Abstract
α-Mangostin, the major xanthone constituent of mangoteen fruit pericarp, has several important pharmaceutical application but its bioavailability is restricted due to its insolubility in water. Herein, we synthesized water soluble α-mangostin-D-glucoside by glycosylation of α-mangostin at hydroxyl group; using amyloglucosidase (3.2.1.3) catalyzed reaction in supercritical carbon dioxide (SC-CO2) media. Response surface methodology (RSM) based on a five-variable central composite rotatable design involving 32 experiments was used to determine the effect of pressure (80–160 bar), temperature (35–75 °C), enzyme concentration (15–45 mg), buffer pH (4.0–8.0) and buffer volume (1.0–5.0 mL). Experimental data fitted the second-order polynomial equation as indicated by R2 value of 0.94. The optimal enzymatic conversion within the experimental range of the variables reached 20.3 % at a pressure of 120 bar, temperature of 55 °C, enzyme concentration of 30 mg, buffer volume of 3 mL and pH 6.0 which is well matched with the predictive yield.
Similar content being viewed by others
References
Chairungsrilerd N, Takeuchi K, Ohizumi Y, Nozoe S, Ohta T (1996) Garcinol, a new prenyl xanthone from Garcinia mangostana. Phytochemistry 43:1099–1102
Devi Sampath P, Vijayaraghavan K (2007) Cardioprotective effect of α-mangostin, a xanthone derivative from mangosteen on tissue defense system against isoproterenol-induced myocardial infarction in rats. J Biochem Mol Toxicol 21:336–339
Iikubo K, Ishikawa Y, Ando N, Umezawa K, Nishiyama S (2002) The first direct synthesis of α-mangostin, a potent inhibitor of the acidic sphingomyelinase. Tetrahedron Lett 43:291–293
Iinuma M, Tosa H, Tanaka T, Asai F, Kobayashi Y, Shimano R, Miyauchi K (1996) Antibacterial activity of xanthones from guttiferaeous plants against methicillin-resistant Staphylococcus aureus. J Pharm Pharmacol 48:861–865
Jessop P, Leitner W (1999) Chemical synthesis using supercritical fluids. Wiley-VCH, Weinheim, p 478
Knez Z (2009) Enzymatic reactions in dense gases. J Supercrit Fluids 47:357–372
Konstantinovic S, Predojevic J, Gojkovic S, Ratkovic Z, Mojsilovic B, Pavlovic V (2001) Synthesis of C7-C16 alkyl 2,3 dideoxy glucosides from glucose and fatty acids. Indian J Chem 40:1242–1244
Mahabusarakam W, Proudfoot J, Taylor W, Croft K (2000) Inhibition of lipoprotein oxidation by prenylated xanthones derived from mangostin. Free Radic Res 33:643–659
Manohar B, Divakar S (2002) Application of central composite rotatable design to lipase catalysed synthesis of m-cresyl acetate. World J Microbiol Biotechnol 18:745–751
Parvathy KS, Negi PS, Srinivas P (2009) Antioxidant, antimutagenic and antibacterial activities of curcumin-β-diglucoside. Food Chem 115:265–271
Peres C, Harper N, Da Silva MDRG, Barreiros S (2005) Effect of zeolites on lipase catalyzed esterification in nonaqueous media. Enzym Microb Tech 37:145–149
Ponrasu T, Manohar B, Divakar S (2009) A response surface methodological study on prediction of glucosylation yields of thiamin using immobilized β-glucosidase. Process Biochem 44:251–255
Sakagamia Y, Iinumab M, Piyasenac KGNP, Dharmaratne HRW (2005) Antibacterial activity of α-mangostin against vancomycin resistant Enterococci (VRE) and synergism with antibiotics. Phytomedicine 12:203–208
Suter M, Richter C (2000) Anti- and pro-oxidative properties of PADMA 28, a Tibetan herbal formula. Redox Rep 5:17–22
Trinca LA, Gilmour SG (2000) An algorithm for arranging response surface designs in small blocks. Comput Stat Data Anal 33:25–43
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zarena, A.S., Sankar, K.U. Synthesis of α − mangostin-D-glucoside in supercritical carbon dioxide media. J Food Sci Technol 52, 6547–6555 (2015). https://doi.org/10.1007/s13197-014-1705-z
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13197-014-1705-z