The system of galactans from Cryptonemia crenulata (Halymeniaceae, Halymeniales) and the structure of two major fractions. Kinetic studies on the alkaline cyclization of the unusual diad G2S→D(L)6S

Mello, Rosiane Guetter; Noseda, Miguel D.; Cerezo, Alberto S.; Duarte, Maria Eugênia R.

doi:10.1016/j.carres.2005.01.010

Cited by 28 publications

(7 citation statements)

References 68 publications

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“…In spite of the close structural similarities between HS and heparin, the antiviral action of C2S-3 is exerted with higher effectiveness than heparin against diverse strains of DENV-2. As previously described [11] C2S-3 presents the diads [®3)-b-D-( 4 C 1 )-Galp-2-OSO 3 -(1®4)-a-L-( 1 C 4 )-Galp-6¢-OSO 3 -(1®] and [®3)-b-D-( 4 C 1 )-Galp-2-OSO 3 -(1®4)-a-D-( 4 C 1 )-Galp-6¢-OSO 3 -(1®]. Both disaccharide units present in C. crenulata polysaccharide are similar to the repeating structures of the minimal sequence of HS necessary to interact with glycoprotein C of herpes simplex virus (HSV) [12].…”

Section: Resultsmentioning

confidence: 99%

“…Chemical and spectroscopic analyses showed that C2S-3 (MW 236 kDa) is constituted of 3-linked b-D-galactose 2-and 2,6-disulfated and 4-linked a-D-and a-L-galactose 6-and 2,6-disulfated besides 3,6-anhydro-a-D-and a-L-galactose. The last unit is C-2 substituted either by sulfate or methoxy groups [11]. Heparin (Sigma-Aldrich Co.; St. Louis, MO, USA) was used as reference substance.…”

Section: Compoundsmentioning

confidence: 99%

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An Algal-Derived DL-Galactan Hybrid is an Efficient Preventing Agent for in vitro Dengue Virus Infection

Talarico¹,

Duarte²,

Mello³

et al. 2007

Planta Med

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The DL-galactan hybrid C2S-3, isolated from the red seaweed Cryptonemia crenulata (Halymeniaceae, Halymeniales), is a potent and selective inhibitor of the multiplication of diverse strains of DENV-2 in Vero cells with higher effectiveness than the reference polysaccharide heparin. The presence of the compound either only at virus adsorption or at virus internalization exerted a significant and dose-dependent inhibition in DENV-2 plaque number. The compound failed to inactivate DENV-2 directly by incubation of virus before cell infection as well as to induce a refractory state by cell pretreatment. Thus, the inhibitory effect was exclusively exerted through a blockade in virus multiplication during the infectious process. When the entry of DENV-2 particles into the cell is bypassed, as occurs in virus RNA transfection, the polysaccharide C2S-3 failed to block the completion of the multiplication cycle. Furthermore, the antiviral properties of C2S-3 are not correlated with anticoagulant activity.

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Section: Resultsmentioning

confidence: 99%

Section: Compoundsmentioning

confidence: 99%

An Algal-Derived DL-Galactan Hybrid is an Efficient Preventing Agent for in vitro Dengue Virus Infection

Talarico¹,

Duarte²,

Mello³

et al. 2007

Planta Med

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“…These polymers are classifi ed according to the stereochemistry of the 4-linked units into agarans (L-enantiomer) and carrageenans (D-enantiomer) (Painter, 1983;Craigie, 1990). Recently, a third group, denominated D/L-hybrids and containing D and L enantiomers of the α-Galp units (Zibetti et al, 2005;Zibetti et al, 2009) has emerged. Agarans and carrageenans can present complex substitution patterns due to the presence of sulfate, methyl, 4,6-O-(1'-carboxyethylidene) and glycosyl groups (Craigie, 1990).…”

Section: Introductionmentioning

confidence: 99%

Production of agaro- and carra-oligosaccharides by partial acid hydrolysis of galactans

Ducatti¹,

Colodi²,

Gonçalves³

et al. 2011

Rev. bras. farmacogn.

