Composition in sugars of white and black garlic from different origins

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GlU

POR

12.a

Reuniao do Grupo de Glucidos

Carboidratos em Portugal

e potencial de diferenciac;ao internacional

Programa e livro de resumos

Universidade de Aveiro

,

Portugal

(2)

GlU

POR

12. a

Reuniao do Grupo de Glucidos

Carboidratos em Portugal e potencial de

diferencia~ao

internacional

Aveiro, 11-13 setembro 2017

(3)

Glll 12.' Reunlao do Grupo de Glucidos PUR Aveiro, 11-13 setembro 2017

COMISSAO 0RGANIZADORA

Chair: Manuel A. Coimbra (UA) Artur Silva (UA) - Presidente da SPQ Ana Moreira (UA)

Carmen Freire (UA) Claudia Nunes (UA) Claudia Passes (UA) Dulce Helena Teixeira (UA) Elisabete Coelho (UA) ldalina Gonc;:alves (UA) Joao Mano (UA) Paula Ferreira (UA)

COMISSAO CIENTiFICA

Manuel A. Coimbra (UA) - Chair

Amelia Rauter (FCUL) -Chair XXIX International Carbohydrate Symposium Artur Silva (UA) - Presidente da SPQ

Dulcineia Ferreira (IPV)- Presidente do Grupo de Glucidos Albertino Figueiredo (UBI)

Ana Maria Gomes (ESB) Angelina Palma (UNL) Ant6nio Vicente (UM) Armando Silvestre (UA) Artur Cavaco-Paulo (UM) Carmen Freire (UA) Fernando Nunes (UTAD) Hans Peter Wessel (UA) lsabel Ferreira (IPB) lsabel lsmael (UBI) Joao Mano (UA)

Jose A. Lopes da Silva (UA) Leticia Estevinho (IPB) Miguel Gama (UM) Pilar Gonc;:alves (FEUP) Rosario Domingues (UA) Victor Freitas (FCUP)

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Oll 12.' Reuniao do Grupo de Glucidos

POI Aveiro, 11-13 setembro 2017

K14 - Role of Cellulosomes in the deconstruction of complex carbohydrates ... .40 K15 -lmmunostimulatory polysaccharides from the hot water extracts of prickled broom (P. tridentatum (l.) Willk) dried inflorescences ... 41

0RAIS ...•...•...•...•...•...•...•.... 43 001 - Bacterial Cellulose: a nature's made nanostructured material for drug delivery ... 45 002 - Development of bacterial cellulose wound dressings with controlled delivery of vitamin D3 •••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••.•••••••••• 46

003- Deciphering ErbB2 Glycosylation Profile in Gastric Cancer Cells ... 47 004 - Sialic acids as immune regulators of antigen presentation in dendritic cells ... .48 005- Apple pomace arabinan- phloridzin binding capacity ... 49 006-Reducing negative volatile phenols in red wine by chitosan: impact on wine quality.50 007 -Dextrin-based hydrogel for the development of an injectable bone substitute ... 51 008- Supramolecular hydrogels based on the eo-assembly of simple carbohydrates and peptide amphiphiles for biological applications ... 52

