Synthesis of the 5-Demethyl-6-deoxy Analogue of Sporogen AO-1, a Sporogenic Substance of<i>Aspergillus oryzae</i>

Tamogami, Shigeru; Katayama, Masato; Marumo, Shingo; Isobe, Mitsuaki

doi:10.1271/bbb.60.1372

Cited by 6 publications

(6 citation statements)

References 2 publications

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“…2012 ), paspaline and β-PC-M6 ( Rank et al . 2012 ), penicillin ( Saito 1946–47 ), speradine B-F ( Hu et al., 2014a , Hu et al., 2014b ), sporogen AO1 ( Tamogami et al . 1996 ), TMC-2A, B & C ( Nonoka et al., 1977 , Asai et al., 1998 ) Asperfuran (CBS 102.22, CBS 134.52, IBT 3629), aspirochlorin (CBS 102.07 T , CBS 134.52, CBS 570.65, CBS 819.72, RIB 40), citreoisocoumarin (CBS 102.22, CBS 570.65, CBS 205.89, NRRL 6270), a cyclopiamide (IBT 3593, IBT 3629, NRRL 695), cyclopiazonic acid (CBS 102.07 T = CBS 110.47 T , CBS 570.65, CBS 205.89, IBT 3593, IBT 3629, NRRL 484), ditryptoleucine (RIB 40), kojic acid (CBS 102.07, CBS 134.52, CBS 570.65, CBS 205.89, IBT 3595, IBT 3629, NRRL 695), miyakamides / oryzamides (CBS 102.07 T = CBS 110.47 T , CBS 570.65, RIB 40), parasiticolides / astellolides (CBS 570.65, CBS 819.72, CBS 205.89, NRRL 695, RIB 40), paspalines (RIB 40), sporogen AO1 (NRRL 6270).…”

Section: Resultsmentioning

confidence: 99%

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Frisvad

Hubka

Ezekiel

et al. 2019

Studies in Mycology

409

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%

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Frisvad

Hubka

Ezekiel

et al. 2019

Studies in Mycology

409

387

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“…From 2-methylcyclohexanone 5, the corresponding imine is quantitatively obtained and condensation with MVK 12, followed by cyclization gives the octalone (+)-16 in 44 % yield with an enantiomeric excess of 76 %. [111] This octalone could then be transformed into a sporogen analog. Similarly, alkylation with EVK 52 yields the corresponding octalone 155 in 86 % yield along with 8 % of the regioisomeric product.…”

Section: Reviewmentioning

confidence: 99%

“…Starting from 2-methylcyclohexanone (5), the corresponding imine is quantitatively obtained and condensation with 12,f ollowed by cyclization gives the octalone (+ +)-16 in 44 %yield with an enantiomeric excess of 76 %. [111] This octalone could then be transformed into as porogen analogue.S imilarly,a lkylation with ethyl vinyl ketone (EVK, 52)yields the corresponding octalone 155 in 86 %yield along with 8% of the regioisomeric product. [112] Successive recrystallizations can increase the enantiopurity to > 99 % ee,a nd three additional steps are required to yield (À)-(2S,4aS,8aR)-1,1,4a-trimethyldecahydronaphthalen-2-ol ((À-TMD).…”

Section: Angewandte Chemiementioning

confidence: 99%

“…The robustness of this method is illustrated well by numerous syntheses (Scheme ). Starting from 2‐methylcyclohexanone ( 5 ), the corresponding imine is quantitatively obtained and condensation with 12 , followed by cyclization gives the octalone (+)‐ 16 in 44 % yield with an enantiomeric excess of 76 % . This octalone could then be transformed into a sporogen analogue.…”

Section: Diastereoselective Pathways To Enantiopure (A)mrapsmentioning

confidence: 99%

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Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors

2017

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The Robinson annulation is a reaction that has been useful for numerous syntheses since its discovery in 1935, especially in the field of steroid synthesis. The products are usually obtained after three consecutive steps: the formation of an enolate (or derivative), a conjugate addition, and an aldol reaction. Over the years, several methodological improvements have been made for each individual step or alternative routes have been devised to access the Robinson annulation products. The first part of this Review outlines the most relevant developments towards the formation of monocarbonyl-derived Robinson annulation products (MRA products, MRAPs) and activated monocarbonyl-derived Robinson annulation products (AMRA products, AMRAPs). The following sections are then devoted to the diastereoselective and enantioselective synthesis of these products, while the last section describes the enantiomeric resolution of racemic mixtures.

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“…[111] Dieses Octalon konnte in ein Sporogenanalogon umgewandelt werden. Aus2 -Methylcyclohexanon (5)w urde das entsprechende Imin quantitativ erhalten, und die Kondensation mit 12 und anschließende Cyclisierung führten zum Octalon (+ +)-16 in 44 %A usbeute mit einem Enantiomerenüberschuss von 76 %.…”

Section: Bildung Von Enantiomerenangereicherten Keto-arentricarbonyl-unclassified

Enantioselektive Synthese von Robinson‐Anellierungsprodukten und Michael‐Addukten als Vorstufen

Gallier

Martel²,

Dujardin³

2017

Angewandte Chemie

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Die Robinson‐Anellierung hat seit ihrer Entdeckung 1935 in zahlreichen Synthesen Anwendung gefunden, besonders auf dem Gebiet der Steroidsynthese. Die Produkte werden gewöhnlich nach drei aufeinanderfolgenden Stufen erhalten: der Bildung eines Enolats (oder Derivats davon), einer konjugierten Addition und einer Aldolreaktion. Im Laufe der Jahre wurden mehrere methodische Verbesserungen für jede einzelne Stufe vorgenommen oder alternative Synthesewege hin zu Robinson‐Anellierungsprodukten entwickelt. Im ersten Teil dieses Aufsatzes werden die wichtigsten Entwicklungen für die Bildung Monocarbonyl‐abgeleiteter Robinson‐Anellierungsprodukte (MRA‐Produkten, MRAPs) und von einer aktivierten Monocarbonylverbindung abgeleiteter Robinson‐Anellierungsprodukte (AMRA‐Produkten, AMRAPs) erläutert. In den folgenden Abschnitten werden diastereoselektive und enantioselektive Synthesen dieser Produkte beschrieben, und im letzten Abschnitt wird die Racematspaltung von Enantiomerenmischungen dargelegt.

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Synthesis of the 5-Demethyl-6-deoxy Analogue of Sporogen AO-1, a Sporogenic Substance ofAspergillus oryzae

Cited by 6 publications

References 2 publications

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors

Enantioselektive Synthese von Robinson‐Anellierungsprodukten und Michael‐Addukten als Vorstufen

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