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Chiral-phase high-performance liquid chromatography of rotenoid racemates

Journal of Chromatography

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DOI: 10.1016/S0021-9673(01)86844-8

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Abstract

The high-performance liquid chromatograhic (HPLC) behavior of parent rotenoids (type I) and the hydroxyl-analogues (type II) on three different chiral stationary phases (CSPs) was studied. Separations of optical isomers were achieved in various degrees depending largely upon the rotenoidal structures and the CSP types employed. Enantiomers of all but elliptone compounds were separable on β-cyclodextrin-bonded silica (CDS). Without exception, the 12a-hydroxyrotenoid antipodes were resolved on Pirkle's phenylglycine-bonded silica (PGS) despite unsuccessful attenmpts to resolve the type I rotenoidal racemates. Conversely, optical resolution of the latter rotenoids was accomplished by using a helical polytriphenylmethylacrylate-coated silica (TPS) column and the observed separation factors (α values) ranged from 1.14 to 1.90. The results from HPLC of type II rotenoids on TPS (α = 1.00–1.63) suggested that variations in E-ring structures had profound influence on the resolution outcome. Conjugated double bonds on the E-ring and the desisopropylation of the five-membered E-ring ot type II rotenoids appeared to be important structural features for chiral recognition involving the TPS substrate. In both reversed-phase (CDS) and normal-pahse (PGS and TPS) HPLC modes, the less polar enantiomers were the 6aβ,12aβ-rotenoids as observed in most cases, though this relationship was reversed in the cases of deguelin and hydroxyelliptone probably due to conformational effects of rotenoidal ring systems.

Additional Publication Details

Publication type:
Article
Publication Subtype:
Journal Article
Title:
Chiral-phase high-performance liquid chromatography of rotenoid racemates
Series title:
Journal of Chromatography
DOI:
10.1016/S0021-9673(01)86844-8
Volume
404
Issue:
1
Year Published:
1987
Language:
English
Contributing office(s):
Upper Midwest Environmental Sciences Center
Description:
11 p.
Larger Work Type:
Article
Larger Work Subtype:
Journal Article
Larger Work Title:
Journal of Chromatography
First page:
133
Last page:
143
Number of Pages:
11