New tricyclic and tetracyclic pyranocoumarins with an unprecedented C-4 substituent. Structure elucidation of tamanolide, tamanolide D and tamanolide P from Calophyllum inophyllum of French Polynesia

Three new pyranocoumarin derivatives, tamanolide (1), tamanolide D (2) and tamanolide P (3), were isolated from the almond seeds of Calophyllum inophyllum L. (Clusiaceae) grown in French Polynesia. These compounds, having an unprecedented C‐4 isobutyl substituent, have been characterized as a new cl...

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Published in:Magnetic resonance in chemistry 2009-11, Vol.47 (11), p.989-993
Main Authors: Leu, T., Raharivelomanana, P., Soulet, S., Bianchini, J.P., Herbette, G., Faure, R.
Format: Article
Language:English
Subjects:
13C NMR
1H NMR
Calophyllum - chemistry
Calophyllum inophyllum
clusiaceae
COSY
HMBC
HMQC
Magnetic Resonance Spectroscopy
NMR
NOESY
Nuts - chemistry
Plant Extracts - chemistry
Polynesia
pyranocoumarin
Pyranocoumarins - analysis
Pyranocoumarins - chemistry
Pyranocoumarins - classification
Seeds - chemistry
tamanolides
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Summary:Three new pyranocoumarin derivatives, tamanolide (1), tamanolide D (2) and tamanolide P (3), were isolated from the almond seeds of Calophyllum inophyllum L. (Clusiaceae) grown in French Polynesia. These compounds, having an unprecedented C‐4 isobutyl substituent, have been characterized as a new class of pyranocoumarins called tamanolides. Their structures were elucidated on the basis of 1D and 2D NMR techniques (COSY, NOESY, HSQC and HMBC) in association with MS (HR‐ESI‐MS) data analysis. Copyright © 2009 John Wiley & Sons, Ltd. A new class of pyranocoumarin bearing an unprecedented isobutyl substituent called tamanolides were isolated from the almond seeds of Calophyllum inophyllum L. (Clusiaceae) grown in French Polynesia. The structures of three pure compounds as tamanolide (1), tamanolide D (2) and tamanolide P (3) were elucidated on the basis of 1D and 2D NMR techniques (COSY, NOESY, HSQC and HMBC) in association with MS (HR‐ESI‐MS) data.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.2482