Skip to main content
SpringerLink
Log in
Book cover

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products pp 77–157Cite as

Diterpenoids of Rabdosia Species

  • Chapter

Abstract

Members of the genus Rabdosia (Labiatae) grow naturally in eastern Asia, but only species found in Japan and China heve been investigated chemically. In Japan, the leaves of Rabdosia japonica and R. trichocarpa are used as a common household medicine for gastrointestinal disorders. The drug is called “enmei-so”, which means “grass effective for prolongation of human life”. In China, some Rabdosia species are used as antitumor and antiphlogistic agents. Species now included in the genus were formerly referred to Plectranthus and Isodon, but since 1972 the genus name Rabdosia has been adopted in accordance with a recommendation by Hara (1).

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Hara, H.: On the Asiatic Species of the Genus Rabdosia (Labiatae). J. Japan Bot. (Shokubutsu Kenkyu Sasshi) 47, 198 (1972).

    Google Scholar 

  2. Yagi, S.: On “Plectranthin”, a Bitter Principle Derived from Plectranthus glaucocalyx Maxim, var. japonicus Maxim. J. Kyoto Med. Soc. 7, 30 (1910).

    Google Scholar 

  3. Tanabe, S., and H. Nishikawa: Screening Tests for Antibiotic Action of Plant Extracts Jpn. J. Bact. 9, 475 (1954).

    CAS  Google Scholar 

  4. Fujita, E.: The Chemistry on Diterpenoids of Isodon Species. Bull. Inst. Chem. Res., Kyoto Univ. 46, 161 (1968).

    CAS  Google Scholar 

  5. Fujita, E.: Diterpenoids of Enmei-so. Kagaku no Ryoiki, Zokan 86 (Chemistry of Natural Products’68), 1968, 173.

    Google Scholar 

  6. Fujita, E., and T. Fujita: The Constituents of Enmei-so (Isodon japonicus Hara and I. trichocarpus Kudo). Proc. Symp. Wakan-Yaku 9, 1 (1975).

    Google Scholar 

  7. Fujita, E., Y. Nagao, and M. Node: Diterpenoids of Isodon and Teucrium Plants. Heterocycles 5, 793 (1976).

    CAS  Google Scholar 

  8. Fujita, E., T. Fujita, and M. Shibuya: Isolation of Enmein and its 3-Acetate from Isodon japonicus. Chem. Commun. 1966, 297; b) Isolation of Enmein and its 3-Acetate from Isodon japonicus Hara. Yakugaku Zasshi 87, 1076 (1967).

    Google Scholar 

  9. Ikeda, T., and S. Kanatomo: Study of Bitter Principles of Isodon trichocarpus. I. Yakugaku Zasshi 78, 1128 (1958).

    CAS  Google Scholar 

  10. Kanatomo, S.: Alkaline Decomposition of Enmein. Chem. Pharm. Bull. (Japan) 6, 680 (1958).

    CAS  Google Scholar 

  11. Naya, K.: Studies on Bitter Principles in Plants (1 st Report). A Bitter Principle in Isodon trichocarpus “Isodonin”. Nippon Kagaku Kaishi 79, 885 (1958).

    CAS  Google Scholar 

  12. Takahashi, M., T. Fujita, and Y. Koyama: Studies on the Components of Isodon japonicus (Burm.) Hara and I. trichocarpus (Maxim.) Kudo. Yakugaku Zasshi 78, 699 (1958).

    CAS  Google Scholar 

  13. Takahashi, M., T. Fujita, and Y. Koyama: Components of Isodon japonicus (Burm.) Hara and I. trichocarpus (Maxim.) Kudo. II. On the Reduction of Enmein and its Derivatives. Yakugaku Zasshi 80, 594 (1960).

    CAS  Google Scholar 

  14. Takahashi, M., T. Fujita, and Y. Koyama: Studies on the Components of Isodon japonicus (Burm.) Hara and I. trichocarpus (Maxim.) Kudo. III. On the Optical Rotatory Dispersion of Dihydroenmein. Yakugaku Zasshi 80, 696 (1960).

    CAS  Google Scholar 

  15. Kanatomo, S.: Studies on Bitter Principles of Isodon trichocarpus. III. Baryta Distillation of Enmein. Yakugaku Zasshi 81, 1437 (1961).

    CAS  Google Scholar 

  16. Takahashi, M.: On the Structure of Enmein. Yakugaku Zasshi 81, 1049 (1961).

    Google Scholar 

  17. Kubota, T., T. Matsuura, T. Tsutsui, and K. Naya: Chemical Constitution of Enmein, a Bitter Principle from Isodon trichocarpus Kudo. Bull. Chem. Soc. Japan 34, 1737 (1961). Idem, Nippon Kagaku Kaishi 84, 353 (1963).

    CAS  Google Scholar 

  18. Kubota, T., T. Matsuura, T. Tsutsui, S. Uyeo, M. Takahashi, H. Irie, A. Numata, T. Fujita, T. Okamoto, M. Natsume, Y. Kawazoe, K. Sudo, T. Ikeda, M. Tomoeda, S. Kanatomo, T. Kosuge, and K. Adachi: The Constitution and Stereochemistry of Enmein. Tetrahedron Letters 1964, 1243.

    Google Scholar 

  19. Kubota, T., T. Matsuura, T. Tsutsui, S. Uyeo, H. Irie, A. Numata, T. Fujita, and T. Suzuki: Constitution and Stereochemistry of Enmein, A Diterpene from Isodon trichocarpus Kudo, Tetrahedron 22, 1659 (1966).

    Google Scholar 

  20. Iitaka, Y., and M. Natsume: The X-ray Study of Acetyl-bromoacetyldihydroenmein. Tetrahedron Letters 1964, 1257; b) The Chrystal and Molecular Structure of Acetylbromoacetyldihydroenmein. Acta Crystallogr. 20, 197 (1966).

