Bioactive Bis-naphtho-γ-pyrones from Rice False
Smut Pathogen Ustilaginoidea virens
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Abstract
Ustilaginoidins
were bis-naphtho-γ-pyrones mycotoxins possessing
an a<i>R</i> configuration of the chiral axis previously
reported from the false smut balls of rice infected by the fungal
pathogen Ustilaginoidea virens. To
investigate the chemical diversity of these metabolites and their
bioactivities, we fermented this fungus on solid rice media, which
afforded the isolation of 13 ustilaginoidins, including seven new
compounds, namely ustilaginoidins K–P, <b>1</b>–<b>6</b>, and E<sub>1</sub>, <b>7</b>, together with the known
ustilaginoidins A, <b>8</b>, D, <b>9</b>, E, <b>10</b>, F, <b>11</b>, and G, <b>12</b>, and isochaetochromin
B<sub>2</sub>, <b>13</b>. The structures of the new compounds
were elucidated by using (1D, 2D) NMR, high-resolution mass spectrometry,
UV, and circular dichroism, as well as by comparison with the literature
data. A plausible biosynthesis pathway was proposed for these dimeric
polyketides. The isolated compounds were evaluated for their antibacterial,
cytotoxic, and radicle elongation inhibitory activities. Ustilaginoidins
K, <b>1</b> and L, <b>2</b> showed cytotoxic activities
on the A2780 human ovarian cancer cell line with IC<sub>50</sub> values
of 4.18 and 7.26 μM, respectively. Ustilaginoidins N, <b>4</b>, D, <b>9</b>, E, <b>10</b>, and G, <b>12</b> were active against the tested pathogenic bacteria with MIC values
in the range of 16–64 μg/mL. Ustilaginoidins O, <b>5</b>, E, <b>10</b>, and F, <b>11</b>, and isochaetochromin
B<sub>2,</sub> <b>13</b> displayed moderate inhibitory activity
on the radicle elongation of rice seeds