Lipase-catalyzed regioselective protection/deprotection of hydroxyl groups of the isoflavone irilone isolated from Iris germanica

Biocatalysis and Biotransformation

Volumn 27, Issue 2, 2009, Pages 118-123

  Nazir, Nighat ^a   Koul, Surrinder ^b   Qurishi, Mushtaq Ahmad ^a   Taneja, Subhash Chandra ^b   Qazi, Ghulam Nabi ^b  

^a UNIVERSITY OF KASHMIR   (India)

^b CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Acetylation; Irilone; Iris germanica; Lipase; Regioselectivity

Indexed keywords

ASPERGILLUS NIGER; BIOLOGICAL ACTIVITIES; CANDIDA; CANDIDA ANTARCTICA; DE PROTECTIONS; DEACYLATION; DERIVATIZATION; ENZYMATIC ACTIONS; EXPERIMENTAL CONDITIONS; HYDROXYL GROUPS; IRILONE; IRIS GERMANICA; ISOFLAVONE; N BUTANOLS; PSEUDOMONAS CEPACIA; REGIO-SELECTIVE; REGIOSELECTIVE ACYLATION;

ACETYLATION; ISOMERS; REGIOSELECTIVITY;

LIPASES;

EID: 61649104375     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420802583457     Document Type: Article

References (31)