    Google Scholar 

  21. Uyeo, S.: The Structure & Stereochemistry of the Diterpenoid Enmein. J. Sci. Indust. Res. (India) 26, 386 (1967).

    CAS  Google Scholar 

  22. Li, G., Y. Wang, Z. Xu, P. Zhang, and W. Zhao: Studies on Chemical Constituents of Isodon amethystoides (Benth) C Y Wu et Hsuan. Yaoxue Xuebao 16, 667 (1981) [Chem. Abstr. 96, 31688s (1982)].

    Google Scholar 

  23. Wang, X., Z. Wang, P. C. Shi, and B. Zhou: Wangzaozine A, a Novel Diterpenoid from Isodon amethystoides. Zhongcaoyao 13, 12 (1982) [Chem. Abstr. 98, 50318d (1983)].

    CAS  Google Scholar 

  24. Chang, T., M. Xu, Y. Lin, and J. Shi: Study on Antitumor Constituents of Rabdosia amethystoides Hara. Yaoxue Tongbao 16, 57 (1981) [Chem. Abstr. 96,118987n (1982)].

    Google Scholar 

  25. Isobe, T., T. KAMIKAWA, and T. KUBOTA: Bitter Components from the Leaves of Isodon Species. Nippon Kagaku Kaishi 1972, 2143.

    Google Scholar 

  26. Kubo, I., T. Kamikawa, T. Isobe, and T. Kubota: Structure of Effusin. Chem. Commun. 1980, 1206.

    Google Scholar 

  27. Fujita, T., Y. Takeda, T. Shingu, and A. Ueno: Structures of Effusanins, Antibacterial Diterpenoids from Rabdosia effusa. Chemistry Letters 1980, 1635.

    Google Scholar 

  28. Wang, Z., and Y. Xu: New Diterpenoid Constituents of Rabdosia eriocalyx. I. Yunnan Zhiwu Yanjiu 4, 407 (1982) [Chem. Abstr. 98, 104285m (1983)].

    Google Scholar 

  29. Sun, H., X. Sun, Z. Lin, Y. Xu, Y. Minami, T. Marunaka, and T. Fujita: Excisanin A and B, New Diterpenoids from Rabdosia excisa. Chemistry Letters 1981, 753.

    Google Scholar 

  30. Kubo, I., K. Nakanishi, T. Kamikawa, T. Isobe, and T. Kubota: The Structure of Inflexin. Chemistry Letters 1977, 99.

    Google Scholar 

  31. Fujita, T., Y. Takeda, E. Yuasa, A. Okumura, T. Shingu, and T. Yokoi: Structure of Inflexinol, a New Cytotoxic Diterpene from Rabdosia inflexa. Phytochem. 21, 903 (1982).

    CAS  Google Scholar 

  32. Fujita, E., T. Fujita, and M. Shibuya: Diterpenoids Constituents of Isodon trichocarpus and Isodon japonicus. Tetrahedron Letters 1977, 3153.

    Google Scholar 

  33. Fujita, E., T. Fujita, and M. Shibuya: Terpenoids. IX. The Structure and Absolute Configuration of Isodocarpin, a New Diterpenoid from Isodon trichocarpus Kudo and I. japonicus Hara. Chem. Pharm. Bull. (Japan) 16, 1573 (1968).

    CAS  Google Scholar 

  34. Fujita, E., T. Fujita, Y. Okada, S. Nakamura, and M. Shibuya: Terpenoids. XXI. The Structure and Stereochemistry of Isodotricin, a Diterpenoid of Isodon trichocarpus and I. japonicus. Chem. Pharm. Bull. (Japan) 20, 2377 (1972).

    CAS  Google Scholar 

  35. Fujita, E., T. Fujita, and M. Shibuya: Terpenoids. VII. The Structure and Absolute Configuration of Nodosin, a New Diterpenoid of Isodon Species. Chem. Pharm. Bull. (Japan) 16, 509 (1968).

    CAS  Google Scholar 

  36. Fujita, E., T. Fujita, H. Katayama, and M. Shibuya: Oridonin, a New Diterpenoid from Isodon Species. Chem. Commun. 1967, 252; b) Fujita, E., T. Fujita, H. Katayama, M. Shibuya, and T. Shingu: Terpenoids. Part XV. Structure and Absolute Configuration of Oridonin Isolated from Isodon japonicus and Isodon trichocarpus. J. Chem. Soc. (C) 1970, 1674.

    Google Scholar 

  37. Fujita, E., M. Taoka, M. Shibuya, T. Fujita, and T. Shingu: Terpenoids. Part XXVII. Structure and Stereochemistry of Ponicidin, a Diterpenoid of Isodon japonicus. J. Chem. Soc., Perkin Trans. I 1973, 2277.

    Google Scholar 

  38. Fujita, E., T. Fujita, M. Taoka, H. Katayama, and M. Shibuya: The Structure and Absolute Configuration of Sodoponin and Epinodosinol, New Minor Diterpenoids of Isodon japonicus. Tetrahedron Letters 1970, 421; b) Terpenoids. XXIV. Isolation of Isodonal and Epinodosin from Isodon japonicus and Structure Elucidation of Sodoponin and Epinodosinol, Novel Diterpenoids of the Same Plant. Chem. Pharm. Bull. (Japan) 21, 1357 (1973).

    Google Scholar 

  39. Fujita, E., M. Taoka, Y. Nagao, and T. Fujita: Terpenoids. Part XXV. Structures and Absolute Configurations of Isodoacetal, Nodosinin, and Odonicin, Novel Diterpenoids of Isodon japonicus. J. Chem. Soc., Perkin Trans. I 1973, 1760.

