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Xyloccensins Q-V, six new 8,9,30-phragmalin ortho ester antifeedants from the Chinese mangrove Xylocarpus granatum
Authors:Jun Wu  Qiang Xiao  Xiang Li  Haixin Ding
Institution:a Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, People's Republic of China
b Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China
Abstract:Six new 8,9,30-phragmalin ortho esters, named xyloccensins Q-V (3-8), have been isolated from the stem bark of a Chinese mangrove Xylocarpus granatum, and their structures were elucidated on the basis of spectroscopic data and chemical means. The absolute stereochemistry of these compounds and xyloccensins O-P (1-2), revised as enantiomeric to all the phragmalins reported so far, was determined by application of the modified MTPA Mosher ester method and circular dichroism analysis. Both xyloccensins P and Q exhibited potent antifeedant activity against the third instar larvae of Mythimna separata (Walker) at a concentration of 500 ppm.
Keywords:Absolute stereochemistry  8  9  30-Phragmalin ortho ester  Xylocarpus granatum  Antifeedant activity
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