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Lamellarins are a group of
pyrrole
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-meth ...
alkaloids first isolated in 1985 from the marine mollusk ''Lamellaria
''Lamellaria'' is a genus of small slug-like sea snails, marine gastropod molluscs in the family Velutinidae.Bouchet, P.; Gofas, S. (2012). Lamellaria. Accessed through: World Register of Marine Species at http://www.marinespecies.org/aphia.php?p ...
'' in the waters of Palau. Over 70 lamellarins and similar compounds were subsequently isolated. Other similar compounds include ningalins, lukianols, polycitones, and storniamides.
Biological activity
These compounds have shown a wide variety ofbiological activity
In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or ...
, including reversal of multidrug resistance, HIV-1 integrase inhibition, and antibiotic activity. Lamellarin D, for example, displays strong cytotoxic activity against tumor cell lines, and is a potent topoisomerase I inhibitor.
Structure
The lamellarins all contain a central pyrrole ring, substituted at the 3 and 4 positions by polyhydroxy- or methoxyphenyls. They are divided into two groups, depending on whether the pyrrole ring is fused or unfused.Synthesis
The lamellarins have been synthesized by a number of groups, including Isibashi, Steglich, Ruchirawat, Banwell, Alvarez, Gupton, Boger, and Handy.Steglich synthesis of lamellarin G trimethyl ether
The Steglich synthesis features an oxidative coupling of two benzylic carbons, as well as a Paal-Knorr pyrrole synthesis.Banwell synthesis of lamellarin K
The Banwell group’s synthesis of lamellarin K includes an intramolecular azomethine ylide cyclization.{{clear-leftGallery
See also
*Pyrrole
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-meth ...
References