    Google Scholar 

  40. Fujita, E., T. Fujita, and M. Shibuya: The Structures of Isodocarpin, Nodosin, Oridonin and Other Constituents of Isodon Trichocarpus and Isodon Japonicus. Abstract Papers of the 10th Symposium on the Chemistry of Natural Products. (Tokyo) P. 224 (1966).

    Google Scholar 

  41. Kubota, T., and I. Kubo: The Structures of Trichodonin and Epinodosin. Chem. Commun. 1968, 763.

    Google Scholar 

  42. Kubo, I., T. Kamikawa, and T. Kubota: Studies on Constituents of Isodon japonicus Hara. The Structures and Absolute Stereochemistry of Isodonal, Trichodonin and Epinodosin. Tetrahedron 30, 615 (1974).

    CAS  Google Scholar 

  43. Kubota, T., and I. Kubo: A New Bitter Principle of Isodon japonicus Hara. Tetrahedron Letters 1967, 3781.

    Google Scholar 

  44. Li, J., C. Liu, X. An, M. Wang, T. Zhao, S. Yu, and G. Zhao: Studies on the Antitumor Constituents of Rabdosia japonica (Burm. f) Hara. I. Structures of rabdosin A and B. Yaoxue Xuebao 17, 682 (1982) [Chem. Abstr. 98, 59801 p (1983)].

    Google Scholar 

  45. Liu, C., J. Li, X. An, R. Cheng, F. Shen, Y. Xu, and D. Wang: Studies on the Antitumor Constituents of Rabdosia japonica (Burm. f) Hara. II. Structure of Rabdosin C. Yaoxue Xuebao 17, 750 (1982) [Chem. Abstr. 98, 77989k (1983)].

    Google Scholar 

  46. Isobe, T., Y. Noda, and T. Kubota: The Constituents from Rabdosia japonica. Nippon Kagaku Kaishi 1982, 883.

    Google Scholar 

  47. Seo, S., Y. Tomita, and K. Tori: Biosynthesis of Oleanene- and Ursene-Type Triterpenes from [4-13C]Mevalonolactone and [l,2-13C2]Acetate in Tissue Cultures of Isodon japonicus Hara. J. Am. Chem. Soc. 103, 2075 (1981).

    CAS  Google Scholar 

  48. Xu, Y., X. Sun, H. Sun, Z. Lin, and D. Wang: Chemical Structures of glaucocalyxin A and B. Yun Nan Zhi Wu Yan Jiu 3, 283 (1981) [Chem. Abstr. 96, 100893 u (1982)].

    Google Scholar 

  49. Fujita, E., and M. Taoka: Terpenoids. XX. The Structure and Absolute Configuration of Lasiokaurin and Lasiodonin, New Diterpenoids from Isodon lasiocarpus (Hayata) Kudo. Chem. Pharm. Bull. (Japan) 20, 1752 (1972).

    CAS  Google Scholar 

  50. Fujita, E., M. Taoka, and T. Fujita: Terpenoids. XXVI. Structures of Lasiokaurinol and Lasiokaurinin, Two Novel Diterpenoids of Isodon lasiocarpus (Hayata) Kudo. Chem. Pharm. Bull. (Japan) 22, 280 (1974).

    CAS  Google Scholar 

  51. Takeda, Y., T. Fujita, and C.-C. Chen: Structures of Lasiocarpanin, Rabdolasional, and Carpalasionin: New Diterpenoids from Rabdosia lasiocarpa. Chemistry Letters 1982, 833.

    Google Scholar 

  52. Fujita, T., Y. Takeda, and T. Shingu: Longikaurin A and B; New, Biologically Active Diterpenoids from Rabdosia longituba. Chem. Commun. 1980, 205.

    Google Scholar 

  53. Fujita, T., Y. Takeda, and T. Shingu: Longikaurin C, D, E, and F; New Antibacterial Diterpenoids from Rabdosia longituba. Heterocycles 16, 227 (1981).

    CAS  Google Scholar 

  54. Cheng, P.-Y, M.-C. Hsu, Y.-T. Lin, and C.-C. Shih: Studies on the Antitumor Components of Rabdosia mactophylla (I.). Yao Hsueh T’ung Pao 15, 43 (1980) [Chem. Abstr. 95, 49257q (1981)].

    Google Scholar 

  55. Cheng, P., M. Xu, Y. Lin, and J. Shi: Antitumor Constituents of Rabdosia macrophylla (Migo). Yaoxue Xuebao 16, 796 (1981) [Chem. Abstr. 96, 48973d (1982)].

    CAS  Google Scholar 

  56. Cheng, P., M. Xu, Y. Lin, and J. Shi: Structure of Rabdophyllin G, an Antitumor Constituent of Rabdosia macrophylla. Yaoxue Tongbao 17, 174 (1982) [Chem. Abstr. 97, 115212r (1982)].

    CAS  Google Scholar 

  57. Cheng, P., M. Xu, Y. Lin, and J. Shi: Studies on Rabdophyllin G, an Antitumor Constituent of Rabdosia macrophylla (II). Yaoxue Xuebao 17, 917 (1982) [Chem. Abstr. 98, 95653a (1983)].

    Google Scholar 

  58. Sun, H., Z. Lin, Y. Minami, T. Marunaka, T. Fujita, and Y. Takeda: Structures of New Diterpenoids isolated from Rabdosia Plants, R. phyllostachys, R. rubescens and R. sculponeata, in China. Abstract Papers of the 25 th Symposium on The Chemistry of Natural Products (Japan) p. 266 (1982).

