Comparative study on enantiomeric excess of main akannin/shikonin derivatives isolated from the roots of three endemic Boraginaceae plants in China

Biomedical Chromatography

Volumn 25, Issue 10, 2011, Pages 1067-1075

  Zhou, Wen ^a   Jiang, Hu Da Gu La ^a   Peng, Ying ^a   Li, Shao Shun ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

Acid treatment; Alkannin; Boraginaceae; Chiral HPLC; Shikonin

Indexed keywords

CHLORINE COMPOUNDS; ENANTIOMERS; KETONES;

ACID TREATMENTS; ALKANNIN; ARNEBIA EUCHROMA; BORAGINACEAE; CHIRAL HPLC; COMPARATIVES STUDIES; ENANTIOMERIC EXCESS; OPTICAL PURITY; SHIKONIN; SHIKONIN DERIVATIVES;

HYDROLYSIS;

(2 ACETOXYISOVALERYL)ALKANNIN; (2,2 DIMETHYLACRYL)ALKANNIN; (3 HYDROXYISOVALERYL)SHIKONIN; ACETYLALKANNINA; ACETYLSHIKONINC; ALKANNIN; ALPHA ETHYLBUTYRYLSHIKONIN; ALPHA METHYLBUTYRYLALKANNIN; BETA ACETOXYISOVALERYLSHIKONIN; BETA HYDROXYISOVALERYLALKANNIN; BETA,BETA DIMETHYLACRYLSHIKONIN; HYDROCHLORIC ACID; SHIKONIN; UNCLASSIFIED DRUG;

ARNEBIA EUCHROMA; ARTICLE; BORAGINACEAE; CHINESE MEDICINE; CHIRALITY; CIRCULAR DICHROISM; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG ISOLATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LITHOSPERMUM ERYTHRORHIZON; ONOSMA CONFERTUM; PLANT ROOT;

ARNEBIA EUCHROMA; BORAGINACEAE; LITHOSPERMUM ERYTHRORHIZON; ONOSMA;

EID: 80052537357     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1570     Document Type: Article

References (17)

1. Ai KH, Li FY, Li Y, Wang WB and Wu YY. Studies on the naphthoquinone constituents of Onosma Confertum W. W. Smithe and quantitative determination of shikonin. Acta Botanica Sinica 1989; 31: 549-553.
2. Ai KH, Jin J and Liu H. Studies on CD spectra derivatives of shikonin and alkannin. Acta Pharmaceutica Sinica 1993; 28: 282-285.
3. Assimopoulou AN and Papageorgiou VP. Study on the enantiomeric ratio of the pharmaceutical substance alkannin and shikonin. Biomedical Chromatography 2004a; 18: 794-799.
4. Assimopoulou AN and Papageorgiou VP. Study on isohexenylnaphthazarins polymerization in alkaline media. Biomedical Chromatography 2004b; 18: 508-522.
5. Brockmann H. Die Konstitution des Alkannins, Shikonins und Alkannans. Annalen der Chemie, Justus Liebigs 1936; 521: 1-47.
6. Fukui H, Tsukada M, Mizukami H and Tabata M. Formation of stereoisomeric mixtures of naphthoquinone derivatives in Echium lycopsis callus cultures. Phytochemistry 1983; 22: 453-456.
7. Jain AC and Mathur SK. Pigment of Arnebia hispidissima. Bulletin of the National Institute of Sciences of India 1965; 28: 52-56.
8. 2 extracted Amebia Euchroma (Royle) John pigment and organic solvents. Food Science 2004; 25: 130-132.
9. Liu J, Zhou W, Li SS, Sun Z, Lin BZ, Lang YY, He JY, Cao XH, Yan TD, Wang L, Lu JM, Han YH, Cao Y, Zhang XK and Zeng JZ. Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues. Cancer Research 2008; 68: 8871-8880.
10. Manabe A, Tokumori T, Sumida Y, Yoshida T, Hatano T, Yazaki K and Okuda T. Application of supercritical fluid extraction to components of crude drugs and plants. III. Extraction of pigments from Lithospermum root and licorice root. Yakugaku Zasshi 1987; 107: 506-510.
11. Mellidis AS and Papageorgiou VP. Naphthazarins from Onosma heterophylla. Journal of Natural Products 1987; 50: 618-619.
12. Papageorgiou VP. Study on the structure of the components of Alkanna Tinctoria Tausch. Chimika Chronika 1978; 7: 45-54.
13. Papageorgiou VP. Naphthoquinones from roots of Macrotomia cephalotes DC. Planta Medica 1979; 37: 259-263.
14. Papageorgiou VP, Assimopoulou AN, Couladouros EA, Hepworth D and Nicolaou KC. The chemistry and biology of alkannin, shikonin and related naphthazarin natural products. Angewandte Chemie, International Edition English 1999; 38: 270-300.
15. Papageorgiou VP, Assimopoulou AN, Samanidou VF and Papadoyannis IN. Analytical methods for the determination of alkannins and shikonins. Current Organic Chemistry 2006; 10: 583-622.
16. Wang WJ, Dai M, Zh u CH, Zhang JG, Lin LP, Ding J and Duan WH. Synthesis and biological activity of novel shikonin analogues. Bioorganic and Medicinal Chemistry Letters 2009; 19: 735-737.
17. Xuan YY and Hu X. Naturally-occurring shikonin analogues-a class of necroptotic inducers that circumvent cancer drug resistance. Cancer Letters 2009; 274: 233-242.