Structure elucidation of a bioactive fucomannogalactan from the edible mushroom Hypsizygus marmoreus

Ruberney S Oliveira; Stellee M P Biscaia; Daniel L Bellan; Sthefany R F Viana; Maria Carolina Di-Medeiros Leal; Ana Flora D Vasconcelos; Luciano M Lião; Edvaldo S Trindade; Elaine R Carbonero

doi:10.1016/j.carbpol.2019.115203

Structure elucidation of a bioactive fucomannogalactan from the edible mushroom Hypsizygus marmoreus

Carbohydr Polym. 2019 Dec 1:225:115203. doi: 10.1016/j.carbpol.2019.115203. Epub 2019 Aug 17.

Authors

Ruberney S Oliveira¹, Stellee M P Biscaia², Daniel L Bellan³, Sthefany R F Viana⁴, Maria Carolina Di-Medeiros Leal⁵, Ana Flora D Vasconcelos⁶, Luciano M Lião⁷, Edvaldo S Trindade⁸, Elaine R Carbonero⁹

Affiliations

¹ Departamento de Química, Universidade Federal de Goiás, Regional Catalão, 75704-020 Catalão, Brazil. Electronic address: [email protected].
² Departamento de Biologia Celular, Universidade Federal do Paraná, 81531-980 Curitiba, Brazil. Electronic address: [email protected].
³ Departamento de Biologia Celular, Universidade Federal do Paraná, 81531-980 Curitiba, Brazil. Electronic address: [email protected].
⁴ Departamento de Engenharia Rural, Faculdade de Ciências Agronômicas, Universidade Estadual Paulista "Júlio de Mesquita Filho", 18610-307 Botucatu, Brazil. Electronic address: [email protected].
⁵ Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, 74001-970 Goiânia, Brazil. Electronic address: [email protected].
⁶ Departamento de Química e Bioquímica, Faculdade de Ciências e Tecnologia, Universidade Estadual Paulista "Júlio de Mesquita Filho", 19060-900 Presidente Prudente, Brazil. Electronic address: [email protected].
⁷ Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, 74001-970 Goiânia, Brazil. Electronic address: [email protected].
⁸ Departamento de Biologia Celular, Universidade Federal do Paraná, 81531-980 Curitiba, Brazil. Electronic address: [email protected].
⁹ Departamento de Química, Universidade Federal de Goiás, Regional Catalão, 75704-020 Catalão, Brazil. Electronic address: [email protected].

PMID: 31521290
DOI: 10.1016/j.carbpol.2019.115203

Abstract

A fucomannogalactan (FMG-Hm), with a molecular weight of 17.1 kDa, obtained from fruiting bodies of Hypsizygus marmoreus exhibited promising in vitro antimelanoma effects. FMG-Hm was not cytotoxic, nor did it alter the cell morphology and proliferation, but was able to inhibit colony-forming ability and cell migration in B16-F10 murine melanoma cells. An analysis of the monosaccharide composition indicated that FMG-Hm was composed of fucose, mannose, and galactose in a ratio of 1.00:1.08:3.17. The FMG-Hm was structurally characterized based on methylation analysis, partial acid hydrolysis, and NMR experiments. The results indicated that FMG-Hm contained a α-(1→6)-linked galactopyranosyl main chain, partially substituted at O-2 by non-reducing ends of α-L-fucopyranose and β-D-mannopyranose. The predicted structure of the heteropolysaccharide was established as.

Keywords: Antimelanoma; B16-F10 cell; Chemical structure; Fucomannogalactan; Hypsizygus marmoreus; Mushroom.

MeSH terms

Agaricales / metabolism*
Animals
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Cell Line, Tumor
Cell Movement / drug effects
Fruiting Bodies, Fungal / metabolism
Galactans / chemistry*
Galactans / isolation & purification*
Galactans / pharmacology*
Molecular Structure
Molecular Weight

Substances

Antineoplastic Agents
Galactans
mannofucogalactan