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Agaro-and carra-oligosaccharides were produced by partial acid hydrolysis of commercial agarose and kappa-carrageenan. Di-and tetrasaccharides were purified by gel filtration chromatography and characterized by NMR (1D and 2D) spectroscopy and ESIMS. The following oligosaccharides were obtained: agarobiose, agarotetraose, kappa-carrabiose and kappa-carratetraose. Agarobiose and agarotetraose were used as standards to develop a high performance size exclusion chromatography (HPSEC) method which was utilized to study the hydrolysis rate of agarose and oligosaccharide production. Six hours of hydrolysis (0.1 M TFA, 65 o C) produced mainly di-and tetrasaccharides. The methodology for oligosaccharide production and evaluation developed in the present work shows good potential for the production of bioactive oligosaccharides. Keywords:agaro-oligosaccharides carra-oligosaccharides partial acid hydrolysis 3,6-anhydro-galactose agarose kappa-carrageenan

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“…Weidner et al (2004) showed that C. seminervis from the same site in the Brazilian coast did not exhibit induced defences against amphipod grazers. However, a series of biologically active galactans was identified from other species of Cryptonemia (C. crenulata, Talarico et al 2004;Zibetti et al 2005), that could play some yet unknown ecological role.…”

Section: Discussionmentioning

confidence: 99%

The effect of epibionts on the susceptibility of the red seaweedCryptonemia seminervisto herbivory and fouling

2008

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Epibiosis or fouling on living organisms can have direct and indirect detrimental effects, in particular on photosynthetic organisms such as seaweeds. It thus seems reasonable to hypothesize that macroalgae have been selected for the presence or induction of antifouling (AF) defences. The red seaweed Cryptonemia seminervis is usually found in nature with an elevated cover of epibionts. To assess the effect of epibiosis on the susceptibility of this seaweed to herbivory and fouling, the abundance of fouling was evaluated and compared to herbivore consumption (by amphipods and sea urchins) of fouled (bryozoan and sponge) and non-fouled C. seminervis. Attachment of the mussel Perna perna to surfaces treated with extracts from seaweeds with and without epibionts was also assessed. Epibiosis corresponded to ca. 51% of the blade surface of C. seminervis, sometimes covering as much as 90% and up to 51% of the thallus weight, encompassing mainly the bryozoan Membranipora membranacea and an unidentified sponge. Algae colonized by M. membranacea were preferred compared to algae devoid of epibionts, a 'shared doom' effect, either by the amphipod Elasmopus brasiliensis or by the urchin Lytechinus variegatus (p < 0.01). Sponge epibiosis also increased consumption by both herbivores (p < 0.001), suggesting that epibionts may act as lures to herbivores, attracting consumers that otherwise would not feed significantly on the seaweed. Foods containing extracts from fouled C. seminervis were preferred by urchins over the alga devoid of epibionts. However, extracts from fouled alga inhibited mussel attachment when compared to epibiont-free alga. Differences might be a direct detrimental effect of the presence of epibionts. On the other hand, epibiosis may induce the production of AF defences in C. seminervis.

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The system of galactans from Cryptonemia crenulata (Halymeniaceae, Halymeniales) and the structure of two major fractions. Kinetic studies on the alkaline cyclization of the unusual diad G2S→D(L)6S

Cited by 28 publications

References 68 publications

An Algal-Derived DL-Galactan Hybrid is an Efficient Preventing Agent for in vitro Dengue Virus Infection

An Algal-Derived DL-Galactan Hybrid is an Efficient Preventing Agent for in vitro Dengue Virus Infection

Production of agaro- and carra-oligosaccharides by partial acid hydrolysis of galactans

The effect of epibionts on the susceptibility of the red seaweedCryptonemia seminervisto herbivory and fouling

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