Abstract
The absolute configuration of the iridoid monoterpene chrysomelidial from the oribatid mite, Austrotritia dentate Aoki, was elucidated by the GC-MS and GC comparisons with four synthetic stereoisomers of this well-known natural product. This identification was made possible by asymmetric synthesis of the known alcohol, (5S,8S)-chrysomelidiol. The GC retention time of diol derived from the natural oribatid dial agreed with that of the synthetic (5S,8S)-chrysomelidiol, confirming that the absolute configurations at C5 and C8 positions of the natural chrysomelidial are both S. Chrysomelidial was detected as a single or a major component in nine oribatid mites examined; thus, this compound is considered to be commonly distributed in Oribotririidae where it serves a defensive role.
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This study was supported by a Grant-in-Aid for Young Scientists (B) [No.20780086 and No.22780106 for NS] from the Japan society for the promotion of Science (JSPS) and by a providing fellowship from the Agricultural Chemical Research Foundation.
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Shimizu, N., Yakumaru, R., Sakata, T. et al. The Absolute Configuration of Chrysomelidial: A Widely Distributed Defensive Component Among Oribotririid Mites (Acari: Oribatida). J Chem Ecol 38, 29–35 (2012). https://doi.org/10.1007/s10886-012-0064-3
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DOI: https://doi.org/10.1007/s10886-012-0064-3