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Identifizierung von Farnesol als Zwischenstufe in der Biosynthese des Cantharidins aus Mevalonsäurelacton. 7.Mitteilung zur Biosynthese des Cantharidins
Author(s) -
Peter Martin G.,
Woggan WolfDietrich,
Schmid Hans
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600827
Subject(s) - farnesol , chemistry , cantharidin , biosynthesis , stereochemistry , sesquiterpene , terpenoid , biochemistry , organic chemistry , enzyme
Identification of farnesol as an intermediate in the biosynthesis of cantharidin from mevalonolactone Simultaneous injection of 2‐[ 14 C]‐mevalonolactone (2‐[ 14 C]‐ 1 ) and ( E , E )‐11′,12‐[ 3 H]‐farnesol (11′,12‐[ 3 H]‐ 2 ) into Lytta vesicatoria L . ( Coleoptera , Meloidae ) yields doubly labelled cantharidin ( 3 ). The remainder of the precursor farnesol, re‐isolated from the insects after the incubation period, has incorporated 14 C‐radioactivity. The labelling pattern in this farnesol, as determined by two independent degradative reaction sequences, is in agreement with the isoprene rule. Since specific incorporation of farnesol ( 2 ) into cantharidin ( 3 ), and of mevalonolactone ( 1 ) into both, farnesol ( 2 ) and cantharidin ( 3 ) is observed, the sesquiterpene alcohol 2 acts as an intermediate in the biosynthesis of the C 10 ‐compound 3 (Scheme 1) .