Two new C13-norisoprenoid compounds, (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (1) and (3S,4S,5S,6S,9S)-3,4-dihydroxy-5,6-dihydro-β-ionol (2), were isolated from the leaves of Apollonias barbujana. The absolute structures were determined by spectroscopic methods and chemical transformations. (3S,4S,5S,6S,9R)-3,4-Dihydroxy-5,6-dihydro-β-ionol (3) was also isolated, the structure of which has been determined by X-ray analysis and whose 1H-NMR, 13C-NMR, and MS data are reported herein.

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In addition to the known compounds (+/-)-threo-guaiacylglycerol and the phenethyl alcohols, 3-methoxy-4-dihydroxyphenethyl alcohol and 3,4-dimethoxyphenethyl alcohol, a new irregular phenylpropanoid 2-(3-methoxy-4-hydroxyphenyl)-1,3-propanediol was isolated from the ethanolic extract of the leaves of Apollonias barbujana (Lauraceae). Their structures were elucidated on the basis of spectroscopic methods and chemical transformations.