METHOXYFLAVONES FROM ORTHOSIPHON STAMINEUS BENTH. AND THEIR PTP1B INHIBITORY ACTIVITIES
Keywords:Orthosiphon stamineus Benth., flavone, ursolic acid, PTP1B inhibitor, type 2 diabetes
AbstractPhytochemical analysis of the methanol extract of the aerial parts of Orthosiphon stamineus Benth. led to the isolation of four flavone compounds including 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (1), 3,5,7,3′,4′-pentamethoxyflavone (2), 3,3′-dihydroxy-5,7,4′-trimethoxyflavone (3), and 3,5,3′-trihydroxy-7,4ʹ-dimethoxyflavone (4). Their chemical structures were determined from the spectroscopic evidences, including 1D-NMR and MS, respectively. The inhibitory effects of the isolates (1‒4) against protein tyrosine phosphatase 1B (PTP1B) enzyme were investigated in vitro using ursolic acid as positive control. Among the isolates, compound 4 exhibited potential activity with IC50 value of 10.12 ± 0.19 μM, the others showed weak activity. In this assay, ursolic acid displayed an IC50 value of 3.42 ± 0.25 μM. This is indicated that 3,3′-dihydroxy-5,7,4′-trimethoxyflavone (4) maybe useful for discovery of PTP1B inhibitors as antidiabetic agent.
IDF Diabetes Atlas. 8th edition, updated 2017. Brussels, Belgium: International Diabetes Federation, 2018. (https://www.idf.org/e-library/epidemiology-research/diabetes-atlas.html)
Day C. - The rising tide of type 2 diabetes, Br J Diabetes Vasc Dis 1 (1) (2001) 37–43.
Coman C., Rugina O. D., Socaciu C. - Plants and natural compounds with antidiabetic action, Not Bot Horti Agrobo 40 (1) (2012).
Xue B., Kim Y. B., Lee A., Toschi E., Bonner-Weir S., Kahn C. R., et al. - Protein tyrosine phosphatase 1B deficiency reduces insulin resistance and the diabetic phenotype in mice with polygenic insulin resistance, J Biol Chem 282 (33) (2007) 23829–23840.
Ahmad F., Azevedo J. L., Cortright R., Dohm G. L., Goldstein B. J. - Alterations in skeletal muscle protein-tyrosine phosphatase activity and expression in insulin-resistant human obesity and diabetes, J Clin Invest 100 (2) (1997) 449–458.
Elchebly M., Payette P., Michaliszyn E., Cromlish W., Collins S., Loy A. L. et al. - Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene, Science (New York, NY) 283 (5407) (1999) 1544–1548.
Johnson T. O., Ermolieff J., Jirousek M. R. - Protein tyrosine phosphatase 1B inhibitors for diabetes, Nat Rev Drug Discov 1 (9) (2002) 696–709.
Newman D. J., Cragg G. M. - Natural products as sources of newdrugs over the last 25 years, J Nat Prod 70 (3) (2007) 461–477.
Jiang C. S., Liang L. F., Guo Y. W. - Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades, Acta Pharmacol Sin 33 (10) (2012) 1217–1245.
Hsu C. L., Hong B. H., Yu Y. S., Yen G. C. - Antioxidant and Anti-Inflammatory Effects of Orthosiphon aristatus and Its Bioactive Compounds, J Agric Food Chem 58 (2010) 2150–2156.
Nguyen P. H., Yang J. L., Uddin M. N., Park S. L., Lim S. I., Jung D. W., Williams D. R., Oh W. K. - Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitors from Morinda citrifolia (Noni) and Their Insulin Mimetic Activity, J Nat Prod 76 (2013) 2080–2087.
Mabry T. J., Markham K. R., Thomas M. B. - The Systematic Identification of Flavonoids, Springer, New York (1970).
Long Cui, Hyun Sun Lee, Derek Tantoh Ndinteh, Joseph Tanyi Mbafor, Young Ho Kim, Thi Van Thu Le, Phi Hung Nguyen,Won Keun Oh. - New Prenylated Flavanones from Erythrina abyssinica with Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity, Planta Med 76 (2010) 713–718.
Bruce A. Bohm, Tod F. Stuessy. Flavonoids of the Sunflower Family (Asteraceae), Springer-Verlag Wien, New York (2001).
Chen L., He T., Han Y., Sheng, J. Z., Jin S., Jin M. W. - Pentamethylquercetin improves adiponectin expression in differentiated 3T3-L1 cells via a mechanism that implicates PPARγ together with TNF-α and IL-6, Molecules 16 (2011) 5754‒5768.
Rao Y. K., Geethangili M., Fang S. H., Tzeng Y. M. - Antioxidant and cytotoxic activities of naturally occurring phenolic and related compounds: A comparative study, Food and Chemical Toxicology 45(9) (2007) 1770‒1776.
Nugroho B. W., Edrada R. A., Wray V., Witte L., Bringmann G., Gehling M., Proksc P. - An insecticidal rocaglamide derivatives and related compounds from Aglaia odorata (Meliaceae), Phytochemistry 51 (1999) 367‒376.
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