Occurrence of juvabione-type and epijuvabione-type sesquiterpenoids in Abies alba |
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Authors: | John Fieve Manville Klaus Bock Ernst von Rudloff |
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Affiliation: | 1. Fisheries and Environment Canada Forestry Directorate, Western Forest Products Laboratory, Vancouver, British Columbia V6T 1X2 Canada;2. Technical University of Denmark, Department of Organic Chemistry, Building 201, 2800 Lyngby, Denmark;3. Frairie Regional Laboratory, National Research Council, Saskatoon, Saskatchewan, S7N 0W9, Canada |
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Abstract: | The petrol-soluble fractions from the branchwood of four Abies alba trees were examined. Only two trees contained sufficient amounts of ‘juvabione-type’ insect juvenile hormone analogues for isolation and characterization. The first contained juvabione (4R, 1′R), 4′-dehydrojuvabione (4R, 1′R) and its 4R, 1′S diastereomer in a ratio of 3:1, and juvabiol (4R, 1′R, 3′S), isojuvabiol (4R, 1′R, 3′R) and epijuvabiol (4R, 1′S, 3′S) in an approximate ratio of 7:3:2. 4′-Dehydroepijuvabione (4R, 1′S) was the only ‘juvabione-type’ compound ioslated from the second tree. If it is accepted that juvabione and epijuvabione are enzymatically reduced forms of dehydrojuvabione and dehydroepijuvabione, respectively; then for these two A. alba our results indicate that only one enzyme which is specific for R chirality at C-1′ is present, since epijuvabione is not observed. |
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Keywords: | leaf oil monoterpene wood extractives sesquiterpenoids insect juvenile hormone analogues biosynthesis stereoconfigurations ORD juvabione. |
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