Hamigerols A and B, unprecedented polysulfate sterol dimers from the Mediterranean sponge Hamigera hamigera

Journal of Natural Products

Volumn 70, Issue 7, 2007, Pages 1195-1199

  Cheng, Jie Fei ^a   Lee, Jong Soo ^b   Sun, Furong ^b   Jares Erijman, Elizabeth A ^b   Cross, Sue ^b   Rinehart, Kenneth L ^b  

^a Tanabe Research Laboratories   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

HAMIGEROL A; HAMIGEROL B; NATURAL PRODUCT; STEROL DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HAMIGERA HAMIGERA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOCHEMISTRY;

ANIMALS; MEDITERRANEAN SEA; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; STEROLS;

HAMIGERA;

EID: 34548037436     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np070027x     Document Type: Article

References (27)

1. (a) D'Auria, M. V.; Minale, L.; Riccio, R. Chem. Rev. 1993, 93, 1839-1895.
2. (b) Ken, R. G.; Baker, B. J. Nat. Prod. Rep. 1991, 8, 465-497.
3. (a) Sun, H. H.; Cross, S. S.; Gunasekera, M.; Koehn, F. E. Tetahedron, 1991, 47, 1185-1190.
4. (b) Koehn, F. E.; Gunasekera, M.; Cross, S. S. J. Org. Chem. 1991, 56, 1322-1325.
5. (c) McKee, T. C.; Cardellina, J. H., II; Tischler, M.; Snader, K. M.; Boyd, M. R. Tetrahedron Lett. 1993, 34, 389-392.
6. (d) McKee, T. C.; Cardellina, J. H.; Riccio, R.; D'Auria, M. V.; Iorizzi, M.; Minale, L.; Moran, R. A.; Gulakowski, R. J.; McMahon, J. B.; Buckheit, T. W., Jr.; Snader, K. M.; Boyd, M. R. J. Med. Chem. 1994, 37, 793-797.
7. (e) Bifulco, G.; Gruno, I.; Minale, L.; Riccio, R. J. Nat. Prod. 1994, 57, 164-167.
8. (a) Fusetani, N.; Matsunaga, S.; Konosu, S. Tetrahedron Lett. 1981, 22, 1985-1988.
9. (b) Kanazawa, S.; Fusetani, N.; Matsunaga, S. Tetrahedron 1992, 48, 5467-5472.
10. (c) Fusetani, N.; Takahashi, M.; Matsunaga, S. Tetrahedron 1994, 50, 7765-7770.
11. The sponge was identified by Dr. M. Vribe. "Hamigera" has also been used as the genus name of a fungus (e.g., Hamigera avellanea).
12. Pure hamigerols proved to be inactive against HIV- 1. The active fractions containing similar steroid sulfates will be reported elsewhere.
13. Tsuda, M.; Schroepfer, G. J., Jr. J. Org. Chem. 1979, 44, 1290-1293.
14. O-Sulfonation causes usually a ca. 8 ppm chemical shift change for monosulfated steroids; see for example: D'Auria, M. V.; Riccio, R.; Minale, L.; BaBarne, S.; Pusset, J. I. J. Org. Chem. 1987, 52, 3947-3952. For glycol-type disulfates the shift values vary with stereochemistry and are 4-6 ppm. Calculated from reported values, the corresponding diols or similar compounds were used as standards.
15. 3CO methyl appeared at δ 2.10 as a singlet.
16. 3 quaternary carbon left for the side chain. For details, see text.
17. There is no report on this ring system in the literature.
18. (a) Vanderah, D. J.; Djerassi, C. J. Org. Chem. 1978, 43, 1442-1448.
19. (b) Koreeda, M.; Koizumi, Z. Tetrahedron Lett. 1978, 19, 1641-1644.
20. (a) Pettit, G. R.; Inoue, M.; Kamano, Y.; Herald, D. L.; Arm, C.; Dufresne, C.; Christie, N. D.; Schmidt, J. M.; Doubek, D. L.; Krupa, T. S. J. Am. Chem. Soc. 1988, 110, 2006-2007.
21. (b) Kobayashi, M.; Kawazoe, K.; Kator, T.; Kitagawa. I. Chem. Pharm. Bull. 1992, 40, 1773-1780.
22. (a) Kawahara, N.; Sekita, S.; Satake, M. Chem. Pharm. Bull. 1993, 41, 1318-1320.
23. (b) Gonzalez, A. G.; Mendoza, J. J.; Luis, J. G.; Ravelo, A. G.; Bazzocchi, I. L. Tetrahedron Lett. 1989, 30, 863-866.
24. (a) Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1994, 59, 6164-6166.
25. (b) Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1995, 60, 608-614.
26. See for example: Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 49, 9149-9152.
27. Witten, J. L.; Schaffer, M. H.; O'Shea, M.; Cook, J. C.; Hemling, M. E.; Rinehart, K. L., Jr. Biochem. Biophvs. Res. Commun. 1984, 124, 350-353.