1. Ardhaoui, M., Falcimaigne, A., Ognier, S., Engasser, JM, Moussou, P. and Pauly, G. (2004) Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids. J Biotechnol, 110, pp. 265-272.
2. Ardhaoui, M., Falcimaigne, A., Engasser, JM, Moussou, P., Pauly, G. and Ghoul, M. (2004) Acylation of natural flavonoids using lipase of Candida antarctica as biocatalyst. J Mol Catal B: Enzym, 29, pp. 63-67.
3. Aviram, M. and Fuhrman, B. (1998) Polyphenolic flavonoids inhibit macrophage-mediated oxidation of LDL and attenuate atherogenesis. Atherosclerosis Suppl, 137, pp. S45-S48.
4. Birt, DF, Hendrich, S. and Wang, W. (2001) Dietary agents in cancer prevention: Flavonoids and isoflavonoids. Pharmacol Ther, 90, pp. 157-177.
5. Casagrande, F. and Darbon, JM (2001) Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: Regulation of cyclin-dependent kinases CDK2 and CDK1. Biochem Pharmacol, 61, pp. 1205-1215.
6. Chebil, L., Humeau, C., Falcimaigne, A., Engasser, J. and Ghoul, M. (2006) Enzymatic acylation of flavonoids. Process Biochem, 41, pp. 2237-2251.
7. Chen, SR, Jin, CF and Yang, XQ (1999) Molecule modification of catechins. J Tea, 25, pp. 76-79.
8. Duan, Y., Du, Z., Yao, Y., Li, R. and Wu, D. (2006) Effect of molecular sieves on lipase-catalyzed esterification of rutin with stearic acid. J Agric Food Chem, 54, pp. 6219-6225.
9. Enaud, E., Humeau, C., Piffaut, B. and Girardin, M. (2004) Enzymatic synthesis of new aromatic esters of phloridzin. J Mol Catal B: Enzym, 27, pp. 1-6.
10. Gaalnur, T., Esra, K., Merve, M. and Erdem, YC (2004) Flavonoids with antinociceptive and anti-inflammatory activities from the leaves of Tilia argentea (silver linden). J Ethnopharmacol, 95, pp. 393-397.
11. Gao, C., Mayon, P., MacManus, DA and Vulfson, EN (2001) Novel enzymatic approach to the synthesis of flavonoid glycosides and their esters. Biotechnol Bioeng, 71, pp. 235-243.
12. Guardia, T., Rotelli, AE, Juarez, AO and Pelzer, LE (2001) Antiinflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat. Il Farmaco, 56, pp. 683-687.
13. Harborne, JB and Williams, CA (2000) Advances in flavonoid research since 1992. Phytochemistry, 55, pp. 481-504.
14. Heim, KE, Pagliaferro, AR and Bobilya, DJ (2002) Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem, 13, pp. 572-584.
15. Hsiao, KF, Yang, FL, Wu, SH and Wang, KT (1996) Selective monoacetylation of diol compounds by Aspergillus niger lipase. Biotechnol Lett, 18, pp. 1277-1282.
16. Kontogianni, A., Skouridou, V., Sereti, V., Stamatis, H. and Kolisis, FN (2003) Lipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain. J Mol Catal B: Enzym, 21, pp. 59-62.
17. Lambusta, D., Nicolosi, G., Patii, A. and Piattelli, M. (1993) Enzyme-mediated regioprotection-deprotection of hydroxyl groups in (+)-catechin. Synthesis, 11, pp. 115-1158.
18. Leslie, EM, Mao, Q., Oleschuk, CJ, Deeley, RG and Cole, SPC (2001) Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and ATPase activities by interaction with dietary flavonoids. Mol Pharmacol, 59, pp. 1171-1180.
19. Li, BQ, Fu, T., Dongyan, Y., Mikovits, JA, Ruscetti, FW and Wang, JM (2000) Flavonoid baicalin inhibits HIV-1 infection at the level of viral entry. Biochem Biophys Res Commun, 276, pp. 534-538.
20. Liang, HR, Vuorela, P., Vuorela, H. and Hiltunen, R. (1997) Isolation and immunomodulatory effect of flavonol glycosides from Epimendium hunananse. Planta Med, 63, pp. 316-319.
21. Manach, C., Williamson, G., Morand, C., Scalbert, A. and Remesy, C. (2005) Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr, 81, pp. 230S-242S.
22. Massaeli, H., Sobrattee, S. and Pierce, GN (1999) The importance of lipid solubility in antioxidants and free radical generating systems for determining lipoprotein peroxidation-epidemiologic evidence. Free Radical Biol Med, 26, pp. 1524-1530.
23. Mazur, A., Bayle, D., Lab, C., Rock, E. and Rayssiguier, Y. (1999) Inhibitory effect of procyanidin-rich extracts on LDL oxidation in vitro. Atherosclerosis, 145, pp. 421-422.
24. Mellou, F., Lazari, D., Skaltsa, H., Tselepis, AD, Kolisis, FN and Stamatis, H. (2005) Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity. J Biotechnol, 116, pp. 295-304.
25. Na, L., Takashi, S., Yuji, T., Yoshihiro, M., Yutaka, S. and Masamichi, Y. (2003) Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol, 65, pp. 2065-2071.
26. Nakajima, N., Ishihara, K., Itoh, T., Furuya, T. and Hamada, H. (1999) Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments. J Biosci Bioeng, 87, pp. 105-107.
27. Natoli, M., Nicolosi, G. and Piattelli, M. (1992) Regioselective alcoholysis of flavonoid acetates with lipase in an organic solvent. J Org Chem, 57, pp. 5776-5778.
28. Sharma, SK, Husain, M., Kumar, R., Samuelson, LA, Kumar, J., Walterson, AC and Parmar, SV (2005) Pure Appl Chem, 77, pp. 209-226.
29. Viljanen, K., Kylli, P., Hubbermann, E., Schwarz, K. and Heinonen, M. (2005) Anthocyanin antioxidant activity and partition behavior in whey protein emulsion. J Agric Food Chem, 53, pp. 2022-2027.
30. Wollenweber, E., Stevens, JF, Klimo, K., Knauft, J., Frank, N. and Gerhauser, C. (2003) Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica. Planta Med, 69, pp. 15-20.
31. Yasukawa, K., Takido, M., Takeuchi, M., Sato, Y., Nitta, K. and Nakagawa, S. (1990) Inhibitory effects of flavonol glycosides on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion. Chem Pharm Bull, 38, pp. 774-776.