17 Oct 2018

Glucosylation of pterostilbene published in Molecules



In this paper was performed the synthesis of a novel α-glucosylated derivative of pterostilbene by a transglycosylation reaction using starch as glucosyl donor, catalyzed by cyclodextrin glucanotransferase (CGTase) from Thermoanaerobacter sp.
Due to the formation of several polyglucosylated products with CGTase, the yield of monoglucoside was increased by the treatment with a recombinant amyloglucosidase (STA1) from Saccharomyces cerevisiae (var. diastaticus).
The glucosylation of pterostilbene enhanced its solubility in water to approximately 0.1 g/L. The α-glucosylation caused a slight loss of antioxidant activity towards ABTS˙+ radicals. Pterostilbene α-D-glucopyranoside was less toxic than pterostilbene for human SH-S5Y5 neurons, MRC5 fibroblasts and HT-29 colon cancer cells, and similar for RAW 264.7 macrophages.


''Enzymatic synthesis of a novel pterostilbene α-glucoside by the combination of cyclodextrin glucanotransferase and amyloglucosidase''. J.L. González-Alfonso, D. Rodrigo-Frutos, E. Belmonte-Reche, P. Peñalver, A. Poveda, J. Jimenez-Barbero, A.O. Ballesteros, Y. Hirose, J. Polaina, J.C. Morales, M. Fernández-Lobato and F. J. Plou. Molecules 25;23(6) (2018)doi:10.3390/molecules23061271 

16 Oct 2018

Our group visited CPhI Worldwide in Madrid

The ABG group visited the pharmaceutical exhibition CPhI Worldwide in Madrid on October 10th 2018. It was an opportunity to connect with pharma professionals and meet companies from around the world.




1 Oct 2018

Glycosylation of hydroxytyrosol published in ChemCatChem

We have investigated the ability of the β-fructofuranosidase pXd-INV from the yeast Xanthophyllomyces dendrorhous to glycosylate the olive biophenol hydroxytyrosol (HT). Two fructosylated derivatives (Fru-HT1 and Fru-HT2) were synthesized.MS and 2D-NMR analyses showed that the major product (Fru-HT1) was fructosylated at the primary OH of HT. The structure of the complexes with the substrates and the product analyzed by crystallography led to the understanding of the molecular determinants regulating the enzymatic mechanism. Product-soaked crystals revealed that the minor derivative (Fru-HT2) was fructosylated at the phenolic p-OH group.  One of the studied mutants (N342Q) was notably more specific for the fructosylation at the phenolic OH than the wild-type.

Reference:“Fructosylation of hydroxytyrosol by the β-fructofuranosidase from Xanthophyllomyces dendrorhous: Insights into the molecular basis of the enzyme specificity”. N. Míguez, M. Ramírez-Escudero, M. Gimeno-Pérez, A. Poveda, J. Jiménez-Barbero, A. O. Ballesteros, M. Fernández-Lobato, J. Sanz-Aparicio* and F. J. Plou* ChemCatChem, http://dx.doi.org/10.1002/cctc.201801171(2018)

26 Jul 2018

Article on glucosylation of epigallocatechin gallate

In this work, the synthesis of various α-glucosyl derivatives of (‒)-epigallocatechin gallate (EGCG), the predominant catechin in green tea, was performed in water at 50 °C by a transglycosylation reaction catalyzed by cyclodextrin glycosyltransferase (CGTase) from Thermoanaerobacter sp. The molecular weight of reaction products was determined by HPLC-MS. Using hydrolyzed potato starch as glucosyl donor, two main monoglucosides were obtained with conversion yields of 58% and 13%, respectively.

“Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.”. J.L. Gonzalez-Alfonso, L. Leemans, A. Poveda, J. Jimenez-Barbero, A.O. Ballesteros and F.J. Plou. Journal of Agricultural and Food Chemistry 66, 7402–7408 (2018), doi:10.1021/acs.jafc.8b02143

28 Jun 2018

II Spanish Meeting on Biocatalysis (JEB 2018)

 The Group has participated actively in the II Spanish Meeting on Biocatalysis (JEB 2018) held in Oviedo (25-26 June 2018). We have contributed in the Scientific Committee, and with an oral presentation by Jose-Luis González, a flash presentation by Fadia Cervantes, and two posters by Noa Míguez and David Fernandez. One of the sessions of the meeting was devoted to Prof. Antonio Ballesteros, pioneer in the development of Biocatalyst in Spain.






25 May 2018

The ABG group in the Science World Exhibition

Our group visited the Science World Exhibition held in Madrid on May 24th 2018. The event showed the latest in iaboratory innovations and laboratory practice and safety.

2 Mar 2018

Publication of a post in the blog "Science to take away"

Francisco J. Plou has published a post describing the application of enzymes in detergents in the CSIC blog "Science to take away". The aim of this blog is to promote the scientific divulgation with the collaboration of the popular newspaper "20 minutos".

https://blogs.20minutos.es/ciencia-para-llevar-csic/2018/03/01/manchas-dificiles-la-solucion-esta-en-las-enzimas/

 https://twitter.com/CSICdivulga/status/969138157391314944

22 Feb 2018

Visit of the Account Manager of Novozymes Spain

Ramiro Martínez, Account Manager of Novozymes Spain, visited the Applied Biocatalysis Group. It was a good opportunity to share the latest developments and applications of industrial enzymes, and to continue the fruitful collaboration of our group with Novozymes. 

14 Jan 2018

Special Issue “Biocatalysis in Spain"

FigureFrancisco Plou is one of the Editors of the  Special Issue “Biocatalysis in Spain:A field of success and innovation” published by the journal Biocatalysis and Biotransformation (Taylor & Francis), which covers the work of several Spanish groups in the field of biocatalysis. Thus, both research articles and reviews allow one to draw an accurate view of the state-of-the-art development of this subject in Spain.

14 Jul 2017

Paloma Santos-Moriano defends her Thesis

Paloma Santos-Moriano defended her Thesis by the Autonomous University of Madrid (UAM) entitled "Biocatalytic processes for the production of bioactive carbohydrates: fructooligosaccharides and chitooligosaccharides", supervised by Dr. Francisco J. Plou. She obtained the maximum qualification (Sobresaliente cum laude). The jury was formed by Dr. Jose L. Copa-Patiño (University of Alcala), Dr. Javier Moreno (CIAL, UAM-CSIC), Dr. Beatriz Gullon (University of Santiago de Compostela), Dr. Pamela Torres (Repsol) and Dr. Miguel Remacha (UAM). CONGRATULATIONS!

7 Jul 2017

Dr. Yoshihiko Hirose visits the Applied Biocatalysis Group

Dr. Yoshihiko Hirose, enzyme application consultant at Enzyme Techno (Japan), visited our laboratories. We have established a collaboration in the field of enzymatic glycosylation of bioactive polyphenols.

29 Jun 2017

Meeting of the Spanish Society of Catalysis (SECAT 2017)

Our PhD student Jose L. González-Alfonso delivered an oral presentation during the celebration of the Meeting of the Spanish Society of Catalysis (SECAT 2017, "Catalysis for a more sustainable world") held in Oviedo (26-28 June 2017). The talk was entitled "Enzymatic glycosylation of two bioactive polyphenols: hydroxityrosol and epigallocatechin gallate", by Noa Míguez, María Gimeno-Pérez, José Luis González-Alfonso, Mercedes Ramírez-Escudero, Laura Leemans, Antonio O. Ballesteros, Julia Sanz-Aparicio, María Fernández-Lobato and Francisco J. Plou.

