Naucline, a new indole alkaloid from the bark of Nauclea officinalis

A new indole alkaloid, naucline (1) together with four known alkaloids, angustine (2), angustidine (3), nauclefine (4) and naucletine (5), were isolated from the bark of Nauclea officinalis. The structures of all isolated compounds were elucidated with various spectroscopic methods such as 1D- and 2...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2012-04, Vol.17 (4), p.4028-4036
Main Authors: Liew, Sook Yee, Mukhtar, Mat Ropi, Hadi, A Hamid A, Awang, Khalijah, Mustafa, Mohd Rais, Zaima, Kazumasa, Morita, Hiroshi, Litaudon, Marc
Format: Article
Language:English
Subjects:
angustidine
angustine
Animals
Aorta, Thoracic - drug effects
Chemical Sciences
In Vitro Techniques
Indole Alkaloids - chemistry
Indole Alkaloids - isolation & purification
Indole Alkaloids - pharmacology
Male
Models, Molecular
nauclefine
naucletine
naucline
Nuclear Magnetic Resonance, Biomolecular
Organic chemistry
Plant Bark - chemistry
Rats
Rats, Wistar
Rubiaceae
Rubiaceae - chemistry
Vasodilator Agents - chemistry
Vasodilator Agents - isolation & purification
Vasodilator Agents - pharmacology
vasorelaxant activity
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Summary:A new indole alkaloid, naucline (1) together with four known alkaloids, angustine (2), angustidine (3), nauclefine (4) and naucletine (5), were isolated from the bark of Nauclea officinalis. The structures of all isolated compounds were elucidated with various spectroscopic methods such as 1D- and 2D- NMR, IR, UV and LCMS-IT-TOF. In addition to that of alkaloid 1, the complete 13C-NMR data of naucletine (5) were also reported. Naucline (1) showed a moderate vasorelaxant activity (90% relaxation at 1 × 10(-5) M) whereas, angustine (2), nauclefine (4), and naucletine (5) showed potent vasorelaxant activity (more than 90% relaxation at 1 × 10(-5) M) on an isolated rat aorta.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules17044028