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Determination of Stereochemical Structure of a Grandidentatin Isomer from Populus alba × glandulosa Bark  

Kwon, Dong-Joo (Dept. of Wood Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University)
Kim, Hyun-Seok (Dept. of Chemistry, College of Natural Sciences, Kangwon National University)
Lee, Phil-Ho (Dept. of Chemistry, College of Natural Sciences, Kangwon National University)
Bae, Young-Soo (Dept. of Wood Science & Engineering, College of Forest and Environmental Sciences, Kangwon National University)
Publication Information
Journal of the Korean Wood Science and Technology / v.37, no.1, 2009 , pp. 114-120 More about this Journal
Abstract
The bark of Populus alba ${\times}$ glandulosa was collected, air-dried and extracted with 70% aqueous acetone. Then it was successively partitioned with n-hexane, $CH_2Cl_2$, EtOAc and $H_2O$. Repeated Sephadex LH-20 column chromatography and preparative TLC on the EtOAc soluble fraction gave a grandidentatin isomer. The structure was elucidated as grandidentatin A (cis-2-hydroxycyclohexyl 6-O-p-coumaroyl-${\beta}$-D-glucopyranoside) on the basis of spectroscopic evidences such as $^1H$-NMR, $^{13}C$-NMR, 2D-NMR and MALDI TOF-MS spectrum followed by acid hydrolysis. Grandidentatin A was identified here for the first time in Populus alba ${\times}$ glandulosa bark, and to the bset of our knowledge it has not been reported in any other literature.
Keywords
Populus alba ${\times}$ glandulosa; grandidentatin isomer; acid hydrolysis; stereochemistry; NMR;
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