22 Jun 2017

Participation in the Spanish Congress of Biotechnology (BIOTEC 2017)

The Applied Biocatalysis Group at CSIC has contributed to the Spanish Congress of Biotechnology (BIOTEC 2017) held in Murcia (18-21 June 2017) with one oral presentation (by Paloma Santos-Moriano) and three poster presentations (by Jose L. Gonzalez-Alfonso, Noa Miguez and Fadia Cervantes). We have presented our latest advances in the synthesis of prebiotic oligosachharides, novel carbohydrates and glycosides of plant polyphenols.

1 Apr 2017

Production of chitooligosaccharides and their bioactive properties

Several commercial enzymes were screened for chitosanolytic activity. The hydrolysis of different chitosans was followed by size exclusion chromatography (SEC-ELSD), mass spectrometry (ESI-Q-TOF), and high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD). Neutrase 0.8L converted 10 g/L of various chitosans into mostly deacetylated oligosaccharides, yielding approximately 2.5 g/L of chitobiose, 4.5 g/L of chitotriose and 3 g/L of chitotetraose. In collaboration with the Institute of Parasitology and Biomedicine "Lopez-Neyra" (CSIC), the synthesized COS were tested in vitro for their neuroprotective and anti-inflammatory activities, and compared with other functional ingredients, namely fructooligosaccharides.

Reference: “Enzymatic production of fully deacetylated chitooligosaccharides and their neuroprotective and anti-inflammatory properties”. P. Santos-Moriano, L. Fernandez-Arrojo, M. Mengibar, E. Belmonte-Reche, P. Peñalver, F.N. Acosta, P. Kidibule, A.O. Ballesteros, J.C. Morales, M. Fernandez-Lobato and F.J. Plou. Biocatalysis and Biotransformation (2017), doi: 10.1080/10242422.2017.1295231

10 Mar 2017

High school students from Cordoba (Spain) visit the Applied Biocatalysis Group

A group of students from the High School IES-Averroes (Cordoba, Spain) have visited the Applied Biocatalysis Group at the Institute of Catalysis and Petrochemistry (CSIC). They have carried out a series of experiments related with the applications of enzymes in the food industry.

10 Oct 2016

XVIII LIGNOCEL Meeting

The XVIII meeting of the LIGNOCEL Network (Biotechnology of Lignocellulolosic Materials),  took place in Jaen (October 6-7 2016), Our group presented the work “Lipase-catalyzed preparation of mono- and diesters of ferulic acid”. The meeting was very fruitful to establish new collaborations between research groups involved in the exploitation of lignocellulosic residues.


27 Sep 2016

Participation in the VI Congress of Industrial Microbiology and Microbial Biotechnology

The Applied Biocatalysis Group has participated in the VI Congress of Industrial Microbiology and Microbial Biotechnology (CMIBM’16) held at the University of Leon, Spain (September 12-14, 2016). The Congress was auspiced by the Spanish Society of Microbiology. Our group presented an abstract entitled "Production of galactooligosaccharides using Kluyveromyces lactis permeabilized cells: effect of entrapment in alginate"

23 Sep 2016

Dual reactor for production of chitosan oligosaccharides


Chitooligosaccharides (COS), obtained by chemical or enzymatic hydrolysis of chitosan, are more soluble and exhibit enhanced biological activities compared with the polysaccharide. COS show antimicrobial, antioxidant, antiangiogenic, antitumoral, anti-inflammatory and prebiotic properties, among others. In this work, a chitosanolytic enzyme was covalently immobilized onto glyoxal agarose beads  and assessed for the continuous production of COS. A two-step process was proposed, in which chitosan was first hydrolyzed in a batch reactor to a viscosity that could flow through a packed-bead reactor (PBR), thus avoiding clogging of the column. This work was performed in collaboration with the Technical University of Denmark

Reference: “Continuous production of chitooligosaccharides by an immobilized enzyme in a dual-reactor system”. P. Santos-Moriano, J.M. Woodley, F.J. Plou. Journal of Molecular Catalysis B: Enzymatic 133, 211-217 (2016), doi:10.1016/j.molcatb.2016.09.001