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Vol. 26 No. 23 (2014)

Copyright (c) 2014 S. Beyaztas1, M. Kucukislamoglu2, F. Sonmez2, M. Nebioglu2, S. Besoluk3, M. Arslan2, M. Zengin2, O. Arslan1

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Total Synthesis of Apigenin Glycosides and the Effect of These Compounds on Polyphenol Oxidase Enzyme Activity

https://doi.org/10.14233/ajchem.2014.18034
S. Beyaztas1
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr
M. Kucukislamoglu2
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr
F. Sonmez2
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr
M. Nebioglu2
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr
S. Besoluk3
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr
M. Arslan2
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr
M. Zengin2
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr
O. Arslan1
1Balikesir University, Science and Art Faculty, Department of Chemistry/Biochemistry Section, Balikesir, Turkey 2Sakarya University, Science and Art Faculty, Department of Chemistry/Organic Chemistry Section, Sakarya, Turkey 3Sakarya University, Faculty of Education, Department of Science Education, Sakarya 54300, Turkey *Corresponding author: Fax: +90 266 6121215; Tel: +90 266 6121278; E-mail: beyaztas@balikesir.edu.tr

Corresponding Author(s) : S. Beyaztas1

Asian Journal of Chemistry, Vol. 26 No. 23 (2014)

Abstract

We have succeeded in total synthesis of apigenin 7-O-b-D-cellobioside (1a) and apigenin 7-O-b-D-cellobiosyl-4'-O-b-D-glucopyranoside (1c) via four and six steps in a total yield of 56 and 76 % from naringenin (2), respectively. We also synthesized apigenin 7-O-b-D-glucopyranoside (1b) and apigenin 7,4'-di-O-b-D-glucopyranoside (1d) from naringenin (2). We also examined two monoglycoside and two diglycoside with polyphenol oxidase (PPO) from potato (Solanum tuberosum). The result showed that 1a inhibited the polyphenol oxidase enzyme activity. The value of IC50 was 1.08 mM. 1b was activator effect on polyphenol oxidase enzyme activity. On the other hand, apigenin 7,4'-di-O-glycosides (1c-d) showed no activator and inhibitor effect on polyphenol oxidase enzyme activity.

Keywords

Apigenin 7-O-b-D-cellobioside Apigenin 7-O-b-D-glucopyranoside Inhibition Polyphenol oxidase.
Beyaztas1, S., Kucukislamoglu2, M., Sonmez2, F., Nebioglu2, M., Besoluk3, S., Arslan2, M., … Arslan1, O. (2014). Total Synthesis of Apigenin Glycosides and the Effect of These Compounds on Polyphenol Oxidase Enzyme Activity. Asian Journal of Chemistry, 26(23), 8219–8222. https://doi.org/10.14233/ajchem.2014.18034
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