The structure of veralomine

Chemistry of Natural Compounds
1975.0

Abstract

We previously reported the isolation of a new alkaloid, veralomine (I, C₃₃H₅₅NO₆, mp 275-277°C, [α]D?54.11°), from the combined bases of the epigeal part of VePatrurn Zobelianurn. Acid hydrolysis of (I) yielded two aglycones, veralomidine (III, C₂₇H₄₅NO, mp 174-175°C, [α]D-53.23°) and veralomidene (IV, C₂₇H₄₃N, mp 175-178°C, [α]D-49.5°), as well as D-glucose. Structural analyses using IR, NMR, mass spectrometry, hydrogenation, acetylation, nitrosation, and other methods showed that veralomidine belongs to the veralkamine type with the verallnine skeleton but differs from verallnine in the configuration of the C₁₇ asymmetric center. Veralomidene, lacking a hydroxy group absorption in its IR spectrum and having a UV spectrum characteristic of a heteroannular diene, is formed by the elimination of a water molecule from veralomidine (from the C₃-OH and C₄-H) during hydrolysis. Comparison of molecular rotations via Klyne's rule revealed that D-glucose in veralomine is linked to the C₃ hydroxy group of veralomidine via a β-glycosidic bond, leading to the conclusion that veralomine is veralomidine 3β-D-glucopyranoside (I).

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