Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends
Oleogels based on sterols such as β-sitosterol blended with the sterol ester γ-oryzanol are a very interesting class of systems, but there are aspects of their formation and structure that remain elusive. It has previously been shown that a methyl group on the C30 position of the sterol-ester plays an important role in gelation. This work explored the effect that having C30 methyl groups on both the sterol and the sterol-ester had on the gelation process and subsequent gel structure. Lanosterol and saponified γ-oryzanol (which was synthesized as part of this study) were identified as materials of interest, as both feature a methyl group on the C30 position of their steroidal cores. It was observed that both sterols formed gels when blended with γ-oryzanol, and also that lanosterol gelled sunflower oil without the addition of γ-oryzanol. All of these gels were significantly weaker than that formed by β-sitosterol blended with γ-oryzanol. To explore why, molecular docking simulations along with AFM and SAXS were used to examine these gels on a broad range of length scales. The results suggest that saponified γ-oryzanol-γ-oryzanol gels have a very similar structure to that of β-sitosterol-γ-oryzanol gels. Lanosterol-γ-oryzanol gels and pure lanosterol gel, however, form with a totally different structure facilitated by the head-to-tail stacking motif exhibited by lanosterol. These results give further evidence that relatively slight changes to the molecular structure of gelators can result in significant differences in subsequent gel properties.
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Language: | English |
Subjects: | fat substitutes, nutraceuticals/functional foods, rheology, structure–functional properties, |
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dig-wur-nl-wurpubs-6007352024-10-02 Matheson, Andrew B. Dalkas, Georgios Lloyd, Gareth O. Hart, Aaliyah Bot, Arjen den Adel, Ruud Koutsos, Vasileios Clegg, Paul S. Euston, Stephen R. Article/Letter to editor JAOCS, Journal of the American Oil Chemists' Society 99 (2022) 11 ISSN: 0003-021X Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends 2022 Oleogels based on sterols such as β-sitosterol blended with the sterol ester γ-oryzanol are a very interesting class of systems, but there are aspects of their formation and structure that remain elusive. It has previously been shown that a methyl group on the C30 position of the sterol-ester plays an important role in gelation. This work explored the effect that having C30 methyl groups on both the sterol and the sterol-ester had on the gelation process and subsequent gel structure. Lanosterol and saponified γ-oryzanol (which was synthesized as part of this study) were identified as materials of interest, as both feature a methyl group on the C30 position of their steroidal cores. It was observed that both sterols formed gels when blended with γ-oryzanol, and also that lanosterol gelled sunflower oil without the addition of γ-oryzanol. All of these gels were significantly weaker than that formed by β-sitosterol blended with γ-oryzanol. To explore why, molecular docking simulations along with AFM and SAXS were used to examine these gels on a broad range of length scales. The results suggest that saponified γ-oryzanol-γ-oryzanol gels have a very similar structure to that of β-sitosterol-γ-oryzanol gels. Lanosterol-γ-oryzanol gels and pure lanosterol gel, however, form with a totally different structure facilitated by the head-to-tail stacking motif exhibited by lanosterol. These results give further evidence that relatively slight changes to the molecular structure of gelators can result in significant differences in subsequent gel properties. en application/pdf https://research.wur.nl/en/publications/exploring-how-changes-to-the-steroidal-core-alter-oleogelation-ca 10.1002/aocs.12624 https://edepot.wur.nl/575196 fat substitutes nutraceuticals/functional foods rheology structure–functional properties https://creativecommons.org/licenses/by/4.0/ https://creativecommons.org/licenses/by/4.0/ Wageningen University & Research |
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fat substitutes nutraceuticals/functional foods rheology structure–functional properties fat substitutes nutraceuticals/functional foods rheology structure–functional properties Matheson, Andrew B. Dalkas, Georgios Lloyd, Gareth O. Hart, Aaliyah Bot, Arjen den Adel, Ruud Koutsos, Vasileios Clegg, Paul S. Euston, Stephen R. Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends |
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Oleogels based on sterols such as β-sitosterol blended with the sterol ester γ-oryzanol are a very interesting class of systems, but there are aspects of their formation and structure that remain elusive. It has previously been shown that a methyl group on the C30 position of the sterol-ester plays an important role in gelation. This work explored the effect that having C30 methyl groups on both the sterol and the sterol-ester had on the gelation process and subsequent gel structure. Lanosterol and saponified γ-oryzanol (which was synthesized as part of this study) were identified as materials of interest, as both feature a methyl group on the C30 position of their steroidal cores. It was observed that both sterols formed gels when blended with γ-oryzanol, and also that lanosterol gelled sunflower oil without the addition of γ-oryzanol. All of these gels were significantly weaker than that formed by β-sitosterol blended with γ-oryzanol. To explore why, molecular docking simulations along with AFM and SAXS were used to examine these gels on a broad range of length scales. The results suggest that saponified γ-oryzanol-γ-oryzanol gels have a very similar structure to that of β-sitosterol-γ-oryzanol gels. Lanosterol-γ-oryzanol gels and pure lanosterol gel, however, form with a totally different structure facilitated by the head-to-tail stacking motif exhibited by lanosterol. These results give further evidence that relatively slight changes to the molecular structure of gelators can result in significant differences in subsequent gel properties. |
format |
Article/Letter to editor |
topic_facet |
fat substitutes nutraceuticals/functional foods rheology structure–functional properties |
author |
Matheson, Andrew B. Dalkas, Georgios Lloyd, Gareth O. Hart, Aaliyah Bot, Arjen den Adel, Ruud Koutsos, Vasileios Clegg, Paul S. Euston, Stephen R. |
author_facet |
Matheson, Andrew B. Dalkas, Georgios Lloyd, Gareth O. Hart, Aaliyah Bot, Arjen den Adel, Ruud Koutsos, Vasileios Clegg, Paul S. Euston, Stephen R. |
author_sort |
Matheson, Andrew B. |
title |
Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends |
title_short |
Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends |
title_full |
Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends |
title_fullStr |
Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends |
title_full_unstemmed |
Exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends |
title_sort |
exploring how changes to the steroidal core alter oleogelation capability in sterol : γ-oryzanol blends |
url |
https://research.wur.nl/en/publications/exploring-how-changes-to-the-steroidal-core-alter-oleogelation-ca |
work_keys_str_mv |
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