Oxodecanoyl histamine

From the leaves of Glochidion philippicum (Euphorbiaceae), a tree that grows in New Guinea, Johns and Lamberton in 1966 isolated four alkaloids (170) glochidine (113), glochidicine (114), Ato-(4-oxodecanoyl)histamine (115), and 7V -cinnamoylhistamine (6). The structures were deduced with the aid of IR, NMR, and mass spectroscopic methods. 

Beispiele fur diese beiden Arten des Ringschlusses (s. Schema 39) sind die gemeinsam in der Euphorbiaceae Glochidion -philippicum neben Na-(4-Oxodecanoyl)-histamin (CCXXXVII) vorkommenden Alkaloide Glo-chidin (CCXXXIX) und Glochidicin (CCXXXVIII) (755, 75(5). 

The isomers glochidine (13) and glochidicine (14) (both with a lactam ring) and A-(4-oxodecanoyl) histamine (15) were isolated from G. philippicum. Structure elucidation was performed by elementary analysis, and NMR and mass... 

Acylation of histamine with 4-oxodecanoyl chloride in pyridine yielded a mixture of 113,114, and 115, which could be separated to yield compounds identical to the respective natural alkaloids. Heating of 113 in dilute acetic acid gave a mixture of 113,114, and 115 further heating finally yielded pure glochidicine (114). One may therefore assume 113 and 114 to be cyclization products of 115. 

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