Journal
FITOTERAPIA
Volume 172, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.fitote.2023.105713
Keywords
Sinoacutine; Salutaridine; Morphinane; Sinomenium acutum
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The study clones the SinSyn gene from Sinomenium acutum and analyzes its catalytic activity, confirming the biosynthetic pathway of sinoacutine and discussing its classification and pharmacological action.
The chemical structure of sinoacutine is formed by a phenanthrene nucleus and an ethylamine bridge. Because it has a similar parent structure to morphine, it is subdivided into morphinane. At present, all reports have pointed out that the basic skeleton of morphine alkaloids is salutaridine (the isomer of sinoacutine), which is generated by the phenol coupling reaction of (R)-reticuline. This study shows that the biosynthetic precursors of sinoacutine and salutaridine are different. In this paper, the sinoacutine synthetase (SinSyn) gene was cloned from Sinomenium acutum and expressed SinSyn protein. Sinoacutine was produced by SinSyn catalyzed (S)-reticuline, according to the results of enzyme-catalyzed experiments. The optical activity, nuclear magnetic resonance, and mass spectrum of sinoacutine and salutaridine were analyzed. The classification and pharmacological action of isoquinoline alkaloids were discussed. It was suggested that sinoacutine should be separated from morphinane and classified as sinomenine alkaloids.
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