Lipopolysaccharide of Pseudomonas solanacearum |
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| Authors: | Yukio Akiyama Shigeki Nishikawaji Shigeru Eda Hiroshi Tanaka Akio Ohnishi Kunio Katō |
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| Institution: | 1. Central Research Institute, The Japan Tobacco and Salt Public Corporation, 6–2 Umegaoka, Midori-ku, Yokohama 227, Japan;2. The Utsunomiya Tobacco Experiment Station, The Japan Tobacco and Salt Public Corporation, Oyama, Tochigi 323, Japan |
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| Abstract: | A novel monoterpene, 2(E)-(4-methyl-3-pentenyl)butenedial (α-acaridial (1) for the trivial name), was isolated from the secretion of the acarid mite Tyrophagus perniciosus. The structure was clarified in the light of spectral data, and the geometry of the double bond in the butenedial moiety was assigned based on the γ-deshielding effect on a methylene and on an aldehyde group. Coupling the Grignard reagent (CH3)2C =CHCH2CH2MgBr to THP-OCH2(C = O)CH2CH2O-THP, and dehydration and deprotection of the OH groups gave α-(E)- and α-(Z)-acaridiol, which were fully assigned byMS and NMR. Matching the spectral data of the synthetic alcohols with those of the alcohol derived from the natural product, or of natural acaridial with those of synthetic α-(E)- and α-(Z)-acaridial, corroborated beyond all doubt the structure of this new monoterpene dial. |
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