Biological activity of trisporoids and trisporoid analogues in Mucor mucedo (-).
In the course of their sexual interactions, zygomycete fungi communicate via an elaborate series of carotene-derived compounds, namely trisporic acid and its biosynthetic progenitors. A novel building-block strategy allowed the systematic generation of structurally modified trisporoids along with putative early biosynthetic precursors for physiological tests. The impact of discrete structural elements was documented by the ability of individual compounds to induce sexually committed hyphae in Mucor mucedo. The activity screening contributed to establish general structure-function relationships for trisporoid action. Most crucial for activity were the dimension of the longer side chain, the polarity of functional groups at C(4) and C(13), and the number of conjugated double bonds in the side chain. The presence of an oxygen substituent at the cyclohexene ring is not essential for function. The overall biological activity apparently results from the combination of the various structural elements.
Schachtschabel
Doreen
D
Abteilung Bioorganische Chemie, Max-Planck-Institut für chemische Okologie, Hans-Knöll-Strasse 8, D-07745 Jena, Germany.
Schimek
Christine
C
Wöstemeyer
Johannes
J
Boland
Wilhelm
W
D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000378:metabolism* / Q000502:physiology*; D015394:Molecular Structure; D009089:Mucor / Q000737:chemistry* / Q000502:physiology*
D005231:Fatty Acids, Unsaturated; C004574:trisporic acid