Revised structure of the alkaloid drymaritin.
In 2004, a new anti-HIV alkaloid named drymaritin was isolated from Drymaria diandra. The authors identified the alkaloid as 5-methoxycanthin-4-one on the basis of spectroscopic data. Here we describe a synthetic approach that unambiguously gave 5-methoxycanthin-4-one, but the synthetic product showed spectroscopic data significantly different from those of the Drymaria alkaloid. Extensive re-evaluation of the spectroscopic data published for this and related alkaloids has led to the conclusion that drymaritin does not have a canthin-4-one backbone, but is identical to the known alkaloid cordatanine (4-methoxycanthin-6-one).
Wetzel
Isolde
I
Center for Drug Research, Department of Pharmacy, Ludwig-Maximilians University of Munich, Butenandtstrasse 5-13, 81377 Munich, Germany.
Allmendinger
Lars
L
Bracher
Franz
F
D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000737:chemistry* / Q000494:pharmacology; D002243:Carbolines / Q000737:chemistry* / Q000494:pharmacology; D029748:Caryophyllaceae / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D000470:Alkaloids; D019380:Anti-HIV Agents; D002243:Carbolines; C489105:drymaritin