Isolation and Structure Determination of Two New Compounds from Zanthoxylum integrifoliolum

Journal of Natural Products
1993.0

Abstract

Two new compounds, tridecanonchelerythrine [1] and conifegrol [2], were isolated from Zanthoxylum integrifoliolum, and their structures were elucidated on the basis of spectroscopic data including 2D nmr. Zanthoxylum integrifoliolum Merr. is a Rutaceous plant growing in the northern Philippines and occasionally in Eastern Taiwan (1). Thirty-two components isolated from this plant have been previously reported (2,3), including triterpenoids, steroids, coumarins, and alkaloids. Two new compounds, tridecanonchelerythrine (6-(2'-oxotridecyl)dihydrochelerythrine [1]) and conifegrol ((trans-4-(3,7-dimethylocta-2,6-dienyl)-3 methoxylphenyl-2-propen-1-ol) [2], were isolated by our group. Compound 1 belongs to the benzo[c]phenanthridine alkaloids. It is a 6-substituted dihydrochelerythrine. The long chain of the 2' oxotridecyl group is interesting, in comparison with other known 6-substituted dihydrochelerythridines, 6-(2'-ketobuty1)dihydrochelerythrine (4) and 6-(2' acetony1)dihydrochelerythrine (5,6). Compound 2, which is fragrant, can be viewed as an ether of a coniferyl alcohol and a geraniol.

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