Novel ring B abeo-sterols as growth inhibitors of Mycobacterium tuberculosis isolated from a Caribbean Sea sponge, Svenzea zeai

Tetrahedron Letters

Volumn 48, Issue 50, 2007, Pages 8851-8854

  Wei, Xiaomei ^a   Rodríguez, Abimael D ^a   Wang, Yuehong ^b   Franzblau, Scott G ^b  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Abeo sterols; Caribbean sponge; Mycobacterium tuberculosis; Svenzea zeai; Tuberculosis

Indexed keywords

ABEOSTEROL DERIVATIVE; PARGUESTEROL A; PARGUESTEROL B; STEROL DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; GROWTH INHIBITION; INHIBITION KINETICS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SPONGE (PORIFERA); STEREOCHEMISTRY; STRUCTURE ANALYSIS; SVENZEA ZEAI;

MYCOBACTERIUM TUBERCULOSIS; SVENZEA;

EID: 36148995894     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.070     Document Type: Article

References (22)

1. Sarma N.S., Krishna M.S.R., and Rao S.R. Mar. Drugs 3 (2005) 84-111
2. Kerr R.G., and Baker B.J. Nat. Prod. Rep. 8 (1991) 465-498
3. Miyamoto T., Kodama K., Aramaki Y., Higuchi R., and Van Soest R.W.M. Tetrahedron Lett. 42 (2001) 6349-6351
4. Blunt J.W., Copp B.R., Hu W.-P., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 24 (2007) 31-86 and previous articles in this series
5. The sponge Svenzea zeai was formerly known as Calyx podatypa, see:. Alvarez B., Van Soest R.W.M., and Rützler K. Contrib. Zool. 71 (2002) 171-176
6. For prior chemical work with this sponge, see:. Doss G.A., and Djerassi C. J. Am. Chem. Soc. 110 (1988) 8124-8128
7. Rodríguez A.D., Cóbar O.M., and Padilla O.L. J. Nat. Prod. 60 (1997) 915-917
8. Rodríguez A.D., Cóbar O.M., and Padilla O.L. J. Nat. Prod. 60 (1997) 1331-1333
9. Carballeira N.M., Pagán M., and Rodríguez A.D. J. Nat. Prod. 61 (1998) 1049-1052
10. To date, the only other reported source of 6-5-6-5 fused rings sterols is the Taiwanese plant Taiwania cryptomerioides, see:. Lin W.-H., Fang J.-M., and Cheng Y.-S. Phytochemistry 48 (1998) 1392-1397
11. Collins L., and Franzblau S.G. Antimicrob. Agents Chemother. 41 (1997) 1004-1009
12. Besides the new abeo-sterols 1 and 2, our specimen contained a complex mixture of sterols which, after careful purification and spectroscopic analysis, were identified as the known sterols 3-8 (see Supplementary data).
13. 2 412.3341, found 412.3348.
14. Lambert J.B., Shurvell H.F., Lightner D.A., and Cooks R.G. Organic Structural Spectroscopy (1998), Prentice Hall, Upper Saddle River, NJ pp 304-344
15. 3 430.3447, found 430.3443.
16. Drahl C. Chem. Eng. News September 24 (2007) 39-43
17. Cantrell C.L., Franzblau S.G., and Fisher N.H. Planta Med. 67 (2001) 685-694
18. Rugutt J.K., and Rugutt K.J. Nat. Prod. Lett. 16 (2002) 107-113
19. Davidson S.M.K., Liu Y., and Regen S.L. J. Am. Chem. Soc. 115 (1993) 10104-10110
20. 50 value of the control drug used (rifampin) in the cytotoxicity assay was 89.3 μg/mL.
21. Copp B.R., and Pearce A.N. Nat. Prod. Rep. 24 (2007) 278-297
22. 37Rv at a concentration of 128 μg/mL. Since 3 is the most plausible biosynthetic precursor to parguesterols A and B, this finding suggests that in active steroids, maximum anti-mycobacterial activity could be attained upon contracting the cyclohexane B-ring, most likely as a result of increasing both the hydrophilic impact and rigidity of the steroidal backbone.