Chiral LC-MS-guided isolation of angular-type pyranocoumarins from Peucedani Radix
10.16438/j.0513-4870.2024-0085
- VernacularTitle:手性色谱-质谱联用导向的前胡中角型吡喃香豆素类化合物分离
- Author:
Yang YANG
1
;
Xing-cheng GONG
1
;
Peng-fei TU
2
;
Wen-jing LIU
3
;
Yue-lin SONG
2
Author Information
1. Modern Research Center for Traditional Chinese Medicine, Beijing Research Institute of Chinese Medicine, Beijing University of Chinese Medicine, Beijing 102400, China; School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 102400, China
2. Modern Research Center for Traditional Chinese Medicine, Beijing Research Institute of Chinese Medicine, Beijing University of Chinese Medicine, Beijing 102400, China
3. School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China
- Publication Type:Research Article
- Keywords:
Peucedani Radix;
chemical component;
angular-type pyranocoumarins;
chiral LC-MS-guided isolation;
enantiomer
- From:
Acta Pharmaceutica Sinica
2024;59(8):2343-2349
- CountryChina
- Language:Chinese
-
Abstract:
This study utilized a chiral liquid chromatography-mass spectrometry (LC-MS)-guided isolation strategy to accurately capture angular-type pyranocoumarins (APs) in Peucedani Radix (Chinese name: Qianhu). Sixteen APs were successfully purified from the ethyl acetate extract of Peucedani Radix through deploying various techniques such as silica gel, ODS, Sephadex LH-20, and achiral (chiral) semi-preparative liquid chromatography. After extensive structural measurements, such as 1H and 13C NMR spectroscopy, their structures were identified as (3′S)-3′-(2-methyl-butyroyl)-4′-oxo-3′,4′-dihydroseselin (1A), (3′R)-3′-(2-methyl-butyroyl)-4′-oxo-3′,4′-dihydroseselin (1B), (3′S)-3′-isovaleryl-4′-oxo-lomatin (2A), (3′R)-3′-isovaleryl-4′-oxo-lomatin (2B), (3′S)-3′-angeloyloxy-4′-oxo-3′,4′-dihydroseselin (3A), (3′R)-3′-angeloyloxy-4′-oxo-3′,4′-dihydroseselin (3B), (3′S,4′S)-praeruptorin B (4A), (3′R,4′R)-praeruptorin B (4B), (3′S,4′S)-praeruptorin E (5A), (3′R,4′R)-praeruptorin E (5B), 3′-isovaleryl-4′-angeloyl-cis-khellactone (6), 3′-angeloyl-4′-(2-methyl-butyroyl)-cis-khellactone (7), (3′S,4′S)-praeruptorin A (8A), (3′R,4′R)-praeruptorin A (8B), (3′S,4′S)-khellactone (9A), and (3′R,4′R)-khellactone (9B), respectively. Thereof, compounds 1A and 1B were new compounds, while compound 2A represents a new configuration for a known planar structure. Compounds 2A and 2B were isolated for the first time from Peucedani Radix. Above all, chiral LC-MS-guided isolation strategy is advantageous at rapid capturing new compounds from herbal medicines, providing an effective means for the separation of novel structures, especially new enantiomers.
