The Halicylindramides, Farnesoid X Receptor Antagonizing Depsipeptides from a Petrosia sp. Marine Sponge Collected in Korea

Journal of Natural Products

Volumn 79, Issue 3, 2016, Pages 499-506

  Hahn, Dongyup ^a   Kim, Hiyoung ^b   Yang, Inho ^b   Chin, Jungwook ^a   Hwang, Hoosang ^b   Won, Dong Hwan ^b   Lee, Byoungchan ^b   Nam, Sang Jip ^c   Ekins, Merrick ^d   Choi, Hyukjae ^e   Kang, Heonjoong ^b  

^a Daegu Gyeongbuk Medical Innovation Foundation   (South Korea)

^b Seoul National University   (South Korea)

^c Ewha Womans University   (South Korea)

^d QUEENSLAND MUSEUM   (Australia)

^e Yeungnam University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DEPSIPEPTIDE; FARNESOID X RECEPTOR; HALICYLINDRAMIDE DERIVATIVE; HALICYLINDRAMIDE F; HALICYLINDRAMIDE G; HALICYLINDRAMIDE H; HORMONE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; CELL RECEPTOR; FARNESOID X-ACTIVATED RECEPTOR; HALICYLINDRAMIDE A;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; ISOLATION AND PURIFICATION; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PETROSIA; PROTON NUCLEAR MAGNETIC RESONANCE; ANIMAL; CHEMISTRY; DRUG EFFECTS; HUMAN; MARINE BIOLOGY; NUCLEAR MAGNETIC RESONANCE; SOUTH KOREA;

ANIMALS; DEPSIPEPTIDES; HUMANS; MARINE BIOLOGY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PETROSIA; RECEPTORS, CYTOPLASMIC AND NUCLEAR; REPUBLIC OF KOREA;

EID: 84962427485     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00871     Document Type: Article

References (30)