    Google Scholar 

  59. Sun, H.-D., Z.-W. Lin, C.-Q. Qin, J.-H. Chao, and Q.-Z. Zhao: Studies on the chemical Constituents of Antitumor Plant Rabdosia rubescens (Hemsl.) Hara. Yun-nan Chih Wu Yen Chiu 3, 95 (1981) [Chem. Abstr. 95, 121032g (1981)].

    Google Scholar 

  60. Chang, T. L., C.-Y. Chen, C.-H. Miau, C.-T. Chao, H.-T. Sun, and C.-W. Liu: Rubescensin B — Another Effective Antitumor Agent in Rabdosia rubescens Hemsl. Kó Hsueh Túng Pao 25, 1051 (1980) [Chem. Abstr. 94, 145226d (1981)].

    Google Scholar 

  61. Sun, H., J. Chao, Z. Lin, T. Marunaka, Y. Minami, and T. Fujita: The Structure of Rubescensin C: A New Minor Diterpenoid isolated from Rabdosia rubescens. Chem. Pharm. Bull. (Japan) 30, 341 (1982).

    CAS  Google Scholar 

  62. Kubota, T., and I. Kubo: The Two Bitter Principles of Isodon shikokianus Kudo. Bull. Chem. Soc. Japan 42, 1778 (1969).

    CAS  Google Scholar 

  63. Isobe, T., T. Kamikawa, I. Kubo, and T. Kubota: The Structure of Shikokianidin, a Minor Component of Isodon shikokianus Hara. Bull. Chem. Soc. Japan 46, 583 (1973).

    CAS  Google Scholar 

  64. Kubo, I., M. J. Pettei, K. Hirotsu, H. Tsuji, and T. Kubota: Structure of Shikodonin, a Unique Anti-Tumor Spiro-secokaurene Diterpenoid. J. Am. Chem. Soc. 100, 628 (1978).

    CAS  Google Scholar 

  65. Ochi, M., M. Okamura, H. Kotsuki, I. Miura, I. Kubo, and T. Kubota: Bitter Diterpenoids from Rabdosia shikokiana (Makino) Hara. Bull. Chem. Soc. Japan 55, 2208 (1982).

    CAS  Google Scholar 

  66. Ochi, M., K. Hirotsu, I. Miura, and T. Kubota: Rabdoepigibberellolide, a Novel Diterpenoid from Rabdosia shikokiana (Makino) Hara. J. Chem. Soc., Chem. Commun. 1982, 810.

    Google Scholar 

  67. Ochi, M., M. Okamura, H. Kotsuki, I. Miura, K. Kubo, and T. Kubota: The Structures of Rabdosianin A, B, and C, Three New Diterpenoids from Rabdosia shikokianus Hara. Bull. Chem. Soc. Japan 54, 2786 (1981).

    CAS  Google Scholar 

  68. Isobe, T., Y. Noda, K. Shibata, and T. Kubota: The Structures of Diterpene Glycoside, Shikokiaside A and B. Chemistry Letters 1981, 1225.

    Google Scholar 

  69. Kubo, I., I. Miura, K. Nakanishi,T. Kamikawa,T. Isobe, andT. Kubota: Structure of Isodomedin, a Novel ent-Kaurenoid Diterpene. J. Chem. Soc., Chem. Commun. 1977, 555.

    Google Scholar 

  70. Fujita, T., Y. Takeda, and T. Shingu: Bitter Diterpenoids from Isodon shikokianus var. intermedius. Phytochem. 18, 299 (1979).

    CAS  Google Scholar 

  71. Fujita,T., Y. Takeda,T. Shingu, M. Kido, and Z. Taira: Structures of Shikodomedin (X-Ray Analysis) and Shikokiamedin: New Cytotoxic 8,9-seco-ent-Kaurenoids from Rabdosia shikokiana. J. Chem. Soc., Chem. Commun. 1982, 162.

    Google Scholar 

  72. Node, M., N. Ito, K. Fuji, and E. Fujita: Three New 8,9-seco-ent-Kaurane Diterpenoids from Rabdosia shikokiana (Labiatae). Chem. Pharm. Bull. (Japan) 30, 2639 (1982).

    CAS  Google Scholar 

  73. Fujita, E., N. Ito, I. Uchida, and K. Fuji: Structures of Shikoccin, a Unique 8,9-seco-ent-Kaurene Diterpenoid, and Shikoccidin (X-Ray Crystallography), a New Pentaoxygenated ent-Kaurene Diterpenoid. Chem. Commun. 1979, 806.

    Google Scholar 

  74. Taga, T., K. Osaki, N. Ito, and E. Fujita: Structure of ent-9,15-Dioxo-8,9-seco-14,16-kauradiene-3α,7β-diol Diacetate (Shikoccin Moncacetate). Acta Crystal. B38, 2941 (1982).

    Google Scholar 

  75. Sun, H., Z. Lin, Y. Minami, Y. Takeda, and T. Fujita: On the Constituents of Rabdosia ternifolia (D. Don) Hara: The structure of a New Diterpenoid, Isodonoic Acid. Yakugaku Zasshi 102, 887 (1982).

    CAS  Google Scholar 

  76. Fujita, T., Y. Takeda, H. Sun, and Y. Minami: The Chemical Structure of a New Diterpene of Rabdosia ternifolia. Abstract Paper of the 103 rd Annual Meeting of Japan Pharmaceutical Society, Tokyo, p. 242 (1983).

    Google Scholar 

  77. Kanatomo, S., and S. Sakai: Studies on Bitter Principles of Isodon trichocarpus. IV. Yakugaku Zasshi 81, 1807 (1961).

