Leporizines A–C: Epithiodiketopiperazines Isolated from an <i>Aspergillus</i> Species

Reátegui, Ricardo; Rhea, Joshua; Adolphson, Janet L.; Waikins, Kathryn; Newell, Ryan; Rabenstein, John; Mocek, Ursula; Luche, Michele; Carr, Grant

doi:10.1021/np300894y

Cited by 7 publications

(6 citation statements)

References 16 publications

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“… CBS 650.74 T A. leporis Antibiotic Y ( Frisvad & Samson, 2000 ), kojic acid ( Frisvad & Samson, 2000 ), leporins ( TePaske et al . 1991 ), leporizines ( Reategui et al . 2013 ), pseurotin A ( Frisvad & Samson, 2000 ) Antibiotic Y, clavatols, 7-hydroxytrichothecolone?, kojic acid, leporine A, leporiziznes, paspalines, pseurotin A CBS 151.66, CBS 349.81, ATCC 76617, IBT 16309, IBT 16585 A. luteovirescens Aflatoxin B 1 , B 2 , G 1 , G 2 ( Pildain et al .…”

Section: Resultsmentioning

confidence: 99%

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Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Frisvad

Hubka

Ezekiel

et al. 2019

Studies in Mycology

408

387

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Aflatoxins and ochratoxins are among the most important mycotoxins of all and producers of both types of mycotoxins are present in Aspergillus section Flavi, albeit never in the same species. Some of the most efficient producers of aflatoxins and ochratoxins have not been described yet. Using a polyphasic approach combining phenotype, physiology, sequence and extrolite data, we describe here eight new species in section Flavi. Phylogenetically, section Flavi is split in eight clades and the section currently contains 33 species. Two species only produce aflatoxin B1 and B2 (A. pseudotamarii and A. togoensis), and 14 species are able to produce aflatoxin B1, B2, G1 and G2: three newly described species A. aflatoxiformans, A. austwickii and A. cerealis in addition to A. arachidicola, A. minisclerotigenes, A. mottae, A. luteovirescens (formerly A. bombycis), A. nomius, A. novoparasiticus, A. parasiticus, A. pseudocaelatus, A. pseudonomius, A. sergii and A. transmontanensis. It is generally accepted that A. flavus is unable to produce type G aflatoxins, but here we report on Korean strains that also produce aflatoxin G1 and G2. One strain of A. bertholletius can produce the immediate aflatoxin precursor 3-O-methylsterigmatocystin, and one strain of Aspergillus sojae and two strains of Aspergillus alliaceus produced versicolorins. Strains of the domesticated forms of A. flavus and A. parasiticus, A. oryzae and A. sojae, respectively, lost their ability to produce aflatoxins, and from the remaining phylogenetically closely related species (belonging to the A. flavus-, A. tamarii-, A. bertholletius- and A. nomius-clades), only A. caelatus, A. subflavus and A. tamarii are unable to produce aflatoxins. With exception of A. togoensis in the A. coremiiformis-clade, all species in the phylogenetically more distant clades (A. alliaceus-, A. coremiiformis-, A. leporis- and A. avenaceus-clade) are unable to produce aflatoxins. Three out of the four species in the A. alliaceus-clade can produce the mycotoxin ochratoxin A: A. alliaceus s. str. and two new species described here as A. neoalliaceus and A. vandermerwei. Eight species produced the mycotoxin tenuazonic acid: A. bertholletius, A. caelatus, A. luteovirescens, A. nomius, A. pseudocaelatus, A. pseudonomius, A. pseudotamarii and A. tamarii while the related mycotoxin cyclopiazonic acid was produced by 13 species: A. aflatoxiformans, A. austwickii, A. bertholletius, A. cerealis, A. flavus, A. minisclerotigenes, A. mottae, A. oryzae, A. pipericola, A. pseudocaelatus, A. pseudotamarii, A. sergii and A. tamarii. Furthermore, A. hancockii produced speradine A, a compound related to cyclopiazonic acid. Selected A. aflatoxiformans, A. austwickii, A. cerealis, A. flavus, A. minisclerotigenes, A. pipericola and A. sergii strains produced small sclerotia containing the mycotoxin aflatrem. Kojic acid has been found in all species in section Flavi, except A. avenaceus and A. coremiiformis. Only six species in the section did not produce any known mycotoxins: A. aspearensis, A. coremii...

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Section: Resultsmentioning

confidence: 99%

“…A. leporis , not being able to produce aspergillic acid, produces leporins more readily. Apart from kojic acid and leporins, A. leporis produces leporizines A, B and C ( Reategui et al. 2013 ).…”

Section: Discussionmentioning

confidence: 99%

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Frisvad

Hubka

Ezekiel

et al. 2019

Studies in Mycology

408

387

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“…7). 89 Ten new carbazole alkaloids, claulansines A (199), B (200), C (201), D (202), E (203), F (204), G (205), H (206), I (207), and J (208) were isolated from the stems of Clausena lansium. Compounds 199, 204, and 206-208 showed selective neuroprotective effects (Fig.…”

Section: Non-tryptaminesmentioning

confidence: 99%

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Ishikura,

Abe,

Choshi

et al. 2015

Nat. Prod. Rep.

213

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“…Thus, the soft rot pathogen is an aporia and a bottle-neck for developing the industrial chain of Amorphophallus rivier in China [ 4 ]. The fungal genus of Aspergillus was widely distributed in soil, plant and ocean environments, and attracted the attention of chemists and pharmacologists because of their enormous metabolites production potential and multifariously biological activities [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. The investigation into the chemical structure and bioassay diversities of the endophytic fungi around the Three Gorges area were performed, we found that the crude extract of the endophytic fungus, Aspergillus versicolor (No.…”

Section: Introductionmentioning

confidence: 99%

Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor

et al. 2018

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Aspergoterpenins A–D (1–4), four new bisabolane sesquiterpenoid derivatives, were obtained from the endophytic fungus, Aspergillus versicolor, together with eight known compounds (5–12), and their structures were elucidated by a comprehensive analysis of their NMR (Nuclear Magnetic Resonance), MS (Mass Spectrum) and CD (Circular Dichroism) spectra. Aspergoterpenin A (1) was the first example with a characteristic ketal bridged-ring part in the degraded natural bisabolane-type sesquiterpene structures. The compounds 1–12 displayed no significant activities against four cancer cell lines (A549, Caski, HepG2 and MCF-7). Further, the antimicrobial activities to Erwinia carotovora sub sp. Carotovora were evaluated, and the results showed that compounds 1–12 displayed antimicrobial activities with MIC values ranging from 15.2 to 85.2 μg/mL.

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Leporizines A–C: Epithiodiketopiperazines Isolated from an Aspergillus Species

Cited by 7 publications

References 16 publications

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Aspergoterpenins A–D: Four New Antimicrobial Bisabolane Sesquiterpenoid Derivatives from an Endophytic Fungus Aspergillus versicolor

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