Agelasines
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Isolated from the marine Sponge Agelas sp. |
Structure of the
known Agelasines A Ð F as well as Ageline B |
Bioactivities |
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Antimicrobial activity Cytotoxic effects Contractive responses of smooth muscles Inhibition of Na,K-ATPase |
We have
synthesized the side chain of Agelasine E as well as the enantiomer (+)
Trixagol isolated from Bellardia trixago (L)
Synthesis of (+)-Trixagol, the
Enantiomer of the (-)-Agelasine E the Terpenoid Side Chain.
Bakkestuen, A. K.; Gundersen, L.-L. Tetrahedron 2003, 59, 115-121.
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Bellardia trixago (L)
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Sage |
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We have published
the first syntheses of Agelasine D and Agelasine E as well as several analogs.
The compounds
display broad spectra of antimicrobial activity, including activity against Mycobactreium
tuberculosis and patogenic protozoa.
¯
Synthesis of (+)-Agelasine D
from (+)-Manool.
Utenova, B. T.; Gundersen, L.-L. Tetrahedron Lett. 2004, 45, 4233-4235.
¯
Synthesis and
Antimycobacterial Activity of Agelasine E and Analogs. Bakkestuen, A.
K.; Gundersen, L.-L.; Petersen, P.; Utenova, B. T.; Vik, A. Org. Biol. Chem. 2005, 3, 1025-1033.
¯
(+)-Agelasine D: Improved
Synthesis and Evaluation of Antibacterial and Cytotoxic Activities.
Vik, A.; Hedner, E.; Charnock, C.; Samuelsen, ¯.; Larsson,
R.; Gundersen, L.-L.; Bohlin. L. J. Nat.
Prod. In press.
Asmarines
Asmarines are isolated from marine sponges (Raspaila sp.).
The known structures are shown below. There are structural
resemblance between agelasines and asmarines.
No total syntheses of asmarines have been published so far and little is known about bioactivities.

Last
updated March 2006, Lise-Lotte Gundersen