Symplostatin 1: A dolastatin 10 analogue from the marine cyanobacterium Symploca hydnoides

Journal of Natural Products

Volumn 61, Issue 9, 1998, Pages 1075-1077

  Harrigan, George G ^a   Luesch, Hendrik ^a   Yoshida, Wesley Y ^a   Moore, Richard E ^a   Nagle, Dale G ^b,c   Paul, Valerie J ^b   Mooberry, Susan L ^d   Corbett, Thomas H ^e   Valeriote, Fred A ^f  

^a UNIVERSITY OF HAWAII   (United States)

^b UNIVERSITY OF GUAM MARINE LABORATORY   (Guam)

^c UNIVERSITY OF MISSISSIPPI   (United States)

^d UNIVERSITY OF HAWAII CANCER CENTER   (United States)

^e WAYNE STATE UNIVERSITY   (United States)

^f WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; DOLASTATIN 10; SYMPLOSTATIN 1; UNCLASSIFIED DRUG;

ARTICLE; CYANOBACTERIUM; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN;

ANTINEOPLASTIC AGENTS; CYANOBACTERIA; DEPSIPEPTIDES; GUAM; HUMANS; KB CELLS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOPEPTIDES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET;

AURICULARIA; DOLABELLA AURICULARIA; SYMPLOCA HYDNOIDES;

EID: 0031668094     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np980321c     Document Type: Article

References (19)

1. (a) Pettit, G. R.; Kamano, Y.; Herald, C. L.; Fujii, Y.; Kizu, H.; Boyd, M. R.; Boettner, F. E.; Doubek, D. L.; Schmidt, J. M.; Chapuis, J.-C.; Michel, C. Tetrahedron 1993, 49, 9151-9170.
2. (b) Pettit, G. R. J. Nat. Prod. 1996, 59, 812-821.
3. (c) Pettit, G. R. In Progress In the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, C., Eds.; Springer-Verlag: Vienna, New York 1997; Vol. 70, pp 1-79.
4. Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems, R. J. J. Am. Chem. Soc. 1987, 709, 6883-6835.
5. (a) Pettit, G. R.; Herald, C. L.; Kamano, Y. US Patent 4,816,444, Mar 28, 1989, 26 pages.
6. (b) Pettit, G. R.; Srirangam, J. K.; Kantoci, D. US Patent 5,663,149, Sept 2, 1997, 50 pages.
7. (c) Sakakibara, K.; Gondo, M.; Miyazaki, K. US Patent 5,654,399, Aug 5, 1997, 48 pages.
8. (a) Carefoot, T. H. Oceanogr. Mar. Biol. Annu. Rev. 1987, 25, 167-284.
9. (b) Faulkner, D. J. In Ecological Roles of Marine Secondary Metabolites; Paul, V. J., Ed; Cornell University Press: Ithaca, NY, 1992; pp 119-163.
10. Harrigan, G. G.; Yoshida, W. Y.; Moore, R. E.; Nagle, D. G.; Park, P. U.; Biggs, J.; Paul, V. J., Mooberry, S. L.; Corbett, T. H.; Valeriote, F. A. J. Nat. Prod. 1998, 61, in press.
11. 2 followed by MeOH. The MeOH fraction was chromatographed on Bond-Elut Si gel, eluting with EtOAc followed by EtOAc-MeOH mixtures containing progressively increasing amounts of MeOH. The EtOAc fraction afforded 3.2 mg of symplostatin 1 (1).
12. 6S, 799.5156).
13. A distinctive feature of 1 and 2 is the presence of the unique dolaphenine unit at one of the terminuses. This novel unit is also found in the cyanobacterial metabolite, barbamide, from a Caribbean variety of Lyngbya majuscula (Orjala, J.; Gerwick, W. H. J. Nat. Prod. 1996, 59, 427-430).
14. Corbett, T. H.; Valeriote, F. A.; Polin, L.; Panchapor, C.; Pugh, S.; White, K., Lowichik, N.; Knight, J.; Bissery, M.-C.; Wozniak, A.; LoRusso, P.; Biernat, L.; Polin, D.; Knight, L.; Biggar, S.; Looney, D.; Demchik, L.; Jones, J.; Jones, L.; Blair, S.; Palmer, K.; Essenmacher, S.; Lisow, L.; Mattes, K. C.; Cavanaugh, P. F.; Rake, J. B.; Baker, L. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development; Valeriote, F. A., Corbett, T. H., Baker, L. H., Eds.; Kluwer Academic Publishers: Norwell, MA, 1993; pp 35-87.
15. Corbett, T.; Vaeriote, F.; LoRusso, P.; Polin, L.; Panchapor, C.; Pugh, S.; White, K.; Knight, J.; Demchik L.; Jones, J.; Jones, L.; Lisow, L. In Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials, and Approval; Teicher, B., Ed.; Humana Press Inc.: Totowa, NJ, 1997; pp 75-99.
16. 2.
17. HMBC data (Table 1) support the attachments of dolaphenine (Doe) to dolaproine (Dap) and dolaisoleuine (Dil) to Val in 2. Although HMBC cross-peak signals are missing between Dap and Dil nuclei and between Val and N,N-dimethylisoleucine (or N,N-dimethylalloisoleucine) nuclei, the sequence of the five units as shown in structure 2 is the only one that can be concluded.
18. The striking similarities of the NMR spectra and biological activities for 1 and 2 strongly suggest that the two compounds have the same relative and absolute stereochemistries.
19. Smith, C. D.; Mooberry, S. L.; Zhang, X.; Helt, A. Cancer Lett. 1994, 79, 213-119.