Alkaloids of Bellendena montana

Abstract

Fourteen alkaloids have been isolated from Bellendena montana, a monotypic proteaceous plant endemic in Tasmania. The structures of ten of these, bellendine (1), isobellendine (2), darlingine (3),5,11-dihydroisobellendine (5), 2,3-dihydrobellendine (6), 2,3-epidihydrobellendine (7), 2,3-dihydrodarlingine(8), 3α-acetoxy-6β-isobutoxytropane (9), 6β-acetoxy-3α-isobutoxytropane (10) and 3α-acetoxy-6β-hydroxytropane (11), have been established.

Natural Products Isolated from Endemic Tasmanian Vascular Plants

“…[41] A separate phytochemical investigation indicated that bellendine (62) was the major alkaloid in B. montana flowers, and its isomer isobellendine (63) represented the major alkaloid of the 'other parts of the plant' examined. [42] An extraction of the upper leaves, flowers, and flowering stems of B. montana provided related alkaloids 62 and 63, darlingine (64), and the pyronotropane alkaloids 5,11-dihydroisobellendine (65), 2,3-dihydrobellendine, 2,3-epidihydrobellendine, 2,3-dihydrodarlingine, (AE)-3a-acetoxy-6b-isobutoxytropane (66), (AE)-6b-acetoxy-3a-isobutoxytropane, and 3a-acetoxy-6b-hydroxytropane. [42] Each of these isolated alkaloids is unique to the family Proteaceae.…”

“…[42] An extraction of the upper leaves, flowers, and flowering stems of B. montana provided related alkaloids 62 and 63, darlingine (64), and the pyronotropane alkaloids 5,11-dihydroisobellendine (65), 2,3-dihydrobellendine, 2,3-epidihydrobellendine, 2,3-dihydrodarlingine, (AE)-3a-acetoxy-6b-isobutoxytropane (66), (AE)-6b-acetoxy-3a-isobutoxytropane, and 3a-acetoxy-6b-hydroxytropane. [42] Each of these isolated alkaloids is unique to the family Proteaceae. In 1979, four alkaloids were isolated from B. montana, which were not characterised.…”

“…In 1979, four alkaloids were isolated from B. montana, which were not characterised. [42] On further study, one of these alkaloids was subsequently identified as the g-lactone 67. [43] However, alkaloid 67 is likely an artefact of isolation, potentially formed by the reaction of ammonia and the lateridentified arbutin derivative 71 during the extraction process (see below).…”

Biogenesis of Proteaceous Alkaloids

“…Since the discovery {1] in 1971 of bellendine (G 2), the first base recorded [1][2][3][4][5] and two endemic in New Caledonia (Knightia deplanchei VIEILL. ex BRONGN. GRIS, Knightia strobilina LABILL.)…”

Synthèses Totales du Knightinol, de l'Acétylknightinol et de la Dihydro-2,3 Darlingine; Alcaloides Tropaniques de Knightia strobilina et de Bellendena montana

“…(Proteaceae), plante endémique de Nouvelle-Calédonie, plusieurs alcaloides tropaniques parmi lesquels le knightinol 1 et l'acétylknightinol 2. Précédemment BIcK et al [3] avaient isolé a partir de Bellendena montana R. BR. (Proteaceae), plante endémique du Queensland, d'autres alcaloIdes tropaniques parmi lesquels Ia dihydro-2,3 darlingine 3a.…”