    CAS  Google Scholar 

  78. Fujita, E., T. Fujita, and M. Shibuya: The structure and Stereochemistry of Trichokaurin, a New Diterpenoid from Isodon trichocarpus Kudo. Chem. Commun. 1967, 148; b) On the Stereochemistry of the Acetoxy-group at C-15 in Trichokaurin. Chem. Commun. 1967, 466; c) The Structure and Absolute Configuration of Trichokaurin and its Chemical Conversion into (—)-Kaurene and Diterpene Alkaloids. Tetrahedron 25, 2517 (1969).

    Google Scholar 

  79. Node, M., M. Sai, K. Fuji, E. Fujita, T. Shingu, W. H. Watson, and D. Grossie: Three New Anti-tumor Diterpenoids, Trichorabdal A, C, and D. Chemistry Letters 1982, 2023.

    Google Scholar 

  80. Fujita, E., K. Fuji, M. Sai, and M. Node: The Structure of Trichorabdal B and its Transformation into a Novel Skeleton; X- Ray Crystal Structures. Chem. Commun. 1981, 899.

    Google Scholar 

  81. Node, M., M. Sai, E. Fujita, and K. Fuji: Structure of New Diterpenoids, Trichorabdals E, F, and G from Rabdosia trichocarpa. Abstract papers of the 27th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics (Japan), p. 70 (1983).

    Google Scholar 

  82. Node, M., M. Sai, N. Ito, K. Fuji, E. Fujita, T. Shingu, S. Takeda, and N. Unemi: Antitumor Active Diterpenoids from Labiatae Plant. Abstract Papers of 4th Symposium on the Development and Application of Naturally Occurring Drug Materials (Japan), p. 37 (1982).

    Google Scholar 

  83. Mori, S., K. Shudo, T. Ageta, T. Koizumi, and T. Okamoto: Studies on the Constituents of Isodon trichocarpus Kudo. I. Isolation of the Constituent and the Structures of Isodonol, Enmedol, and Enmenol. Chem. Pharm. Bull. (Japan) 18, 871 (1970).

    CAS  Google Scholar 

  84. Mori, S., T. Koizumi, K. Shudo, and T. Okamoto: Studies on the Constituents of Isodon trichocarpus Kudo. II. The Structures of Enmenin, Enmelol, and Ememodin. Chem. Pharm. Bull. (Japan) 18, 884 (1970).

    CAS  Google Scholar 

  85. Fujita, T., Y. Takeda, and K. Takeda: The Chemical Structures of New Minor Diterpenes of Rabdosia trichocarpa. Abstract Papers of the 25 th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics (Japan), p. 104 (1981); b) The Chemical Structure of Minor Diterpenoid from Rabdosia trichocarpa. Abstract Paper of the 29th Meeting of Japan Pharmacognosy Society, p. 71 (1982).

    Google Scholar 

  86. Fujita, E., Y. Nagao, S. Nakano, Y. Masada, K. Hashimoto, and T. Inoue: Change of Quantity of Each Major Diterpenoid During Growth of Isodon trichocarpus Kudo, its Exploration by GC and GC-MS. Yakugaku Zasshi 92, 1400 (1972).

    CAS  Google Scholar 

  87. Fujita, E., T. Fujita, and N. Ito: Studies on the Constituents of the Stems of Isodon trichocarpus Kudo. Yakugaku Zasshi 87, 1150 (1967).

    CAS  Google Scholar 

  88. Kubo, I., T. Kamikawa, T. Isobe, and T. Kubota: Bitter Principles of Isodon umbrosus Hara. The Structures of Umbrosin A and B. Bull. Chem. Soc. Japan 47, 1277 (1974).

    CAS  Google Scholar 

  89. Takeda, Y., T. Fujita, and A. Ueno: A New Diterpenoid from Rabdosia umbrosa var. latifolia. Abstract Paper of the 21st Chugoku-Shikoku Regional Meeting of Pharmaceutical Society of Japan, p. 53 (1982).

    Google Scholar 

  90. Hirotsu, K., T. Kamikawa, T. Kubota, and A. Shimada: Mebadonin, a New ent-Kaurane Diterpenoid from Isodon kameba Okuyama. Chemistry Letters 1973, 255.

    Google Scholar 

  91. Kubo, I., I. Miura, T. Kamikawa, T. Isobe, and T. Kubota: The Structure of Kamebanin, a New Antitumor ent-Kaurenoid from Isodon kameba Okuyama. Chemistry Letters 1977, 1289.

    Google Scholar 

  92. Takeda, Y., T. Fujita, and A. Ueno: Structures of Leukamenins. Chemistry Letters 1981, 1229.

    Google Scholar 

  93. Fujita, T., T. Ichihara, Y. Takeda, Y. Takaishi, Y. Minato, and T. Shingu: The Chemical Structure of a New Diterpene, Kamebakaurin from Isodon kameba. Abstract papers of the 21st Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics (Japan), p. 24 (1977).

    Google Scholar 

  94. Fujita, T., T. Ichihara, Y. Takeda, Y. Takaishi, and T. Shingu: Study on the Constituents of Isodon kameba; Structure of A New Diterpene, Kamebakaurinin. Abstract paper of the 98 th Annual Meeting of Pharmaceutical Society of Japan, p. 331 (1978).

    Google Scholar 

  95. Fujita, T., T. Ichihara, Y. Takeda, Y. Takaishi, and T. Shingu: Chemical Structures of New Diterpenes, Kamebacetal A and B from Isodon kameba. Abstract papers of the 23 rd Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics (Japan), p. 279 (1979).

    Google Scholar 

  96. Kubo, I., I. Ganjian, and T. Kubota: Chemotaxonomic Significance of ent-Kaurene Derivatives in Rabdosia umbrosus Varieties. Phytochemistry 21, 81 (1982).

