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Acylation of Antioxidant of Bamboo Leaves with Fatty Acids by Lipase and the Acylated Derivatives' Efficiency in the Inhibition of Acrylamide Formation in Fried Potato Crisps.

Ma X, Wang E, Lu Y, Wang Y, Ou S, Yan R - PLoS ONE (2015)

Bottom Line: Both thin layer chromatography and high-performance liquid chromatography analyses confirmed the high efficiency of the isolation process with the purified orientin-6″-laurate, isoorientin-6″-laurate, vitexin-6″-laurate, and isovitexin-6″-laurate that were obtained.The addition of AOB and acylated AOB reduced acrylamide formation in fried potato crisps.Results showed that 0.05% AOB and 0.05% and 0.1% acylated AOB groups significantly (p < 0.05) reduced the content of acrylamide in potato crisps by 30.7%, 44.5%, and 46.9%, respectively.

View Article: PubMed Central - PubMed

Affiliation: Department of Food Science and Engineering, College of Science and Engineering, Jinan University, Guangzhou, 510632, China.

ABSTRACT
This study selectively acylated the primary hydroxyl groups on flavonoids in antioxidant of bamboo leaves (AOB) using lauric acid with Candida antarctica lipase B in tert-amyl-alcohol. The separation and isolation of acylated derivatives were performed using silica gel column chromatography with a mixture of dichloromethane/diethyl ether/methanol as eluents. Both thin layer chromatography and high-performance liquid chromatography analyses confirmed the high efficiency of the isolation process with the purified orientin-6″-laurate, isoorientin-6″-laurate, vitexin-6″-laurate, and isovitexin-6″-laurate that were obtained. The addition of AOB and acylated AOB reduced acrylamide formation in fried potato crisps. Results showed that 0.05% AOB and 0.05% and 0.1% acylated AOB groups significantly (p < 0.05) reduced the content of acrylamide in potato crisps by 30.7%, 44.5%, and 46.9%, respectively.

No MeSH data available.


Related in: MedlinePlus

Acylation of orientin, virexin, isoorientin, and isovitexin with CALB.
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pone.0130680.g002: Acylation of orientin, virexin, isoorientin, and isovitexin with CALB.

Mentions: Fig 2 shows the acylation of orientin, virexin, isoorientin, and isovitexin with lauric acids. All four flavonoids have a glucose moiety, and acylation occurred at the 6″-OH on the glucose moiety as a result of the high reactivity of the primary hydroxyl groups and the good selectivity of CALB. Ardhaoui et al. [22] and Gao et al. [23] also reported similar results for the acylation of other glycoside flavonoids and showed that with CALB, acylation occurs at the primary hydroxyl group on the glucose. Solvents and acyl donors are the two major concerns during this type of biosynthesis reaction. Gayot et al. [24] and Xu et al. [25] found that tert-amyl-alcohol was the most suitable solvent for the acylation of flavonoids with fatty acids due to tert-amyl-alcohol’s ideal log P (1.15), which is less prone to destroy the enzymes’ stabilization water layers. In contrast, other solvent candidates such as tert-butanol and acetone have log P values of 0.8 and −0.23, respectively, which have negative effects on the stability of enzymes [26]. In terms of the acyl donors, Ardhaoui et al. [22] found that for fatty acids with a carbon chain shorter than 12, both acylation yields and initial reaction rates increased progressively to peaks at 76% and 3.5 × 10−3 mM h -1 with lauric acid (C12). For fatty acids with longer carbon chains (C14-C18), no significant difference was observed. Mellou et al. [27] also found that when conducting acylation through transesterification using various vinyl fatty acid esters, the reaction rate and yields with vinyl laurate (C12) were higher than with vinyl decanoate (C10) and vinyl stearate (C18).


Acylation of Antioxidant of Bamboo Leaves with Fatty Acids by Lipase and the Acylated Derivatives' Efficiency in the Inhibition of Acrylamide Formation in Fried Potato Crisps.

Ma X, Wang E, Lu Y, Wang Y, Ou S, Yan R - PLoS ONE (2015)

Acylation of orientin, virexin, isoorientin, and isovitexin with CALB.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4476655&req=5

pone.0130680.g002: Acylation of orientin, virexin, isoorientin, and isovitexin with CALB.
Mentions: Fig 2 shows the acylation of orientin, virexin, isoorientin, and isovitexin with lauric acids. All four flavonoids have a glucose moiety, and acylation occurred at the 6″-OH on the glucose moiety as a result of the high reactivity of the primary hydroxyl groups and the good selectivity of CALB. Ardhaoui et al. [22] and Gao et al. [23] also reported similar results for the acylation of other glycoside flavonoids and showed that with CALB, acylation occurs at the primary hydroxyl group on the glucose. Solvents and acyl donors are the two major concerns during this type of biosynthesis reaction. Gayot et al. [24] and Xu et al. [25] found that tert-amyl-alcohol was the most suitable solvent for the acylation of flavonoids with fatty acids due to tert-amyl-alcohol’s ideal log P (1.15), which is less prone to destroy the enzymes’ stabilization water layers. In contrast, other solvent candidates such as tert-butanol and acetone have log P values of 0.8 and −0.23, respectively, which have negative effects on the stability of enzymes [26]. In terms of the acyl donors, Ardhaoui et al. [22] found that for fatty acids with a carbon chain shorter than 12, both acylation yields and initial reaction rates increased progressively to peaks at 76% and 3.5 × 10−3 mM h -1 with lauric acid (C12). For fatty acids with longer carbon chains (C14-C18), no significant difference was observed. Mellou et al. [27] also found that when conducting acylation through transesterification using various vinyl fatty acid esters, the reaction rate and yields with vinyl laurate (C12) were higher than with vinyl decanoate (C10) and vinyl stearate (C18).

Bottom Line: Both thin layer chromatography and high-performance liquid chromatography analyses confirmed the high efficiency of the isolation process with the purified orientin-6″-laurate, isoorientin-6″-laurate, vitexin-6″-laurate, and isovitexin-6″-laurate that were obtained.The addition of AOB and acylated AOB reduced acrylamide formation in fried potato crisps.Results showed that 0.05% AOB and 0.05% and 0.1% acylated AOB groups significantly (p < 0.05) reduced the content of acrylamide in potato crisps by 30.7%, 44.5%, and 46.9%, respectively.

View Article: PubMed Central - PubMed

Affiliation: Department of Food Science and Engineering, College of Science and Engineering, Jinan University, Guangzhou, 510632, China.

ABSTRACT
This study selectively acylated the primary hydroxyl groups on flavonoids in antioxidant of bamboo leaves (AOB) using lauric acid with Candida antarctica lipase B in tert-amyl-alcohol. The separation and isolation of acylated derivatives were performed using silica gel column chromatography with a mixture of dichloromethane/diethyl ether/methanol as eluents. Both thin layer chromatography and high-performance liquid chromatography analyses confirmed the high efficiency of the isolation process with the purified orientin-6″-laurate, isoorientin-6″-laurate, vitexin-6″-laurate, and isovitexin-6″-laurate that were obtained. The addition of AOB and acylated AOB reduced acrylamide formation in fried potato crisps. Results showed that 0.05% AOB and 0.05% and 0.1% acylated AOB groups significantly (p < 0.05) reduced the content of acrylamide in potato crisps by 30.7%, 44.5%, and 46.9%, respectively.

No MeSH data available.


Related in: MedlinePlus