Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars

Phytochemical Analysis

Volumn 15, Issue 6, 2004, Pages 397-406

  Derksen, Goverdina C H ^a   Lelyveld, Gerrit P ^a   van Beek, Teris A ^a   Capelle, Anthony ^a   de Groot, Æde ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Alizarin; Cultivars; HPLC; Madder; Quantitative analysis; Ruberythric acid; Rubia tinctorum

Indexed keywords

AROMATIC COMPOUNDS; EXTRACTION; SUGARS;

AGLYCONES; CULTIVAR; EXTRACTION METHOD; HPLC; HPLC METHOD; HPLC-UV; MADDER; MADDER ROOT; RUBERYTHRIC ACID; RUBIA TINCTORA;

KETONES;

ALIZARIN; ANTHRAQUINONE DERIVATIVE; LUCIDIN; METHANOL; MUNJISTIN; NORDAMNACANTHAL; PLANT GLYCOSIDE; PSEUDOPURPURIN; PURPURIN; RUBERYTHRIC ACID; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CULTIVAR; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTERMETHOD COMPARISON; NONHUMAN; PLANT ROOT; QUANTITATIVE ANALYSIS; RUBIA TINCTORUM; RUBIACEAE; VALIDATION PROCESS;

RUBIA TINCTORIUM; RUBIA TINCTORUM;

EID: 9944249530     PISSN: 09580344     EISSN: None     Source Type: Journal    
DOI: 10.1002/pca.800     Document Type: Article

References (36)

