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. 2016:2016:5782942.
doi: 10.1155/2016/5782942. Epub 2016 Feb 21.

Improved Chiral Separation of (R,S)-Goitrin by SFC: An Application in Traditional Chinese Medicine

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Improved Chiral Separation of (R,S)-Goitrin by SFC: An Application in Traditional Chinese Medicine

Lixing Nie et al. J Anal Methods Chem. 2016.

Abstract

Like chemical drugs, research and development of herbal medicine also have a need to resolve enantiomers. To help illustrating the antiviral bioactivity of Isatidis Radix, a widely used traditional Chinese medicine (TCM), supercritical fluid chromatography (SFC) was used for analytical and preparative separation of (R,S)-goitrin, which was reported as the active ingredient of the herbal. Improved resolution was achieved on Chiralpak IC column, using acetonitrile as the organic modifier, representing a tenfold increase in speed, compared to the previous normal phase HPLC (NPLC) method. The newly developed chromatographic method was validated in terms of linearity, precision, limit of detection (LOD), and limit of quantitation (LOQ). Scale-up purification of (R)-goitrin and (S)-goitrin was performed on a preparative column with >90% total recovery. The absolute stereochemical assignment of the purified isomers was determined through optical rotation study. This attempt explored SFC's application in chiral research of traditional Chinese medicine.

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Figures

Figure 1
Figure 1
Chemical structures of (+)-(R)-goitrin (epigoitrin) and (−)-(S)-goitrin (goitrin).
Figure 2
Figure 2
Chiral separation of (R,S)-goitrin using improved SFC method. (1) (S)-goitrin; (2) (R)-goitrin. Chiralpak IC 4.6 × 250 mm column, 5 μm; ACN/CO2 (15 : 85, v/v); 3.5 mL/min, 35°C, 100 bar, UV detection 245 nm.
Figure 3
Figure 3
Chiral separation of (R,S)-goitrin using previous NPLC method. (1) (R)-goitrin; (2) (S)-goitrin. Chiralpak IC 4.6 × 250 mm column, 5 μm; n-hexane/isopropanol (90 : 10, v/v); 0.8 mL/min, 20°C, UV detection 245 nm.
Figure 4
Figure 4
Preparative chiral separation of (R,S)-goitrin. Chiralpak IC 20 × 250 mm column, 5 μm; ACN/CO2 (15 : 85, v/v); 9.0 mL/min, 35°C, 100 bar, UV detection 245 nm.

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