    CAS  Google Scholar 

  97. Ganjian, I., I. Kubo, and T. Kubota: Rapid and Micro Identification of Biologically Active Diterpenes in Rabdosia umbrosus var. excisinflexus (Labiatae) by Reversed-phase High-performance Liquid Chromatography. J. Chromatogr. 200, 250 (1980).

    CAS  Google Scholar 

  98. Triveda, G. K., I. Kubo, and T. Kubota: High Performance Liquid Chromatography of Isodon Diterpenoids. J. Chromatogr. 179, 219 (1979).

    Google Scholar 

  99. Shudo, K., M. Natsume, and T. Okamoto: Conversion of Enmein to (-)-Kaurane. The Absolute Stereochemistry of Enmein. Chem. Pharm. Bull. (Japan) 13, 1019 (1965).

    CAS  Google Scholar 

  100. Fujita, E., T. Fujita, K. Fuji, and N. Ito: The Absolute Configuration of Enmein. Transformation of Enmein into (-)-Kaurane. Chem. Pharm. Bull. (Japan) 13, 1023 (1965); b) Terpenoids —II. The Chemical Conversion of Enmein into (-)-Kaurane. The Absolute Configuration of Enmein. Tetrahedron 22, 3423 (1966).

    Google Scholar 

  101. Fujita, E., T. Fujita, and H. Katayama: Formal Chemical Conversion of Enmein into ent-Kaurene, Atisine, Garryine and Veatchine. Tetrahedron Letters 1969, 2577; b) Terpenoids — XIV. Formal Chemical Conversion of Enmein into ent-Kaurene, Atisine, Garryine and Veatchine. Tetrahedron 26, 1009 (1970).

    Google Scholar 

  102. Fujita, E., T. Fujita, and M. Shibuya: The Chemical Conversion of Trichokaurin into (-)-Kaurene, Atisine, Garryine, and Veatchine. Chem. Commun. 1967, 468.

    Google Scholar 

  103. Fujita, E., T. Fujita, and Y. Nagao: Terpenoids XIX. Chemical Conversion of Enmein into ent-15-Kaurene and ent-16-Kaurene. Tetrahedron 28, 555 (1972).

    CAS  Google Scholar 

  104. Fujita, E., and Y. Nagao: Terpenoids XXIII. Reduction of Kaurene with Hydrazine and Hydrazine Hydrochloride. Yakugaku Zasshi 92, 1405 (1972).

    CAS  Google Scholar 

  105. Fujita, E., T. Fujita, and H. Katayama: Synthesis of Abietane and Transformation of Enmein into enantio-Abietane. Chem. Commun. 1967, 968; b) Fujita, E.,T. Fujita, H. Katayama, and Y. Nagao: Terpenoids-X. Chemical Conversion of Enmein into enantio-Abietane and Total Synthesis of Abietane. Tetrahedron 25, 1335 (1969).

    Google Scholar 

  106. Shudo, K., M. Natsume, and T. Okamoto: Synthesis of Gibbane Derivatives from Enmein. Chem. Pharm. Bull. (Japan) 14, 311 (1966).

    CAS  Google Scholar 

  107. Somei, M., and T. Okamoto: A Novel Method for Attacking Non-activated C-H Bond and its Application to the Synthesis of Gibberellin-A15 from Enmein. Chem. Pharm. Bull. (Japan) 18, 2135 (1970); b) A Novel Method for Functionalization of Non-activated C — H Bond and its Application to the Synthesis of Gibberellin-A15 (Chemical Studies on Diterpenoids. I). Yakugaku Zasshi 92, 397 (1972).

    Google Scholar 

  108. Node, M., H. Hori, and E. Fujita: Syntheses of Methyl Esters of Gibberellin A15 and Gibberellin A37. Chem. Commun. 1975, 898; b) Fujita, E., M. Node, and H. Hori: Terpenoids. Part 39. Total Synthesis of Gibberellins A15 and A37. J. Chem. Soc. Perkin Trans. I 1977, 611;c) Fujita, E., and M. Node: Synthesis of Gibberellins. Heterocycles 7, 709 (1977).

    Google Scholar 

  109. Node, M., H. Hori, and E. Fujita: Demethylation of Aliphatic Methyl Ethers with a Thiol and Boron Trifluoride. J. Chem. Soc. Perkin Trans. I 1976, 2237.

    Google Scholar 

  110. Node, M., H. Hori, and E. Fujita: Terpenoids. XXXVII. Hypoiodite Reactions with 6-Hydroxy-17-norkaurane- and 7-Norgibberellane-derivatives. Chem. Pharm. Bull. (Japan) 24, 2149 (1976).

    CAS  Google Scholar 

  111. Node, M., H. Hori, and E. Fujita: Terpenoids. Part XXXVIII. Ring B Contraction of Kauranolides and Related Compounds into Gibberellane-type Compounds. J. Chem. Soc. Perkin Trans. I 1976, 2144.

    Google Scholar 

  112. Fujita, E., T. Fujita, and H. Katayama: Terpenoids. Part XVI. Chemical Conversion of Oridonin into Isodocarpin. J. Chem. Soc. (C) 1970, 1681.

    Google Scholar 

  113. Fujita, E., T. Fujita, and Y. Nagao: Terpenoids. XVII. Chemical Conversion of Trichokaurin into Isodocarpin via a Direct Pathway. Chem. Pharm. Bull. (Japan) 18, 2343 (1970).

    CAS  Google Scholar 

  114. Fujita, E., and S. Nakamura: Terpenoids. XXXIII. Chemical Conversion of Enmein into Enmelol. Chem. Pharm. Bull. (Japan) 23, 858 (1975).

