PITHECOLOBINE, THE ALKALOID OF PITHECOLOBIUMSAMAN BENTH. I

Abstract

Pithecolobine, C22H46N4O2, has a lactam group, one primary and two secondary amino groups, and a hydroxyl group. Lithium aluminum hydride converts it into a monocyclic saturated compound, desoxypithecolobine, C22H48N4. Hofmann degradation of this compound gives tetramethylputrescine, trimethyl amine, a doubly unsaturated base C16H31N with a terminal methylene group, and a base C16H34N2. Heating with selenium yields a hydrocarbon, C12;H24–26, with a sequence of six or more CH2 groups. A crystalline oxygen-free compound with two nitrogens (m.p.94 °C.) is also obtained, the ultraviolet spectrum of which is almost identical with aminopyridine.

Biological Activity of Novel Macrocyclic Alkaloids (Budmunchiamines) from Albizia amara Detected on the Basis of Interaction with DNA

“…These materials, assigned the trivial names budmunchiamines A-C, belong to the pithecolobine class of alkaloids, previously isolated from Pithecolobium saman (syn. Samanta saman) (8)(9)(10). [The name budmunchiamine (11) commemorates the collaboration between Budapest, Munich, and Chicago that led to the discovery of these alkaloids.]…”

“…Budmunchiamines belong to the class of pithecolobine alkaloids reported by Wiesner and co-workers (8)(9)(10). In determining the structures of budmunchiamines A-C (Figure 1), we have recently delineated all of the 'Hand 13C-nmr spectral parameters associated with the compounds (11).…”

Structure of pithecolobine. II

“…Our first full paper on the alkaloid of Pitlzecolobium saman Benth' was published sixteen years ago (1). Since that time we have solved the structure in principle (2,3) and corroborated the solution by synthetic work (4).…”

Evaluation of Antimicrobial and Antioxidant Properties of Pithecolobine Isolated fromAlbizia saman

“…A wide range biological activities of A. saman and pithecolobine have been reported previously (23,26,27). Pithecolobine isolated from S. saman demonstrated antimicrobial activity against B. subtilis and plant pathogenic molds (2).…”

“…The leaves are used in folk remedy for stomach cancer, common cold, diarrhoea, headache, intestinal ailments, sore throat, stomach ache, and wounds (18). Some biological activities of this plant have been reported in aqueous and solvent extracts (3-5, 10, 17, 19, 24), and phytochemical analysis of this species revealed pithecolobine as the main alkaloid (26,27). Some biological activities have been reported for pithecolobine (2).…”