2000
DOI: 10.1021/np990534h
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Phytotoxic Compounds from the New Coprophilous Fungus Guanomyces polythrix

Abstract: Bioactivity-directed fractionation of the fermentation broth and mycelium of the coprophilous fungus Guanomyces polythrix led to the isolation of several phytotoxic compounds, including five new naphthopyranone derivatives (1-5). In addition, rubrofusarin B, emodin, citrinin, and 4-hydroxybenzoic acid methyl ester were obtained. The structures of the new compounds were established by spectral and chiroptical methods. The isolates caused significant inhibition of radicle growth of two weed seedlings (Amaranthus… Show more

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Cited by 38 publications
(43 citation statements)
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“…1 These results seem to indicate that hydroxylation of the lactone core at C-2 decreases the phytotoxic activity. Compounds 1-3 interacted with bovine brain-calmodulin as detected in a SDS-PAGE electrophoresis [14][15][16] (Figure 3). Calmodulin treated with the lactones had lower electrophoretic mobility than untreated calmodulin.…”
Section: Resultsmentioning
confidence: 99%
“…1 These results seem to indicate that hydroxylation of the lactone core at C-2 decreases the phytotoxic activity. Compounds 1-3 interacted with bovine brain-calmodulin as detected in a SDS-PAGE electrophoresis [14][15][16] (Figure 3). Calmodulin treated with the lactones had lower electrophoretic mobility than untreated calmodulin.…”
Section: Resultsmentioning
confidence: 99%
“…[15][16][17] Bibenzyls 23-25, 28, 29, and 33. 4′-Hydroxy-3,3′,5-trimethoxybibenzyl (23), 3,3′,4′,5-tetramethoxybibenzyl (24), 3,3′-dihydroxy-4′,5-dimethoxybibenzyl (25), 3,4′-dihydroxy-5-methoxybibenzyl (29), 3,3′,4′,5-tetrahydroxybibenzyl (28), and 3,4′,5-trihydroxybibenzyl (33) were prepared as previously described. [15][16][17][18][19] In all cases, the spectroscopic properties of the synthetic materials were identical to those described in the literature.…”
mentioning
confidence: 99%
“…Moreover, the position of glucose at C-8 was confirmed by HMBC correlations between H-1' glc (δ H 4.93) and C-8 (δ C 161.4). The CD spectrum of 1 showed a negative Cotton effect around 319 nm (See Supporting Information), similarly to those of (2S)-5-hydroxy-6,8-dimethoxy-2-methyl-4H-2,3-dihydronaphtho[2,3-b]-pyran-4-one, 12 suggested the configuration at C-2 to be S. In addition, the aglycone 1a can be determined by comparing the optical rotation of 1a with those of series of 2-methylchroman-4-one as well as the optical rotation of (R) dihydroeleutherinol ( = +8.8).…”
mentioning
confidence: 68%