Very-long-chain hydroxyaldehydes from the cuticular wax of Taxus baccata needles.
In the cuticular wax of Taxus baccata needles, homologous series of very-long-chain 1,5-alkanediols and 5-hydroxyaldehydes were identified by various chemical transformations with product assignment using GC-MS. The 1,5-alkanediols had chain lengths ranging from C(28) to C(38), with strong predominance of even carbon numbers and a maximum at C(32) (29%). The series of 5-hydroxyaldehydes comprised chain lengths C(24) and C(26)-C(36), and showed a pronounced prevalence of even-numbered homologues. 5-Hydroxyoctacosanal was the most abundant compound of the series (42%). The 5-hydroxyaldehydes together amounted to 0.4 microg/cm(2), corresponding to 1.2% of total wax of the needles. A polyketide-like biosynthetic pathway is proposed based on the (similar) chain length distributions and functional group patterns for both compound classes.
Wen
Miao
M
Department of Botany, University of British Columbia, 6270 University Blvd., Vancouver, Canada V6T 1Z4.
Jetter
Reinhard
R
D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000447:Aldehydes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000473:Alkanes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D013329:Structure-Activity Relationship; D020946:Taxus / Q000737:chemistry*; D014885:Waxes / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes; D000473:Alkanes; D014885:Waxes