• Food Science and Biotechnology
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• v.15 no.3
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• pp.424-430
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• 2006

Low molecular weight polyphenols were isolated from hot water extracts of radiata pine (Pinus radiata) bark using a Sephadex LH-20 column and characterized by $^1H$ and $^{13}C$ NMR, UV, FT-IR, and GC-MS analyses. Major compounds isolated and identified were protocatechuic acid, trans-taxifolin, and quercetin. Trans-taxifolin, an important intermediate in biosynthetic route of proanthocyanidin (PA), was isolated in large quantities and indicates that PA is a major component of radiata pine bark. Small amounts of polyphenols were identified by GC-MS analysis. The presence of p-hydroxybenzoic acid, vanillic acid, protocatechuic acid, cis- and trans-feruic acid, p-coumaric acid, trans-caffeic acid, (-)-epicatechin, (+)-catechin, trans- and cis-taxifolin, (+)-gallocatechin, and quercetin was confirmed by comparison of mass fragmentation patterns and retention times (RT) with authentic samples. In addition, the presence of astringenin, astringenin glycoside, trans- and cis-leucodelphinidin was strongly assumed from characteristic mass fragment ions due to their conjugated structure and retro Diels-Alder reaction, and also from biosynthetic route of PA. GC-MS analysis allowed us to detect small amounts of phenolic acids and flavonoids and eventually discriminate trans- and cis-configuration in the identified polyphenols.

• Korean Journal of Food Science and Technology
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• v.45 no.2
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• pp.174-179
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• 2013

Three low-molecular compounds were isolated from methanol extracts of pear (Pyrus pyrifolia N. cv. Chuhwangbae) fruit peels using solvent fractionation, various types of column chromatogrphy (Diaion HP-20, Sephadex LH-20, and silica gel), and high performance liquid chromatography with an assay guided by 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity. The isolated compounds were identified as 2-carboxyl-4(1H)-quinolinone (kynurenic acid, 1) from butanol fraction, cis-p-coumaric acid (2) from ethyl acetate-acidic fraction, and vanillin (3) from the ethyl acetate-phenolic fraction, respectively. These isolated compounds were confirmed on the basis of the spectroscopic data of electrospray ionization mass spectrometry and nuclear magnetic resonance. This is the first time that compounds 1-3 were isolated and identified in pear.

• Food Science and Biotechnology
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• v.18 no.2
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• pp.463-470
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• 2009

Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.