The structure of the products of transformation of suberosin and their possible biogenesis
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When suberosin is allowed to stand in chloroform at room temperature with access of atmospheric oxygen, photooxidation takes place with the formation of at least three substances: (II), C15H16O4, mp 172–174°C; (III), C15H16O5, mp 184–185°C; and (IV).
It has been established by NMR and mass spectroscopy and also by their chemical properties, that (II) is 6-(3′-hydroxyisopent-2′-en-1′-yl)-7-methoxycoumarin (trans-suberenol) and (III) is 6-(1′,2′-epoxy-3′-hydroxyisopentyl)-7-methoxycoumarin (lophopterol). The nature of (IV) has not yet been determined.
It has been shown experimentally that no such oxidation takes place with an isomer of (I) — osthole (IX). A scheme for the biogenesis of coumarins in the organism of the plant investigated has been put forward.
KeywordsCoumarin Glacial Acetic Acid Atmospheric Oxygen HMDS Chloroform Solution
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