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Annosqualine: a Novel Alkaloid from the Stems of Annona squamosa

✍ Scribed by Yu-Liang Yang; Fang-Rong Chang; Yang-Chang Wu

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
149 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Annosqualine (=(10′b__R__)‐1′,5′,6′,10′b‐tetrahydro‐9′‐hydroxy‐7′,8′‐dimethoxyspiro[cyclohexa‐2,5‐diene‐1,2′‐pyrrolo[2,1‐a]isoquinoline]‐3′,4‐dione; 1), a novel alkaloid with an unprecedented skeleton, and a new amide, dihydrosinapoyltyramine (=3‐(4‐hydroxy‐3,5‐dimethoxyphenyl)‐N‐[2‐(4‐hydroxyphenyl)ethyl]propanamide; 2), were isolated from the stems of Annona squamosa L., together with six known alkaloids. The structures of all compounds were elucidated spectroscopically by means of optical rotation, ^1^H‐, ^13^C‐, and 2D‐NMR, and by EI‐MS, or by comparison with the spectral data of authentic samples. A possible biogenetical pathway towards annosqualine (1) is proposed.

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