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Tricalysiolide G and tricalysiols A and B: rearranged ent-kaurane-type and ent-kaurane-type diterpenoids from the leaves of Tricalysia dubia (Lindl.) Ohwi

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Abstract

Three rearranged ent-kaurane diterpenes with the cafestol-type framework have been isolated from the leaves of Tricalysia dubia. Two were found to be known diterpenoids, tricalysiolides B and C. Tricalysiolide B was isolated as colorless prisms in this experiment and its three-dimensional structure was determined by X-ray crystallography. The remaining diterpenoid was a new compound and was named tricalysiolide G. Two new ent-kaurane-type diterpenoids, given the trivial names tricalysiol A and tricalysiol B, were also isolated. The structures of the new compounds were elucidated from spectroscopic evidence.

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References

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Acknowledgments

The authors are grateful for access to the superconducting NMR instrument in the Analytical Center of Molecular Medicine of the Graduate School of Biomedical Sciences, Hiroshima University. This work was supported in part by grant-in-aids from the Ministry of Education, Science, Sports, Culture and Technology of Japan (No. 18590117 and 18032050). Thanks are also due to the Astellas Foundation for financial support with a Research Grant on Medicinal Resources.

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Authors and Affiliations

  1. Department of Pharmacognosy, Graduate School of Biomedical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan

    Dong-Hui He, Katsuyoshi Matsunami & Hideaki Otsuka

  2. Subtropical Field Science Center, Faculty of Agriculture, University of the Ryukyus, 1 Senbaru, Nishihara-cho, Nakagami-gun, Okinawa, 903-0213, Japan

    Takakazu Shinzato

  3. Iriomote Station, Tropical Biosphere Research Center, University of the Ryukyus, 870 Aza Uehara, Taketomi-cho, Yaeyama-gun, Okinawa, 907-1541, Japan

    Mitsunori Aramoto

  4. Medicinal Chemistry Research Institute, Otsuka Pharmaceutical Co. Ltd, 463-10 Kagasuno, Kawauchi-cho, Tokushima, 771-0192, Japan

    Masahiko Bando

  5. Faculty of Integrated Arts and Sciences, The University of Tokushima, 1-1 Minamijosanjima-cho, Tokushima, 770-8502, Japan

    Yoshio Takeda

Authors
  1. Dong-Hui He
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  2. Katsuyoshi Matsunami
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  3. Hideaki Otsuka
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  4. Takakazu Shinzato
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  5. Mitsunori Aramoto
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  6. Masahiko Bando
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  7. Yoshio Takeda
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Corresponding author

Correspondence to Hideaki Otsuka.

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He, DH., Matsunami, K., Otsuka, H. et al. Tricalysiolide G and tricalysiols A and B: rearranged ent-kaurane-type and ent-kaurane-type diterpenoids from the leaves of Tricalysia dubia (Lindl.) Ohwi. J Nat Med 61, 46–50 (2007). https://doi.org/10.1007/s11418-006-0016-8

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  • DOI: https://doi.org/10.1007/s11418-006-0016-8

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