Potent HGF/c-Met axis inhibitors from Eucalyptus globulus: The coupling of phloroglucinol and sesquiterpenoid is essential for the activity

Journal of Medicinal Chemistry

Volumn 55, Issue 18, 2012, Pages 8183-8187

  Yang, Sheng Ping ^a   Zhang, Xiao Wei ^a   Ai, Jing ^a   Gan, Li She ^b   Xu, Jin Biao ^a   Wang, Ying ^a   Su, Zu Shang ^a   Wang, Lu ^a   Ding, Jian ^a   Geng, Mei Yu ^a   Yue, Jian Min ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

10ALPHA DIHYDROXYAROMADENDRANE; EUCALYPTIN A; EUGLOBAL IIC; EUGLOBAL T1; GLOBULOL; GRANDINOL; JENSENONE; MACROCARPAL A; MACROCARPAL B; PHLOROGLUCINOL; PROTEIN INHIBITOR; SCATTER FACTOR RECEPTOR; SESQUITERPENOID; UNCLASSIFIED DRUG; UROKINASE;

ANIMAL CELL; ARTICLE; BRANCHING MORPHOGENESIS; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CELL MIGRATION; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; EUCALYPTUS GLOBULUS; FRUIT; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PROTEIN PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SIGNAL TRANSDUCTION; STEREOCHEMISTRY; WOUND HEALING;

ANIMALS; CELL MOVEMENT; CELL PROLIFERATION; DOGS; EUCALYPTUS; HEPATOCYTE GROWTH FACTOR; HUMANS; MADIN DARBY CANINE KIDNEY CELLS; PHLOROGLUCINOL; PLANT EXTRACTS; PROTEIN KINASE INHIBITORS; PROTO-ONCOGENE PROTEINS C-MET; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP; UROKINASE-TYPE PLASMINOGEN ACTIVATOR;

EID: 84866875425     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3007454     Document Type: Article

References (26)

