Tigloylshikonin, a New Minor Shikonin Derivative, from the Roots and the Commercial Root Extract of Lithospermum erythrorhizon

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  • Ito Yusai
    Division of Food Additives, National Institute of Health Sciences
  • Onobori Kenichi
    Division of Food Additives, National Institute of Health Sciences
  • Yamazaki Takeshi
    Division of Food Additives, National Institute of Health Sciences
  • Kawamura Yoko
    Division of Food Additives, National Institute of Health Sciences

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Tigloylshikonin, a new shikonin derivative esterified with tiglic acid ((E)-2-methylbut-2-enoic acid), was isolated as a minor pigment from a food colorant “Shikon color,” a commercial root extract from Lithospermum erythrorhizon SIEBOLD et ZUCCARINI. The structure of tigloylshikonin was elucidated using 1H, 13C, the difference nuclear Overhauser effect (NOE), and 2D NMR techniques. Its stereochemistry was determined by chiral-phase HPLC analysis. Tigloylshikonin was also found in the roots of L. erythrorhizon, which indicated that this new shikonin derivative is a typical component of naphthoquinone pigments in the roots of L. erythrorhizon.

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