009 - Cyclodextrins: impact on anthocyanins thermal and gastrointestinal stability ... 53 010- The glycosylic profile of edible flowers while alternative foods ... 54 011 -Mimicking Plusiotis Resplendens Cuticule with a New Photonic Properties of Cellulose Nanocrystals Films ... 55 012- Designing of a laccase super-catalyst ... 56 013- The role of choline chloride-based Deep Eutectic Solvent (DES) and curcumin on chitosan films properties ... 57 014- "POTATOPLASTIC": Development of starch-based bioplastics using potato chips industry byproducts ... 58 015 - Hemicellulose extraction using Deep Eutectic Solvents for Biorefinery purposes ... 59 016- Straw pentoses for the production of added-value products ... 60 017 "Identification and structural-functional characterization of a new chitin-binding protein module from Clostridium thermocel/um ...... 61 018- Glycan recognition in the human gut- A combined approach to unravel microbiome strategies ... 62 019- Potential ofthiol-amphiphile glycosaminoglycans as redox-sensitive nanoparticles.63 020- Modification of cyclo-oligosaccharides for drug encapsulation ... 64 021 - Carclnoembryonic antigen carries a2-3 linked sialic acid on type 11 chains and is implicated in the metastatic potential of gastric cancer cells ... 65 022- Hypoxia enhances the malignant nature of bladder cancer cells and concomitantly antagonizes protein 0-glycosylation extension ... 66 023 -Targeted 0-glycoproteomics explored increased sialylation and identified MUC16 as a poor prognosis biomarker in advanced stage bladder tumours ... 67 024- Structural Basis for the Highly Selective Recognition of Di-Giucosylated N-glycans by Human Malectin in the Endoplasmic Reticulum ... 68 025 - Magnetic and electrical conductive chitosan-based bionanocomposites ... 69 026 -Cellulose nanocrystals coated with gold nanoparticles and folic acid-conjugated chitosan as candidates for nanotheranostic systems ... 70 027-In vitro digestions to predict the glycemic index of rice ... 71

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llU "' 12.• Reuniao do Grupo de GIUcidos

PUB_ Avelro, 11-13 setembro 2017

028 - The effect of immobilized Hyaluronic Acid on CD44-overexpressing MKN45 gastric cancer cell line ... 72 029 -Influence of ionizing radiation on the free sugars content of several aromatic and medicinal plants ... , ... 73 030- Composition in sugars of white and black garlic from different origins ... 74 031 - Structural characterization of polysaccharides from Nannochloropsis oculata and their use in microarrays ... 75

032 - Incorporation of an extract rich in rosmarinic acid into cupcakes: Influence on the sugars and total carbohydrates composition ... 76 033- Protein-Glycan driven qui nary interactions under macromolecular crowding unveiled by NMR Spectroscopy ... 77 034- Non-enzymatic transglycosylation reactions and Maillard reaction: a competition with relevance for coffee melanoid ins formation ... 78 035 -Which arabinogalactans structural features can contribute to in vitro

immunostimulatory activity of coffee? ... 79 036 - Chemical synthesis of GaiNAc mimetics aimming macrophage galactose C-type lectin and block viral infections ... 80

P6STERES •••••••••••••••··••••••••··•••••••••••••••·•···•···•···•···•···•···•··•···•···•··· 81

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GlB 12.' Reuniao do Grupo de Glucldos

PO~- Aveiro, 11-13 setembro 2017

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09h30 10h30 Chairperson: Hans-Peter Wessel

Anfiteatro 30A 1 .14

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G/ycotmmuno/ogy crackmg sugars to develop noveftmmunotheraptes 10h00 10h30 _{G/ycosy/atton m}_cancerPL08- Celso Re1s _{molecular mechamsms and clinicaftmplicattons}(13SUP)

10h30 11h30 Cafe + P6steres

Sessoes Paralelas Biorefinery 11h30 12h50 Chairperson: Carmen Freire

Anf1teatro 30A 1 14 K07 - Florbela Carvalheiro (LNEG)

11h30 11h50 Btomass denved o/igosaccharides m the Biorefinery context Production and future prospects

013- Cl<'wdio Almeida (UP)

11h50 12h05 The role of Choline Chloride-based Deep Eutectic Solvent (DES) and Curcumin on chitosan films properties

014 - ldalina Gon9alves (UA)

12h05 12h20 "POTATOPLASTIC": Development of starch-based bioplastics using potato chips industry

byproducts

12h20 12h35 _{Hemicellulose extraction using Deep Eutectic Solvents for Biorefinery purposes}015- Eduarda Serra Morais (UA)

12h35 12h50 _{Straw pentoses for the production of}016-Patricia Moniz (CEBAL) _{added-value products}

