Unusual phenethylamine-containing alkaloids from Elaeocarpus tectorius

From the leaves of Elaeocarpus tectorius (Lour.) Poir. four previously undescribed phenethylamine-containing alkaloids were isolated, namely, tectoricine, possessing an unprecedented isoquinuclidinone ring system incorporating a phenethylamine moiety, tectoraline, representing a rare alkamide incorp...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2018-02, Vol.146, p.75-81
Main Authors: Ezeoke, Margret Chinonso, Krishnan, Premanand, Sim, Dawn Su-Yin, Lim, Siew-Huah, Low, Yun-Yee, Chong, Kam-Weng, Lim, Kuan-Hon
Format: Article
Language:English
Subjects:
Alkaloids
Amidine
Elaeocarpaceae
Elaeocarpus tectorius
Formamidine
Isoquinuclidinone
Phenethylamine
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Summary:From the leaves of Elaeocarpus tectorius (Lour.) Poir. four previously undescribed phenethylamine-containing alkaloids were isolated, namely, tectoricine, possessing an unprecedented isoquinuclidinone ring system incorporating a phenethylamine moiety, tectoraline, representing a rare alkamide incorporating two phenethylamine moieties, and tectoramidines A and B, representing the first naturally occurring trimeric and dimeric phenethylamine alkaloids incorporating an amidine function. The structures of these alkaloids were established by detailed spectroscopic analysis. The absolute configuration of tectoricine was determined by comparison of the experimental and calculated ECD spectra. Plausible biosynthetic pathways to the four alkaloids are proposed. Four unusual phenethylamine-containing alkaloids were isolated from the leaves of Elaeocarpus tectorius (Lour.) Poir. [Display omitted] •Tectoricine possesses an isoquinuclidinone ring system incorporating a phenethylamine moiety.•Tectoraline represents a rare alkamide incorporating two phenethylamine moieties.•Tectoramidines A and B are trimeric and dimeric phenethylamines possessing an amidine function.•This represents the first isolation of phenethylamine-containing alkaloids from Elaeocarpus.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2017.12.003