Natural acetylenes. Part XXII. trans-Dehydromatricaria ester as a biosynthetic precursor of some fungal polyacetylenes

Abstract

trans-[1-¹⁴C]Dehydromaticaria ester (CH₃·[CC]₃·CH[graphic omitted]CH·CO₂Me) is specifically converted in cultures of (i)Tricholoma grammopodium(Bull.) Fr. into dehydromatricarianol (CH₃·[CC]₃·CH[graphic omitted]CH·CH₂·OH), (ii)T. paneolum Fr. to 10-hydroxydehydromatricaria acid (HO·CH₂·[CC]₃·CH[graphic omitted]CH·CO₂H), (iii)Merulius lacrymans(Jacq.) Fr. to the dicarboxylic acid (HO₂C·[CC]₃·[CH₂]₂·CO₂H) and (iv)Coprinus quadrifidus Pk. to the C₉-triol {HCC·[CC]₂·CH(OH)·CH(OH)·CH₂OH}. The incorporations (3·4–46%) indicate that the above ester or a close relative is a precursor of the fungal C₁₀(and C₉) polyacetylenes.