Secondary mould metabolites. Part 16. Stemphyltoxins, new reduced perylenequinone metabolites from Stemphylium botryosum var. Lactucum

Arnone, Alberto; Nasini, Gianluca; Merlini, L.; Assante, Gemma

doi:10.1039/p19860000525

Cited by 50 publications

(61 citation statements)

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“…13 Many Alternaria sp. have been reported to contain perylene oxides and alterperylenols 14–19 which are known to possess antibacterial, 16 antifungal, 17 mutagenic, 14,15 and phytotoxic 17–19 activities. A recent report described the isolation of altertoxin II ( 4 ) and altertoxin IV ( 6 ) from an endophytic strain of A. tenuissima occurring in the medicinal plant, Tribulus terrestris .…”

Section: Introductionmentioning

confidence: 99%

Altertoxins with potent anti-HIV activity from Alternaria tenuissima QUE1Se, a fungal endophyte of Quercus emoryi

Bashyal

Wellensiek

Ramakrishnan

et al. 2014

Bioorganic & Medicinal Chemistry

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Screening of a small library of natural product extracts derived from endophytic fungi of the Sonoran desert plants in a cell-based anti-HIV assay involving T-cells infected with the HIV-1 virus identified the EtOAc extract of a fermentation broth of Alternaria tenuissima QUE1Se inhabiting the stem tissue of Quercus emoryi as a promising candidate for further investigation. Bioactivity-guided fractionation of this extract led to the isolation and identification of two new metabolites, altertoxins V (1) and VI (2) together with the known compounds, altertoxins I (3), II (4), and III (5). The structures of 1 and 2 were determined by detailed spectroscopic analysis and those of 3–5 were established by comparison with reported data. When tested in our cell-based assay at concentrations insignificantly toxic to T-cells, altertoxins V (1), I (3), II (4), and III (5) completely inhibited replication of the HIV-1 virus at concentrations of 0.50, 2.20, 0.30, and 1.50 μM respectively. Our findings suggest that the epoxyperylene structural scaffold in altertoxins may be manipulated to produce potent anti-HIV therapeutics. 2014 Elsevier Ltd. All rights reserved.

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Section: Introductionmentioning

confidence: 99%

Altertoxins with potent anti-HIV activity from Alternaria tenuissima QUE1Se, a fungal endophyte of Quercus emoryi

Bashyal

Wellensiek

Ramakrishnan

et al. 2014

Bioorganic & Medicinal Chemistry

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“…Based on the literature, the biosynthesis of partially reduced perylenequinones occurs by oxidative aromatic coupling of two pentaketide-derived moieties. 25,27 However, this coupling has been proposed to occur in a quite specific way, by prior formation of two tetralone derivative intermediates, which undergo head-to-head or tail-to-head coupling, giving rise to those reported perylenequinones containing biphenyl or dihydroanthracene scaffolds, respectively. 25,27 The non-reduced perylenequinone derivative 3 might be produced from a partially reduced perylenequinone, such as alterperylenol (i) (hypothesis 1), or, instead, it would be a pathway intermediate of the biosynthesis of partially reduced perylenequinones (hypothesis 2) (Fig.…”

Section: Resultsmentioning

confidence: 98%

“…S28) and also in previously reported compounds. 16,17,[25][26][27] Thus, based on UV spectra, it was determined that compound 1 possesses a dihydroanthracene framework. Therefore, compound 1 is different from the previously reported stemphytriol (f) (Fig.…”

Section: Resultsmentioning

confidence: 99%

New perylenequinone derivatives from the endophytic fungus Alternaria tenuissima SS77

Chagas

Dias

Pupo

2016

Tetrahedron Letters

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“…3 water hyacinth {Eichornia crassipes); the latter are obtained from Stemphylium botryosum var. Lactucum, an organism that causes leaf spot of lettuce and is an international economic problem in lettuce cultivation.…”

Section: Dihydrotentoxin (Alternaria Citri)mentioning

confidence: 99%

Unusual plant‐growth regulators from microorganisms

Cutler¹,

Wells

1988

Critical Reviews in Plant Sciences

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For at least 35 years, five major plant-growth regulators have predominated the field of plant growth and development. One of the reasons for the preoccupation with indole-3-acetic acid, the gibberellins (especially GA 3 ), abscisic acid, the cytokinins, and ethylene has been the relatively large quantities with which these metabolites can be obtained from either natural sources or by synthesis. The bulk of the literature attests to the availability of these compounds. For example, the literature concerning gibberellins had already amounted to 632 abstracts and articles by 1957 66 when gibberellin, specifically GA 3 , was a relatively newly discovered compound compared to indole-3-acetic acid and ethylene.It is significant that the five major plant-growth regulators have, at last, all been found in microorganisms. Indole-3-acetic acid was discovered in Rhkopus suinis n early in the developmental history of plant-growth regulators and was called rhizopin. Gibberellins were isolated from Gibberella fujikuori (Fusarium moniliforme). 5 Ethylene has been found emanating from numerous fungi. 30 Abscisic acid and its metabolites have been recent topics of discussion relative to their identification and large titer in Cercospora cruenta.' 9 "-54 This organism produces mostly 2-cis-( + )-abscisic acid, which is the active isomer, as opposed to 2-trans-{ -)-abscisic acid which is inactive. The last well-known metabolites to be isolated from microorganisms, the cytokinins, have only recently been reported. These include transzeatin, franj-zeatin riboside, and the novel cytokinin 6-(4-hydroxy-l,3-dimethyIbut-frarc.y-2-enyIamino)-9-B-D-ribofuranosylpurine 6lf from Pseudomonas syringae pv. savastanoi, the causal organism of olive knot, which includes stem galls in ash, oleander, privet, and jasmine. Initial studies with crude ethyl acetate extracts of the culture filtrate showed that olive and tobacco callus cultures were stimulated and this indicated the probable presence of a cytokinin. Thus, all of the "major" classes of plant-growth regulators have been accounted for in microorganisms. Furthermore, it appears that the genetic influence governing the production of these important compounds has not been deleted during the evolutionary process. Until recently, it was believed that these compounds were almost totally responsible for events taking place in the differentiation and development of plants including, in certain cases, the etiology of plant diseases.Any discussion of plant-growth regulators that includes compounds other than these five often raises a hue and cry among certain circles of scientists. But the evidence supports the facts to show that there are fungal and bacterial metabolites that promote plant growth and others that inhibit it. Earlier, we reviewed the literature on (+ )-hexylitaconic acid, from Aspergillus niger K-88, that promoted lettuce root growth by approximately 250%, relative

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Secondary mould metabolites. Part 16. Stemphyltoxins, new reduced perylenequinone metabolites from Stemphylium botryosum var. Lactucum

Abstract: The structures of five new metabolites, stemphyltoxins (I)‐(IV) [(Ia)‐(Ic), (II)] and stemphyperylenol (III), are elucidated by analysis of their 1H and 13C NMR spectra [the relative configuration of (II) is unknown].

Cited by 50 publications

References 1 publication

Altertoxins with potent anti-HIV activity from Alternaria tenuissima QUE1Se, a fungal endophyte of Quercus emoryi

Altertoxins with potent anti-HIV activity from Alternaria tenuissima QUE1Se, a fungal endophyte of Quercus emoryi

New perylenequinone derivatives from the endophytic fungus Alternaria tenuissima SS77

Unusual plant‐growth regulators from microorganisms

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