Naturally Occurring Coumaranochroman-4-Ones: A New Class Of Isoflavonoids From Lupins And Jamaican Dogwood

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  • Satoshi Tahara
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University, Kita-ku, Sapporo 060, Japan
  • Masaaki Moriyam
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University, Kita-ku, Sapporo 060, Japan
  • Sunao Orihara
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University, Kita-ku, Sapporo 060, Japan
  • John L. Ingham
    Department of Food Science, University of Reading, P. O. Box 226, Whiteknights, Reading RG 6 2 AP, England
  • Jun Kawabata
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University, Kita-ku, Sapporo 060, Japan
  • Junya Mizutani
    Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University, Kita-ku, Sapporo 060, Japan

書誌事項

公開日
1991-06-01
権利情報
  • http://creativecommons.org/licenses/by-nc-nd/3.0/
DOI
  • 10.1515/znc-1991-5-602
公開者
Walter de Gruyter GmbH

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説明

<jats:p>A further investigation of the isoflavonoid components of Piscidia erythrina, Lupinus alhus and L. luteus has revealed the presence of 3-hydroxy- and 3-methoxy-coumaranochroman- 4-ones. These compounds are the first known representatives of a new type of naturally occurring isoflavonoid. Using a combination of chemical and spectroscopic methods, the com pounds were identified as 3,5,7,4′-tetrahydroxy-5′-methoxy-3′-(3,3-dimethylallyl)coumaranochroman- 4-one (piscerythrol, 1), 3,5,7,4′-tetrahydroxy-6,3′-di(3,3-dimethylallyl)coumaranochroman- 4-one (lupinol A, 3), 5,7,4′-trihydroxy-3-methoxy-6,3′-di(3,3-dimethylallyl)- coumaranochroman-4-one (lupinol B, 6) and 3,5,7,4′-tetrahydroxy-6-(3,3-dimethylallyl)- coumaranochroman-4-one (lupinol C, 7). All four isoflavonoids were found to have the cis relative configuration at C-2/C-3. Possible biogenetic relationships between the coumaranochroman- 4-ones and other isoflavonoids (isoflavones and coumaronochrom ones) found in Piscidia and Lupinus are briefly discussed</jats:p>

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