Stephen M. Poling

Antimicrobial Activity of Pyrrocidines from Acremonium zeae Against Endophytes and Pathogens of Maize

Acremonium zeae produces pyrrocidines A and B, which are polyketide-amino acid-derived antibiotics, and is recognized as a seedborne protective endophyte of maize which augments host defenses against microbial pathogens causing seedling blights and stalk rots. Pyrrocidine A displayed significant in vitro activity against Aspergillus flavus and Fusarium verticillioides in assays performed using conidia as inoculum, with pyrrocidine A being more active than B. In equivalent assays performed with conidia or hyphal cells as inoculum, pyrrocidine A revealed potent activity against major stalk and ear rot pathogens of maize, including F. graminearum, Nigrospora oryzae, Stenocarpella (Diplodia) maydis, and Rhizoctonia zeae. Pyrrocidine A displayed significant activity against seed-rotting saprophytes A. flavus and Eupenicillium ochrosalmoneum, as well as seed-infecting colonists of the phylloplane Alternaria alternata, Cladosporium cladosporioides, and Curvularia lunata, which produces a damaging leaf spot disease. Protective endophytes, including mycoparasites which grow asymptomatically within healthy maize tissues, show little sensitivity to pyrrocidines. Pyrrocidine A also exhibited potent activity against Clavibacter michiganense subsp. nebraskense, causal agent of Gosss bacterial wilt of maize, and Bacillus mojaviense and Pseudomonas fluorescens, maize endophytes applied as biocontrol agents, but were ineffective against the wilt-producing bacterium Pantoea stewartii.

Structure--activity relationships of chemical inducers of carotenoid biosynthesis☆

Abstract Fifteen amines having a profound effect on carotenogenesis in Marsh seedless grapefruit are reported. The compounds fall into three series: Et2N(CH2)nMe (n = 4–8), Et2N(CH2)nPh (n = 1–5), and Et2NCH2CH2OC6H4R (R=H, p-Me, p-Et, p-iso-Pr, p-tert-Bu), There was up to an 11-fold increase in the total carotene content. Lycopene, not normally accumulated, became a major pigment. The inducing ability of the amines on carotenoid biosynthesis is correlated with the octanol-water partition coefficient. The mode of action appears to be similar to that of 2-(4-chlorophenylthio)triethylamine hydrochloride.

Acremonium zeae, a protective endophyte of maize, produces dihydroresorcylide and 7-hydroxydihydroresorcylides.

Acremonium zeae has been characterized as a protective endophyte of maize and displays antifungal activity against other fungi. Pyrrocidines A and B were discovered to be the metabolites accounting for this activity. During a population survey of A. zeae isolates from maize seeds produced in nine states to determine their ability to produce pyrrocidines, another metabolite of A. zeae, unrelated to the pyrrocidines, was found to have widespread occurrence (105 of 154 isolates) and to be produced in amounts comparable to the pyrrocidines. Further chemical studies of fermentation extracts of an A. zeae isolate (NRRL 45893) from maize led to the identification of a new compound, dihydroresorcylide, the saturated analogue of cis-resorcylide. Also identified were the two diastereomers of 7-hydroxydihydroresorcylide. Dihydroresorcylide and pyrrocidines A and B were detected by LC-APCI-MS in symptomatic maize kernels from ears that were wound-inoculated in the milk stage with A. zeae NRRL 34559.

Analytical Determination of Fumonisins and Other Metabolites Produced by Fusarium moniliforme and Related Species on Corn

Fumonisins, secondary metabolites of the fungus Fusarium moniliforme are potent toxins that can be found in fungal contaminated corn. The detection and measurement of these toxins by HPLC with detection by an evaporative light scattering detector and by electrospray MS is reported. The light scattering detector had enough sensitivity to analyze culture materials, however, clean-up was necessary to detect fumonisins at sub-ppm levels in naturally contaminated corn extracts. The detection limit for FB1 with the light scattering detector was in the low ng range (10-50) while the detection limit of less than 1 ng injected was observed for the electrospray detector. Several previously unreported fumonisin isomers were observed in electrospray chromatograms of culture extracts. Two of these compounds, FA3 and FA4 were isolated and their proposed structure confirmed by NMR experiments.

