PTP1B inhibitory activity of kaurane diterpenes isolated from Siegesbeckia glabrescens

References

• Johnson TO, Ermolieff J, Jirousek MR. Protein tyrosine phosphatase 1B inhibitors for diabetes. Nat Rev Drug Discov 2002; 1: 696–709
   PubMed Web of Science ®Google Scholar
• Asante-Appiah E, Kennedy BP. Protein tyrosine phosphatases: The quest for negative regulators of insulin action. Am J Physiol Endocrinol Metab 2003; 284: E663–E670
   PubMed Web of Science ®Google Scholar
• Ahmad F, Azevedo JJ, Cortright R, Dohm G, Goldstein B. Alterations in skeletal muscle protein-tyrosine phosphatase activity and expression in insulin-resistant human obesity and diabetes. J Clin Invest 1997; 100: 449–458
   PubMed Web of Science ®Google Scholar
• Byon JCH, Kusari AB, Kusari J. Protein-tyrosine phosphatase-1B acts as a negative regulator of insulin signal transduction. Mol Cell Biochem 1998; 182: 101–108
   PubMed Web of Science ®Google Scholar
• Elchebly M, Payette P, Michaliszyn E, Cromlish W, Collins S, Loy AL, Normandin D, Cheng A, Himms-Hagen J, Chan CC, Ramachandran C, Gresser MJ, Tremblay ML, Kennedy BP. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science 1999; 283: 1544–1548
   PubMed Web of Science ®Google Scholar
• Ukkola O, Santaniemi M. Protein tyrosine phosphatase 1B: A new target for the treatment of obesity and associated co-morbidities. J Intern Med 2002; 251: 467–475
   PubMed Web of Science ®Google Scholar
• Cook WS, Unger RH. Protein tyrosine phosphatase 1B: A potential leptin resistance factor of obesity. Dev Cell 2002; 2: 385–387
   PubMed Web of Science ®Google Scholar
• Taylor SD, Hill B. Recent advances in protein tyrosine phosphatase 1B inhibitors. Expert Opin Invest Drugs 2004; 13: 199–214
   PubMed Web of Science ®Google Scholar
• Chen RM, Hu LH, An TY, Li J, Shen Q. Natural PTP1B inhibitors from Broussonetia papyrifera. Bioorg Med Chem Lett 2002; 12: 3387–3390
   PubMed Web of Science ®Google Scholar
• Kim YC, Oh H, Kim BS, Kang TH, Ko EK, Han YM, Kim BY, Ahn JS. In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia. Planta Med 2005; 71: 87–89
   PubMed Web of Science ®Google Scholar
• Hong JH, Lee MS, Bae EY, Kim YH, Oh H, Oh WK, Kim BY, Ahn JS. Screening of the inhibitory activity of medicinal plants against protein tyrosine phosphatase 1B. Kor J Pharmacogn 2004; 35: 16–21
   Google Scholar
• Bae K. The medicinal plants of Korea. Seoul: Kyo-Hak Publishing Co.; 2000. p 512.
