PMID- 22809749 OWN - NLM STAT- MEDLINE DCOM- 20130625 LR - 20180816 IS - 1872-7077 (Electronic) IS - 1382-6689 (Linking) VI - 34 IP - 2 DP - 2012 Sep TI - Synthesis of phenolic acid conjugated chitooligosaccharides and evaluation of their antioxidant activity. PG - 519-527 LID - S1382-6689(12)00075-0 [pii] LID - 10.1016/j.etap.2012.05.004 [doi] AB - In this study, eight kinds of phenolic acid conjugated chitooligosaccharides (PA-c-COSs) with different substitution groups, including p-hydroxyl hydroxybenzoic acid-c-COS (HBA-c-COS), p-coumaric acid-c-COS (PCA-c-COS), 3,4-dihydroxyl protocatechuic acid-c-COS (PTA-c-COS), caffeic acid-c-COS (CFA-c-COS), 3-methoxyl-4-hydroxyl vanillic acid-c-COS (VNA-c-COS), ferulic acid-c-COS (FRA-c-COS) and 3,5-dimethoxyl-4-hydroxy syringic acid-c-COS (SRA-c-COS), sinapinic acid-c-COS (SNA-c-COS), were prepared by amide coupling reaction. Their antioxidant properties were evaluated using several in vitro models such as 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl (OH) and nitric oxide (NO) radicals scavenging and reducing power assays. The structures of the synthesized compounds were confirmed by UV, FT-IR and (1)H NMR data. CFA-c-COS showed 81.6% and 89.8% scavenging against DPPH and NO radical formation, respectively. CFA-c-COS also showed higher reducing power and hydroxyl radical scavenging activity compared to those of other compounds. Hence, CFA-c-COS can be a potential antioxidant compound. CI - Crown Copyright (c) 2012. Published by Elsevier B.V. All rights reserved. FAU - Eom, Tae-Kil AU - Eom TK AD - Marine Bioprocess Research Center, Pukyong National University, Busan 608-737, Republic of Korea. FAU - Senevirathne, Mahinda AU - Senevirathne M AD - Marine Bioprocess Research Center, Pukyong National University, Busan 608-737, Republic of Korea. FAU - Kim, Se-Kwon AU - Kim SK AD - Marine Bioprocess Research Center, Pukyong National University, Busan 608-737, Republic of Korea; Department of Chemistry, Pukyong National University, Busan 608-737, Republic of Korea. Electronic address: sknkim@pknu.ac.kr. LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20120529 PL - Netherlands TA - Environ Toxicol Pharmacol JT - Environmental toxicology and pharmacology JID - 9612020 RN - 0 (Antioxidants) RN - 0 (Biphenyl Compounds) RN - 0 (Hydroxybenzoates) RN - 0 (Oligosaccharides) RN - 0 (Picrates) RN - 31C4KY9ESH (Nitric Oxide) RN - 9012-76-4 (Chitosan) RN - DFD3H4VGDH (1,1-diphenyl-2-picrylhydrazyl) RN - I3P9R8317T (phenolic acid) SB - IM MH - Antioxidants/*chemistry MH - Biphenyl Compounds/chemistry MH - Chitosan/*chemistry MH - Hydroxybenzoates/*chemistry MH - Nitric Oxide/chemistry MH - Oligosaccharides/*chemistry MH - Picrates/chemistry EDAT- 2012/07/20 06:00 MHDA- 2013/06/26 06:00 CRDT- 2012/07/20 06:00 PHST- 2011/11/04 00:00 [received] PHST- 2012/05/16 00:00 [revised] PHST- 2012/05/19 00:00 [accepted] PHST- 2012/07/20 06:00 [entrez] PHST- 2012/07/20 06:00 [pubmed] PHST- 2013/06/26 06:00 [medline] AID - S1382-6689(12)00075-0 [pii] AID - 10.1016/j.etap.2012.05.004 [doi] PST - ppublish SO - Environ Toxicol Pharmacol. 2012 Sep;34(2):519-527. doi: 10.1016/j.etap.2012.05.004. Epub 2012 May 29.