Comparative study on enantiomeric excess of main akannin/shikonin derivatives isolated from the roots of three endemic Boraginaceae plants in China.[Pubmed: 21308700]

This work systematically investigated the enantiomeric excess (e.e.) of main components isolated from the roots of three endemic Boraginaceae plants distributed extensively in China, named Arnebia euchroma (Royle) Johnst (A.e.), Lithospermum erythrorhizon Sieb. et Zucc. (L.e.) and Onosma confertum W. W. Smith (O.c.), and the optical purity of their hydrolysis products separately, by means of three different approaches. The influence of HCl on the e.e. values of the major constituents was also studied. Analysis of the absolute configurations and e.e. values of all the derivatives acquired was performed by CD and chiral-HPLC respectively. The results of the main constituents demonstrated that A.e. mainly yields S-form naphthoquinone derivatives, while the R-form is predominant in the derivatives of L.e. and O.c. The optical purity of alkannin and shikonin and their derivatives was not influenced by acid treatment in the course of separation and hydrolysis. Additionally, it was found that 100% e.e. of shikinon could be acquired from a specific shikinon ester derivative, β,β-dimethylacrylshikonin occurring in the roots of O.c., as did 100% e.e. of alkannin from β,β-dimethylacrylalkannin contained in the roots of A.e.

[Studies on CD spectra of derivatives of shikonin and alkannin].[Pubmed: 8213171]

The circular dichroism (CD) and electronic absorption spectra of seven derivatives of shikonin and alkannin isolated from the roots of Onosma confertum W.W. Smith (from Sichuan) and Arnebia euchroma (Royle) Johust (from Xinjiang) were described. Each pair of CD spectra obtained was exact mirror images and the UV spectra of these compounds were very similar. In comparison with the CD spectra of shikonin given in literature, the configuration of the pigments from Sichuan was assigned R and from Xinjiang were all S.