2′-Epi-uscharin from the latex of Calotropis gigantea with HIF-1 inhibitory activity

Scientific Reports

Volumn 4, Issue , 2014, Pages

  Parhira, Supawadee ^a   Zhu, Guo Yuan ^a   Jiang, Ren Wang ^b   Liu, Liang ^a   Bai, Li Ping ^a   Jiang, Zhi Hong ^a  

^a MACAU UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Macao)

^b JINAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARDENOLIDE; HYPOXIA INDUCIBLE FACTOR 1; LATEX; PLANT EXTRACT;

ANOXIA; ANTAGONISTS AND INHIBITORS; CALOTROPIS; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; GENE EXPRESSION; GENETIC TRANSCRIPTION; GENETICS; HUMAN; METABOLISM; NUCLEAR MAGNETIC RESONANCE; REPORTER GENE;

ANOXIA; CALOTROPIS; CARDENOLIDES; CELL LINE; GENE EXPRESSION; GENES, REPORTER; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1; LATEX; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT EXTRACTS; TRANSCRIPTION, GENETIC;

EID: 84899053930     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep04748     Document Type: Article

References (26)

1. Pari, K., Rao, P. J., Devakumar, C. & Rastogi, J. N. A novel insect antifeedant nonprotein amino acid from Calotropis gigantea. J. Nat. Prod. 61, 102-104 (1998). (Pubitemid 28086985)
2. Lhinhatrakool, T. & Sutthivaiyakit, S. 19-Nor- and 18, 20-epoxy-cardenolides from the leaves of Calotropis gigantea. J. Nat. Prod. 69, 1249-1251 (2006). (Pubitemid 44409809)
3. Silva, M. C. C. et al. Therapeutic and biological activities of Calotropis procera (Ait.) R. Br. Asian Pac. J. Trop. Med. 3, 332-336 (2010).
4. Seiber, J. N., Nelson, C. J. & Lee, S. M. Cardenolides in the latex and leaves of seven Asclepias species and Calotropis procera. Phytochemistry 21, 2343-2348 (1982).
5. Wang, Z. N., Wang, M. Y., Mei, W. L., Han, Z. & Dai, H. F. A new cytotoxic pregnanone from Calotropis gigantea. Molecules 13, 3033-3039 (2008).
6. Thakur, S., Das, P., Itoh, T., Imai, K. & Matsumoto, T. Latex extractables of Calotropis gigantea. Phytochemistry 23, 2085-2087 (1984).
7. Bhaskara Rama Murti, P. & Seshadri, T. R. Chemical composition of Calotropis gigantea. Part I. Wax and resin components of the latex. Proc. Indian Acad. Sci., Section A 18, 145-159 (1943).
8. Cheung, H. T. A., Chiu, F. C. K., Watson, T. R. & Wells, R. J. Cardenolide glycosides of the Asclepiadaceae. New glycosides from Asclepias fruticosa and the stereochemistry of uscharin, voruscharin and calotoxin. J. Chem. Soc., Perkin Trans. 1, 2827-2835 (1983).
9. Bruschweiler, F., Stocklin, W., Stockel, K. & Reichstein, T. Glycosides of Calotropis procera R. Br. Glycosides and aglycones. Helv. Chim. Acta. 52, 2086-2106 (1969).
10. Bruschweiler, F., Stockel, K. & Reichstein, T. Calotropis glycosides, probable partial structure. Glycosides and aglycones. Helv. Chim. Acta. 52, 2276-2303 (1969).
11. Cheung, H. T. A., Chiu, F. C. K., Watson, T. R. & Wells, R. J. Reduction of hemiacetal ring-opened forms of Asclepiadaceae cardenolide glycosides. J. Chem. Soc., Perkin Trans. 1, 55-59 (1986).
12. Lichtenthaler, F. W., Cuny, E. & Sakanaka, O. A concise and general method for doubly attaching 2-ketosugars to aglycon diols: synthesis of the gomphosides and spectinomycin. Angew. Chem. Int. Ed. Engl. 44, 4944-4948 (2005). (Pubitemid 41138686)
13. Zhang, H. et al. Digoxin and other cardiac glycosides inhibit HIF-1 a synthesis and block tumor growth. Proc. Natl. Acad. Sci. USA. 105, 19579-19586 (2008).
14. Semenza, G. L. Hypoxia-inducible factors in physiology and medicine. Cell 148, 399-408 (2012).
15. Strieter, R. M. Masters of angiogenesis. Nat. Med. 11, 925-927 (2005). (Pubitemid 41294434)
16. Giaccia, A., Siim, B. G. & Johnson, R. S. HIF-1 as a target for drug development. Nat. Rev. Drug Discov. 2, 803-811 (2003). (Pubitemid 37361812)
17. Zhao, T. et al. HIF-1-mediated metabolic reprogramming reduces ROS levels and facilitates the metastatic colonization of cancers in lungs. Sci. Rep. 4, 3793; DOI:10.1038/srep03793 (2014).
18. Takeda, T., Okuyama, H., Nishizawa, Y., Tomita, S. & Inoue, M. Hypoxia inducible factor-1α is necessary for invasive phenotype in Vegf-deleted islet cell tumors. Sci. Rep. 2, 494; DOI:10.1038/srep00494 (2012).
19. Zhang, C., Li, Y., Cornelia, R., Swisher, S. & Kim, H. Regulation of VEGF expression by HIF-1α in the femoral head cartilage following ischemia osteonecrosis. Sci. Rep. 2, 650; DOI:10.1038/srep00650 (2012).
20. Bienes-Martínez, R. et al. Autocrine stimulation of clear-cell renal carcinoma cell migration in hypoxia via HIF-independent suppression of thrombospondin-1. Sci. Rep. 2, 788; DOI:10.1038/srep00788 (2012).
21. Saito, M. et al. Prostatic ischemia induces ventral prostatic hyperplasia in the SHR; possible mechanism of development of BPH. Sci. Rep. 4, 3822; DOI:10.1038/srep03822 (2014).
22. Chan, D. S. et al. Structure-based discovery of natural-product-like TNF-α inhibitors. Angew. Chem. Int. Ed. Engl. 49, 2860-2864 (2010).
23. Leung, C. H. et al. A natural product-like inhibitor of NEDD8-activating enzyme. Chem. Commun. 47, 2511-2513 (2011).
24. Leung, C. H. et al. A metal-based inhibitor of tumor necrosis factor-α. Angew. Chem. Int. Ed. Engl. 51, 9010-9014 (2012).
25. Welsh, S. J. et al. Inhibition of the hypoxia-inducible factor pathway by a Gquadruplex binding small molecule. Sci. Rep. 3, 2799; DOI:10.1038/srep02799 (2013).
26. Kim, H. J. et al. Inhibition of endoplasmic reticulum stress alleviates lipopolysaccharide-induced lung inflammation through modulation of NF-kB/HIF-1α signaling pathway. Sci. Rep. 3, 1142; DOI:10.1038/srep01142 (2013).