1. Giordano, S.; Ponzetto, C.; Di Renzo, M. F.; Cooper, C. S.; Comoglio, P. M. Tyrosine kinase receptor indistinguishable from the c- met protein Nature 1989, 339, 155-156
2. Birchmeier, C.; Birchmeier, W.; Gherardi, E.; Vande Woude, G. F. Met, metastasis, motility and more Nature Rev. Mol. Cell Biol. 2003, 4, 915-925
3. Longati, P.; Comoglio, P. M.; Bardelli, A. Receptor tyrosine kinases as therapeutic targets: the model of the MET oncogene Curr. Drug Targets 2001, 2, 41-55
4. Dai, Y.; Siemann, D. W. BMS-777607, a small-molecule Met kinase inhibitor, suppresses hepatocyte growth factor-stimulated prostate cancer metastatic phenotype in vitro Mol. Cancer Ther. 2010, 9, 1554-1561
5. Comoglio, P. M.; Giordano, S.; Trusolino, L. Drug development of MET inhibitors: targeting oncogene addiction and expedience Nature Rev. Drug Discovery 2008, 7, 504-516
6. Lesko, E.; Majka, M. The biological role of HGF-MET axis in tumor growth and development of metastasis Front. Biosci. 2008, 13, 1271-1280
7. Matsumoto, K.; Nakamura, T. Hepatocyte growth factor and the Met system as a mediator of tumor-stromal interactions Int. J. Cancer 2006, 119, 477-483
8. Zeng, J. F.; Liu, S. Q. In Chinese Flora (Zhongguo Zhiwu Zhi); Science Press: Beijing, 1984; Vol. 53, Chapter 1, pp 31-52.
9. Yin, S.; Xue, J. J.; Fan, C. Q.; Miao, Z. H.; Ding, J.; Yue, J. M. Eucalyptals A-C with a new skeleton isolated from Eucalyptus globulus Org. Lett. 2007, 9, 5549-5552
10. Ghisalberti, E. L. Bioactive acylphloroglucinol derivatives from Eucalyptus species Phytochemistry 1996, 41, 7-22
11. Nishizawa, M.; Emura, M.; Kan, Y.; Yamada, H.; Ogawa, K.; Hamanaka, N. Macrocarpals: HIV-RTase inhibitors of Eucalyptus globulus Tetrahedron Lett. 1992, 33, 2983-2986
12. 2, -Ib, -Ic, -IIa, -IIb and -IIc Chem. Pharm. Bull. 1982, 30, 1952-1963
13. Kozuka, M.; Sawada, T.; Mizuta, E.; Kasahara, F.; Amano, T.; Komiya, T.; Goto, M. The granulation-inhibiting principles from Eucalyptus globulus LABILL. III. The structures of euglobal-III, -IVb and -VII Chem. Pharm. Bull. 1982, 30, 1964-1973
14. Takasaki, M.; Konoshima, T.; Fujitani, K.; Yoshida, S.; Nishimura, H.; Tokuda, H.; Nishino, H.; Iwashima, A.; Kozuka, M. Inhibitors of skin-tumor promotion. VIII. Inhibitory effects of euglobals and their related compounds on Epstein-Barr virus activation (1) Chem. Pharm. Bull. 1990, 38, 2737-2739
15. Umehara, K.; Singh, I. P.; Etoh, H.; Takasaki, M.; Konoshima, T. Five phloroglucinol-monoterpene adducts from Eucalyptus grandis Phytochemistry 1998, 49, 1699-1704
16. Osawa, K.; Yasuda, H.; Morita, H.; Takeya, K.; Itokawa, H. Macrocarpals H, I, and J from the leaves of Eucalyptus globulus J. Nat. Prod. 1996, 59, 823-827
17. Crow, W. D.; Osawa, T.; Paton, D. M.; Willing, R. R. Structure of grandinol: a novel root inhibitor from Eucalytus grandis Tetrahedron Lett. 1977, 12, 1073-1074
18. Kokumai, M.; Konoshima, T.; Kozuka, M.; Haruna, M.; Ito, K. Euglobal T1, a new euglobal from Eucalyptus tereticornis J. Nat. Prod. 1991, 54, 1082-1086
19. Murata, M.; Yamakoshi, Y.; Homma, S.; Aida, K.; Hori, K.; Ohashi, Y. Macrocarpal A, a novel antibacterial compound from Eucalyptus macrocarpa Agric. Biol. Chem. 1990, 54, 3221-3226
20. Diedrich, C.; Grimme, S. Systematic Investigation of Modern Quantum Chemical Methods to Predict Electronic Circular Dichroism Spectra J. Phys. Chem. A 2003, 107, 2524-2539
21. Faure, R.; Ramanoelina, A. R. P.; Rakotonirainy, O.; Bianchini, J.-P.; Gaydou, E. M. Two-dimensional nuclear magnetic resonance of sesquiterpenes. 4. Application to complete assignment of proton and carbon-13 NMR spectra of some aromadendrane derivatives Magn. Reson. Chem. 1991, 29 (9) 969-971
22. Beechan, C. M.; Djerassi, C. Terpenoids-LXXIV: The sesquiterpenes from the soft coral Sinularia mayi Tetrahedron 1978, 34, 2503-2508
23. Nagashima, F.; Tanaka, H.; Toyota, M.; Hashimoto, T.; Kan, Y.; Takaoka, S.; Tori, M.; Asakawa, Y. Sesqui- and diterpenoids from Plagiochila species Phytochemistry 1994, 36, 1425-1430
24. Boland, D. J.; Brophy, J. J.; Fookes, C. J. R. Jensenone, a ketone from Eucalyptus jensenii Phytochemistry 1992, 31, 2178-2179
25. Webb, C. P.; Hose, C. D.; Koochekpour, S.; Jeffers, M.; Oskarsson, M.; Sausville, E.; Monks, A.; Vande Woude, G. F. The geldanamycins are potent inhibitors of the hepatocyte growth factor/scatter factor-met-urokinase plasminogen activator-plasmin proteolytic network Cancer Res. 2000, 60, 342-349
26. Zhang, Y. W.; Vande Woude, G. F. HGF/SF-met signaling in the control of branching morphogenesis and invasion J. Cell Biochem. 2003, 88, 408-417