Alertenone, a Dimer of Suberosenone from Alertigorgia sp.

Alertenone, a Dimer of Suberosenone from Alertigorgia sp.

Bioassay-guided fractionation of organic extracts of the gorgonian Alertigorgia sp. has yielded the previously known suberosenone (1), a cytotoxic tricyclic sesquiterpene of the quadrone class, and alertenone (2), a dimer of suberosenone. The structure of 2 was determined by spectral analysis; the 1...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) Vol. 62; no. 4; pp. 633 - 635
Main Authors: Bokesch, Heidi R, Blunt, John W, Westergaard, Chandra K, Cardellina, John H, Johnson, Tanya R, Michael, Jennifer A, McKee, Tawnya C, Hollingshead, Melinda G, Boyd, Michael R
Format: Journal Article
Language:English
Published: United States American Chemical Society 01-04-1999
Subjects:
alertenone
Alertigorgia
Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Cnidaria - chemistry
Drug Screening Assays, Antitumor
Humans
Magnetic Resonance Spectroscopy
Mass Spectrometry
Models, Molecular
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Sesquiterpenes - pharmacology
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
suberosenones
Tumor Cells, Cultured
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Summary:Bioassay-guided fractionation of organic extracts of the gorgonian Alertigorgia sp. has yielded the previously known suberosenone (1), a cytotoxic tricyclic sesquiterpene of the quadrone class, and alertenone (2), a dimer of suberosenone. The structure of 2 was determined by spectral analysis; the 1D TOCSY experiment was particularly useful in the structure elucidation. Comparison of the in vitro cytotoxicity of alertenone and suberosenone revealed that the dimeric alertenone was devoid of cytotoxicity below 35 μg/mL. In a hollow-fiber assay model of in vivo activity, suberosenone exhibited some growth inhibition of two of six tumor cell lines tested.
Bibliography:istex:46253B0A06BF2F85C810C65FD7B312A3298E5108
Dedicated to the memory of Michael A. Westergaard, who lost his battle with prostate cancer on September 6, 1997.
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ISSN:0163-3864
1520-6025
DOI:10.1021/np980464z