Plant growth regulators from the fruiting bodies of Tricholoma flavovirens

Abstract

A novel indole derivative (1) and three known compounds (2-4) were isolated from the fruiting bodies of Tricholoma flavovirens. Their structures were determined or identified by the interpretation of spectroscopic data. Compounds 1 and 2 promoted root growth of lettuce and inhibited hypocotyl growth at 1 μmol/paper. Compound 3 inhibited hypocotyl and root growth at 100 nmol/paper.

Secondary Metabolites Isolated fromTricholomaSpecies (Basidiomycota, Tricholomatacee): A Review

“…T. equestre) [84]. Further investigations of the same extract led to the isolation of the new indole 103 together with the known acetamidophthalide 104 and indoles 94 and 105 [85]. The last two compounds had been previously isolated from injured fruiting bodies of T. sciodes [86].…”

“…The last two compounds had been previously isolated from injured fruiting bodies of T. sciodes [86]. Compounds 94, 100, 101and103 possessed similar growth regulation activity against lettuce, inhibiting the growth of hypocotyl and promoting the growth of root [84,85]. Instead, phthalide 104 inhibited hypocotyl and root growth at 100 nmol/paper [85].…”

“…The configuration of the stereocenter C(7) in saponaceolide C (13) was established with the aid of molecular mechanics calculations, using Allinger's MM2 (85) program, through conformational analysis of two model compounds possessing the two possible configurations of the carbinol [19].…”

“…Upon standing in CHCl 3 containing a catalytic amount of HCl, compound 85 slowly converted to phenol 86 [69]. The bicyclic tricholomenyn B (88) likely originates biosynthetically from a hypothetical precursor 87 formed by regiospecific oxidation of the C(8')-methyl group of tricholomenyn A (85). In fact, the characteristic 12-membered ansa ring of tricholomenyn B (88) may result from the regio-and stereospecific internal attack of the carboxylic acid group of 87 onto the epoxide ring.…”

Synthesis of three Tricholoma-derived indoles via an ortho-quinone methide

“…1,2 Several indole alkaloids harbouring a methyl group at the C2-position have been isolated from species of Tricholoma, a selection of which (1)(2)(3)(4) can be seen in Figure 1A. [3][4][5][6] Unlike most indole alkaloids, the Tricholoma indoles are not biosynthetically derived from tryptophan, but instead assembled via a biosynthetic pathway that involves lascivol (5), a bitter component isolated from Tricholoma lascivum that likely serves as a predation deterrent. 7 Tellingly, lascivol degrades into the natural product 5-methoxy-2,4-dimethylindole (1) and dimethylglutamate upon treatment with acid in methanol ( Figure 1B).…”