Studies in mycological chemistry. Part XXIII. The structure of flavomannin, a metabolite of Penicillium wortmanni Klöck

Atherton, John H.; Bycroft, Barrie W.; Roberts, John C.; Roffey, Partick; Wilcox, M. E.

doi:10.1039/j39680002560

Cited by 13 publications

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“…28 It was recently discovered by Bara et al that the Talaromyces wortmannii fungus, an endosymbiont of Egyptian Aloe vera (Asphodeloideae), contained several bioactive atropisomeric compounds; and the group conducted extensive studies to determine any potential medicinal application. 29 Analysis of the isolated products 26 found that they were similar to that of previously-reported avomannin, 30 allowing for general structural assignment (Fig. 5, Compounds 11 and 12).…”

Section: Flavomannins and Talaromannins: Potential Novel Route For An...supporting

confidence: 74%

“…Further analysis indicated these were heterodimers composed of one atrochrysone unit, and one unit of either an ether derivative of atrochrysone, named flavomannins C and D ( ECD analysis of the compounds resulted in three pairs of almost mirror-image spectra, suggesting they are atropdiastereomers. Given that the [α] D of one of the compounds matched the value previously reported for flavomannin A (11), 30 the corresponding compound was thought to be its atropdiastereomer, and dubbed flavomannin B (12). Using TD-DFT (B3LYP, BH&HLYP, PBE0/TZVP) ECD calculation protocols, the simulated ECD spectra of both atropisomeric configurations matched well with the experimental ECD data, assuming identical point chirality at C3/C3ʹ.…”

Section: Flavomannins and Talaromannins: Potential Novel Route For Ansupporting

confidence: 74%

“…5 atropdiastereomers. Given that the [a] D of one of the compounds matched the value previously reported for avomannin A (11), 30 the corresponding compound was thought to be its atropdiastereomer, and dubbed avomannin B (12). Using TD-DFT (B3LYP, BH&HLYP, PBE0/TZVP) ECD calculation protocols, the simulated ECD spectra of both atropisomeric congurations matched well with the experimental ECD data, assuming identical point chirality at C3/C3 0 .…”

Section: Flavomannins and Talaromannins: Potential Novel Route For An...supporting

confidence: 71%

“…However, the two spectra did not appear as the expected mirror-images of each other; instead they were both similar to the ECD of 33, a phenomenon attributed to the symmetry of the 9-carbazole, the orientation of which is similar Fig. 10 The absolute structures of marinopyrroles A (28) and B ( 29), with their composite monomeric precursor monodeoxypyoluteorin (30).…”

Section: Dixiamycins: Atropisomeric N-c and N-n Coupled Dimers From M...mentioning

confidence: 98%

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A twist of nature – the significance of atropisomers in biological systems

2015

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. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583. A twist of nature-the significance of atropisomers in biological systems AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized. AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

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Section: Flavomannins and Talaromannins: Potential Novel Route For An...supporting

confidence: 74%

Section: Flavomannins and Talaromannins: Potential Novel Route For Ansupporting

confidence: 74%

Section: Flavomannins and Talaromannins: Potential Novel Route For An...supporting

confidence: 71%

Section: Dixiamycins: Atropisomeric N-c and N-n Coupled Dimers From M...mentioning

confidence: 98%

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A twist of nature – the significance of atropisomers in biological systems

2015

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“…On the other hand, mitorubrin ( 2 ), mitorubrinol ( 3 ), and mitorubrinol acetate ( 5 ) were isolated as yellow pigments on the ascomata of T. emodensis , T. hachijoensis , and T. wortmannii var. sublevisporus , along with duclauxin from the former fungus, FDM from the middle, and flavomanin from the latter. The optical rotation of mitorubrin derivatives from the three above fungi were all positive (Table ).…”

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confidence: 97%

Mitorubrin Derivatives on Ascomata of Some Talaromyces Species of Ascomycetous Fungi

et al. 1999

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Two groups, producers of (+)- and (-)-mitorubrin derivatives, coexist in the series Lutei of the genus Talaromyces. The optical rotations of mitorubrins from T. emodensis, T. hachijoensis, and T. wortmannii var. sublevisporus, which produced mitorubrinol acetate (5), were all positive, whereas those from T. austrocalifornicus and T. convolutus, which produced mitorubrinal (3) and mitorubrinic acid (4), were all negative.

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Chemistry and Bioactivities of Secondary Metabolites from the Genus Talaromyces

Lan

2020

Chemistry & Biodiversity

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Fungi have especially captured the interest and fascination of natural product chemists in that they produce a dizzying array of natural organic molecules with many unique functional groups and atom arrangements. In this review, we focus on the genus Talaromyces (Trichocomaceae) which has been a hot spot of natural product studies over the last three decades. This review summarized the discovery, structures, and bioactivities of various classes of 151 compounds isolated from both terrestrial and marine derived fungal strains of the genus Talaromyces reported from 1994 to 2019.

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Studies in mycological chemistry. Part XXIII. The structure of flavomannin, a metabolite of Penicillium wortmanni Klöck

Abstract: dim et hy I -2,Z'b ia n t h race n e-8 (7H) ,8' (7'H)d i o n e ( XI1 Ia) .

Cited by 13 publications

References 0 publications

A twist of nature – the significance of atropisomers in biological systems

A twist of nature – the significance of atropisomers in biological systems

Mitorubrin Derivatives on Ascomata of Some Talaromyces Species of Ascomycetous Fungi

Chemistry and Bioactivities of Secondary Metabolites from the Genus Talaromyces

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