   Google Scholar
• Xiang Y, Fan C-Q, Yue J-M. Novel sesquiterpenoids from Siegesbeckia orientalis. Helv Chim Acta 2005; 88: 160–170
   Google Scholar
• Jiang X, Yunbao M, Yunlong X. Diterpenoids from Siegesbeckia pubescens. Phytochemistry 1992; 31: 917–921
   Web of Science ®Google Scholar
• Xiang Y, Zhang H, Fan C-Q, Yue J-M. Novel diterpenoids and diterpenoid glycosides from Siegesbeckia orientalis. J Nat Prod 2004; 67: 1517–1521
   PubMed Web of Science ®Google Scholar
• Kang BK, Lee EH, Kim HM. Inhibitory effects of Korean folk medicine ‘Hi-Chum’ on histamine release from mast cells in vivo and vitro. J Ethnopharmacol 1997; 57: 73–79
   PubMed Web of Science ®Google Scholar
• Kim HM, Lee JH, Won JH, Park EJ, Chae HJ, Kim HR, Kim CH, Baek SH. Inhibitory effect on immunoglobulin E production in vivo and in vitro by Siegesbeckia glabrescens. Phytother Res 2001; 15: 572–576
   PubMedGoogle Scholar
• Oh H, Kim BS, Bae EY, Kim MS, Kim BY, Lee HB, Kim CJ, Ahn JS. Inhibition of PTP1B by metabolites from Micromucor ramannianus var. angulisporus CRM000232. J Antibiot 2004; 57: 528–531
   PubMedGoogle Scholar
• Lee MS, Oh WK, Kim BY, Ahn SC, Kang DO, Sohn CB, Osada H, Ahn JS. Inhibition of VHR dual-specificity protein tyrosine phosphatase activity by flavonoids isolated from Scutellaria baicalensis: Structure-activity relationships. Planta Med 2002; 68: 1063–1065
   PubMed Web of Science ®Google Scholar
• Murakami T, Isa T, Satake T. Eine neuuntersuchung der inhaltsstoffe von Siegesbeckia pubescens Makino. Tetrahedron Lett 1973; 50: 4991–4994
   Google Scholar
• Guo DA, Zhang ZG, Ye GQ, Lou ZC. Studies on liposoluble constituents from the aerial parts of Siegesbeckia orientalis L. Acta Pharm Sin 1997; 32: 282–285
   Google Scholar
• Cai XF, Shen G, Dat NT, Kang OH, Lee YM, Lee JJ, Kim YH. Inhibitory effect of kaurane type diterpenoids from Acanthopanax koreanum on TNF-α secretion from trypsin-stimulated HMC-1 cells. Arch Pharm Res 2003; 26: 731–734
   PubMed Web of Science ®Google Scholar
• Etse JT, Gray AI, Waterman PG. Chemistry in the Annonaceae, XXIV. Kaurane and kaur-16-ene diterpenes from the stem bark of Annona reticulata. J Nat Prod 1987; 50: 979–983
   Google Scholar
• Hamaguchi T, Sudo T, Osada H. RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1phase. FEBS Lett 1995; 372: 54–58
   PubMed Web of Science ®Google Scholar
• Wiesmann C, Barr KJ, Kung J, Zhu J, Erlanson DA, Shen W, Fahr BJ, Zhong M, Taylor L, Randal M, McDowell RS, Hansen SK. Allosteric inhibition of protein tyrosine phosphatase 1B. Nat Struc Mol Biol 2004; 11: 730–737
   PubMed Web of Science ®Google Scholar
• Hwang BY, Lee JH, Koo TH, Kim HS, Hong YS, Ro JS, Lee KS, Lee JJ. Kaurane diterpenes from Isodon japonicus inhibit nitric oxide and prostaglandin E2 production and NF-B activation in LPS-stimulated macrophage RAW264.7 cells. Planta Med 2001; 67: 406–410
   PubMed Web of Science ®Google Scholar
• Suzuki I, Kondoh M, Nagashima F, Fujii M, Asakawa Y, Watanabe Y. A comparison of apoptosis and necrosis induced by ent-kaurane-type diterpenoids in HL-60 cells. Planta Med 2004; 70: 401–406
   PubMed Web of Science ®Google Scholar
• Wu Y-C, Hung Y-C, Chang F-R, Cosentino M, Wang H-K, Lee K-H. Identification of ent-16,17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa. J Nat Prod 1996; 59: 635–637
   PubMed Web of Science ®Google Scholar
• Yang Y-L, Chang F-R, Wu C-C, Wang W-Y, Wu Y-C. New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa. J Nat Prod 2002; 65: 1462–1467
   PubMed Web of Science ®Google Scholar
• Xiang W, Na Z, Li S-H, Li M-L, Li R-T, Tian Q-E, Sun H-D. Cytotoxic diterpenoids from Isodon enanderianus. Planta Med 2003; 69: 1031–1035
   PubMed Web of Science ®Google Scholar