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■ DNA-based Isolation and the Structure Elucidation of the Budmunchiamines, Novel Macrocyclic Alkaloids from Albizia amara

John M. Pezzuto,* Woongchon Mar, Long-Ze Lin, Geoffrey A. Cordell, Andras Neszmélyi, and Hildebert Wagner

*Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, 833 South Wood St., Chicago, IL 60612-7231, U.S.A.

Abstract

On the basis of DNA affinity, a novel isolate was obtained from an extract prepared from the seeds of Albizia amara. As determined by a series of spectroscopic techniques, the isolate was structurally defined as a mixture of three macrocyclic alkaloids of the pithecolobine type that differed only in the length of the aliphatic side chain. The ¹H - and ¹³C-nmr spectral parameters were unambiguously assigned to these alkaloids, which were given the trivial names budmunchiamine A, B or C. With the exception of former studies performed with Pithecolobium saman, this is the only other report of pithecolobine alkaloids being found in nature.