sym-Homospermidine, a naturally occurring polyamine.

1,9-Diamino-5-azanonane (1, H2N(CH2)4NH(CH2)4NH2), symmetrical “homospermidine,” previously unreported in nature, has now been discovered in sandal (Santalum album L.), where it comprises 0.5-1.5% of the weight of the dried leaves. The new polyamine is conveniently isolated from an aqueous extract of the leaves by ion-exchange 1^) uring a routine examination of the amino acids from an ethanolic extract of the leaves of the sandalwood tree, a prominent ninhydrin-positive spot (spot 5 in Figure 1), hitherto unrecognized, was observed in two-dimensional chromatograms. However, when an aqueous extract was examined, which had been desalted on a column of Dowex 50 (H+ form) by elution with 1.0 n ammonia, this spot was absent in otherwise unchanged chromatograms. The unknown, strongly basic compound could be eluted with 1.0 m piperidine. Repetition of this procedure afforded a chromatographically homogeneous product whose characterization as sym-homospermidine forms the subject of this paper.