Palauolol, a new anti-inflammatory sesterterpene from the sponge Fascaplysinopsis sp. from Palau

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 3951-3954

  Schmidt, Eric W ^a   Faulkner, D John ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FASCAPHYSIN; PALAUOLIDE; PALAUOLOL; PHOSPHOLIPASE A2; SESTERTERPENE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SPONGE;

APOIDEA; FASCAPLYSINOPSIS;

EID: 0029955176     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00718-6     Document Type: Article

References (14)

1. Sullivan, B.; Faulkner D.J. Tetrahedron Lett. 1982, 23, 907.
2. Roll, D.M.; Ireland C.M.; Lu, H.S.M.; Clardy, J. J. Org. Chem. 1988, 53, 3276.
3. Jimènez, C.; Quiñoà, E.; Adamczeski, M.; Hunter, L.M.; Crews, P. J. Org. Chem. 1991, 56, 3403.
4. Jimènez, C.; Quiñoà, E.; Crews, P. Tetrahedron Lett. 1991, 32, 1843.
5. + requires 420.2875.
6. de Silva, E.D.; Scheuer, P.J. Tetrahedron Lett. 1981, 22, 3147.
7. Dale, J.A.; Mosher H.S. J. Am. Chem. Soc. 1973, 95, 512. Ohtani, I.; Kusumi, T.; Kashman, Y., Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
8. Dale, J.A.; Mosher H.S. J. Am. Chem. Soc. 1973, 95, 512. Ohtani, I.; Kusumi, T.; Kashman, Y., Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
9. All new compounds gave satisfactory analytical and spectral data.
10. Luibrand, R.T.; Erdman, T.R.; Vollmer, JJ.; Scheuer, P.J.; Finer, J.; Clardy, J. Tetrahedron 1979, 35, 609.
11. Although Capon and MacLeod (J. Org. Chem. 1987, 52, 5060) caution against using weak Cotton effects associated with 4-keto derivatives derived from ilimaquinone, the stronger π-π* Cotton effect used to determine the absolute configuration of avarol (de Rosa, S.; Minale, L.; Riccio, R.; Sodano, G. J. Chem. Soc., Perkin Trans I 1976, 1408) appears reliable.
12. Although Capon and MacLeod (J. Org. Chem. 1987, 52, 5060) caution against using weak Cotton effects associated with 4-keto derivatives derived from ilimaquinone, the stronger π-π* Cotton effect used to determine the absolute configuration of avarol (de Rosa, S.; Minale, L.; Riccio, R.; Sodano, G. J. Chem. Soc., Perkin Trans I 1976, 1408) appears reliable.
13. Potts, B.C.M.; Faulkner, D.J.; Jacobs, R.S. J. Nat. Prod. 1992, 55, 1701.
14. We thank Mary Kay Harper for identifying the sponge and for performing the antimicrobial assays, Bryan Wylie and Dr. Robert S. Jacobs (UC Santa Barbara) for performing the antiinflammatory assays, and Barbara Doerner and Behrouz Forood (Torrey Pines Institute for Molecular Studies) for assistance with CD measurements. We thank the Republic of Palau and the State of Koror for collecting permits and Larry Sharron of the Coral Reef Research Foundation, Palau for invaluable assistance with collections. This research was supported by the California Sea Grant College Program (NOAA grant NA36RG0537, project R/MP-60).