New Tryptophan Metabolites from Cultures of the Lipophilic Yeast Malassezia furfur

Helvetica Chimica Acta
2005.0

Abstract

<jats:title>Abstract</jats:title><jats:p>Eleven new indole alkaloids were isolated from cultures of the human pathogenic yeast <jats:italic>Malassezia furfur</jats:italic> after addition of <jats:sc>L</jats:sc>‐tryptophan as the sole N‐source: pityriacitrin B (<jats:bold>2</jats:bold>), the malassezindoles A (<jats:bold>3</jats:bold>) and B (<jats:bold>4</jats:bold>), malassezialactic acid (<jats:bold>6</jats:bold>), the malasseziazoles A (<jats:bold>7</jats:bold>), B (<jats:bold>8</jats:bold>), and C (<jats:bold>9</jats:bold>), pityriazole (<jats:bold>10</jats:bold>), malasseziacitrin (<jats:bold>11</jats:bold>), and malassezione (<jats:bold>12</jats:bold>), along with the known <jats:sc>d‐</jats:sc>indole‐3‐lactic acid (=(<jats:italic>α</jats:italic>R)‐<jats:italic>α</jats:italic>‐hydroxy‐1<jats:italic>H</jats:italic>‐indole‐3‐propanoic acid <jats:bold>5</jats:bold>), and 2‐hydroxy‐1‐(1<jats:italic>H</jats:italic>‐indol‐3‐yl)ethanone (<jats:bold>13</jats:bold>). The structural elucidation of these compounds was performed by spectroscopic methods (MS as well as 1D‐ and 2D‐NMR). The biogenetic relationships (<jats:italic>Scheme</jats:italic>) and biological activities of the new metabolites are discussed.

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