Effects of amines on the carotenogenesis in Blakeslea trispora

Abstract Six amines profoundly affected carotenogenesis in Blakeslea trispora . When cultures were treated with the amines, namely 4-[β-(diethylamino)-ethoxy]-benzaldehyde, 4-[β-(diethylamino)-ethoxy]-acetophenone hydrochloride, 4-β-(diethylamino)-ethoxy]-benzophenone hydrochloride, triethylamine hydrochloride, α-diethylaminopropiophenone hydrochloride and tributylamine hydrochloride, an increase in the lycopene accumulation was observed. The modes of action of these amines appear to be similar to that of 2-(4-chlorophenylthio)triethylamine hydrochloride (CPTA); however, they difrer in relative effectiveness.

Cytokinins Inhibit Abscisic Acid Biosynthesis in Cercospora Rosicola

Summary The fungus Cercospora rosicola produces the plant hormone, abscisic acid (ABA), as a secondary metabolite. We developed C. rosicola into a convenient system to determine the effects of compounds on the biosynthesis of ABA. Another important group of plant hormones, the cytokinins, inhibited ABA biosynthesis in C. rosicola. The inhibition of ABA biosynthesis was concentration dependent and, in studies using farnesyl-[1-14C]pyrophosphate, appeared to be specific rather than resulting from a general blocking of terpenoid biosynthesis. Inhibitors of ABA biosynthesis have not previously been reported. Knowledge that cytokinins have the ability to inhibit ABA biosynthesis in this fungal system indicates the need for further studies to determine if cytokinin inhibition of ABA biosynthesis occurs in plants and is an element of the hormonal action of cytokinins.

New chemical inducers of carotenoid biosynthesis

Abstract Five compounds having a striking effect on the color of Marsh seedless grapefruit are reported. The compounds, namely [β-(diethylamino)-ethoxy]-benzene, [γ-(diethylamino)-propoxy]-benzene, [δ-(diethylamino)-butoxy]-benzene, 4-[β-(diethylamino)-ethoxy]-benzaldehyde, and diethylaminoethyl anisolate caused a 5- to 12-fold increase in the carotene content. Lycopene, not normally accumulated, became the major pigment. The mode of action appears to be similar to that of CPTA.

Metabolism of abscisic acid: Bacterial conversion to dehydrovomifoliol and vomifoliol dehydrogenase activity

Abstract A species of Corynebacterium , capable of metabolizing abscisic acid (ABA), was isolated from soil. The organism converted ABA to dehydrovomifoliol [(±)-1′-hydroxy-4′-keto-α-ionone] as the major metabolise. A cell-free extract exhibited vomifoliol dehydrogenase activity. This suggests that vomifoliol is most likely the immediate precursor of dehydrovomifoliol.

New bioregulators of gibberellin biosynthesis in Gibberella fujikuroi

Abstract A number of new inhibitors of gibberellin (GA) biosynthesis in Gibberella fujikuroi are reported, including secondary, tertiary and quaternary amines. Octyltrimethylammonium iodide and 3-chloropropyltrimethylammonium iodide were equally as effective as 2-chloroethyltrimethylammonium chloride (CCC). At least two of the other inhibitors reported, diethyloctylamine hydrochloride and octyltriethylammonium iodide, showed a different pattern of accumulation of GAs and kaurenoic acids than did CCC.

Chemical induction of β-carotene biosynthesis

Abstract Marsh white seedless grapefruit were treated with the 2-diethylaminoethanol esters of the following acids: benzoic, phenylacetic, hydrocinnamic, 4-phenylbutyric, 5-phenylvaleric, valeric, hexanoic, heptanoic, octanoic, nonanoic, 5-chlorovaleric, cyclohexanecarboxylic, phenoxyacetic, p -chlorophenoxyacetic, 3-phenoxypropionic, cinnamic and p -chlorocinnamic. Several of these esters, in particular the hexanoate, 4-phenylbutyrate and cinnamate, caused the accumulation of large amounts of β-carotene. The effects of the hexanoate and of 2-phenoxytriethylamine, which causes only lycopene accumulation, were studied as functions of time. The hexanoate caused the rapid accumulation of lycopene during the first day. The amount of lycopene then began to decrease and that of β-carotene increased until, after 14 days, β-carotene was the major pigment. 2-Phenoxytriethylamine caused rapid lycopene accumulation during the first day and a slow steady increase afterwards. Thus, the mode of action of the β-carotene inducers may be similar to that of the lycopene inducers except that the former are probably rapidly hydrolysed by the esterase(s) in the flavedo, so that they no longer inhibit the cyclase(s), and β-carotene is accumulated at the expanse of lycopene.