Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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α-Glucosidase inhibitory caged xanthones from the resin of Garcinia hanburyi

  • Jin, Young Min (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) ;
  • Kim, Jeong Yoon (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) ;
  • Lee, Soo Min (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) ;
  • Tan, Xue Fei (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) ;
  • Park, Ki Hun (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University)
  • Received : 2019.01.16
  • Accepted : 2019.01.22
  • Published : 2019.03.31
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Abstract

A yellow resin (gamboge) from Garcinia hanburyi has been widely used as folk medicine due to its antibacterial and antitumor activities. We isolated four ${\alpha}$-glucosidase inhibitory compounds from the methanol extract of gamboge. The compounds (1-4) were identified as gambogoic acid (1), moreollic acid (2), gambogic acid (3), and 10-methoxygambogenic acid (4), respectively through spectroscopic data including 2D-NMR and HREIMS. All compounds were examined in the enzyme inhibition assay against ${\alpha}$-glucosidase to identify their inhibitory potencies and kinetic behavior. All compounds (1-4) showed enzyme inhibition against ${\alpha}$-glucosidase, but the activity was significantly affected by the methoxy group on C-10 of ring A and pentenyl pyran moiety of ring D. For example, compound 1 ($IC_{50}=41.4{\mu}M$) bearing pyran ring eight times effective that 4 ($IC_{50}=350.6{\mu}M$) having geranyl group itself. Most active compound was found out to be gambogoic acid (1) which was analyzed most abundant metabolite in gamboge by LC-ESI-MS/MS. In kinetic study, compounds 1 and 2 were proved as noncompetitive inhibitors.

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References

  1. Bojarova P, Kren V (2009) Glycosidases: a key of tailored carbohydrates. Trends Biotechnol 27(4): 199-209 https://doi.org/10.1016/j.tibtech.2008.12.003
  2. Van de Larr FA, Lucassen PL, Akkermans RP, Van de Lisdonk EH, Rutten GE, Van Weel C (2005) Alpha-glucosidase inhibitors for type 2 diabetes mellitus. Cochrane Database Sys Rev 2: CD003639
  3. Papandreou MJ, Barbouche R, Guieu R, Kieny MP, Fenouillet E (2002) The $\alpha$-glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step. Mol Pharmacol 61(1): 186-193 https://doi.org/10.1124/mol.61.1.186
  4. Fischer PB, Collin M, Karlsson GB, James W, Butters TD, Davis SJ, Gordon S, Dwek RA, Platt FM (1995) The $\alpha$-glucosidase inhibitor Nbuthyldeoxynojirimycin inhibits human immunodeficiency virus entry at the level of post-CD4 binding. J Virol 69: 5791-5797 https://doi.org/10.1128/JVI.69.9.5791-5797.1995
  5. Fischer PB, Karlsson GB, Dwek RA, Platt FM (1996) Nbutyldeoxynojirimycin-mediated inhibition of human immunodeficiency virus entry correlates with impaired gp120 shedding and gp41 exposure. J Virol 70(10): 7153-7160 https://doi.org/10.1128/jvi.70.10.7153-7160.1996
  6. Duke JA (1985) Handbook of Medical Herbs. Library of Congress, New York
  7. Evan WC (1996) Trease and Evans Pharmacognosy, 14th ed. Saunders Company Limited, Nottingham
  8. Reutrakul V, Anantachoke N, Pohmakotr M, Jaipetch T, Sophasan S, Yoosook C, Kasisit J, Napaswat C, Santisuk T, Tuchinda P (2007) Cytotoxic and anti-HIV-1 caged xanthones from the resin and fruits of Garcinia hanburyi. Plant Med 73(1): 33-40 https://doi.org/10.1055/s-2006-951748
  9. Sukpondma Y, Rukachaisirikul V, Phongpaichit S (2005) Antibacterial caged-tetraprenylated xanthones from the fruits of Garcinia hanburyi. Chem Pharm Bull (Tokyo) 53(7): 850-852 https://doi.org/10.1248/cpb.53.850
  10. Panthong A, Norkaew P, Kanjanapothi D, Taesotikul T, Anantachoke N, Reutrakul V (2007) Anti-inflammatory, analgesic and antipyretic activities of the extract of gamboge from Garcinia hanburyi Hook f. J Ethnopharmacol 111(2): 335-340 https://doi.org/10.1016/j.jep.2006.11.038
  11. Han Q, Yang L, Liu Y, Wang Y, Qiao C, Song J, Xu L, Yang D, Chen S, Xu H (2006) Gambogic acid and epigambogic acid, C-2 epimers with novel anticancer effects from Garcinia hanburyi. Planta Med 72(3): 281-284 https://doi.org/10.1055/s-2005-916193
  12. Tan XF, Uddin Z, Park C, Song YH, Son M, Lee KW, Park KH (2017) Competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors, prenylated caged xanthones from Garcinia hanburyi and their inhibitory mechanism. Bioorg Med Chem 25(8): 2498-2506 https://doi.org/10.1016/j.bmc.2017.03.010
  13. Kim JY, Lee JW, Kim YS, Lee Y, Ryu YB, Kim S, Ryu HW, Curtis-Long MJ, Lee KW, Lee WS, Park KH (2010) A novel competitive class of $\alpha$-glucosidase inhibitors: (E)-1-phenyl-3-(4-styrylphenyl)urea derivatives. ChemBioChem 11: 2125-2131 https://doi.org/10.1002/cbic.201000376
  14. Waley SG (1982) A quick method for the determination of inhibition constants. Biochem J 205(3): 631-633 https://doi.org/10.1042/bj2050631
  15. Zhou Y, Liu X, Yang J, Han QB, Song JZ, Li SL, Qiao CF, Ding LS, Xu HX (2008) Analysis of caged xanthones from the resin of Garcinia hanburyi using ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Anal Chim Acta 629(1-2): 104-118 https://doi.org/10.1016/j.aca.2008.09.044
  16. Han QB, Zhou Y, Feng C, Xu G, Huang SX, Li SL, Qiao CF, Song JZ, Chang DC, Luo KQ, Xu HX (2009) Bioassay guided discovery of apoptosis inducers from gamboge by high-speed counter-current chromatography and high-pressure liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry. J Chromatogr B Anlyt Technol Biomed life Sci 877(4): 401-407 https://doi.org/10.1016/j.jchromb.2008.12.046
  17. Yang J, Ding L, Hu L, Jin S, Liu W, You Q, Guo Q (2012) Rapid characterization of caged xanthones in the resin of Garcinia hanburyi using multiple mass spectrometric scanning modes: the importance of biosynthetic knowledge based prediction. J Pharm Biomed Anal 60: 71-79 https://doi.org/10.1016/j.jpba.2011.10.035