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Natural arylterpenes and their biological activity

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Chemistry of Natural Compounds Aims and scope

Abstract

Information on naturally occurring aromatic mono-, sesqui-, and diterpenes was systematized. The types of their biological activity and possible practical applications were described. Possible synthetic pathways to the most important terpenes were examined.

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References

  1. Y. Asakawa, M. Toyota, T. Takemoto, H. Fujiki, and T. Sugimura, Planta Med., 39, No. 3, 233 (1980); Ref. Zh. Biol., 21, X441 (1980).

    Google Scholar 

  2. Y. Asakawa, M. Toyota, and T. Takemoto, Expxerientia, 34, No. 2, 155 (1978).

    CAS  Google Scholar 

  3. F. Taura, S. Morimoto, Y. Shoyama, and R. Mechoulam, J. Am. Chem. Soc., 117, No. 38, 9766 (1995).

    Article  CAS  Google Scholar 

  4. F. Taura, S. Morimoto, and Y. Shoyama, Phytochemistry, 39, No. 2, 457 (1995); Ref. Zh. Khim., 24, E69 (1995).

    Article  CAS  Google Scholar 

  5. F. Tomas-Lorente, E. Iniesta-Sanmartin, F. A. Tomas-Barberan, W. Trowitzsch-Kienast, and V. Wray, Ger. Offen. No. 3907543, MKI5 C 07 D 309/36 A 01 N 43/16; Appl. 08 Mar. 89, Publ. 13 Sep. 90.

  6. M. Tada, K. Chiba, H. Yamada, and H. Maruyama, Phytochemistry, 30, No. 8, 2559 (1991); Ref. Zh. Khim., 2, E97 (1992).

    Article  CAS  Google Scholar 

  7. V. Mahiou, F. Roblot, R. Hocquemiller, A. Cave, A. R. De Arias, A. Inchausti, G. Yaluff, and A. Fournet, J. Nat. Prod., 59, No. 7, 694 (1996); Ref. Zh. Khim., 8, E208 (1997).

    Article  CAS  PubMed  Google Scholar 

  8. J. Nakano, K. Uchida, and Y. Fujimoto, Heterocycles, 29, No. 3, 427 (1989).

    CAS  Google Scholar 

  9. H. Shibuya, Y. Takeda, R.-S. Zhang, R.-X. Tong, and I. Kitagawa, Chem. Pharm. Bull., 40, No. 9, 2325 (1992); Ref. Zh. Khim., 10, E71 (1993).

    CAS  PubMed  Google Scholar 

  10. C.-J. Chou, L.-C. Lin, K.-T. Chen, and C.-F. Chen, J. Nat. Prod., 55, No. 6, 795 (1992); Ref. Zh. Khim., 14, E146 (1993).

    Article  CAS  Google Scholar 

  11. C. Tringali, M. Piattelli, C. Geraci, and G. Nicolosi, J. Nat. Prod., 52, No. 5, 941 (1989); Ref. Zh. Khim., 12, E180 (1990).

    CAS  PubMed  Google Scholar 

  12. A. Maxwell and D. Rampersad, J. Nat. Prod., 52, No. 3, 614 (1989); Ref. Zh. Khim., 1, E198 (1990).

    Article  CAS  Google Scholar 

  13. L. M. Murray, A. Johnson, M. C. Diaz, and P. Crews, J. Org. Chem., 62, No. 16, 5638 (1997).

    Article  CAS  Google Scholar 

  14. J. Perez Baz, L. M. Canedo, and D. Tapiolas, J. Nat. Prod., 59, No. 10, 960 (1996); Ref. Zh. Khim., 11, E231 (1997).

    CAS  Google Scholar 

  15. G. J. Hooper and M. T. Davies-Coleman, Tetrahedron Lett., 36, No. 18, 3165 (1995); Ref. Zh. Khim., 21, E48 (1995).

    Article  CAS  Google Scholar 

  16. V. Amico, F. Cunsolo, P. Neri, M. Piattelli, and G. Ruberto, Phytochemistry, 27, No. 5, 1327 (1988); Ref. Zh. Khim., 12, E219 (1988).

    Article  CAS  Google Scholar 

  17. J. G. Urones, P. Basabe, I. S. Marcos, J. Pineda, A. M. Lithgow, R. F. Moro, N. M. Garrido, M. E. M. Araujo, and M. D. G. Gravalos, Phytochemistry, 31, No. 1, 179 (1992); Ref. Zh. Khim., 16, E93 (1992).

