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Chemical structure of the complex pyruvylated and sulfated agaran from the red seaweed Palisada flagellifera (Ceramiales, Rhodophyta).
Carbohydr Res. 2012 Jan 10; 347(1):83-94.CR

Abstract

A homogeneous agaran fraction from Palisada flagellifera (Laurencia complex, Rhodomelaceae, Ceramiales) was obtained by aqueous room-temperature extraction, followed by ion-exchange chromatography. This galactan presents a highly complex structure with at least 18 different types of derivatives. The A units were found mostly pyruvylated, 2-sulfated (∼34%), and 6-methylated (∼34%), with the latter partially 2- and 2,4-sulfated. Minor amounts of β-D-galactopyranosyl units 2-, 6- and 2,6-sulfated, 6-glycosylated, and non-substituted are also present. The B-units are L-sugars composed predominantly of their cyclized derivatives, 3,6-anhydrogalactose and 3,6-anhydro-2-O-methylgalactose (∼56%). The former are linked to β-D-galactosyl (6-methyl) (6-glycosylated) units, as well as to 4,6-O-(1-carboxyethylidene)-β-D-galactose 2-sulfate in the proportion of 3:1.8, respectively. A significant amount (∼18%) of the α-L-galactopyranosyl units are linked to pyruvylated β-D-galactose 2-sulfate residues. An important part of the B-units (20%) is represented by α-L-galactose 6-sulfate substituted on C-3 by xylosyl, galactosyl and/or 2,3-di-O-methylgalactose units or sulfate groups that preclude their cyclization to 3,6-anhydrogalactosyl derivative. The precursor units are present in relatively low percentages. Kinetic studies suggest that in P. flagellifera agaran the cyclizable units are linked to 6-O-methyl-β-D-galactosyl and/or β-D-galactosyl units (6-glycosylated). The structural complexity of this polysaccharide is increased by the presence of 2- and 3,6-sulfated α-L-galactoses, with the latter additionally 2-O-methylated. Therefore, the major subfraction obtained from the cold extract contains structurally complex sulfated, methylated, and pyruvylated agaran.

Authors+Show Affiliations

Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, PO Box: 19046, CEP: 81531-990 Curitiba, Paraná, Brazil.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22055816

Citation

Ferreira, Luciana G., et al. "Chemical Structure of the Complex Pyruvylated and Sulfated Agaran From the Red Seaweed Palisada Flagellifera (Ceramiales, Rhodophyta)." Carbohydrate Research, vol. 347, no. 1, 2012, pp. 83-94.
Ferreira LG, Noseda MD, Gonçalves AG, et al. Chemical structure of the complex pyruvylated and sulfated agaran from the red seaweed Palisada flagellifera (Ceramiales, Rhodophyta). Carbohydr Res. 2012;347(1):83-94.
Ferreira, L. G., Noseda, M. D., Gonçalves, A. G., Ducatti, D. R., Fujii, M. T., & Duarte, M. E. (2012). Chemical structure of the complex pyruvylated and sulfated agaran from the red seaweed Palisada flagellifera (Ceramiales, Rhodophyta). Carbohydrate Research, 347(1), 83-94. https://doi.org/10.1016/j.carres.2011.10.007
Ferreira LG, et al. Chemical Structure of the Complex Pyruvylated and Sulfated Agaran From the Red Seaweed Palisada Flagellifera (Ceramiales, Rhodophyta). Carbohydr Res. 2012 Jan 10;347(1):83-94. PubMed PMID: 22055816.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chemical structure of the complex pyruvylated and sulfated agaran from the red seaweed Palisada flagellifera (Ceramiales, Rhodophyta). AU - Ferreira,Luciana G, AU - Noseda,Miguel D, AU - Gonçalves,Alan G, AU - Ducatti,Diogo R B, AU - Fujii,Mutue T, AU - Duarte,Maria E R, Y1 - 2011/10/14/ PY - 2011/07/06/received PY - 2011/10/05/revised PY - 2011/10/06/accepted PY - 2011/11/8/entrez PY - 2011/11/8/pubmed PY - 2012/5/5/medline SP - 83 EP - 94 JF - Carbohydrate research JO - Carbohydr Res VL - 347 IS - 1 N2 - A homogeneous agaran fraction from Palisada flagellifera (Laurencia complex, Rhodomelaceae, Ceramiales) was obtained by aqueous room-temperature extraction, followed by ion-exchange chromatography. This galactan presents a highly complex structure with at least 18 different types of derivatives. The A units were found mostly pyruvylated, 2-sulfated (∼34%), and 6-methylated (∼34%), with the latter partially 2- and 2,4-sulfated. Minor amounts of β-D-galactopyranosyl units 2-, 6- and 2,6-sulfated, 6-glycosylated, and non-substituted are also present. The B-units are L-sugars composed predominantly of their cyclized derivatives, 3,6-anhydrogalactose and 3,6-anhydro-2-O-methylgalactose (∼56%). The former are linked to β-D-galactosyl (6-methyl) (6-glycosylated) units, as well as to 4,6-O-(1-carboxyethylidene)-β-D-galactose 2-sulfate in the proportion of 3:1.8, respectively. A significant amount (∼18%) of the α-L-galactopyranosyl units are linked to pyruvylated β-D-galactose 2-sulfate residues. An important part of the B-units (20%) is represented by α-L-galactose 6-sulfate substituted on C-3 by xylosyl, galactosyl and/or 2,3-di-O-methylgalactose units or sulfate groups that preclude their cyclization to 3,6-anhydrogalactosyl derivative. The precursor units are present in relatively low percentages. Kinetic studies suggest that in P. flagellifera agaran the cyclizable units are linked to 6-O-methyl-β-D-galactosyl and/or β-D-galactosyl units (6-glycosylated). The structural complexity of this polysaccharide is increased by the presence of 2- and 3,6-sulfated α-L-galactoses, with the latter additionally 2-O-methylated. Therefore, the major subfraction obtained from the cold extract contains structurally complex sulfated, methylated, and pyruvylated agaran. SN - 1873-426X UR - https://www.unboundmedicine.com/medline/citation/22055816/Chemical_structure_of_the_complex_pyruvylated_and_sulfated_agaran_from_the_red_seaweed_Palisada_flagellifera__Ceramiales_Rhodophyta__ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(11)00489-7 DB - PRIME DP - Unbound Medicine ER -