Unusual phenethylamine-containing alkaloids from Elaeocarpus tectorius

Ezeoke, Margret Chinonso and Krishnan, Premanand and Sim, Dawn Su Yin and Lim, Siew Huah and Low, Yun Yee and Chong, Kam Weng and Lim, Kuan Hon (2018) Unusual phenethylamine-containing alkaloids from Elaeocarpus tectorius. Phytochemistry, 146. pp. 75-81. ISSN 0031-9422, DOI https://doi.org/10.1016/j.phytochem.2017.12.003.

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Official URL: https://doi.org/10.1016/j.phytochem.2017.12.003


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.

Item Type: Article
Uncontrolled Keywords: Elaeocarpus tectorius; Elaeocarpaceae; Alkaloids; Phenethylamine; Isoquinuclidinone; Amidine; Formamidine
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 27 Aug 2019 04:00
Last Modified: 27 Aug 2019 04:00
URI: http://eprints.um.edu.my/id/eprint/22099

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