Sansalvamide: A new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2913-2916

  Belofsky, Gilbert N ^a,b   Jensen, Paul R ^a   Fenical, William ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF TULSA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; DEPSIPEPTIDE; SANSALVAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG SYNTHESIS; FUNGUS; FUSARIUM; STRUCTURE ANALYSIS;

FUNGI; FUSARIUM; HALODULE WRIGHTII; HALOPHILA;

EID: 0033538036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00393-7     Document Type: Article

References (23)

1. Current Address: Department of Chemistry, University of Tulsa, 600 South College Ave., Tulsa, OK 74104.
2. a) Fenical, W. Chem. Rev. 1993, 93, 1673.
3. b) Davidson, B. S. Curr. Opin. Biotech. 1995, 6, 284.
4. (c) Liberra, K.; Lindequist, U. Pharmazie 1995, 50, 583.
5. c) Okami, Y. J. Mar. Biotechnol. 1993, 1, 59.
6. d) Biabani, M. A. F.; Laatsch, H. J. Prakt. Chem. 1998, 340, 589.
7. a) Wang, G Y.S.; Abrell, L. M.; Avelar, A.; Borgeson, B.M.; Crews, P. Tetrahedron 1998, 54, 7335.
8. b) Wang, G.; Borgeson, B. M.; Crews, P. Tetrahedron Lett. 1997, 38, 8449.
9. c) Numata, A,; Amagata, T.; Minoura, K.; Ito, T. Tetrahedron Lett. 1997, 38, 5675.
10. d) Numata, A.; Takahashi, C.; Matsushita, T.; Miyamoto, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Inoue, M.; Ohishi, H.; Shingu, T. Tetrahedron Lett. 1992, 33:1621.
11. a) Belofsky, G. N.; Jensen, P. R.; Renner, M. K.; Fenical, W. Tetrahedron, 1998, 54, 1715.
12. b) Takahashi, C.; Minoura, K.; Yamada, T.; Numata, A.; Kushida, K.; Shingu, T.; Hagishita, S.; Nakai, H.; Sato, T.; Harada, H. Tetrahedron, 1995, 51, 3483.
13. c) Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355.
14. FAME (Fatty Acid Methyl Ester) analysis (Microbial ID Inc., Newark, DE), similarity index 0.845. The identification was also confirmed by Professor E. B. Gareth Jones.
15. The fungus was cultured for 20 days (static) at 28 °C in YPG+C medium: yeast extract (0.5%), peptone (0.5%), glucose (1.0%), crab meal (0.2%), and seawater (100%).
16. 6, 587.3808 (Δ -6.0 mDa).
17. 7, 604.4].
18. Alltech Kit cat# 18093. See: Ibrahim, K. E.; Couch, M. W.; William, C. M.; Budd, M.; Yost, R. A.; Midgley, J. M. Anal. Chem. 1984, 56, 1695.
19. 3 were generally poorly resolved. Clear signals for N-H and α-protons were seen only at high concentrations (e.g. >50 mg/mL) suggesting increased order in solution due to inter- or intramolecular hydrogen bonding. All observed NOESY correlations agreed with the proposed sequence for 1.
20. Hamano, K.; Kinoshita, M.; Tanzawa, K.; Yoda, K.; Ohki, Y.; Nakamura, T.; Kinoshita, T. J. Antibiotics 1992, 45, 906.
21. D = -29.0° (c 0.002 g/mL, 1N NaOH, for both samples).
22. Boyd, M. R.; Paull, K. D. Drug Development Res. 1995, 34, 91.
23. Data for known anticancer agents are available on the World Wide Web: http://ctep.info.nih.gov/ and http://epnws1.ncifcrf.gov/.