Synthesis of three bromophenols from red algae as PTP1B inhibitors

Chinese Journal of Oceanology and Limnology

Volumn 29, Issue 1, 2011, Pages 68-74

  Guo, Shuju ^a,b   Li, Jing ^a   Li, Ting ^a,b   Shi, Dayong ^a   Han, Lijun ^a  

^a INSTITUTE OF OCEANOLOGY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

bromophenols; PTP1B inhibitory activity; synthesis

Indexed keywords

ALGAE; RHODOPHYTA;

EID: 79955549935     PISSN: 02544059     EISSN: 19935005     Source Type: Journal    
DOI: 10.1007/s00343-011-9996-7     Document Type: Article

References (32)

1. Choi J S, Park H J, Jung H A, Chung H Y, Jung J H, Choi W C. 2000. A cyclohexanonyl bromophenol from the red alga Symphyocladia latiuscula. J. Nat. Prod., 63: 1 705-1 706.
2. Dadke S, Chernoff J. 2003. Protein-tyrosine phosphatase 1B as a potential drug target for obesity. Curr. Drug Targets, 3: 299-304.
3. Elchebly M, Payette P, Michaliszyn E, Cromlish W, Collins S, Loy A L, Normandin D, Cheng A, Himms-Hagen J, Chan C C, Ramachandran C, Gresser M J, Tremblay M L, Kennedy B P. 1999. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science, 283: 1 544-1 548.
4. Fan X, Xu N J, Shi J G. 2003a. Bromophenols from the red alga Rhodomela confervoides. J. Nat. Prod., 66: 455-458.
5. Fan X, Xu N J, Shi J G. 2003b. Two new bromophenols from red alga Rhodomela confervoides. Chin. Chem. Lett., 14: 939-941.
6. Fan X, Liu Q W, Han L J, Zhang T, Ma C J. 2006. 3-bromo-4-(3-bromo-4, 5-dihydroxyphenylmethyl)-5-(Ethoxymethyl)-1, 2-benzenediol, and its Preparation Method and Applications. Prospectus of invention patent applications (Faming Zhuanli Shenqing Gongkai Shuomingshu), China, 200410087506. 7.
7. Flodin C, Whitfield F B. 1999. Biosynthesis of bromophenols in marine algae. Water Science and Technology, 40: 53-58.
8. Ford P W, Davidson B S. 1993. Synthesis of varacin, a cytotoxic naturally occurring benzopentathiepin isolated from a marine ascidian. J. Org. Chem., 58: 4 522-4 523.
9. Fürstner A, Stelzer F, Rumbo A, Krause H. 2002. Total synthesis of the turrianes and evaluation of their DNA-cleaving properties. Chem. Eur. J., 8: 1 856-1 871.
10. Glombitza K W, Sukopp I, Wiedenfeld H. 1985. Antibiotics from algae XXXVII. rhodomelol and methylrhodomelol from Polysiphonia lanosa1. Planta Med., 51: 437-440.
11. Hattori T, Konno A, Adachi K, Shizuri Y. 2001. Four new bioactive bromophenols from the palauan sponge Phyllospongia dendyi. Fisheries Science, 67: 899-903.
12. Kim H O, Blaskovich M A. 2002. Recent discovery and development of protein tyrosine phosphatase inhibitors. Expert Opin. Ther. Patents, 12: 871-905.
13. Kim K Y, Choi K S, Kurihara H, Kim S M. 2008. beta-glucuronidase inhibitory activity of bromophenols purified from Grateloupia elliptica. Food Science and Biotechnology, 17: 1 110-1 114.
14. Klaman L D, Boss O, Peroni O D, Kim J K, Martino J L, Zabolotny J M, Moghal N, Lubkin M, Kim Y B, Sharpe A H, Stricker-Krongrad A, Shulman G I, Neel B G, Kahn B B. 2000. Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1b-deficient mice. Mol. Cell. Biol., 20: 5 479-5 489.
15. Kubo I, Ochi M, Shibata K, Hanke F J, Nakatsu T, Tan K-S, Taniguchi M, Kamikawa T, Yamagiwa Y, Arizuka M, Wood W F. 1990. Effect of a marine algal constituent on the growth of lettuce and rice seedlings. J. Nat. Prod., 53: 50-56.
