Lamellarin D Explained

Lamellarins are a group of pyrrole alkaloids first isolated in 1985 from the marine mollusk Lamellaria in the waters of Palau. Over 70 lamellarins and similar compounds were subsequently isolated. Other similar compounds include ningalins, lukianols, polycitones, and storniamides.^[1]

Biological activity

These compounds have shown a wide variety of biological activity, 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.^[2]

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.^[3]

Synthesis

The lamellarins have been synthesized by a number of groups, including Isibashi, Steglich, Ruchirawat, Banwell, Alvarez, Gupton, Boger, and Handy.^[4]

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.^[5]

See also

• Pyrrole

References

1. Bailly . Christian . Newman . David J. . Download Limit Exceeded . PDF . Marine Drugs . 2015 . 13 . 3 . . 1105–1123 . en . 2015-02-19 . 10.3390/md13031105 . 25706633 . 4377975 . 1660-3397. free .
2. Reddy . Venkata M. . Rao . Rama M. . Rhodes . Denise . Hansen . Mark S. . Rubins . Kathleen . Bushman . Frederic D. . Venkateswarlu . Yenamandra . Faulkner . John D. . November 24, 1999 . 1999 . Lamellarin r 20-Sulfate, an Inhibitor of HIV-1 Integrase Active against HIV Virus in Cell Culture . live . . . 42 . 11 . 1901–1907 . 10.1021/jm9806650 . 10354398 . 0022-2623 . 1520-4804 . https://web.archive.org/web/20220811222101/https://media.iupac.org/symposia/proceedings/phuket97/ruchirawat.pdf . 2022-08-11 . 2022-08-11.
3. Bailly . Christian . 2004-07-04 . Lamellarins, from A to Z: a family of anticancer marine pyrrole alkaloids . live . Current Medicinal Chemistry. Anti-Cancer Agents . 4 . 4 . 363–378 . 10.2174/1568011043352939 . 1568-0118 . 15281908 . https://web.archive.org/web/20220811214702/https://pubmed.ncbi.nlm.nih.gov/15281908/ . 2022-08-11.
4. Ruchirawat . Somsak . Mutarapat . Thumnoon . Sahakitpichan . Poolsak . Bhavakul . Vanida . Mahidol . Chulabhorn . 1997-11-13 . The Syntheses of Lamellarins and Isoindolobenzazepine Alkaloids . live . . . 70 . 11 . 6 . https://web.archive.org/web/20220811222101/https://media.iupac.org/symposia/proceedings/phuket97/ruchirawat.pdf . 2022-08-11 . 2022-08-11 . IUPAC.
5. Padwa . Albert . 2017-11-29 . Use of nitrogen and oxygen dipole ylides for alkaloid synthesis . PDF . . en . 2018-02-06 . 5 . 1 . 23–49 . 10.24820/ark.5550190.p010.416 . 2022-08-11 . ARKAT USA. free .