Biotechnology and Glycomics

11h30 12h50 Chairperson: Rosario Oomingues

Anfiteatro 30A.2 05

11h30 11h50 KOB -Mariana Oliveira (UA)

Sequenttalfy moldable alginate-chitosan hydroge/s compatible with cell encapsulation

017- Diana Ribeiro (UNL)

11h50 12h05 Identification and structural-functional characterization of a new chitin-binding protein module from Clostridium thermocellum

018 - Viviana Correia (UNL)

12h05 12h20 Glycan recognition in the human gut- A combined approach to unravel microbiome

· strategies

12h20 12h35 _{Potential ofthiol-amphiphile glycosaminoglycans}019-Ana Margarida Carvalho (UM}

as redox-sensitive nanoparticles

12h35 12h50 _{Modification of cyc/o-oligosaccharides for drug encapsulation}020 - Jennifer Noro (UM)

Glycobiology

11h30 12h50 Chairperson: Paula Videira

sala 308 2 16 K09-Miguel Ribeiro (UTAD)

11h30 11h50 Btomsptred gluten-chitosan supramolecular assembftes· effect on the functtonaftty, digestibtfity and release of ceftac disease active peptides

021 - Catarina Games (13SUP)

11h50 12h05 Carcinoembryonic antigen carries a2-3 linked sialic acid on type If chains and is implicated in the metastatic potential of gastric cancer cells

022 -Andreia Peixoto (!PO}

12h05 12h20 Hypoxia enhances the malignant nature of bladder cancer cells and concomitantly antagSJnizes protein 0-glycosy/ation extension

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G LU 12.' Reuniao do Grupo de Glucidos

POR Aveiro, 11-13 setembro 2017

023- Rita Azevedo (I PO)

12h20 12h35 Targeted 0-glycoproteomics explored increased sialylation and identified MUC16 as a

poor proqnosis biomarker in advanced staqe bladder tumours

024 - Benedita Pinheiro (UNL)

12h35 12h50 Structural basis for the highly selective recognition of di-glucosylated N-glycans by human

malectin in the endoplasmic reticulum

12h50 14h30 Almo!fo

14h30 15h30 Chairperson: Ant6nio Vicente

Anfrteatro 30A 1 14

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--14h30 15h00 _Cyclodextn_n_{s based rr:ate}_fiPL09- Helena Marques (Ff'UL) _als_in_dru_g_c!_s_t_i_very_·_s_{l3te af the art and future perspectiVes}

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---15h00 15h30 _TallonngPL 10_c- CI.Sud1a _hito_s_an-_bNunes (UA) _a_ee_{d mate}_n_'_a_l_s

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Sessoes Paralelas Biomaterials

15h30 16h20 Chaiperson: Pilar Gon~alves

Anf1teatro 30A 1 14

15h30 15h50 _{In vitro and m v1vo stud1es of dextran-based mater}K10- Jorge Coelho (FCTUC) _i_{als for penpheral nerve regeneration}

15h50 16h05 _{Magnetic and electrical conductive chitosan-based bionanocomposites}025 -Ana Barra (UA) 026- Ricardo Pinto (UA)

16h05 16h20 Cellulose nanocrystals coated with gold nanoparticles and folic acid-conjugated chitosan as candidates for nanotheranostic systems

Gastric digestion and cell interaction devices

15h30 16h20 Chairperson: Albertino Figueiredo

Anf1teatro 30A.2 05 K11 -Ana Cnstma P1nheiro (UM)

15h30 15h50 Dynam1c gastromtestmal system as a tool to evaluate the behavwur of carbohydrates after

ingestion from macro to nano scale

15h50 16h05 _{In vitro digestions to predict the glycemia index of rice}027 - Daniel Madalena (UM) 028 - Sara Amorim (UM)

