Biosynthesis of phenols

Secondary Metabolites from the Sponge Tedania anhelans: Isolation and Characterization of Two Novel Pyrazole Acids and Other Metabolites

“…p -Hydroxybenzaldehyde, phenylacetamide, phenylpropionic acid, 3-( p -hydroxyphenyl)propionic acid, and 3-( p -methoxyphenyl)propionic acid were readily identified by the analysis of MS, NMR, and IR data. p -Hydroxybenzaldehyde had been previously reported to be produced by the fungus Ceratocystis clavigera, associated with blue disease of pine, and phenylacetamide from terrestrial plants − as well as the fungus Streptoverticillium olivoreticuli. …”

“…p-Hydroxybenzaldehyde, phenylacetamide, 3 phenylpropionic acid, 3-(p-hydroxyphenyl)propionic acid, and 3-(p-methoxyphenyl)propionic acid were readily identified by the analysis of MS, NMR, and IR data. p-Hydroxybenzaldehyde had been previously reported to be produced by the fungus Ceratocystis clavigera, 7 associated with blue disease of pine, and phenylacetamide from terrestrial plants [8][9][10][11][12] as well as the fungus Streptoverticillium olivoreticuli. 13 The IR spectrum of 1, which was quite different from the aromatic acids or other diketopiperazines, showed multiple bands in the region 3150-2650 and 1650-1300 cm -1 , indicating the presence of aromatic ring and amino groups.…”

Aromatic Secondary Metabolites from the Sponge Tedania ignis

“…2-Phenylacetamide [1], 1-methyl-carbazole [2], and 1-acetyl-ß-carboline [31 were readily identified by analysis of the ms, nmr, and ir data and comparison to literature reports. Compound 1 had been previously reported from terrestrial plants (6)(7)(8) and microorganisms (9,10); similarly, compounds 2 (11-13) and 3 (14) were previously known, but none of the three compounds had been isolated from the marine biosphere.…”

“…While a novel compound, it resembles 9, a microbial transformation product of ß-ionone ( 24) and a constituent of the volatiles from grape brandies (25), preserved prunes (26) and other fruit (27). The aromatic substitution pattern of 8 is found in at least three carotenoids of Tedania digitata (28)(29)(30)(31), including tedanin [10] (28,29). Mikami's microbial conversion of ß-ionone to 9 (24) suggests a similar biosynthetic process in the Tedania carotenoids; compound 8 is very likely a degradation product of carotenoids.…”