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Isoheleproline: a new amino acid-sesquiterpene adduct from Inula helenium

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Abstract

A new amino acid–sesquiterpene adduct, isoheleproline (1), was isolated from the roots of Inula helenium (elecampane), together with four known sesquiterpene lactones (2–5). The planar configuration of 1 was elucidated on the basis of spectroscopic data analysis, and the relative configuration of 1 was determined by performing a detailed analysis of NOESY correlations and comparing its physicochemical data with the d- and l-proline adducts of 2 obtained by Michael addition. This is the first report of a new amino acid–sesquiterpene adduct from Inula plants.

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Acknowledgments

This study was supported by a Health and Labour Science Research Grant.

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Authors and Affiliations

  1. Division of Pharmacognosy, Phytochemistry and Narcotics, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501, Japan

    Kazumasa Zaima, Daigo Wakana, Yukie Kumeta, Hiroyuki Kamakura, Takuro Maruyama & Yukihiro Goda

  2. Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501, Japan

    Yosuke Demizu & Masaaki Kurihara

Authors
  1. Kazumasa Zaima
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  2. Daigo Wakana
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  3. Yosuke Demizu
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  4. Yukie Kumeta
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  5. Hiroyuki Kamakura
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  6. Takuro Maruyama
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  7. Masaaki Kurihara
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  8. Yukihiro Goda
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Correspondence to Yukihiro Goda.

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Zaima, K., Wakana, D., Demizu, Y. et al. Isoheleproline: a new amino acid-sesquiterpene adduct from Inula helenium . J Nat Med 68, 432–435 (2014). https://doi.org/10.1007/s11418-013-0806-8

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  • DOI: https://doi.org/10.1007/s11418-013-0806-8

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