Chemical and enzymatic hydrolysis of anthraquinone glycosides from Madder roots

Phytochemical Analysis

Volumn 14, Issue 3, 2003, Pages 137-144

  Derksen, Goverdina C H ^a   Naayer, Martijn ^a   van Beek, Teris A ^a   Capelle, Anthony ^a   Haaksman, Ingrid K ^b   van Doren, Henk A ^b   de Groot, Æde ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b TNO   (Netherlands)

Author keywords

Alizarin; Hydrolysis; Lucidin; Madder root; Nordamnacanthal; Ruberythric acid

Indexed keywords

AROMATIC COMPOUNDS; ENZYMATIC HYDROLYSIS; KETONES; SUSPENSIONS (FLUIDS);

AGLYCONES; DYE COMPONENTS; LUCIDIN; MADDER ROOT; NATIVE ENZYMES; NORDAMNACANTHAL; RUBERYTHRIC ACID; STRONGEST ACID;

SUGARS;

ACID; ALIZARIN; ANTHRAQUINONE DERIVATIVE; BASE; DYE; GLUCOSIDASE; GLYCOSIDE; OXIDOREDUCTASE; PLANT EXTRACT; PURPURIN DERIVATIVE; WATER; XYLAN 1,4 BETA XYLOSIDASE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME KINETICS; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MUTAGENICITY; NONHUMAN; PLANT ROOT; ROOM TEMPERATURE; SUSPENSION;

RUBIA TINCTORUM;

EID: 0037620533     PISSN: 09580344     EISSN: None     Source Type: Journal    
DOI: 10.1002/pca.694     Document Type: Article

References (29)

1. Bianco A, Guiso M, Iavarone C, Passacantilli P and Trogolo C. 1978. Iridoids XXV. New iridoid glucosides from Rubiaceae. Gaz Chim Ital 108: 13-16.
2. Brown JP. 1980. A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat Res 75: 243-277.
3. Brown JP and Brown RJ. 1976. Mutagenesis by 9, 10-anthraquinone derivatives and related compounds in Salmonella typhimurium. Mutat Res 40: 203-224.
4. Brown JP and Dietrich PS. 1979. Mutagenicity of anthraquinone and benzanthrone derivatives in the salmonella/microsome test; activation of anthraquinone glycosides by enzymic extracts of rat fecal bacteria. Mutat Res 66: 9-24.
5. Derksen GCH and van Beek TA. 2002. Rubia tinctorum L. In Studies in Natural Product Chemistry Vol 26, Rahman A-U (ed.). Elsevier: Amsterdam; 629-684.
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. El-Emary NA and Backheet EY. 1998. Three hydroxymethyl-anthraquinone glycosides from Rubia tinctorum. Phyto-chemistry 49: 277-279.
9. Guo W, Yamauchi K, Watanabe N, Usui T, Luo S and Sakata K. 1995. A primeverosidase as a main glycosidase concerned with the alcoholic aroma formation in tea leaves. Biosci Biotech Biochem 59: 962-964.
10. 1mice. Toxicol Industr Health 11: 449-458.
11. Kawasaki Y, Goda Y, Yoshihira K and Noguchi H. 1990. A new anthraquinone from Rubia tinctorum. Shoyakugaku Zasshi 44: 95-97.
12. Kawasaki Y, Goda Y and Yoshihira K. 1992. The mutagenic constituents of Rubia tinctorum. Chem Pharm Bull 40: 1504-1509.
13. Leistner E. 1975. Isolierung, Identifizierung und Biosynthese von Anthrachinonen in Zellsuspensionkulturen von Morinda citrifolia. Planta Med Suppl: 214-223.
14. Masawaki T, Taya M and Tone S. 1996. Selective solvent extraction of ruberythric acid from madder roots and subsequent hydrolysis with β-glucosidase. J Ferment Bioengng 81: 567-569.
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. Ogawa K, Ijima Y, Guo W, Watanabe N, Usui T, Dong S, Tong Q and Sakata K. 1997. Purification of a β-primeverosidase concerned with alcoholic aroma formation in tea leaves (cv. shuixian) to be processed to oolong tea. J Agric Food Chem 45: 877-882.
17. Poginsky B. 1989. Vorkommen und Genotoxizität von Anthracen-Derivaten in Rubia tinctorum L. PhD Thesis, University of Hamburg.
18. 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 Ed 9: 242.
19. 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 tinctorurn L. Carcinogrenesis 12: 1265-1271.
20. Schweppe H. 1993. Handbuch der Naturfarbstoffe. Ecomed: Landsberg.
21. Tessier AM, Delaveau P and Champion B. 1981. Nouvelles anthraquinones des racines de Rubia cordifolia. Planta Med 41: 337-343.
22. Thomson RH. 1971. Naturally Occurring Quinones, 2nd edn. Academic Press: London.
23. Tikkanen L, Matsushima T and Natori S. 1983. Mutagenicity of anthraquinones in the Salmonella pre-incubation test. Mutat Res 116: 297-304.
24. 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.
25. 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.
26. Westendorf J, Marquardt H, Poginsky B, Dominiak M, Schmidt J and Marquardt H. 1990. Genotoxicity of naturally occurring hydroxyanthraquinones. Mutat Res 240: 1-12.
27. Wijnsma R and Verpoorte R. 1986. Anthraquinones in the Rubiaceae - review. In Progress in the Chemistry of Organic Natural Products, Vol 49, Hill RA, Krebs HC. (eds). Springer: Wien; 79-141.
28. Wölfle 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.
29. Yasui Y and Takeda N. 1983. Identification of a mutagenic substance, in Rubia tinctorum L. (madder) root, as lucidin. Mutat Res 121: 185-190.