4 research outputs found
Condensation of Macrocyclic Polyketides Produced by <i>Penicillium</i> sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway
Application of a refined procedure
of experimental design and chemometric
analysis to improve the production of curvularin-related polyketides
by a marine-derived <i>Penicillium</i> sp. DRF2 resulted
in the isolation and identification of cyclothiocurvularins <b>6</b>ā<b>8</b> and cyclosulfoxicurvularins <b>10</b> and <b>11</b>, novel curvularins condensed with a
mercaptolactate residue. Two additional new curvularins, <b>3</b> and <b>4</b>, are also reported. The structures of the sulfur-bearing
curvularins were unambiguously established by analysis of spectroscopic
data and by X-ray diffraction analysis. Analysis of stable isotope
feeding experiments with [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine confirmed the presence of the 2-hydroxy-3-mercaptopropanoic
acid residue in <b>6</b>ā<b>8</b> and the oxidized
sulfoxide in <b>10</b> and <b>11</b>. Cyclothiocurvularins
A (<b>6</b>) and B (<b>7</b>) are formed by spontaneous
reaction between 10,11-dehydrocurvularin (<b>2</b>) and mercaptopyruvate
(<b>12</b>) obtained by transamination of cysteine. High ratios
of [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine
incorporation into cyclothiocurvularin B (<b>7</b>), the isolation
of two diastereomers of cyclothiocurvularins, the lack of cytotoxicity
of cyclothiocurvularin B (<b>7</b>) and its methyl ester (<b>8</b>), and the spontaneous formation of cyclothiocurvularins
from 10,11-dehydrocurvularin and mercaptopyruvate provide evidence
that the formation of cyclothiocurvularins may well correspond to
a 10,11-dehydrocurvularin detoxification process by <i>Penicillium</i> sp. DRF2
Condensation of Macrocyclic Polyketides Produced by <i>Penicillium</i> sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway
Application of a refined procedure
of experimental design and chemometric
analysis to improve the production of curvularin-related polyketides
by a marine-derived <i>Penicillium</i> sp. DRF2 resulted
in the isolation and identification of cyclothiocurvularins <b>6</b>ā<b>8</b> and cyclosulfoxicurvularins <b>10</b> and <b>11</b>, novel curvularins condensed with a
mercaptolactate residue. Two additional new curvularins, <b>3</b> and <b>4</b>, are also reported. The structures of the sulfur-bearing
curvularins were unambiguously established by analysis of spectroscopic
data and by X-ray diffraction analysis. Analysis of stable isotope
feeding experiments with [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine confirmed the presence of the 2-hydroxy-3-mercaptopropanoic
acid residue in <b>6</b>ā<b>8</b> and the oxidized
sulfoxide in <b>10</b> and <b>11</b>. Cyclothiocurvularins
A (<b>6</b>) and B (<b>7</b>) are formed by spontaneous
reaction between 10,11-dehydrocurvularin (<b>2</b>) and mercaptopyruvate
(<b>12</b>) obtained by transamination of cysteine. High ratios
of [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine
incorporation into cyclothiocurvularin B (<b>7</b>), the isolation
of two diastereomers of cyclothiocurvularins, the lack of cytotoxicity
of cyclothiocurvularin B (<b>7</b>) and its methyl ester (<b>8</b>), and the spontaneous formation of cyclothiocurvularins
from 10,11-dehydrocurvularin and mercaptopyruvate provide evidence
that the formation of cyclothiocurvularins may well correspond to
a 10,11-dehydrocurvularin detoxification process by <i>Penicillium</i> sp. DRF2
Condensation of Macrocyclic Polyketides Produced by <i>Penicillium</i> sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway
Application of a refined procedure
of experimental design and chemometric
analysis to improve the production of curvularin-related polyketides
by a marine-derived <i>Penicillium</i> sp. DRF2 resulted
in the isolation and identification of cyclothiocurvularins <b>6</b>ā<b>8</b> and cyclosulfoxicurvularins <b>10</b> and <b>11</b>, novel curvularins condensed with a
mercaptolactate residue. Two additional new curvularins, <b>3</b> and <b>4</b>, are also reported. The structures of the sulfur-bearing
curvularins were unambiguously established by analysis of spectroscopic
data and by X-ray diffraction analysis. Analysis of stable isotope
feeding experiments with [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine confirmed the presence of the 2-hydroxy-3-mercaptopropanoic
acid residue in <b>6</b>ā<b>8</b> and the oxidized
sulfoxide in <b>10</b> and <b>11</b>. Cyclothiocurvularins
A (<b>6</b>) and B (<b>7</b>) are formed by spontaneous
reaction between 10,11-dehydrocurvularin (<b>2</b>) and mercaptopyruvate
(<b>12</b>) obtained by transamination of cysteine. High ratios
of [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine
incorporation into cyclothiocurvularin B (<b>7</b>), the isolation
of two diastereomers of cyclothiocurvularins, the lack of cytotoxicity
of cyclothiocurvularin B (<b>7</b>) and its methyl ester (<b>8</b>), and the spontaneous formation of cyclothiocurvularins
from 10,11-dehydrocurvularin and mercaptopyruvate provide evidence
that the formation of cyclothiocurvularins may well correspond to
a 10,11-dehydrocurvularin detoxification process by <i>Penicillium</i> sp. DRF2
Condensation of Macrocyclic Polyketides Produced by <i>Penicillium</i> sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway
Application of a refined procedure
of experimental design and chemometric
analysis to improve the production of curvularin-related polyketides
by a marine-derived <i>Penicillium</i> sp. DRF2 resulted
in the isolation and identification of cyclothiocurvularins <b>6</b>ā<b>8</b> and cyclosulfoxicurvularins <b>10</b> and <b>11</b>, novel curvularins condensed with a
mercaptolactate residue. Two additional new curvularins, <b>3</b> and <b>4</b>, are also reported. The structures of the sulfur-bearing
curvularins were unambiguously established by analysis of spectroscopic
data and by X-ray diffraction analysis. Analysis of stable isotope
feeding experiments with [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine confirmed the presence of the 2-hydroxy-3-mercaptopropanoic
acid residue in <b>6</b>ā<b>8</b> and the oxidized
sulfoxide in <b>10</b> and <b>11</b>. Cyclothiocurvularins
A (<b>6</b>) and B (<b>7</b>) are formed by spontaneous
reaction between 10,11-dehydrocurvularin (<b>2</b>) and mercaptopyruvate
(<b>12</b>) obtained by transamination of cysteine. High ratios
of [Uā<sup>13</sup>C<sub>3</sub><sup>15</sup>N]-l-cysteine
incorporation into cyclothiocurvularin B (<b>7</b>), the isolation
of two diastereomers of cyclothiocurvularins, the lack of cytotoxicity
of cyclothiocurvularin B (<b>7</b>) and its methyl ester (<b>8</b>), and the spontaneous formation of cyclothiocurvularins
from 10,11-dehydrocurvularin and mercaptopyruvate provide evidence
that the formation of cyclothiocurvularins may well correspond to
a 10,11-dehydrocurvularin detoxification process by <i>Penicillium</i> sp. DRF2