Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin
© 2015 Sangpheak et al; licensee Beilstein-Institut. The aim of this work is to improve physical properties and biological activities of the two flavanones hesperetin and naringenin by complexation with β-cyclodextrin (β-CD) and its methylated derivatives (2,6-di-O-methyl-β-cyclodextrin, DM-β-CD and...
Saved in:
Main Authors: | , , , , , , , , |
---|---|
Format: | Journal |
Published: |
2018
|
Subjects: | |
Online Access: | https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84961848296&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/43959 |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Institution: | Chiang Mai University |
id |
th-cmuir.6653943832-43959 |
---|---|
record_format |
dspace |
spelling |
th-cmuir.6653943832-439592018-04-25T07:44:10Z Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin Waratchada Sangpheak Jintawee Kicuntod Roswitha Schuster Thanyada Rungrotmongkol Peter Wolschann Nawee Kungwan Helmut Viernstein Monika Mueller Piamsook Pongsawasdi Agricultural and Biological Sciences © 2015 Sangpheak et al; licensee Beilstein-Institut. The aim of this work is to improve physical properties and biological activities of the two flavanones hesperetin and naringenin by complexation with β-cyclodextrin (β-CD) and its methylated derivatives (2,6-di-O-methyl-β-cyclodextrin, DM-β-CD and randomly methylated-β-CD, RAMEB). The free energies of inclusion complexes between hesperetin with cyclodextrins (β-CD and DM-β-CD) were theoretically investigated by molecular dynamics simulation. The free energy values obtained suggested a more stable inclusion complex with DM-β-CD. The vdW force is the main guest-host interaction when hesperetin binds with CDs. The phase solubility diagram showed the formation of a soluble complex of A L type, with higher increase in solubility and stability when hesperetin and naringenin were complexed with RAMEB. Solid complexes were prepared by freeze-drying, and the data from differential scanning calorimetry (DSC) confirmed the formation of inclusion complexes. The data obtained by the dissolution method showed that complexation with RAMEB resulted in a better release of both flavanones to aqueous solution. The flavanones-β-CD/DM-β-CD complexes demonstrated a similar or a slight increase in anti-inflammatory activity and cytotoxicity towards three different cancer cell lines. The overall results suggested that solubilities and bioactivities of both flavanones were increased by complexation with methylated β-CDs. 2018-01-24T04:36:30Z 2018-01-24T04:36:30Z 2015-12-29 Journal 18605397 2-s2.0-84961848296 10.3762/bjoc.11.297 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84961848296&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/43959 |
institution |
Chiang Mai University |
building |
Chiang Mai University Library |
country |
Thailand |
collection |
CMU Intellectual Repository |
topic |
Agricultural and Biological Sciences |
spellingShingle |
Agricultural and Biological Sciences Waratchada Sangpheak Jintawee Kicuntod Roswitha Schuster Thanyada Rungrotmongkol Peter Wolschann Nawee Kungwan Helmut Viernstein Monika Mueller Piamsook Pongsawasdi Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin |
description |
© 2015 Sangpheak et al; licensee Beilstein-Institut. The aim of this work is to improve physical properties and biological activities of the two flavanones hesperetin and naringenin by complexation with β-cyclodextrin (β-CD) and its methylated derivatives (2,6-di-O-methyl-β-cyclodextrin, DM-β-CD and randomly methylated-β-CD, RAMEB). The free energies of inclusion complexes between hesperetin with cyclodextrins (β-CD and DM-β-CD) were theoretically investigated by molecular dynamics simulation. The free energy values obtained suggested a more stable inclusion complex with DM-β-CD. The vdW force is the main guest-host interaction when hesperetin binds with CDs. The phase solubility diagram showed the formation of a soluble complex of A L type, with higher increase in solubility and stability when hesperetin and naringenin were complexed with RAMEB. Solid complexes were prepared by freeze-drying, and the data from differential scanning calorimetry (DSC) confirmed the formation of inclusion complexes. The data obtained by the dissolution method showed that complexation with RAMEB resulted in a better release of both flavanones to aqueous solution. The flavanones-β-CD/DM-β-CD complexes demonstrated a similar or a slight increase in anti-inflammatory activity and cytotoxicity towards three different cancer cell lines. The overall results suggested that solubilities and bioactivities of both flavanones were increased by complexation with methylated β-CDs. |
format |
Journal |
author |
Waratchada Sangpheak Jintawee Kicuntod Roswitha Schuster Thanyada Rungrotmongkol Peter Wolschann Nawee Kungwan Helmut Viernstein Monika Mueller Piamsook Pongsawasdi |
author_facet |
Waratchada Sangpheak Jintawee Kicuntod Roswitha Schuster Thanyada Rungrotmongkol Peter Wolschann Nawee Kungwan Helmut Viernstein Monika Mueller Piamsook Pongsawasdi |
author_sort |
Waratchada Sangpheak |
title |
Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin |
title_short |
Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin |
title_full |
Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin |
title_fullStr |
Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin |
title_full_unstemmed |
Physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin |
title_sort |
physical properties and biological activities of hesperetin and naringenin in complex with methylated p-cyclodextrin |
publishDate |
2018 |
url |
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84961848296&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/43959 |
_version_ |
1681422470490357760 |