Iriomoteolide-1a, a potent cytotoxic 20-membered macrolide from a benthic dinoflagellate Amphidinium species

Journal of Organic Chemistry

Volumn 72, Issue 12, 2007, Pages 4469-4474

  Tsuda, Masashi ^a,b   Oguchi, Keiko ^b   Iwamoto, Rie ^b   Okamoto, Yumiko ^b   Kobayashi, Jun'ichi ^b   Fukushi, Eri ^b   Kawabata, Jun ^b   Ozawa, Tomoko ^c   Masuda, Atsunori ^c   Kitaya, Yoshiaki ^d   Omasa, Kenji ^e  

^a KOCHI UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c Yanmar Co Ltd   (Japan)

^d Osaka Prefecture University   (Japan)

^e UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IRIOMOTEOLIDE-1A; MACROLIDE; MOSHER'S METHOD;

CHEMICAL MODIFICATION; CONFORMATIONS; CYTOTOXICITY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

ANTIBIOTICS;

DOXORUBICIN; IRIOMOTEOLIDE 1A; MACROLIDE; UNCLASSIFIED DRUG;

AMPHIDINIUM; ARTICLE; B LYMPHOCYTE; CHEMICAL STRUCTURE; CYTOTOXICITY; DINOFLAGELLATE; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TUMOR CELL;

ANIMALS; DINOFLAGELLIDA; MACROLIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 34250207333     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070414b     Document Type: Article

References (53)

1. Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Princep, M. R. Nat. Prod. Rep. 2006, 23, 26-78 and its previous reviews.
2. Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77-93 and references cited therein.
3. (a) Ishibashi, M.; Ohizumi, Y.; Hamashima, M.; Nakamura, H. Hirata, Y.; Sasaki, T.; Kobayashi, J. J. Chem. Soc, Chem. Commun. 1987, 1127-1129.
4. (b) Kobayashi, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Yamasu, T.; Hirata, Y.; Sasaki, T.; Ohta, T.; Nozoe, S. J. Nat. Prod. 1989 , 52, 1036-1041.
5. (c) Bauer, I.; Maranda, L.; Shimizu, Y.; Peterson, R. W.; Cornell, L.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 2657-2658.
6. (a) Kobayashi, J.; Shigemori, H.; Ishibashi, M.; Yamasu, T.; Hirota, H.; Sasaki, T. J. Org. Chem. 1991, 56, 5221-5224.
7. (b) Kobayashi, J.; Shimbo, K.; Sato, M.; Shiro, M.; Tsuda, M. Org. Lett. 2000, 2, 2805-2807.
8. (c) Kobayashi, J.; Shimbo, K.; Sato, M.; Tsuda, M. J. Org. Chem. 2002, 67, 6585-6592.
9. Ishibashi, M.; Yamaguchi, N.; Sasaki, T.; Kobayashi, J. J. Chem. Soc, Chem. Commun. 1994, 1445-1446.
10. Bauer, I.; Maranda, Y.; Young, K. A.; Shimizu, Y.; Fairchild, C.; Cornell, L.; MacBeth, J.; Huang, S. J. Org. Chem. 1995, 60, 1084-1086.
11. Total synthesis of amphidinolides: (a) Amphidiolide, A: Trost, B. M.; Harrington, P. E.; Chrisholm, J. D.; Wrobleski, S. T. J. Am. Chem. Soc 2005, 127, 13598-13610.
12. (b) Trost, B. M.; Wrobleski, S. T.; Chrisholm, J. D.; Harrington, P. E.; Jung, M. J. Am. Chem. Soc 2005, 127, 13589-13597.
13. (c) Trost, B. M.; Harrington, P. E. J. Am. Chem. Soc. 2004, 126, 5028-5029.
14. (d) Maleczeka, R. E., Jr.; Terrell, L. R.; Gang, F.; Ward, J. S., III. Org. Lett. 2002, 4, 2841-2844.
15. (e) Lam, H. W.; Pattenden, G. Angew. Chem., Int. Ed. 2002, 41, 508-811.
16. (f) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420-12421.
17. (g) Amphidinolide E: Va, P.; Roush, W. R. J. Am. Chem. Soc. 2006, 128, 15960-15961.
18. (h) Amphidinolide J.; Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198-11199.
19. (e) Amphidinolide K: Williams, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765-766.
20. (f) Amphidinolide P: Williams, D. R.; Myers, B. J. Org. Lett. 2000, 2, 945-948.
21. (g) Amphidinolide T1: Ghosh, A. K.; Liu, C. J. Am. Chem. Soc. 2003, 125, 2374-2375.
22. (h) Amphidinolide T4: Fürstner, A.; Aïssa, C.; Riveiros, R.; Ragot, J. Angew. Chem., Int. Ed. 2002, 41, 4763-4766.
23. (a) Rein, K. S.; Borrone, J. Comp. Biochem. Physiol., Part B: Biochem. Mol. Biol. 1999, 124, 117-131.
24. (b) Snyder, R. V.; Gibbs, P. D.; Palacio, A.; Abiy, L.; Dickey, R.; Lopez, J. V.; Rein, K. S. Mar. Biotechnol. 2003, 5, 1-12.
25. (c) Kubota, T.; Iinuma, Y.; Kobayashi, J. Biol. Pharm. Bull. 2006, 29, 1314-1318.
26. Iwamoto, R.; Kobayashi, J.; Horiguchi, T.; Tsuda, M. Phycologia 2005, 44, 104.
27. (a) Fiehn, O. Plant Mol. Biol. 2002, 48, 155-171.
28. (b) Reo, N. V. Drug Chem. Toxicol. 2002, 25, 375-382.
29. (c) Kikuchi, J.; Shinozaki, K.; Hirayama, T. Plant Cell Physiol. 2004, 45, 1099-1104.
30. (a) Davis, D. G. J. Magn. Reson. 1991, 91, 665.
31. (b) Fukushi, E.; Tanabe, S.; Watanabe, M. Kawabata, J. Magn. Reson. Chem.1998, 36, 741-746.
32. (a) Tsuda, M.; Nozawa, K.; Shimbo, K.; Ishiyama, H.; Fukushi, E.; Kawabata, J.; Kobayashi, J. Tetrahedron Lett. 2003, 44, 1395-1399.
33. (b) Nozawa, K.; Tsuda, M.; Ishiyama, H.; Sasaki, T.; Tsuruo, T.; Kobayashi, J. Bioorg. Med. Chem. 2006, 14, 1063-1067.
34. (a) Otting, G.; Wüthrich, K. Quart. Rev. Biophys. 1990, 23, 39-96.
35. (b) Wollborn, U.; Leibfritz, D. J. Magn. Reson. 1992, 98, 142-146
36. . (c) Kurz, M.; Schmieder, P.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1329-1331.
37. Williamson, R. T.; Marquez, B. L.; Gerwick, W. H.; Martin, G. E.; Krishnamurthy, V. V. Magn. Reson. Chem. 2001, 39, 127-132.
38. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866-876.
39. CH values were 6 to ∼8 and 1 to ∼3 Hz, respectively. For review, see: Hansen, P. E. Prog. NMR Spectrosc. 1981, 14, 175-296.
40. Although the modulus of J(C-19/H-18) was obtained from the J-IMPEACH MBC spectrum, the sign was not determined.
41. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4095.
42. 1 branches were found to be derived from C-2 of acetate. Vicinally located C1 branches were also derived from C-2 of acetate: (a) Kobayashi, J.; Takahashi, M.; Ishibashi, M. J. Chem. Soc., Chem. Commun. 1995, 1639-1640.
43. (b) Sato, M.; Shimbo, K.; Tsuda, M.; Kobayashi, J. Tetrahedron Lett. 2000, 41, 503-506.
44. (c) Kubota, T.; Tsuda, M.; Kobayashi, J. Tetrahedron 2001, 57, 5975-5977.
45. (d) Tsuda, M.; Kubota, T.; Sakuma, Y.; Kobayashi, J. Chem. Pharm. Bull. 2001, 49, 1366-1367.
46. Kobayashi, J.; Shimbo, K.; Sato, M.; Tsuda, M. J. Org. Chem. 2002, 67, 6585-6592.
47. West, L. M.; Northcote, P. T.; Battershill, C. N. J. Org. Chem. 2000, 65, 445-449.
48. (a) Hood, K. A.; West, L. M.; Rouwe, B.; Northcote, P. T.; Berridge, M. V.; Qakefield, S. J.; Miller, J. H. Cancer Res. 2002, 62, 3356-3360.
49. (b) Gaitanos, T. N.; Buey, R. M.; Diaz, J. F.; Northcote, P. T.; Teesdale-Spittle, P.; Andreu, J. M.; Miller, J. H. Cancer Res. 2004, 64, 5063-5067.
50. (c) Miller, J. H.; Rouwe, B.; Gaitanos, T. N.; Hood, K. A.; Crume, K. P.; Backstrom, B. T.; La Flamme, A. C.; Berridge, M. V.; Northcote, P. T. Apoptosis 2004, 9, 785-796.
51. (a) Pineda, O.; Farras, J.; Maccari, L.; Manetti, F.; Botta, M.; Vilarrasa, J. Bioorg. Med. Chem. Lett. 2004, 14, 4825-4829.
52. (b) Hamel, E.; Day, B. W.; Miller, J. H.; Jung, M. K.; Northcote, P. T.; Ghosh, A. K.; Curran, D. P.; Cushman, M.; Nicolaou, K. C.; Paterson, I.; Sorensen, E. J. Mol. Pharmcol. 2006, 70, 1555-1564.
53. Shaka, A. J.; Pines, A. J. Magn. Reson. 1987, 71, 495-503.