    CAS  Google Scholar 

  115. Fujita, E., T. Fujita, Y. Nagao, P. Coggan, and G. A. Sim: On the Stereoisomers of Some Enmein Derivatives. Tetrahedron Letters 1968, 4191; b) Fujita, E., T. Fujita, and Y. Nagao: Terpenoids —XII. The Stereochemistry of Some Alcohols Derived from Enmein. Tetrahedron 25, 3717 (1969).

    Google Scholar 

  116. Coggon, P., and G. A. Sim: Molecular Conformations. IX. Bicyclo[3.2.1]octene System: X-Ray Analysis of Enmein Derivative. J. Chem. Soc. (B) 1969, 413.

    Google Scholar 

  117. Fujita, E., and Y. Nagao: A Common Stereoelectronic Requirement in Epimerisations with Some Diterpene Alcohols. Chem. Commun. 1970, 1112; b) Terpenoids. Part XVIII. A Common Stereoelectronic Requirement in Epimerizations and Retro-Dieckmann-type Cleavages of Some Diterpene Alcohol and Ketones. J. Chem. Soc. (C) 1971, 2902.

    Google Scholar 

  118. Fujita, E., I. Uchida, and T. Fujita: Reactions of Enmein-type Compounds with Lead Tetraacetate and Iodine under Irradiation. Chem. Pharm. Bull. (Japan) 22, 1656 (1974).

    CAS  Google Scholar 

  119. Katayama, H.: Studies on Inter-conversion of Kaurane Type and B-Secokaurane Type Diterpenoids and on the Structure of Oridonin. Dissertation (Kyoto Univ.), p. 21 (1969).

    Google Scholar 

  120. Isobe, T., and T. Kubota: Dehydrobromination of 16-Bromodihydroenmein-type Compounds. Bull. Chem. Soc. Japan 48, 949 (1975).

    CAS  Google Scholar 

  121. Shibuya, M., and E. Fujita: Terpenoids. Part XXX. Chemical Conversion of Enmein into an Important Relay Compound for its Total Synthesis. J. Chem. Soc. Perkin Trans. I 1974, 178.

    Google Scholar 

  122. Fujita, E., M. Shibuya, S. Nakamura, Y. Okada, and T. Fujita: Total Synthesis of Enmein. Chem. Commun. 1972, 1107; b) Terpenoids. Part XXVIII. Total Synthesis of Enmein. J. Chem. Soc. Perkin Trans. I 1974, 165.

    Google Scholar 

  123. Fujita, E., M. Node, Y. Nagao, and T. Fujita: Terpenoids. XXXI. Biogenetic Classification of Isodon Diterpenoids. Yakugaku Zasshi 94, 788 (1974).

    CAS  Google Scholar 

  124. Fujita, T., S. Takao, and E. Fujita: Biosynthesis of the Diterpenes Enmein and Oridonin from ent- 16-Kaurene. Chem. Commun. 1973, 434.

    Google Scholar 

  125. Fujita, T., I. Masuda, S. Takao, and E. Fujita: Biosynthesis of Natural Products. Part 1. Incorporations of ent-Kaur-16-ene and ent-Kaur-16-en-15-one into Enmein and Oridonin. J. Chem. Soc. Perkin Trans. I 1976, 2098.

    Google Scholar 

  126. Fujita, T., S. Takao, Y. Nagao, and E. Fujita: Biosynthesis of Enmein and Oridonin from 15-Oxygenated Kaurenoids and 14-Deoxyoridonin. J. Chem. Soc. Chem. Commun. 1974, 666.

    Google Scholar 

  127. Fujita, T., S. Takao, and E. Fujita: Biosynthesis of Natural Products. Part 2. Syntheses of 14C- or 3H-Labelled ent-Kaur-16-ene Derivatives Oxygenated at C-7, or at C-7 and C-15, from Epicandicandiol. J. Chem. Soc. Perkin Trans. I 1979, 910.

    Google Scholar 

  128. Fujita, T., S. Takao, and E. Fujita: Biosynthesis of Natural Products. Part 4. Biosynthesis of Enmein and Oridonin from Mono- or Di-oxygenated Kaurenoids. J. Chem. Soc. Perkin Trans. I 1979, 2468.

    Google Scholar 

  129. Fujita, T., I. Masuda, S. Takao, and E. Fujita: Biosynthesis of Natural Products. Part 3. Syntheses of ent-[17-14C] Kaur-16-en-20-ol from Enmein and ent-[17-14C] Kaur-16-ene Derivatives oxygenated at C-3 from ent-Kaur-16-ene-3β, 19-diol. J. Chem. Soc. Perkin Trans. I 1979, 915.

    Google Scholar 

  130. Nagao, Y., and E. Fujita: Studies for Exploitation of the Biologically Active Components in “Enmei-so” (Rabdosia japonica Hara and R. trichocarpa Kudo) and Related Plants. Proc. Symp. Wakan-Yaku 13, 79 (1980).

    CAS  Google Scholar 

  131. Ohyama, A., Y. Furumoto, S. Chikugo, A. Ishiga, Y. Takami, M. Nomura, S. Yokota, F. Liao, T. Awai, A. Fuwa, M. Yamada, Y. Ueda, N. Ishii, T. Kurimura, and S. Tanama: Antimicrobial activity of extracts of Amethystanthus trichocarpus Nakai (Action of Enmein and C1 Upon Some Bacteria and Fungi). Bull. Kobe Med. College 13, 253 (1958).

    CAS  Google Scholar 

  132. Arai, T., Y. Koyama, T. Suenaga, and H. Kaji: Studies on antitumor substance in I. trichocarpus. II. Chemotherapy 9, 404 (1961).

    Google Scholar 

  133. Arai, T., Y. Koyama, T. Suenaga, and T. Morita: Antitumor Activity of the Components of Isodon trichocarpus and Related Plants. J. Antibiotics Ser. A 16, 132 (1963).

