Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity

Biocatalysis and Biotransformation

Volumn 27, Issue 3, 2009, Pages 170-178

  Xanthakis, Epameinondas ^a   Magkouta, Sophia ^b   Loutrari, Heleni ^b   Stamatis, Haralambos ^c   Roussos, Charis ^b   Kolisis, Fragiskos N ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

^b UNIVERSITY OF ATHENS MEDICAL SCHOOL   (Greece)

^c UNIVERSITY OF IOANNINA   (Greece)

Author keywords

Antitumor growth activity; Enzymatic glucosylation acylation; Glucosidase; Lipase B; Perillyl alcohol

Indexed keywords

ANTI-ANGIOGENIC ACTIVITY; ANTI-TUMOR; ANTIPROLIFERATIVE ACTIVITIES; ANTITUMOR GROWTH ACTIVITY; BIOSYNTHETIC PATHWAY; CHEMOPREVENTIVE; CONVERSION YIELD; ENZYMATIC GLUCOSYLATION/ACYLATION; ENZYMATIC REACTION; ENZYMATIC SYNTHESIS; FATTY ESTERS; GLUCOSIDASE; GLUCOSYLATION; HYDROXYL GROUPS; LAURATE; LEWIS LUNG CARCINOMATA; LIPASE B FROM CANDIDA ANTARCTICA; LOW-WATER SYSTEMS; MONOTERPENE; PERILLYL ALCOHOL; PHYSICOCHEMICAL PROPERTY; PHYTOCHEMICALS; PROLIFERATION ACTIVITY; TERPENOID;

CELL MEMBRANES; CELL PROLIFERATION; ESTERIFICATION; GLUCOSE;

ESTERS;

ANTINEOPLASTIC AGENT; BETA GLUCOSIDASE; GLUCOSE; LAURIC ACID DERIVATIVE; LIPASE B; PERILLYL ALCOHOL; PERILLYL GLUCOSIDE; PERILLYL GLUCOSIDE LAURIC ESTER; TERPENE; UNCLASSIFIED DRUG;

ALMOND; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOCATALYST; BIOTRANSFORMATION; CANDIDA ANTARCTICA; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME KINETICS; ESTERIFICATION; GLYCOSYLATION; GROWTH INHIBITION; LEWIS CARCINOMA; MOUSE; NONHUMAN; PROCESS OPTIMIZATION;

CANDIDA ANTARCTICA; PRUNUS DULCIS;

EID: 68049106060     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420902811089     Document Type: Article

References (23)

1. Ardhaoui M, Falcimaigne A, Engasser JM, Moussou P, Pauly G, Ghoul M. 2004. Acylation of natural flavonoids using lipase of Candida antarctica as biocatalyst. J Mol Catal B Enzym 29: 63-67.
2. Belanger JT. 1998. Perillyl alcohol: Applications in oncology. Altern Med Rev 3:448-457.
3. Budde CL, Khmelnitsky YL. 1999. Aldolase stability in the presence of organic solvents. Biotechnol Lett 21:77-80.
4. Carrea G, Ottolina G, Riva S. 1995. Role of solvent in the control of enzyme selectivity in organic media. Tribtech 13:63-70. Crowell PL. 1999. Prevention and therapy of cancer by dietary monoterpenes. J Nutr 129:775-778.
5. Danieli B, Bellis P, Carrea G, Riva S. 1990. Enzyme mediated regioselective acylations of flavonoid disaccharide monoglycosides. Helv Chim Acta 73:1837-1844.
6. Griffin WC. 1949. Classification of surface active agents by HLB. J Soc Cosmet Chem 1:311-326.
7. Gunata Z, Vallier MJ, Sapis JC, Baumes R, Bayonove C. 1994. Enzymatic synthesis of montherpenyl β-D-glucosides by various b-glucosidades. Enzyme Microb Technol 16:1055-1058.
8. Gupta MN, Roy I. 2004. Enzymes in organic media - forms, functions and applications. Eur J Biochem 271:2575-2583.
9. Gupta MN, Batra R, Tyagi R, Sharma A. 1997. Polarity index: The guiding solvent parameter for enzyme stability in aqueous- organic cosolvent mixtures. Biotechnol Prog 13:284-288.
10. Katsoura MH, Polydera AC, Katapodis P, Kolisis FN, Stamatis H. 2007. Effect of different reaction parameters on the lipasecatalyzed selective acylation of polyhydroxylated natural compounds in ionic liquids. Process Biochem 42:1326-1334.
11. Kise H, Hayakawa A, Noritomi H. 1990. Protease catalyzed synthetic reactions and immobilization-activation of the enzymes in hydrophilic organic solvents. J Biotechnol 14:239-254.
12. Kris-Etherton PM, Hecker KD, Bonanome A, Coval SM, Binkoski AE, Hilpert KF, Griel AE, Etherton TD. 2002. Bioactive compounds in foods: Their role in the prevention of cardiovascular disease and cancer. Am J Med 113 Suppl 9B:71-88.
13. Liu G, Oettel K, Bailey H, Ummersen LV, Tutsch K, Staab MJ, Horvath D, Alberti D, Arzoomanian R, Rezazadeh H. 2003. Phase II trial of perillyl alcohol (NSC 641066) administered daily in patients with metastatic androgen independent prostate cancer. Invest New Drugs 21:367-372.
14. Loutrari H, Hatziapostolou M, Skouridou V, Papadimitriou E, Roussos C, Kolisis FN, Papapetropoulos A. 2004. Perillyl alcohol is an angiogenesis inhibitor. J Pharmacol Exp Ther 311:568-575.
15. Mo H, Elson CE. 2004. Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention. Exp Biol Med (Maywood) 229:567-585.
16. Otto RT, Scheib H, Bornscheuer UT, Pleiss J, Syldatk C, Schmid RD. 2000. Substrate specificity of lipase B from Candida antarctica in the synthesis of arylaliphatic glycolipids. J Mol Catal B Enzym 8:201-211.
17. Ripple GH, Gould MN, Arzoomanian RZ, Alberti D, Feierabend C, Simon K, Binger K, Tutsch KD, Pomplun M, Wahamaki A. 2000. Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. Clin Cancer Res 6: 390-396.
18. Stamatis H, Sereti V, Kolisis FN. 2001. Enzymatic synthesis of hydrophilic and hydrophobic derivatives of natural phenolic acids in organic media. J Mol Catal B Enzym 11:323-328.
19. Srivastava V, Negi AS, Kumar JK, Gupta MM, Khanuja SP. 2005. Plant-based anticancer molecules: A chemical and biological profile of some important leads. Bioorg Med Chem 13: 5892-5908.
20. Surh YJ. 2003. Cancer chemoprevention with dietary phytochemicals. Nat Rev Cancer 3:768-780.
21. Vermue MH, Tramper J. 1995. Biocatalysis in non-conventional media: medium engineering aspects. Pure Appl Chem 67: 345-373.
22. Vic G, Biton J, Le Beller D, Michel JM, Thomas D. 1995. Enzymatic glucosylation of hydrophobic alcohols in organic medium by the reverse hydrolysis reaction using almond-β-Dglucosidase. Biotechnol Bioeng 46:109-116.
23. Wescott CR, Klibanov AM. 1994. The solvent dependence of enzyme specificity. Biochim Biophys Acta 1206:1-9.