Enantioseparation and Absolute Configuration Determination of Angular-Type Pyranocoumarins from Peucedani Radix Using Enzymatic Hydrolysis and Chiral HPLC-MSMS Analysis.docVIP
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Enantioseparation and Absolute Configuration Determination of Angular-Type Pyranocoumarins from Peucedani Radix Using Enzymatic Hydrolysis and Chiral HPLC-MSMS Analysis
Molecules 2012, 17, 4236-4251; doi:10.3390/moleculeOPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Enantioseparation and Absolute Configuration Determination
of Angular-Type Pyranocoumarins from Peucedani Radix Using
Enzymatic Hydrolysis and Chiral HPLC-MS/MS Analysis
Yue-Lin Song 1, Qing-Wen Zhang 1, Ya-Ping Li 1, Ru Yan 1,* and Yi-Tao Wang 1,2,*
1
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences,
University of Macau, Taipa, Macao SAR, 999078, China
2
School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100029, China
* Authors to whom correspondence should be addressed; E-Mails: ruyan@umac.mo (R.Y.);
ytwang@umac.mo (Y.-T.W.); Tel.: +853-8397-4876 (R.Y.); Fax: +853-2884-1358 (R.Y.);
Tel.: +853-8397-4691 (Y.-T.W.); Fax: +853-2884-1358 (Y.-T.W.).
Received: 27 February 2012; in revised form: 29 March 2012 / Accepted: 31 March 2012 /
Published: 10 April 2012
Abstract: Angular-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
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