1. Ebada, S. S.; Proksch, P. In Handbook of Marine Natural Products; Fattorusso, E.; Gerwick, W. H.; Taglialatela-Scafati, O., Eds.; Springer: New York, 2012; Vol. 1, Chapter 4, pp 191-293.
2. Kobayashi, M.; Aoki, S.; Ohyabu, N.; Kurosu, M.; Wang, W.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 7969-7972 10.1016/0040-4039(94)80024-3
3. Anderson, H. J.; Coleman, J. E.; Andersen, R. J.; Roberge, M. Cancer Chemother. Pharmacol. 1997, 39, 223-226 10.1007/s002800050564
4. Randazzo, A.; Bifulco, G.; Giannini, C.; Bucci, M.; Debitus, C.; Cirino, G.; Gomez-Paloma, L. J. Am. Chem. Soc. 2001, 123, 10870-10876 10.1021/ja010015c
5. Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254 10.1016/0040-4039(94)88295-9
6. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Waelchli, M. J. Am. Chem. Soc. 1989, 111, 2582-2588 10.1021/ja00189a035
7. Gunasekera, S. P.; Pomponi, S. A.; McCarthy, P. J. J. Nat. Prod. 1994, 57, 79-83 10.1021/np50103a011
8. Li, H.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343 10.1021/jm00002a015
9. Scott, V. R.; Boehme, R.; Matthews, T. R. Antimicrob. Agents Chemother. 1998, 32, 1154-1157 10.1128/AAC.32.8.1154
10. Plaza, A.; Bifulco, G.; Keffer, J. L.; Lloyd, J. R.; Baker, H. L.; Bewley, C. A. J. Org. Chem. 2009, 74, 504-512 10.1021/jo802232u
11. Ford, P. W.; Gustafson, K. R.; McKee, M. C.; Shigematsu, N.; Maurizi, L. K.; Pannell, L. K.; Williams, D. E.; de Silva, D.; Lassota, P.; Allen, T. M.; van Soest, R.; Andersen, R. J.; Boyd, M. R. J. Am. Chem. Soc. 1999, 121, 5899-5909 10.1021/ja990582o
12. Zampella, A.; Sepe, V.; Luciano, P.; Bellotta, F.; Monti, M. C.; D'Auria, M. V.; Jepsen, T.; Petek, S.; Adeline, M.; Laprévote, O.; Aubertin, A.; Debitus, C.; Poupat, C.; Ahond, A. J. Org. Chem. 2008, 73, 5319-5327 10.1021/jo800583b
13. Makishima, M.; Okamoto, A. Y.; Repa, J. J.; Tu, H.; Learned, R. M.; Luk, A.; Hull, M. V.; Lustig, K. D.; Mangelsdorf, D. J.; Shan, B. Science 1999, 284, 1362-1365 10.1126/science.284.5418.1362
14. Parks, D. J.; Blanchard, S. G.; Bledsoe, R. K.; Chandra, G.; Consler, T. G.; Kliewer, S. A.; Stimmel, J. B.; Willson, T. M.; Zavacki, A. M.; Moore, D. D.; Lehmann, J. M. Science 1999, 284, 1365-1368 10.1126/science.284.5418.1365
15. Liu, Y.; Binz, J.; Numerick, M. J.; Dennis, S.; Luo, G.; Desai, B.; MacKenzie, K. I.; Mansfield, T. A.; Kliewer, S. A.; Goodwin, B.; Jones, S. A. J. Clin. Invest. 2003, 112, 1678-1687 10.1172/JCI18945
16. Fiorucci, S.; Antonelli, E.; Rizzo, G.; Renga, B.; Mencarelli, A.; Riccardi, L.; Orlandi, S.; Pellicciari, R.; Morelli, A. Gastroenterology 2004, 127, 1497-1512 10.1053/j.gastro.2004.08.001
17. Fiorucci, S.; Distrutti, E.; Ricci, P.; Giuliano, V.; Donini, A.; Baldelli, F. Expert Opin. Ther. Targets 2014, 18, 1449-1459
18. Siemion, I. Z.; Wieland, T.; Pook, K. Angew. Chem., Int. Ed. Engl. 1975, 14, 702-703 10.1002/anie.197507021
19. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596 10.1007/BF02908688
20. Fuji, K.; Ikai, Y.; Oka, H.; Suzuki, M.; Harada, K. Anal. Chem. 1997, 69, 5146-5151 10.1021/ac970289b
21. Edman, P. Acta Chem. Scand. 1950, 4, 283-293 10.3891/acta.chem.scand.04-0283
22. Simat, T. J.; Steinhart, H. J. Agric. Food Chem. 1998, 46, 490-498 10.1021/jf970818c
23. Labroo, R. B.; Cohen, L. A. J. Org. Chem. 1990, 55, 4901-4904 10.1021/jo00303a027
24. Takayama, H.; Shimizu, T.; Sada, H.; Harada, Y.; Kitajima, M.; Aimi, N. Tetrahedron 1999, 55, 6841-6846 10.1016/S0040-4020(99)00337-3
25. Robinson, S. J.; Morinaka, B. I.; Amagata, T.; Tenney, K.; Bray, W. M.; Gassner, N. C.; Lokey, R. S.; Crews, P. J. Med. Chem. 2010, 53, 1651-1661 10.1021/jm9013554
26. Urizar, N. L.; Liverman, A. B.; Dodds, D. T.; Silva, F. V.; Ordentlich, P.; Yan, Y.; Gonzalez, F. J.; Heyman, R. A.; Mangelsdorf, D. J.; Moore, D. D. Science 2002, 296, 1703-1706 10.1126/science.1072891
27. Burris, T. P.; Montrose, C.; Houck, K. A.; Osborne, H. E.; Bocchinfuso, W. P.; Yaden, B. C.; Cheng, C. C.; Zink, R. W.; Barr, R. J.; Hepler, C. D.; Krishnan, V.; Bullock, H. A.; Burris, L. L.; Galvin, R. J.; Bramlett, K.; Stayrook, K. R. Mol. Pharmacol. 2005, 67, 948-954 10.1124/mol.104.007054
28. Choi, H.; Pereira, A. R.; Gerwick, W. H. In Handbook of Marine Natural Products; Fattorusso, E.; Gerwick, W. H.; Taglialatela-Scafati, O., Eds.; Springer: New York, 2012; Vol. 1, Chapter 2, pp 55-152.
29. Fujino, T.; Sato, Y.; Une, M.; Kanayasu-Toyoda, T.; Yamaguchi, T.; Shudo, K.; Inoue, K.; Nishimaki-Mogami, T. J. Steroid Biochem. Mol. Biol. 2003, 87, 247-252 10.1016/j.jsbmb.2003.09.008
30. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63 10.1016/0022-1759(83)90303-4