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Epicuticular waxes from Agropyron dasystachyum,agropyron riparium and Agropyron elongatum
Authors:Alexander P Tulloch
Institution:National Research Council of Canada, Prairie Regional Laboratory, Saskatoon, Saskatchewan, Canada, S7N 0W9
Abstract:Epicuticular waxes from whole plants of Agropyron dasystachyum var. psammophylum, A. riparium and A. elongatum contain hydrocarbons (5–8 %), long chain esters (12–15%) and free acids (2–5%). The major esters are C34C56 esters derived from C16C30 acids and alcohols (1-hexacosanol is the major alcohol) but C31, C33 and C35 esters (3–11%) are also present. The latter esters are C18 and C20 acid esters of C13 and C15 2-alkanols. A. dasystachyum wax contains 2% free alcohols, that of A. riparium contains 17% and that of A. elongatum 11% (1-hexacosanol is the major alcohol in each). Diesters (2%), C8C12 diols esterified by (E)-2-alkenoic acids, are present in A. riparium wax. Hentriacontane-14,16-dione is present: 29% in A. dasystachyum wax and 32% in A. riparium wax, but only 5% in A. elongatum wax. 25-Oxohentriacontane-14,16-dione forms 14% of A. dasystachyum wax and 27% of A. elongatum wax but the oxo β-diketones of A. riparium wax (5%) consist of both 10-oxo- and 25-oxohentriacontane-14,16-diones in the ratio 4:1. Hydroxy β-diketones of the waxes are 25- and 26-hydroxyhentriacontane-14,16-diones; in A. dasystachyum (20%) the ratio is 3:1, in A. elongatum (20%) the ratio is 9:1 but in A. riparium (5%) it is ca 1:2. The configuration of the hydroxyl group in the 26-hydroxy β-diketone is opposite to that in the 25-hydroxy derivative. The unusual composition of the oxygenated β-diketones of A. riparium confirms that this species should be regarded as separate from A. dasystachyum. Wax from A. elongatum also contains 4-hydroxy-25-oxohentriacontane-14,16-dione (4%) and an unusual oxo-β-ketol, 18-hydroxy-7,16-hentriacontanedione (2%), both these components are probably derived biosynthetically from the 25-oxo β-diketone which is the major component of this wax. Syntheses of racemic 18-hydroxy-7,16-hentriacontanedione and of a model β-ketol, 12-hydroxy-10-pentacosanone, are described.
Keywords:Gramineae  epicuticular wax  25-hydroxy-hentriacontane-14  16-dione  26-hydroxyhentriacontane-14  16-dione  10-oxohentriacontane-14  16-dione  25-oxohentriacontane-14  16-dione  4-hydroxy-25-oxohentriacontane-14  16-dione  18-hydroxy-7  16-hentriacontanedione  
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