Characterization of Low Molecular Weight Polyphenols from Pine (Pinus radiata) Bark


Mun, Sung-Phil, Ku, Chang-Sub

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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 13C 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.


 Materials and Methods
 Results and Discussion


  • Mun, Sung-Phil Division of Forest Science, College of Agriculture and Life Sciences, Chonbuk National University
  • Ku, Chang-Sub Department of Advanced Organic Materials Engineering, Chonbuk National University


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