Song Yue-Lin, Jing Wang-Hui, Tu Peng-Fei, Wang Yi-Tao
a State Key Laboratory of Quality Research in Chinese Medicine , Institute of Chinese Medical Sciences, University of Macau , Macao , SAR , P.R. China.
Nat Prod Res. 2014;28(8):545-50. doi: 10.1080/14786419.2014.883397. Epub 2014 Feb 6.
Enantiomers and diastereoisomers of angular-type pyranocoumarins (APs) are abundant in Peucedani Radix (Chinese name: Qian-hu), eliciting distinct activities in vitro and in vivo. Our ongoing investigation on APs yielded eight pairs of enantiomers (1a and 1b, 2a and 2b, 3a and 3b, 4a and 4b, 5a and 5b, 6a and 6b, 7a and 7b and 8a and 8b) via enantiomeric separation of trans-3'-angeloylkhellactone (1), trans-3'-acetyl-4'-isobutyrylkhellactone (2), trans-3'-acetyl-4'-angeloyl-khellactone (3), 3'-angeloyloxy-4'-oxo-3',4'-dihydroseselin (4), cis-3'-acetyl-4'-angeloylkhellactone (5), cis-3'-isovaleryl-4'-acetylkhellactone (6), cis-3'-angeloyl-4'-isovalerylkhellactone (7) and cis-3',4'-diisovalerylkhellactone (8), respectively, using semi-preparative AD-RH chiral column. All the compounds (1-8) were enantioseparated for the first time, while the absolute configurations of 2a, 2b, 6a and 8b were reported first.
角型吡喃香豆素（APs）的对映体和非对映异构体在中药前胡中含量丰富，在体外和体内表现出不同的活性。我们对APs的持续研究通过使用半制备型AD-RH手性柱分别对反式-3'-当归酰基凯内酯（1）、反式-3'-乙酰基-4'-异丁酰基凯内酯（2）、反式-3'-乙酰基-4'-当归酰基凯内酯（3）、3'-当归酰氧基-4'-氧代-3',4'-二氢蛇床子素（4）、顺式-3'-乙酰基-4'-当归酰基凯内酯（5）、顺式-3'-异戊酰基-4'-乙酰基凯内酯（6）、顺式-3'-当归酰基-4'-异戊酰基凯内酯（7）和顺式-3',4'-二异戊酰基凯内酯（8）进行对映体分离，得到了八对对映体（1a和1b、2a和2b、3a和3b、4a和4b、5a和5b、6a和6b、7a和7b以及8a和8b）。所有化合物（1-8）均首次实现对映体分离，同时首次报道了2a、2b、6a和8b的绝对构型。
