. NOSEDA, M. D.; CEREZO, A. S. Alkali modification of carrageenans-II. The cyclization of model compounds containing non-sulfated -D-galactose units. Carbohydr. Polym., v. 26, p. 1-3, 1995. NYBERG, K.; EKBLAD, M.; BERGSTRM, T.; FREEMAN, C.; PARISH, C. R.; FERRO, V.; TRYBALA, E. The low molecular weight heparan sulfate-mimetic, PI88, inhibits cell-to-cell spread of herpes simplex virus. Antiviral Res., v. 63, p. 15-24, 2004. PAINTER, T.J. Algal Polysaccharides. In: ASPINALL, G. The polysaccharides, v. 2, p. 195-285, 1982. PARISH, C. R.; FREEMAN, C.; BROWN, K. J.; COWDEN, W. B., Identification of sulfated oligosaccharides-based inhibitors of tumor growth and metastasis using novel in vitro assays for angiogenesis and heparanase activity. Cancer Res., v. 59, p. 34333441, 1999. PENMAN, A.; REES, D. A. Carrageenans. Part XI. Mild oxidative hydrolysis of and -carrageenans and the characterisation of oligosaccharide sulphates. J. Chem. Soc., v. 19, p. 2191-2196, 1973. RAVEN, P.H.; EVERT, R.F.; EICHORN, S.E. Biologia vegetal, 5 edio. Guanabara/Koogan, Rio de Janeiro, 728 p. 1996.

111

RENN, D. Biotechnology and the red seaweed polysaccharide industry: status, needs and prospects. Trends Biotechnol., v. 15, p. 9-14, 1997. ROCHAS, C.; LAHAYE, M.; YAPHE, W. 13C-nmr spectroscopic investigation of agarose oligomers. Carbohydr. Res., v. 148, p. 199-207, 1986. SAKAMOTO, T.; SAKAI, T. Analysis of stucture of sugar-beet pectin by enzymatic methods. Phytochemistry, v. 39, p. 821-823, 1995. SHUKLA, D.; LIU, J.; BLAIKLOCK, P.; SHWORAK, N. W.; BAI, X.; ESKO, J. D.; COHEN, G. H.; EISENBERG, R. J.; ROSENBERG, R. D.; SPEAR, P. G. A novel role for 3-O-sulfated heparan sulfate in herpes simplex virus 1 entry. Cell, v. 99, p. 1322, 1999. STAHL, E. Thin-layer chromatography. Springer-Verlag, New York, 1965. STANEK, J.; CERNY, M.; PACAK, J. The oligosaccharides. First Edition. Academic Press, New York, 567 p., 1965. STEVENSON, T.; FURNEAUX, R. Chemical methods for the analysis of sulphated galactans from red algae. Carbohydr. Res., v. 210, p. 277-298, 1991. STORTZ, C. A.; CEREZO, A. S. Novel findings in carrageenans, agaroids and hybrid red seaweed galactans. Curr. Top. Phytoch., v. 4, p. 121-134, 2000. TAKANO, R.; HAYASHI, K.; HARA, S. Highly methylated agars with a high gelmelting point from the red seaweed, Gracilaria eucheumoides. Phytochemistry, v. 40, p. 487-490, 1995. TURVEY, J. R. Sulfates of the simple sugars. Advan. Carbohydrate Chem., v. 20, p. 183-218, 1965. URYU, T.; IKUSHIMA, N.; KATSURAYA, K.; SHOJI, T.; TAKAHASHI, N.; YOSHIDA, T.; KANNO, K.; MURAKAMI, T.; NAKASHIMA, H.; YAMAMOTO, N. Sulfated alkyl oligosaccharides with potent inhibitory effects on human immunodeficiency virus infection. Biochem. Pharmacol., v. 43, p. 2385-2392, 1992. USOV, A. I.; ELASHVILI, M.Y. Polysaccharides of algae 44. Investigation of sulfated galactan from Laurencia nipponica Yamada (Rhodophyta, Rhodomelaceae)., using partial reductive hydrolysis. Bot. Mar., v. 34, p. 553-560, 1991. VALIENTE, O.; FERNNDEZ, L. E.; PEREZ, R. M.; MARQUINA, G.; VELEZ H. Agar polysaccharides from the red seaweeds Gracilaria domingensis Sonder ex Ktzing and Gracilaria mammillaris (Montagne) Howe. Bot. Mar., v. 35, p. 77-81, 1992.

112

VAN de VELDE, F.; KNUTSEN, S. H.; USOV, A. I.; ROLLEMA, H. S.; CEREZO, A. S. 1H and 13C high resolution NMR spectroscopy of carrageenans: application in research and industry. Trends Food Sci. Technol., v. 13, p. 73-92, 2002. VIANA, A. G. Estudo de uma porfirana com estrutura no usual obtida da alga vermelha Porphyra columbina Montagne (Bangiales, Rhodophyta). Dissertao (Mestrado em Cincias, Bioqumica) Setor de Cincias Biolgicas, Universidade Federal do Paran, 97p., 2001. VIANA, A. G.; NOSEDA, M. D.; DUARTE, M. E. R.; CEREZO, A. S. Alkali modification of carrageenans. Part V. The iota-nu hybrid carrageenan from Eucheuma denticulatum and its cyclization to iota-carrageenan. Carbohydr. Polym., v. 58, p. 455-460, 2004. WALL, D.; DOUGLAS, S.; FERRO, V.; COWDEN, W.; PARISH, C. Characterisation of the anticoagulant properties of a range of structurally diverse sulfated oligosaccharides. Thromb. Res., v. 103, p. 325-335, 2001. WITCZAK, Z. J. Carbohydrates as new and old targets for future drug design. In: WITCZAK, Z. J.; NIEFORTH, K. A. Carbohydrates in drug design. M. Dekker, New York, 703 p., 1997. WITVROUW, M.; PANNECOUQUE, C.; DE CLERCQ, E. Polysulfates: chemistry and potential as antiviral drugs. In: WITCZAK, Z. J.; NIEFORTH, K. A. Carbohydrates in drug design. M. Dekker, New York, 703 p., 1997. YANG, B. Y.; BRAND, J.; MONTGOMERY, R. Pyruvated galactose and oligosaccharides from Erwinia chrysanthemi Ech6 extracellular polysaccharide. Carbohydr. Res., v. 331, p. 59-67, 2001. YOUNG, K.S.; BHATTACHARJEE, S. S.; YAPHE, W. Enzymic cleavage of the linkages in agarose, to yield agaro-oligosaccharides. Carbohydr. Res., v. 66, p. 207212, 1978. YU, G.; GUAN, H.; IOANOVICIU, A.S.; SIKKANDER, S.A.; THANAWIROON, C.; TOBACMAN, J.K.; TOIDA, T.; LINHARDT, R.J. Structural studies on carrageenan derived oligosaccharides. Carbohydr. Res., v. 337, p. 433-440, 2002. ZENG, Y.; LI, A.; KONG, F. A concise synthesis of arabinogalactan with -(16) galactopyranose backbone and -(12) arabinofuranose side chains. Tetrahedron Letters, v. 44, p. 8325-8329, 2003.

113

ZHANG, Q.; LI, N.; LIU, X.; ZHAO, Z.; LI, Z.; XU, Z. The structure of a sulfated galactan from Porphyra haitanensis and its in vivo antioxidant activity. Carbohydr. Res., v. 339, p. 105-111, 2004.