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Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum.

ABSTRACT: Spiroscytalin (1), a new tetramic acid that possesses an uncommon spiro-ring fusion between a polyketide-derived octalin ring system and a 2,4-pyrrolidinedione, along with two known compounds, leporin B (2) and purpactin A (3), were isolated from a solid phase culture of the fungus Scytalidium cuboideum (MSX 68345). The molecular connectivity of 1-3 was determined using NMR spectroscopy and mass spectrometry. The relative configurations of 1 and 2 were determined by NOESY experiments. The absolute configuration of 1 was determined by electronic circular dichroism (ECD) via a combination of experimental measurements and computational calculations. While leporin B was known, it displayed activities that had not been reported previously, including cytotoxicity against three human tumor cell lines and antibacterial activity against Candida albicans and Staphylococcus aureus.

SUBMITTER: Sy-Cordero AA

PROVIDER: S-EPMC4624200 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum.

Sy-Cordero Arlene A AA Figueroa Mario M Raja Huzefa A HA Meza Aviña Maria Elena ME Croatt Mitchell P MP Adcock Audrey F AF Kroll David J DJ Wani Mansukh C MC Pearce Cedric J CJ Oberlies Nicholas H NH

Tetrahedron 20151101 47

Spiroscytalin (1), a new tetramic acid that possesses an uncommon spiro-ring fusion between a polyketide-derived octalin ring system and a 2,4-pyrrolidinedione, along with two known compounds, leporin B (2) and purpactin A (3), were isolated from a solid phase culture of the fungus Scytalidium cuboideum (MSX 68345). The molecular connectivity of 1-3 was determined using NMR spectroscopy and mass spectrometry. The relative configurations of 1 and 2 were determined by NOESY experiments. The absolu ...[more]

PMID: 26525642

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Project description:Pigments from wood-decay fungi (specifically spalting fungi) have a long history of use in wood art, and have become relevant in modern science due to their longevity and colorfastness. They are presently under investigation as colorants for wood, bamboo, oils, paints and textiles. Major hurdles to their commercialization have been color repeatability (in that the same strain of the same species of fungus may produce different colors over time), and the binding of the pigments to glass storage containers. This is persistent as they do not naturally exist in a loose form. Due to these issues, the 'standard' color for each was historically determined not by the amount of pigment, but by the color in a solution of dichloromethane (DCM), using the CIE L*a*b colorspace. This method of standardization severely limited the use of these pigments in industrial applications, as without a dry form, standard methodologies for repeatable color processing into other materials could not be easily implemented. Recent studies have developed a method to crystalize the red pigment from Scytalidium cuboideum (Sacc. & Ellis) Sigler & Kang, producing a highly pure (99%) solid crystal named 'Dramada'. Herein a method is detailed to compare the molarity of this crystallized pigment to variations in the color, to determine a color saturation curve (by weight) for the pigment from S. cuboideum in DCM and acetone. The molarities for this experiment ranged from 0.024 mM to 19 mM. Each molarity was color read and assigned a CIEL*a*b* value. The results showed that there was a correlation between the molarity and color difference, with the maximum red color occurring between 0.73 mM and 7.3 mM in DCM and between 0.97 mM to 0.73 mM in acetone. Extremely low molarities of pigment produced strong coloration in the solvent, and changes in molarity significantly affected the color of the solution. Having a saturation and color curve for the crystal 'Dramada' from S. cuboideum will allow for the reliable production of distinct colors from a known quantity (by weight) of pigment, erasing the final hurdle towards commercial development of the crystallized pigment from S. cuboideum as an industrial dyestuff.

Dataset Information

Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum.

Publications

Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum.

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