The new homogentisic acid derivatives miliusol (1b) and miliusolide (2) from Miliusa balansae were isolated and structurally determined by spectroscopic means. The relative configurations of the new 1b and its known acetate 1a were established. Furthermore, the symmetric ether bis(2-hydroxyphenyl)methyl ether 3, which was isolated for the first time from a natural source, the known flavonoids pachypodol and chrysosplenol C, and sodium benzoate were identified.
Two new compounds named miliubisstyryl A and miliubisstyryl B were isolated from leaves and branches of Miliusa balansae Fin. & Gagn. (Annonaceae) in addition to octacosanoic acid. Their structures were elucidated by spectroscopic methods, especially 2D NMR spectroscopy. The rare cyclobutane skeletons of these compounds are derived from a styryl compound which is also present in this plant.
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