Efficient regioselective acylation of andrographolide catalyzed by immobilized Burkholderia cepacia lipase

Process Biochemistry

Volumn 45, Issue 3, 2010, Pages 415-418

  Chen, Zhi Gang ^a   Tan, Ren Xiang ^b   Huang, Ming ^a  

^a NANJING AGRICULTURAL UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

14 Acetylandrographolide; Andrographolide; Burkholderia cepacia lipase; Organic media; Regioselective acylation

Indexed keywords

ACYLATION REACTIONS; ANDROGRAPHOLIDE; BURKHOLDERIA CEPACIA; ELEMENTAL ANALYSIS; FT-IR SPECTRUM; IMMOBILIZED LIPASE; INITIAL RATE; OPERATIONAL STABILITY; ORGANIC MEDIA; REACTION TEMPERATURE; REACTION TIME; REGIOSELECTIVE ACYLATION; SUBSTRATE CONVERSION; VINYL ACETATES; WATER ACTIVITY;

ACETONE;

ACYLATION;

BURKHOLDERIA CEPACIA;

EID: 74449093845     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2009.09.022     Document Type: Article

References (17)

1. Pelletier S.W., Chappell R.L., and Prabhakar S. A stereoselective synthesis of racemic andrographolide lactone. J Am Chem Soc 90 (1968) 2889-2895
2. Chang K.T., Lii C.K., Tsai C.W., Yang A.J., and Chen H.W. Modulation of the expression of the π class of glutathione s-transferase by Andrographis paniculata extracts and andrographolide. Food Chem Toxicol 46 (2008) 1079-1088
3. Chen L., Zhu H., Wang R., Zhou K., Jing Y., and Qiu F. ent-Labdane diterpenoid lactone stereoisomers from Andrographis paniculata. J Nat Prod 71 (2008) 852-855
4. Rajagopal S., Ajaya kumar R., Deevi D.S., Satyanarayana C., and Rajagopalan R. Andrographolide, a potential cancer therapeutic agent isolated from Andrographis paniculata. J Exp Ther Oncol 3 (2003) 147-158
5. Jada S.R., Subur G.S., Matthews C., Ahmad Sazali Hamzah, Lajis N.H., Saad M.S., et al. Semisynthesis and in vitro anticancer activities of andrographolide analogues. Phytochemistry 68 (2007) 904-912
6. Chen J.H., Hsiao G., Lee A.R., Wu C.C., and Yen M.H. Andrographolide suppresses endothelial cell apoptosis via activation of phosphatidyl inositol-3-kinase/Akt pathway. Biochem Pharmacol 67 (2004) 1337-1345
7. Wiart C., Kumar K., Yusof M.Y., Hamimah H., Fauzi Z.M., and Sulaiman M. Antiviral properties of ent-labdene diterpenes of Andrographis paniculata nees, inhibitors of herpes simplex virus type 1. Phytother Res 19 (2005) 1069-1070
8. Gupta P.P., Tandon J.S., and Patnaik G.K. Antiallergic activity of andrographolides isolated from Andrographis paniculata (Burm.f.) Wall. Pharm Biol 36 (1998) 72-74
9. Reyes B.A., Bautista N.D., Tanquilut N.C., Anunciado R.V., Leung A.B., Sanchez G.C., et al. Anti-diabetic potentials of Momordica charantia and Andrographis paniculata and their effects on estrous cyclicity of alloxan-induced diabetic rats. J Ethnopharmacol 105 (2006) 196-200
10. Xu Y., Chen A., Fry S., Barrow R.A., Marshall R.L., and Mukkur T.K. Modulation of immune response in mice immunised with an inactivated Salmonella vaccine and gavaged with Andrographis paniculata extract or andrographolide. Int Immunopharmacol 7 (2007) 515-523
11. Nanduri S., Nyavanandi V.K., Thunuguntla S.S.R., Kasu S., Pallerla M.K., Ram P.S., Rajagopal S., Kumar R.A., Ramanujam R., Moses B.J., Vyas K., Devi A.S., Reddyc G.O., and Akella V. Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents. Bioorg Med Chem Lett 14 (2004) 4711-4717
12. Zaks A., and Klibanov A.M. Enzymatic catalysis in organic media at 100 °C. Science 224 (1984) 1249-1251
13. Klibanov A.M. Improving enzymes by using them in organic solvents. Nature 409 (2001) 241-246
14. Persson M., Costes D., Wehtje E., and Adlercreutz P. Effects of solvent, water activity and temperature on lipase and hydroxynitrile lyase enantioselectivity. Enzyme Microb Technol 30 (2002) 916-923
15. Lee M.Y., and Dordick J.S. Enzyme activation for nonaqueous mediums. Curr Opin Biotechnol 13 (2002) 376-384
16. Therisod M., and Klibanov A.M. Facile enzymatic preparation of monoacylated sugars in pyridine. J Am Chem Soc 108 (1986) 5638-5640
17. Rasalkar M.S., Potdar M.K., and Salunkhe M.M. Pseudomonas cepacia lipase-catalysed resolution of racemic alcohols in ionic liquid using succinicanhydride: role of triethylamine in enhancement of catalytic activity. J Mol Catal B-Enzyme 27 (2004) 267-270