Sulfated heterorhamnans from the green seaweed Gayralia oxysperma: partial depolymerization, chemical structure and antitumor activity

被引:37
作者
Ropellato, Juliana [1 ]
Carvalho, Mariana M. [1 ]
Ferreira, Luciana G. [1 ]
Noseda, Miguel D. [1 ]
Zuconelli, Cristiane R. [2 ]
Goncalves, Alan G. [3 ]
Ducatti, Diogo R. B. [1 ]
Kenski, Juliana C. N. [2 ]
Nasato, Pauline. L. [1 ]
Winnischofer, Sheila M. B. [2 ]
Duarte, Maria E. R. [1 ]
机构
[1] Univ Fed Parana, Dept Bioquim & Biol Mol, Lab Glicobiol Estrutural Carboidratos Algas Marin, BR-81531980 Curitiba, Parana, Brazil
[2] Univ Fed Parana, Dept Bioquim & Biol Mol, Lab Cult Celular, BR-81531980 Curitiba, Parana, Brazil
[3] Univ Fed Parana, Dept Farm, BR-81531980 Curitiba, Parana, Brazil
关键词
Sulfated polysaccharides; Partial depolymerization; Chemical structure; Antitumor activity; Gayralia oxysperma; Green seaweed; RHAMNAN SULFATE; ANTICOAGULANT ACTIVITY; POLYSACCHARIDES; MANNANS; ALGAE;
D O I
10.1016/j.carbpol.2014.09.089
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Sulfated heterorhamnans produced by Gayralia oxysperma were utilized for the preparation of two homogeneous and highly sulfated Smith-degraded products (Mwof 109 and 251 kDa), which were constituted principally by 3-linked alpha-L-rhamnosyl units 2- or 4-sulfate and 2-linked alpha-L-rhamnosyl units 4- or 3,4-sulfate, in different percentages. The homogeneous products and the crude extracts containing the sulfated heterorhamnans showed cytotoxic effect against U87MG cells. These sulfated polysaccharides induced an increase in the number of cells in G1 phase with concomitant increase of the mRNA levels of p53 and p21. The presence of 2-linked disulfated rhamnose residues together with the molecular weight could be important factors to be correlated with the inhibitory effect on human glioblastoma cells. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:476 / 485
页数:10
相关论文
共 35 条
[1]   A RADIOCHEMICAL APPROACH TO THE DETERMINATION OF CARBOXYLIC-ACID GROUPS IN POLYSACCHARIDES [J].
ANDERSON, MA ;
STONE, BA .
CARBOHYDRATE POLYMERS, 1985, 5 (02) :115-129
[2]   Complete 1H and 13C NMR assignment of digeneaside, a low-molecular-mass carbohydrate produced by red seaweeds [J].
Ascêncio, SD ;
Orsato, A ;
França, RA ;
Duarte, MER ;
Noseda, MD .
CARBOHYDRATE RESEARCH, 2006, 341 (05) :677-682
[3]   Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma [J].
Cassolato, Juliana E. F. ;
Noseda, Miguel D. ;
Pujolb, Carlos A. ;
Pellizzaric, Franciane M. ;
Damonte, Elsa B. ;
Duarte, Maria E. R. .
CARBOHYDRATE RESEARCH, 2008, 343 (18) :3085-3095
[4]   Relationship between Oversulfation and Conformation of Low and High Molecular Weight Fucoidans and Evaluation of Their in Vitro Anticancer Activity [J].
Cho, Myoung Lae ;
Lee, Boo-Yong ;
You, SangGuan .
MOLECULES, 2011, 16 (01) :291-297
[5]   Overview of Anticoagulant Activity of Sulfated Polysaccharides from Seaweeds in Relation to their Structures, Focusing on those of Green Seaweeds [J].
Ciancia, M. ;
Quintana, I. ;
Cerezo, A. S. .
CURRENT MEDICINAL CHEMISTRY, 2010, 17 (23) :2503-2529
[6]   A SIMPLE AND RAPID METHOD FOR THE PERMETHYLATION OF CARBOHYDRATES [J].
CIUCANU, I ;
KEREK, F .
CARBOHYDRATE RESEARCH, 1984, 131 (02) :209-217
[7]   Sulfated seaweed polysaccharides as antiviral agents [J].
Damonte, EB ;
Matulewicz, MC ;
Cerezo, AS .
CURRENT MEDICINAL CHEMISTRY, 2004, 11 (18) :2399-2419
[8]   Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties [J].
de Araujo, Cristiano A. ;
Noseda, Miguel D. ;
Cipriani, Thales R. ;
Goncalves, Alan G. ;
Duarte, Maria Eugenia R. ;
Ducatti, Diogo R. B. .
CARBOHYDRATE POLYMERS, 2013, 91 (02) :483-491
[9]   A NOTE ON DETERMINATION OF ESTER SULPHATE CONTENT OF SULPHATED POLYSACCHARIDES [J].
DODGSON, KS ;
PRICE, RG .
BIOCHEMICAL JOURNAL, 1962, 84 (01) :106-&
[10]   A COLORIMETRIC METHOD FOR THE DETERMINATION OF SUGARS [J].
DUBOIS, M ;
GILLES, K ;
HAMILTON, JK ;
REBERS, PA ;
SMITH, F .
NATURE, 1951, 168 (4265) :167-167