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Natural acetylenes. Part XXVII. An antifungal acetylenic furanoid keto-ester (wyerone) from shoots of the broad bean (Vicia faba L.; Fam. Papilionaceae)
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1968
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BiosynthesisPart XxviiEngineeringBiochemistryAntifungal AgentVicia Faba L.Secondary MetaboliteNatural Product BiosynthesisNatural AcetylenesFungitoxic PrincipleBroad BeanPhytochemistryPharmacologyBiomolecular EngineeringNatural Product Synthesis
The isolation and determination of the structure of the fungitoxic principle of the broad bean, Vicia faba L., is described. The natural material is the acetylenic keto-ester R[graphic omitted]·CH[graphic omitted]CH·CO2Me (R =cis-EtCH:CH·C⋮C·CO), contaminated with about 2% of the more saturated ketone (R = BuC⋮C·CO). In addition, the alcohol (R =cis-EtCH:CH·C⋮C·CHOH) was found in the shoot extract. These compounds, as well as the lower homologue (R =cis-MeCH:CH·C⋮C·CO), its trans-isomer, the aldehyde (R = OCH·C⋮C), the alcohol (R = HO·CH2·C⋮C), and the close thiophen analogue MeCH[graphic omitted]CH·C⋮C·CO·[graphic omitted]·CH[graphic omitted]CH·CO2Me were synthesised, and their fungitoxic properties were compared.