    CAS  Google Scholar 

  134. Kubo, I., M. Taniguchi, Y. Satomura, and T. Kubota: Antibacterial Activity and Chemical Structure of Diterpenoids. Agr. Biol. Chem. 38, 1261 (1974).

    CAS  Google Scholar 

  135. Yamaguchi, M., M. Taniguchi, I. Kubo, and T. Kubota: Inhibitory Effect of Antibacterial and Antitumor Diterpenoids on Oxidative Phosphorylation in Mitochondria Isolated from Rat Liver. Agr. Biol. Chem. 41, 2475 (1977).

    CAS  Google Scholar 

  136. Fujita, E., Y. Nagao, K. Kaneko, S. Nakazawa, and H. Kuroda: The Antitumor and Antibacterial Activity of the Isodon Diterpenoids. Chem. Pharm. Bull. (Japan) 24, 2118 (1976).

    CAS  Google Scholar 

  137. Arai, T., Y. Koyama, T. Morita, and H. Kaji: Studies on Antitumor Substance in I. trichocarpus. I. Chemotherapy 9, 403 (1961).

    Google Scholar 

  138. Aiso, K., T. Arai, and Y. Koyama: Studies on Antitumor Substance in I. trichocarpus. III. Chemotherapy 9, 404 (1961).

    Google Scholar 

  139. Arai, T., Y. Koyama, T. Suenaga, and T. Morita: Studies on Antitumor Substance in I. trichocarpus. IV. Chemotherapy 10, 197 (1962).

    Google Scholar 

  140. Fujita, E., Y. Nagao, M. Node, K. Kaneko, S. Nakazawa, and H. Kuroda: Antitumor Activity of the Isodon Diterpenoids: Structural Requirements for the Activity. Experientia 32, 203 (1976).

    CAS  Google Scholar 

  141. Fujita, E., Y. Nagao, T. Kohno, M. Matsuda, and M. Ozaki: Antitumor Activity of Acylated Oridonin. Chem. Pharm. Bull. (Japan) 29, 3208 (1981).

    CAS  Google Scholar 

  142. Node, M., M. Sai, K. Fuji, E. Fujita: S. Takeda, and N. Unemi: Antitumor Activity of Diterpenoids, Trichorabdal A, B, and C, and the Related Compounds: Synergism of Two Active Sites. Chem. Pharm. Bull. (Japan) 31, 1433 (1983).

    CAS  Google Scholar 

  143. Fujita,T., Y.Takeda, H.-D. Sun, Y. Minami, T. Marunaka, S. Takeda, Y. Yamada, and T. Togo: Structures and Antitumor Activity of Diterpenoids from Rabdosia (Labiatae) Plants. Abstract papers of 4th Symposium on the Development and Application of Naturally Occurring Drug Materials (Japan), p. 34 (1982).

    Google Scholar 

  144. Itokawa, H., K. Watanabe, and S. Mihashi: Screening Test for Antitumor Activity of Crude Drugs (I). Shoyakugaku Zasshi 33, 95 (1979).

    Google Scholar 

  145. Nagao, Y., N. Ito, T. Kohno, H. Kuroda, and E. Fujita: Antitumor Activity of Rabdosia and Teucrium Diterpenoids against P. 388 Lymphocytic Leukemia in Mice. Chem. Pharm. Bull. (Japan) 30, 111 (1982).

    Google Scholar 

  146. Fujita, E., K. Fuji, M. Node, and M. Sai: unpublished results.

    Google Scholar 

  147. Fujita, T., Y. Takeda, and T. Shingu: Biologically Active Diterpenoids from I. longitubus. Abstract papers of 2nd Symposium on the Development and Application of Naturally Occurring Drug Materials (Japan), p. 16 (1978).

    Google Scholar 

  148. Taniguchi, M., M. Yamaguchi, I. Kubo, and T. Kubota: Inhibitory Effect of Isodon Diterpenoids on Growth and Mitochondrial Oxidative Phosphorylation in Lepidopterous Insects. Agr. Biol. Chem. 43, 71 (1979).

    CAS  Google Scholar 

  149. Kubo, I., M. Taniguchi, and T. Kubota: The Biological Activities of the Isodon Diterpenoids. Rev. Latinoamer. Quim. 9, 157 (1978).

    CAS  Google Scholar 

  150. Kubota, T., and I. Kubo: Bitterness and Chemical Structure. Nature 223, 97 (1969).

    CAS  Google Scholar 

  151. Kubo, I., and T. Kubota: The Structural Basis for Bitterness in the Isodon Diterpenes. J. Food Chem. 4, 235 (1979).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute for Chemical Research, Kyoto University, Uji, Kyoto-fu, Japan

    E. Fujita & M. Node

Authors
  1. E. Fujita
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Node
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz (Professor of Chemistry) (Professor of Chemistry)

  2. Biologisches Institut II, Lehrstuhl für Biochemie der Pflanzen, Albert-Ludwigs-Universität, Freiburg i. Br., Federal Republic of Germany

    H. Grisebach

  3. Chemistry Department, The University, Glasgow, Scotland

    G. W. Kirby Sc. D. (Regius Professor of Chemistry) (Regius Professor of Chemistry)

  4. Institut für Organische Chemie, Universität Basel, Basel, Switzerland

    Ch. Tamm

Rights and permissions

Reprints and permissions

Copyright information

© 1984 Springer-Verlag/Wien

About this chapter

Cite this chapter

Fujita, E., Node, M. (1984). Diterpenoids of Rabdosia Species. In: Herz, W., Grisebach, H., Kirby, G.W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 46. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8759-3_3

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8759-3_3

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8761-6

  • Online ISBN: 978-3-7091-8759-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation