Microbial transformation of bioactive anthraquinones - A review

Biosciences Biotechnology Research Asia

Volumn 10, Issue 2, 2013, Pages 577-582

  Sultan, Sadia ^a,b   Ghani, Nurunajah Ab ^b,c   Shah, Syed Adnan Ali ^a,b   Ismail, Nor Hadiani ^b,c   Noor, Mohd Zaimi ^a,b   Naz, Humera ^a,b  

^a Faculty of Pharmacy   (Malaysia)

^b Atta ur Rahman Institute for Natural Product Discovery UiTM Kampus Puncak Alam   (Malaysia)

^c UNIVERSITI TEKNOLOGI MARA   (Malaysia)

Author keywords

Anthraquinone; Biotransformation; Fungi; Glycoside

Indexed keywords

1 AMINOANTHRAQUINONE; 1,2 DIAMINOANTHRAQUINONE; ALIZARIN; ALOE EMODIN; ANTHRAQUINONE DERIVATIVE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; CHRYSOPHANIC ACID; DANTRON; EMODIN; PHYSCION; RHEIN; UNCLASSIFIED DRUG;

ABSIDIA COERULEA; ANTICOAGULATION; ANTIFUNGAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BEAUVERIA BASSIANA; BIOTRANSFORMATION; CHINESE MEDICINE; COLUBRINA GREGGII; DRUG SOLUBILITY; DRUG TRANSFORMATION; MICROBIAL BIOTRANSFORMATION; MUCOR SPINOSUS; NONHUMAN;

EID: 84905439451     PISSN: 09731245     EISSN: None     Source Type: Journal    
DOI: 10.13005/bbra/1167     Document Type: Article

References (39)

1. Ali A. M., El-Sharkawy S. H., Hamid J. A., Ismail N. H., Lajis N. H., Antimicrobial activity of selected Malaysian plants. Pertanika Journal of Tropical Agricultural Science, 1995; 18: 57-61.
2. Ayo R. G., Amupitan J. O., Zhao Y., Cytotoxicity and antimicrobial studies of 1, 6, 8-trihydroxy-3-methyl-anthraquinone (emodin) isolated from the leaves of Cassia nigricans Vahl. African Journal of Biotechnology, 2007; 6: 1276-1279.
3. Garcia-Sosa K., Villarreal-Alvarez N., Lubben P., Pena-Rodrigues L. M., Chrysophanol, an antimicrobial anthraquinone from the root extract of Colubrina greggii. Journal of Mexican Chemical Society, 2006; 50: 76-78.
4. Kanokmedhakul K., Kanokmedhakul S., Phatchana R., Biological activity of anthraquinones and triterpenoids from Prismatomeris fragrans. Journal of Ethnopharmacology, 2005; 100: 284-288.
5. Ahmad R., Mahbob E. N. M., Noor Z. M., Ismail N. H., Lajis N. H., Shaari K., Evaluation of antioxidant potential of medicinal plants from Malaysian Rubiaceae (subfamily Rubioideae). African Journal of Biotechnology, 2010; 9: 7948-7954.
6. Ali A. M., Mackeen M. M., El-Sharkawy S. H., Hamid J. A., Ismail N. H., Ahmad F. B. H., Lajis N. H., Antiviral and cytotoxic activities of some plants used in Malaysian indigenous medicine. Pertanika Journal of Tropical Agricultural Science, 1996; 19: 129-136.
7. Stringfellow D. A., Weed S. D., Underwood G. E., Antiviral and interferon-inducing properties of 1, 5-diamino anthraquinones. Antimicrobial Agents and Chemotheraphy, 1979; 15: 111-118.
8. Huang Y. H., Zhen Y. S., Rhein induces apoptosis in cancer cells and shows synergy with mitomycin. Acta Pharmaceutica Sinica, 2001; 36: 334-338.
9. Eyong K. O., Folefoc G. N., Kuete V., Beng V. P., Krohn K., Hussain H., Nkengfack A. E., Saeftel, M., Sarite S. R., Hoerauf A., Newbouldiaquinone A: A naphthoquinone-anthraquinone ether coupled pigment, as a potential antimicrobial and antimalarial agent from Newbouldia laevis. Phytochemistry, 2006; 67: 605-609.
10. Osman C. P., Ismail N. H., Ahmad R., Ahmat N., Awang K., Jaafar F. M., Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae). Molecules, 2010; 15: 7218-7226.
11. Ji-Hua L., Bo-Yang Y., Biotransformation of bioactive natural products for pharmaceutical Lead compounds. Curr Org Chem, 2010; 14: 1400-6.
12. Liu J. H., Yu B. Y., Biotransformation of bioactive natural products for pharmaceutical lead compounds. Current Organic Chemistry, 2010; 14: 1400-1406.
13. Rozzell J. D., Commercial scale biocatalysis: myths and realities. Bioorganic and Medicinal Chemistry, 1999; 7: 2253-2261.
14. Sultan S., Choudhary M. I., Khan S. N., Fatima U., Ali R. A., Atif M., Atta-ur-Rahman, Fatmi M. Q., Fungal transformation of cedryl acetate and alpha-glucosidase inhibition assay, quantum mechanical calculations and molecular docking studies of its metabolites. European Journal of Medicinal Chemistry, 2013; 62: 764-770.
15. Shah S. A. A., Sultan S., Noor Z. M., Biotransformation of tissue-specific hormone tibolone with fungal culture Trichothecium roseum. Journal of Molecular Structure 2013; 1042: 118-112.
16. Gerardo M, Casanola-Martin, Marrero-Ponce Y., Khan M. T. H., Ather A., Sultan S., Torrens F., Rotondo R., TOMOCOMD-CARD description-based virtual screening of tyrosinse inhibitors: Evaluation of different classification model combinations using bond-based linear indices. Bioorganic and Medicinal Chemistry, 2007; 15: 1483-1503.
17. Choudhary M. I., Sultan S., Hassan M. T., Atta-ur-Rahman., Metabolism of 17-ethynyl-and 17a-ethylsteroids. Steroids, 2005; 70: 792-800.
18. Choudhary M. I., Sultan S., Jalil, S., Anjum S., Rahman A. A., Fun H. K., and Atta-ur-Rahman, Microbial transformation of mesterolone. Chemistry & Biodiversity, 2005; 2: 392-400.
19. Choudhary M. I., Sultan S., Hassan M. T., Yasin A., Shaheen F., Atta-ur-Rahman, Biotransformation of (+)-androst-4-ene-3, 17-dione. Natural Product Research, 2004; 18: 529.
20. Choudhary M. I., Sultan S., Yaqoob M., Musharraf, S. G., Yasin, A., Shaheen F., Atta-ur-Rahman., Microbial transformation of cortisol and prolyl endopeptidase activity of transformed productst. Natural Product Research, 2003; 17: 389.
21. Sosa K. G., Alvarez N. V., Lubben P., Rodriguez L. M. P., Chrysophanol, an antimicrobial anthraquinone from the root extract of Colubrina greggii Journal of Mexican Chemical Society, 2006; 50: 76-78.
22. Kim S. J., Kim M. C., Lee B. J., Park D. H., Hong S. H., Um J. Y., Anti-inflammatory activity of chrysophanol through the suppression of NF-kB/caspase-1 activation in vitro and in vivo. Molecules 2010; 15: 6436-6451.
23. Zhang W., Ye M., Zhan J., Chen Y., Guo D., Microbial glycosylation of four free anthraquinones by Absidia coerulea. Biotechnology Letters, 2004; 26: 127-131.
24. Zhang W., Zhan J. X., Chen Y. J., Guo D. A., Biotransformation of three free anthraquinones by Mucor spinosus. Chinese Journal of Natural Medicines, 2003; 1: 219-223.
25. Seo E. J., Ngoc T. M., Lee S. M., Kim Y. S., Jung Y. S., Chrysophanol-8-O-glucoside, an anthraquinone derivative in Rhubarb, has antiplatelet and anticoagulant activities. Journal of Pharmacological Sciences, 2012; 118: 245-254.
26. Beattie K. D., Rouf R., Gander L., May T. W., Ratkowsky D., Donner C. D., Gill M., Grice I. D., Tiralongo E., Antibacterial metabolites from Australian macrofungi from the genus Cortinarius. Phytochemistry, 2010; 71: 948-955.
27. Manojlovic N., Markovic Z., Duric M., Regioselective synthesis and antimicrobial activity of O-alkylated physcion's derivatives. Journal of the Chilean Chemical Society, 2007; 52: 1330-1331.
28. Muto A., Hori M., Sasaki Y., Saitoh A., Yasuda I., Maekawa T., Uchida T., Asakura K., Nakazato T., Kaneka T., Kizaki M., Ikeda Y., Yoshida T., Emodin has a cytotoxic activity against human multiple myeloma as a Janus-activated kinase 2 inhibitor. Molecular Cancer Therapeutics, 2007; 6: 987-994.
29. Duraipandiyan V., Ignacimuthu S., Paulraj M. G., Antifeedant and larvicidal activities of Rhein isolated from the flowers of Cassia fistula L. Saudi Journal of Biological Sciences, 2011; 18: 129-133.
30. Lai W. W., Yang J. S., Lai K. C., Kuo C..L, Hsu C. K., Wang C. K., Chang C. Y., Lin J. Y., Tang N. Y., Chen P. Y., Huang W. W., Chung J. G., Rhein induced apoptosis through the endoplasmic reticulum stress, caspase- and mitochondria-dependent pathways in SCC-4 human tongue squamous cancer cells. In Vivo, 2009; 23: 309-316.
31. Duraipandiyan V., Ignacimuthu S., Antifungal activity of rhein isolated from Cassia fistula L. flower. Webmed Central Pharmacology, 2010; 1: 1-15.
32. Yin Z. Q., Wang L., Ye W. C., Zhang J., Zhou C. L., Zhao S. X., A new anthraquinone glycoside biotransformed by Beauveria bassiana. Chinese Journal of Natural Medicines, 2008; 6: 103-104.
33. Mori H., Sugie S., Niwa K., Yoshimi N., Tanaka T., Hirono I., Carcinogenicity of chrysazin in large intestine and liver of mice. Japanese Journal of Cancer Research Gann, 1986; 77: 871-876.
34. Zhan J., Gunatilaka A. A. L., Microbial transformation of amino- and hydroxyanthra-quinones by Beauveria bassiana ATCC 7159. Journal of Natural Products, 2006; 69: 1525-1527.
35. Zhang J., Shen X., Antioxidant activities of baicalin, green tea polyphenols and alizarin in vitro and in vivo. Journal of Nutritional and Environmental Medicine, 1997; 7: 79-90.
36. Fotia C., Avnet S., Granchi D., Baldini N., The natural compound alizarin as an osteotropic drug for the treatment of bone tumors. Journal of Orthopaedic Research, 2012; 30: 1486-1492.
37. Hilgert I., Cudlin J., Steinerova N., Vanek Z., Antitumour and immunosuppressive activity of hydroxyanthraquinones and their glucosides. Folia Biol (Praha), 1977; 23: 99-109.
38. Centelles J. J., Fernandez-Cancio M., Imperial S., Spectrophotometric determination of nitrites in biological samples using 1, 2-diaminoanthraquinone. Potential application to the determination of nitric oxide synthase activity. Analytical Letters, 2003; 36: 2139-2149.
39. Drogovoz S. M., Slyshkov V. V., Ranhel S. E., Bezuglyi P. A., Shtefan L. M., Brigida N. V., The synthesis and pharmacological activity of anthraquinonemalonamic acid derivatives. Farmatsevtichnii Zhurnal (Kiev), 1992; 43-47.