2024-03-29T15:24:59Z
https://kitami-it.repo.nii.ac.jp/oai
oai:kitami-it.repo.nii.ac.jp:00008488
2022-12-13T02:22:00Z
1:87
Synthesis of hydroxycinnamoyl β-D-xylopyranosides and evaluation of their antioxidant properties
Shimotori, Yasutaka
Hoshi, Masayuki
Soga, Kouji
Osawa, Yosuke
Miyakoshi, Tetsuo
Hydroxycinnamic acids
Hydroxycinnamoyl β-d-xylopyranosides
Lipase
Regioselective transesterification
Antioxidant properties
Various hydroxycinnamoyl β-d-xylopyranosides were efficiently prepared from 2,3,4-tri-O-acetyl-α-d-xylopyranosyl bromide (TAXB) with amine by amine-promoted glycosylation. The resulted acetylated hydroxycinnamoyl β-d-xylopyranosides with acetoxy groups at C-2, C-3, and C-4 were regioselectively deacetylated at C-4 position with Novozym 435. Antioxidant activities of free hydroxycinnamic acids and the respective β-d-xylopyranosides were evaluated by DPPHradical dot radical scavenging activity as well as their inhibitory effect on autoxidation of bulk methyl linoleate. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPHradical dot) decreased in the order ferulic acid > caffeic acid ≈ caffeoyl β-d-xylopyranosides ≈ sinapinic acid > sinapoyl β-d-xylopyranosides ≈ feruloyl β-d-xylopyranosides > p-coumaric acid > p-coumaroyl β-d-xylopyranosides. In bulk methyl linoleate, the antioxidant activity order against autoxidation was almost consistent with the scavenging activity order. The results showed that caffeoyl β-d-xylopyranosides and sinapoyl β-d-xylopyranosides were as effective as free caffeic acid, sinapinic acid, and ferulic acid.
journal article
Elsevier
2014-03
application/pdf
Carbohydrate Research
388
138
146
https://kitami-it.repo.nii.ac.jp/record/8488/files/No4.pdf
eng
https://doi.org/10.1016/j.carres.2013.12.014
c 2013 Elsevier