16h05 16h20 The effect of immobilized Hyaluronic Acid on CD44-overexpressing MKN45 gastric cancer

cell line

Sugars origins and occurrence

15h30 16h20 Chairperson: Jorge Justino

sala 308 216

15h30 15h50 _{The early t}_i_{mes of sc1ent1fic research on sugar chemistry}K12- Joao Ol1ve~ra (UA) 029- Eliana Pereira (IPB)

15h50 16h05 Influence of ionizing radiation on the free sugars content of several aromatic and medicinal

plants

16h05 16h20 030- Joana Betas (IPB)

Composition in sugars of white and black garlic from different origins

16h20 17h30 Cafe + P6steres

17h30 18h30 Chairperson: Artur Silva

Anf1teatro 30A. 1 14

17h30 18h00 PL 11 - Manuela P1ntado (ESB)

Opportunities m polysacchandes towards the preb10f1c act1v1ty

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ILU 12.' Reunlao do Grupo de Glucidos

Pll Avelro, 11·13 setembro 2017

030 -Composition in sugars of white and black garlic from different

origins

Joana Botas, Ange/a Fernandes, Lillian Barros, Ana Maria Carvalho, /sabel C.F.R. Ferreira

• Centro de lnvestigar;ao de Montanha (CIMO), ESA, lnstituto Politecnico de Braganr;a. Campus de Santa Apol6nia, 5300-253 Braganr;a, Portugal

*iferreira@ipb.pt

Allium sativum L., commonly known as garlic, has been used by populations for dietary

purposes and also for its medicinal interest, since antiquity. Garlic presents an interesting

nutritional profile as well as bioactive compounds related to its medicinal properties:

antimicrobial, antiseptic, antiviral, antioxidant, anticancer, immunostimulatory,

cardioprotective and hypoglycemic [1).

This study has tested (i) three samples of fresh white garlic, from different origins: Spain

(commercial variety), Tn3s-os-Montes and Algarve, Portugal (both traditional cultivated

varieties); (ii) and a sample of black garlic. Black garlic is the result of a thermic treatment

in which garlic bulbs are subjected to controlled temperature and humidity, resulting in organoleptic changes such as colour and flavour. Nutritional and chemical compositions

also suffer changes in this process [2]. The samples were tested to determine free sugars

content, using high performance liquid chromatography coupled to a refraction index

detector (HPLC-RI).

Four different sugars were identified: fructose, sucrose, xylose and glucose. Fructose was

the most abundant sugar in black garlic (BG), while sucrose was the most abundant in

commercial garlic (CG), followed by the traditional cultivated garlic from Algarve (TGA) and

traditional cultivated sample from Tras-os-Montes (TGTM). Xylose was only detected in

BG sample. Sucrose was found in higher concentration in TGA sample and at lower levels

in BG sample. The highest content of glucose and fructose was found in BG, while the

lowest content was observed in TGA. Total sugars content was significantly higher in BG

sample (33.55 g/1 00 g of fresh weight), than in the other samples: CG (1.32 g/1 00 g fw),

TGA ( 1 .48 g/1 00 g fw) and TGTM (0. 70 g/1 00 g fw).

These results show some variability on the sugars content, less relevant between the white garlic samples when compared to the black garlic sample. This study shows the

possible variations in the sugars' profile accordingly to various factors, such as variety or

processing treatments. Therefore, these experiments are highly important to have a better

understanding of the products used in our diet.

Acknowledgments: The authors are grateful to the Foundation for Science and Technology (FCT, Porlugal) and FEDER under Program PT2020 for financial supporl to CIMO {UID/AGR/0069012013), A.F grant (SFRH/BPD/11475312016) and L. B contract.

References:

1. Martins, N., Petropoulos, S., Ferreira, I.C.F.R. Chemical composijion and bioactive compounds of garlic (Allium sativum L.) as affected by pre-and pas-harvest conditions: A review. Food Chemistry, 2016, 211, 41·50.

2. Choi, I.S., Cha, H.S., Lee, Y.S. Physicochemical and antioxidant properties of black garlic. Molecules, 2014, 19, 16811-16823.