16. Kurata K, Taniguchii K, Takashima K, Hayashi I, Suzuki M. 1997. Feeding-deterrent bromophenols from Odonthalia corymbifera. Phytochemistry, 45: 485-487.
17. Li J, Guo S J, Su H, Han L J, Shi D Y. 2008. Total synthesis of bis-(2, 3-dibromo-4, 5-dihydroxyphenyl)-methane as potent PTP1B inhibitor. Chin. Chem. Lett., 19: 1 290-1 292.
18. Li K, Li X M, Ji N Y, Wang B G. 2007. Natural bromophenols from the marine red alga Polysiphonia urceolata (Rhodomelaceae): Structural elucidation and DPPH radical-scavenging activity. Bioorganic & Medicinal Chemistry, 15: 6 627-6 631.
19. Lim C, Lee J, Cho Y. 2000. Structures and some properties of the antimicrobial compounds in the red alga, Symphyocladia latiuscula. Journal-Korean Fisheries Society, 33: 280-287.
20. Lundgren L, Olsson K, Theander, O. 1979. Synthesis of some bromophenols present in red algae. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, B33: 105-108.
21. Ma M, Zhao J L, Wang S J, Li S, Yang Y C, Shi H G, Fan X, He L. 2006. Bromophenols coupled with methyl gamma-ureidobutyrate and bromophenol sulfates from the red alga Rhodomela confervoides. J. Nat. Prod., 69: 206-210.
22. Oh K B, Lee J H, Chung S C, Shin J, Shin H J, Kim H K, Lee H S. 2008. Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives. Bioorganic & Medicinal Chemistry Letters, 18: 104-108.
23. Oh K B, Lee J H, Lee J W, Yoon K M, Chung S C, Jeon H B, Shin J, Lee H S. 2009. Synthesis and antimicrobial activities of halogenated bis(hydroxyphenyl)methanes. Bioorganic & Medicinal Chemistry Letters, 19: 945-948.
24. Pei Z, Liu G, Lubben T H, Szczepankiewicz B G. 2004. Inhibition of protein tyrosine phosphatase 1B as a potential treatment of diabetes and obesity. Curr. Pharm. Design, 10: 3 481-3 504.
25. Popplewell W L, Northcote P T. 2009. Colensolide A: a new nitrogenous bromophenol from the New Zealand marine red alga Osmundaria colensoi. Tetrahedron Letters, 50: 6 814-6 817.
26. Saltiel A R, Kahn C R. 2001. Insulin signalling and the regulation of glucose and lipid metabolism. Nature, 414: 799-806.
27. Shi D Y, Xu F, He J, Li J, Fan X, Han L J. 2008. Inhibition of bromophenols against PTP1B and anti-hyperglycemic effect of Rhodomela confervoides extract in diabetic rats. Chin. Sci. Bull., 16: 2 476-2 479.
28. Takenaka Y, Tanahashi T, Nagakura N, Hamada N. 2003. Phenyl ethers from cultured lichen mycobionts of Graphis scripta var. serpentina and G. rikuzensis. Chem. Pharm. Bull., 51: 794-797.
29. Teclechiel D, Sundstrom M, Marsh G. 2009. Synthesis of polybrominated diphenyl ethers via symmetrical tetra- and hexabrominated diphenyliodonium salts. Chemosphere, 74: 421-427.
30. Xu N J, Fan X, Yan X J, Li X C, Niu R L, Tseng C K. 2003. Antibacterial bromophenols from the marine red alga Rhodomela confervoides. Phytochemistry, 62: 1 221-1 224.
31. Yang L, Williams D E, Mui A, Ong C, Krystal G, van Soest R, Andersen R J. 2005. Synthesis of pelorol and analogues: activators of the inositol 5-phosphatase SHIP. Org. Lett., 7: 1 073-1 076.
32. Zhao J L, Ma M, Wang S J, Li S, Cao P, Yang Y C, Lu Y, Shi J G, Xu N J, Fan X, He L. 2005. Bromophenols coupled with derivatives of amino acids and nucleosides from the red alga Rhodomela confervoides. J. Nat. Prod., 68: 691-694.