1. Angelini LG, Pistelli L, Belloni P, Bertoli A and Panconesi S. 1997. Rubia tinctorum a source of natural dyes: agronomic evaluation, quantitative analysis of alizarin and industrial assays. Industr Crops Prod 6: 303-311.
2. Bosáková Z, Persl J and Jegorov A. 2000. Determination of lucidin in Rubia tinctorum aglycones by an HPLC method with isocratic elution. J High Resol Chromatogr 23: 600-602.
3. Brown JP. 1980. A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat Res 75: 243-277.
4. Brown JP and Brown RJ. 1976. Mutagenesis by 9, 10-anthraquinone derivatives and related compounds in Salmonella typhimurium. Mutat Res 40: 203-224.
5. Brown JP and Dietrich PS. 1979. Mutagenicity of anthraquinones and benzanthrone derivatives in the salmonella/microsome test; activation of anthraquinone glycosides by enzymic extracts of rat fecal bacteria. Mutat Res 566: 9-24.
6. Derksen GCH, van Beek TA, de Groot Æ and Capelle A. 1998. High-performance liquid chromatographic method for the analysis of anthraquinone glycosides and aglycones in madder root (Rubia tinctorum L.). J Chromatogr A 816: 277-281.
7. Derksen GCH, Niederländer HAG and van Beek TA. 2002. Separation and identification of anthraquinones in roots of Rubia tinctorum L. by means of high-performance liquid chromatography coupled on-line with UV, diode-array or mass spectrometric detection. J Chromatogr A 978: 119-127.
8. Derksen GCH, Naayer M, van Beek TA, Capelle A, Haaksman IK, van Doren HA and de Groot Æ. 2003. Chemical and enzymatic hydrolysis of anthraquinone glycosides from madder roots. Phytochem Anal 14 137-144.
9. 1mice. Toxicol Industr Health 11: 449-458.
10. Khouri HE, Ibrahim RK and Rideau M. 1986. Effects of nutritional and hormonal factors on growth and production of anthraquinone glucosides in cell suspension cultures of Cinchona succirubra. Plant Cell Rep 5: 423-426.
11. Krizsán K, Szókán G, Tóth ZA, Hollósy F, László M and Khlafulla A. 1996. HPLC analysis of anthraquinone derivatives in madder root (Rubia tinctorum) and its cell cultures. J Liq Chromatogr Rel Technol 19: 2295-2314.
12. Kuzovkina IN, Mantrova OV, Al'terman IE and Yakimov SA. 1996. Culture of genetically transformed hairy roots derived from anthraquinone-producing European madder plants. Russ J Plant Physiol 43: 291-298.
13. Leistner E. 1975. Isolierung, Identifizierung und Biosynthese von Anthrachinonen in Zellsuspensionkulturen von Morinda citrifolia. Planta Med Suppl: 214-223.
14. Lodhi AH, Sant'Ana AEG and Charlwood BV. 1994. Quantitative analysis of alizarin in tissue cultures of Rubia species by high performance liquid chromatography. Phytochem Anal 5: 261-265.
15. Murti VVS, Seshadri TR and Sivakumaran S. 1970. A study of madder, the roots of Rubia tinctorum L. Ind J Chem 8: 779-782.
16. Novotná P, Pacáková V, Bosáková Z and Stulík K. 1999. High-performance liquid chromatographic determination of some anthraquinone and naphtthoquinone dyes occurring in historical textiles. J Chromatogr A 863: 235-241.
17. Poginsky B, Westendorf OJ, Kraus L and Marquardt H. 1987. Detection of lucidin, a genotoxic principle in root extracts of Rubia tinctorum and the conversion to its ethyl ether during ethanol extraction. Pharm Weekblad Sci Edn 9: 242.
18. Poginsky B, Westendorf J, Blömeke B, Marquardt H, Hewer A, Grover PL and Phillips DH. 1991. Evaluation of DNA-binding activity of hydroxyanthraquinones occurring in Rubia tinctorum L. Carcinogenesis 12: 1265-1271.
19. Ramos-Valdivia AC, van der Heijden R and Verpoorte R. 1998. Isopentyl diphosphate isomerase and prenyltransferase activities in rubiaceous and apocynaceous cultures. Phytochemistry 48: 961-969.
20. Schulte U, El-Shagi H and Zenk MH. 1984. Optimization of 19 Rubiaceae species in cell culture for the production of anthraquinones. Plant Cell Rep 3: 51-54.
21. Schweppe H. 1993. Handbuch der Naturfarbstoffe. Ecomed: Landsberg.
22. Strobel J, Hieke M, Gebauer E, Wind E and Gröger D. 1990. The influence of organic and inorganic chemical factors on cell growth and anthraquinone formation in suspension cultures of Galium vernum. Biochem Physiol Pflanzen 186: 117-124.
23. Suzuki H, Matsumoto T and Mikami Y. 1984. Effects of nutritional factors on the formation of anthraquinones by Rubia cordifolia plant cells in suspension culture. Agric Biol Chem 48: 603-610.
24. Thomson RH. 1971. Naturally Occurring Quinones, 2 edn. Academic Press: London.
25. Tikkanen L, Matsushima T and Natori S. 1983. Mutagenicity of anthraquinones in the Salmonella pre-incubation test. Mutat Res 116: 297-304.
26. Tóth ZA, Raatikainen O, Naaranlathi T and Auriola S. 1993. Isolation and determination of alizarin in cell cultures of Rubia tinctorum and emodin in Dermocybe sanguinea using solid-phase extraction and high-performance liquid chromatography. J Chromatogr 630: 423-428.
27. van Beek TA, van Veldhuizen A, Lelyveld GP, Piron I and Lankhorst PP. 1993. Quantitation of bilobalide and ginkgolides A, B, C and J by means of nuclear magnetic resonance spectroscopy. Phytochem Anal 4: 261-268.
28. van der Heijden R, Verpoorte R, Hoekstra SS and Hoge JHC. 1994. Nordamnacanthal, a major anthraquinone from an Agrobacterium rhizogenes induced root culture of Rubia tinctorum. Plant Physiol Biochem 32: 399-404.
29. van der Plas LHW, Hagendoom MJM and Jamar DCL. 1998. Anthraquinone glycosylation and hydrolysis in Morinda citrifolia cell suspensions: regulation and function. J Plant Physiol 152 235-241.
30. Westendorf J, Poginsky B, Marquardt H, Groth G and Marquardt H. 1988. The genotoxicity of lucidin, a natural component of Rubia tinctorum L. and lucidinethylether, a component of ethanolic Rubia extracts. Cell Biol Toxicol 4: 225-239.
31. Westendorf J, Marquardt H, Poginsky B, Dominiak M, Schmidt J and Marquardt H. 1990. Genotoxicitiy of naturally occurring hydroxyanthraquinones. Mutat Res 240: 1-12.
32. Wijnsma R, Go JTKA, van Weerden IN, Harkes PAA, Verpoorte R, and Baerheim Svendsen A. 1985. Antraquin-ones as phytoalexins in cell and tissue cultures of Cinchona spec. Plant Cell Rep 4: 241-244.
33. Wölfe D, Schmutte C, Westendorf J and Marquardt H. 1990. Hydroxyanthraquinones as tumour promoters: enhancement of malignant transformation of C3H mouse fibroblasts and growth stimulation of primary rat hepatocytes. Cancer Res 50: 6540-6544.
34. Yasui Y and Takeda N. 1983. Identification of a mutagenic substance, in Rubia tinctorum L. (madder) root, as lucidin. Mutat Res 121: 185-190.
35. Zenk MH, El-Shagi H and Schulte U. 1975. Anthraquinone production by cell suspension cultures of Morinda citrifolia. Planta Med Supp 79-101.
36. Zuurdeeg JP. 1995. Ode aan de meekrap: Sint-Annaland.