Absolute configurations of asperlin, a metabolite of Aspergillus nidulans, and its related compounds.

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概要

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• The structures of asperlin (<B>1</B>) C<SUB>10</SUB>H<SUB>12</SUB>O<SUB>5</SUB> and asperlinol (<B>2</B>) C<SUB>10</SUB>H<SUB>14</SUB>O<SUB>6</SUB>, isolated from <I>Aspergillus nidulans</I>, and a chloro derivative of asperlin (<B>3</B>) C<SUB>10</SUB>H<SUB>13</SUB>O<SUB>5</SUB>Cl have been studied by the X-ray diffraction method. The absolute configuration of <B>3</B> has been determined by the Bijvoet method by utilizing the anomalous scattering of chlorine atom for Cu <I>K</I>α radiation. The present analysis has verified the configurations of the atoms in an αβ-unsaturated δ-lactone ring as suggested by spectroscopy. In each compound, the acetoxyl group occupies a quasi-axial and the three-carbon side chain a quasi-equatorial position on the lactone ring. All the crystals are orthorhombic, space group P2<SUB>1</SUB>2<SUB>1</SUB>2<SUB>1</SUB>with <I>Z</I>=4. The cell dimensions are <I>a</I>=26.536, <I>b</I>=5.955, <I>c</I>=6.973 Å for <B>1</B>, <I>a</I>=25.496, <I>b</I>=7.097, <I>c</I>=6.329 Å for <B>2</B>, and <I>a</I>=26.050, <I>b</I>=5.899, <I>c</I>=7.548 Å for <B>3</B>. The structures of <B>1</B>, <B>2</B>, and <B>3</B> were refined by the block-diagonal least-squares method to <I>R</I>=0.068 for 1084 reflections, <I>R</I>=0.056 for 1127 reflections, and <I>R</I>=0.051 for 831 reflections, respectively.

• 公益社団法人 日本化学会の論文

著者

• Fukuyama Keiichi

  Faculty Of Engineering Tottori University

• Hatsuda Yuichi

  Faculty Of Agriculture Tottori University

• Hamasaki Takashi

  Faculty Of Agriculture Tottori University

• Hatsuda Yuichi

  Faculty of Agriculture, Tottori University

• KATSUBE Yukiteru

  Faculty of Engineering, Tottori University

• Noda Akihiro

  Faculty of Agriculture, Tottori University

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