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Enantioseparation and absolute configuration determination of angular-type pyranocoumarins from Peucedani radix using enzymatic hydrolysis and chiral HPLC-MS/MS analysis
Song Y.-L.2; Zhang Q.-W.2; Li Y.-P.2; Yan R.2; Wang Y.-T.2
2012-04-01
Source PublicationMolecules
ISSN14203049
Volume17Issue:4Pages:4236-4251
AbstractAngular-type pyranocoumarins from Peucedani Radix (Chinese name: Qian-hu) have exhibited potential for use on treatment of cancer and pulmonary hypertension. Due to the existence of C-3′ and C-4′ chiral centers, compounds belonging to this chemical type commonly exist in enantiomers and/or diastereoisomers, which may elicit distinct activities during their interactions with the human body. In the present study, a new method, which combines enzymatic hydrolysis with chiral LC-MS/MS analysis, has been developed to determine the absolute configurations of these angular-type pyranocoumarins. Pyranocoumarins isolated from Qian-hu, their enantiomers, or metabolites were individually incubated with rat liver microsomes. As the common end product from enzymatic hydrolysis of all tested pyranocoumarins, cis-khellactone was collected and its absolute configuration was determined by comparison with (+)-cis-khellactone and (-)-cis-khellactone using chiral LC-MS/MS. The absolute configurations of all tested parent pyranocoumarins were determined by combination of LC-MS/MS, NMR and polarimetric analysis. The results revealed that the metabolite cis-khellactone retained the same absolute configurations of the stereogenic carbons as the respective parent compound. This method was proven to be rapid and sensitive and also has advantages in discriminating single enantiomers and mixtures of optical isomers with different ratios. © 2012 by the authors.
KeywordAbsolute configuration Angular-type pyranocoumarins Chiral LC-MS/MS Cis-khellactone Enzymatic hydrolysis
DOI10.3390/molecules17044236
URLView the original
Language英語
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Cited Times [WOS]:28   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionUniversity of Macau
Affiliation1.Beijing University of Chinese Medicine
2.Universidade de Macau
Recommended Citation
GB/T 7714
Song Y.-L.,Zhang Q.-W.,Li Y.-P.,et al. Enantioseparation and absolute configuration determination of angular-type pyranocoumarins from Peucedani radix using enzymatic hydrolysis and chiral HPLC-MS/MS analysis[J]. Molecules,2012,17(4):4236-4251.
APA Song Y.-L.,Zhang Q.-W.,Li Y.-P.,Yan R.,&Wang Y.-T..(2012).Enantioseparation and absolute configuration determination of angular-type pyranocoumarins from Peucedani radix using enzymatic hydrolysis and chiral HPLC-MS/MS analysis.Molecules,17(4),4236-4251.
MLA Song Y.-L.,et al."Enantioseparation and absolute configuration determination of angular-type pyranocoumarins from Peucedani radix using enzymatic hydrolysis and chiral HPLC-MS/MS analysis".Molecules 17.4(2012):4236-4251.
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