Malonylated Glycerolipids from the Glandular Trichome Exudate of Ceratotheca triloba

Chemical investigation of the glandular trichome exudate from Ceratotheca triloba (Pedaliaceae) led to the identification of nine 1‐O‐acetyl‐2‐O‐[(R)‐3‐acetyloxy‐fatty acyl]‐3‐O‐malonylglycerols. Among these, 1‐O‐acetyl‐2‐O‐[(R)‐3‐acetyloxyicosanoyl]‐3‐O‐malonylglycerol (7) was the most abundant con...

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Bibliographic Details
Published in:Chemistry & biodiversity 2012-08, Vol.9 (8), p.1611-1617
Main Authors: Ohkawa, Akiko, Sakai, Takaomi, Ohyama, Kiyoshi, Fujimoto, Yoshinori
Format: Article
Language:English
Subjects:
Ceratotheca triloba
Fatty Acids - chemistry
Fatty Acids - isolation & purification
Glandular trichome
Glycerides
Glycerol - analogs & derivatives
Glycerol - isolation & purification
Glycerolipids
Lipids
Malonates - chemistry
Malonates - isolation & purification
Pedaliaceae - chemistry
Plant Extracts - chemistry
Plant Extracts - isolation & purification
Stereoisomerism
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Summary:Chemical investigation of the glandular trichome exudate from Ceratotheca triloba (Pedaliaceae) led to the identification of nine 1‐O‐acetyl‐2‐O‐[(R)‐3‐acetyloxy‐fatty acyl]‐3‐O‐malonylglycerols. Among these, 1‐O‐acetyl‐2‐O‐[(R)‐3‐acetyloxyicosanoyl]‐3‐O‐malonylglycerol (7) was the most abundant constituent (41%), followed by 1‐O‐acetyl‐2‐O‐[(R)‐(3‐acetyloxyoctadecanoyl)‐3‐O‐malonylglycerol (2; 21%). Compounds having iso‐ and anteiso‐type structures in the 3‐acetyloxy‐fatty acyl groups in the fatty acyl moiety were also characterized as minor constituents. This is the first report of the isolation of malonylated glycerolipids as natural products.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.201200097