Structure and biosynthesis of the penitrems A–F, six novel tremorgenic mycotoxins from Penicillium crustosum

Jesus, Amelia E. de; Steyn, Pieter S.; Heerden, Fanie R. van; Vleggaar, Robert; Wessels, Philippus L.; Hull, William E.

doi:10.1039/c39810000289

Cited by 58 publications

(27 citation statements)

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“…After a concentration step, the crude extract was subjected to flash chromatography with subsequent final separation of the penitrems by preparative HPLC-UV. The structures of the isolated penitrems were proven by spectroscopic methods and were in agreement with previously reported data [ 42 , 43 ] (see Tables S1 and S2 in the Supplementary Materials ). Penitrems A–F with a purity of ≥96% were obtained and applied as external standards for the subsequent quantitative analysis ( Figure 3 a,b).…”

Section: Resultssupporting

confidence: 89%

Influence of Environmental Factors on the Production of Penitrems A–F by Penicillium crustosum

Kalinina

Jagels

Cramer

et al. 2017

Toxins

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Filamentous fungi produce a multitude of secondary metabolites, some of them known as mycotoxins, which are toxic to vertebrates and other animal groups in low concentrations. Among them, penitrems, which belong to the group of indole-diterpene mycotoxins, are synthesized by Penicillium and Aspergillus genera and exhibit potent tremorgenic effects. This is the first complex study of the penitrems A–F production under the influence of different abiotic factors, e.g., media, incubation time, temperature, pH, light, water activity, and carbon and nitrogen source as well as oxidative and salt stress. For this purpose, penitrems A–F were isolated from Penicillium crustosum cultures and used as analytical standards. Among the carbon sources, glucose supplemented to the media at the concentration of 50 g/L, showed the strongest inducing effect on the biosynthesis of penitrems. Among nitrogen sources, glutamate was found to be the most favorable supplement, significantly increasing production of these secondary metabolites. CuSO4-promoted oxidative stress was also shown to remarkably stimulate biosynthesis of all penitrems. In contrast, the salt stress, caused by the elevated concentrations of NaCl, showed an inhibitory effect on the penitrem biosynthesis. Finally, cheese model medium elicited exceptionally high production of all members of the penitrems family. Obtained results give insides into the biosynthesis of toxicologically relevant penitrems A–F under different environmental factors and can be utilized to prevent food contamination.

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Section: Resultssupporting

confidence: 89%

Influence of Environmental Factors on the Production of Penitrems A–F by Penicillium crustosum

Kalinina

Jagels

Cramer

et al. 2017

Toxins

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“…Mycotoxins are produced by several Penicillium species: P. crustosum, P. brevicompactum, P. chrysogenum, P. expansum, P. roqueforti, P. spinulosum, P. viridicatum, P. commune, P. citrinum, and P. solitum, including mycophenolic acid, roquefortine C, penitrems A-F (53)(54)(55)(56)(57)(58) and thomitrems A and E (61 and 62) [99][100][101][102][103][104][105][106][107]. Penitrem G (59), a new alkaloid, has been isolated together with the already known mycotoxins penitrems A-D and F from the mycelium of P. crustosum [108].…”

Section: Terrestrial Cyclobutane-containing Alkaloidsmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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The present review describes research on novel natural cyclobutane-containing alkaloids and synthetic compounds isolated from terrestrial and marine species. More than 210 compounds have been confirmed to show antimicrobial, antibacterial, anticancer, and other activities. Structures, origins, biosynthesis, photodimerization, and biological activities of a selection of cyclobutane-containing alkaloids and selected synthetic analogs of natural alkaloids are reviewed.

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“…Penitrems are found in several species of fungi and have been described particularly well in the case of Penicillium crustosum [73,74]. Penitrem A is the most tremorgenic and abundant of the penitrems (Figure 5) [54,75].…”

Section: Reported Animal Toxicity For Indole-diterpenesmentioning

confidence: 99%

Tremorgenic Mycotoxins: Structure Diversity and Biological Activity

Reddy

Guthridge

Vassiliadis

et al. 2019

Toxins

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Indole-diterpenes are an important class of chemical compounds which can be unique to different fungal species. The highly complex lolitrem compounds are confined to Epichloë species, whilst penitrem production is confined to Penicillium spp. and Aspergillus spp. These fungal species are often present in association with pasture grasses, and the indole-diterpenes produced may cause toxicity in grazing animals. In this review, we highlight the unique structural variations of indole-diterpenes that are characterised into subgroups, including paspaline, paxilline, shearinines, paspalitrems, terpendoles, penitrems, lolitrems, janthitrems, and sulpinines. A detailed description of the unique biological activities has been documented where even structurally related compounds have displayed unique biological activities. Indole-diterpene production has been reported in two classes of ascomycete fungi, namely Eurotiomycetes (e.g., Aspergillus and Penicillium) and Sordariomycetes (e.g., Claviceps and Epichloë). These compounds all have a common structural core comprised of a cyclic diterpene skeleton derived from geranylgeranyl diphosphate (GGPP) and an indole moiety derived from tryptophan. Structure diversity is generated from the enzymatic conversion of different sites on the basic indole-diterpene structure. This review highlights the wide-ranging biological versatility presented by the indole-diterpene group of compounds and their role in an agricultural and pharmaceutical setting.

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Structure and biosynthesis of the penitrems A–F, six novel tremorgenic mycotoxins from Penicillium crustosum

Abstract: The structures of six new mycotoxins, penitrems A-F, isolated from cultures of Penicillium crustosum are deduced from their 13C and lH n.m.r. spectra and from biosynthetic results.

Cited by 58 publications

References 1 publication

Influence of Environmental Factors on the Production of Penitrems A–F by Penicillium crustosum

Influence of Environmental Factors on the Production of Penitrems A–F by Penicillium crustosum

Bioactive cyclobutane-containing alkaloids

Tremorgenic Mycotoxins: Structure Diversity and Biological Activity

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