    CAS  Google Scholar 

  18. J. G. Urones, D. Diez, I. S. Marcos, P. Basabe, A. M. Lithgow, R. F. Moro, N. M. Garrido, and R. Escarcena, Tetrahedron, 51, No. 12, 3691 (1995); Ref. Zh. Khim., 2, E34 (1996).

    Article  CAS  Google Scholar 

  19. A. Praud, R. Valls, L. Piovetti, B. Banaigs, and J.-Y. Benaim, Phytochemistry, 40, No. 2, 495 (1995); Ref. Zh. Khim., 8, E37 (1996).

    Article  CAS  Google Scholar 

  20. V. Amico, P. Neri, G. Oriente, and M. Piattelli, Phytochemistry, 28, No. 1, 215 (1989); Ref. Zh. Khim., 9, E314 (1989).

    CAS  Google Scholar 

  21. K. Inaoka, Y. Nisizawa, H. Tone, and T. Kamitani, Jpn. Pat. No. 449259, MKI5, C 07 s 39/19 50/26, No. 2, 155745; Appl. 14 June, 1990, Publ. 18 Feb. 1992; Ref. Zh. Khim., 20, O165P (1995).

    Google Scholar 

  22. G. Koren-Goldshlager, P. Klein, A. Rudi, Y. Benayahu, M. Schleyer, and Y. Kashman, J. Nat. Prod., 59, No. 3, 262 (1996); Ref. Zh. Khim., 18, E220 (1996).

    Article  Google Scholar 

  23. V. Amico, M. Piattelli, P. Neri, and G. Ruberto, J. Nat. Prod., 53, No. 2, 517 (1990); Ref. Zh. Khim., 5, E184 (1991).

    Article  CAS  Google Scholar 

  24. J.-Z. Deng, D.-A. Sun, S. R. Starck, S. M. Hecht, R. L. Cerny, and J. R. Engen, J. Chem. Soc., Perkin Trans. 1, No. 9, 1147 (1999); Ref. Zh. Khim., 21, E43 (1999).

  25. S. Takanashi and K. Mori, Liebigs Ann., No. 5, 825 (1997); Ref. Zh. Khim., 1, E204 (1998).

  26. H. Besl, G. Hoefle, B. Jendrny, E. Jaegers, and W. Steglich, Chem. Ber., 110, No. 12, 3770 (1977).

    CAS  Google Scholar 

  27. H. Takayanagi, Y. Kitano, and Y. Morinaka, US Pat. No. 5399724, Appl. No. 128266, 28 Sep. 1993; Publ. 21 Mar. 1995; Ref. Zh. Khim., 3, O90P (1997).

    Google Scholar 

  28. M. Kodama, Jpn. Pat. No. 01-233245, No. 63, Ser. 3(2), 78, 285 (1989); Ref. Zh. Khim., 9 O111P (1992).

  29. H. Takayanagi, Y. Kitano, and Y. Morinaka, US Pat. No. 5292911, Appl. No. 849576; 10 Mar. 1992, Publ. 8 Mar. 1994; Ref. Zh. Khim., 15, O134P (1995).

    Google Scholar 

  30. B. C. Pearce, US Pat. No. 5318993, Appl No. 48695, 16 Apr. 1993, Publ. 7 Jun. 1994; Ref. Zh. Khim., 6, O14P (1996).

  31. Y. Akinuki, RF Pat. No. 97115259/14, MPK6, A 61 K 31/00, Appl. 1 Jul. 1996, Publ. 10 Apr. 1999; Ref. Zh. Khim., 24, 054P (1999).

  32. B. C. Pearce, US Pat. No. 5393776, Appl. No. 242213, 13 May 1994, Publ. 28 Feb. 1995; Ref. Zh. Khim., 16, O24P (1996).

  33. S.-Y. Sit, J. J. Wright, and J. A. Field, US Pat. No. 5321046, Appl. No. 970594, 27 Oct. 1992, Publ. 14 Jun. 1994; Ref. Zh. Khim., 21, O78P (1995).

    Google Scholar 

  34. G. J. Samuels, J.-C. Lee, C. Lee, S. Berry, and P. J. Jarosz, US Pat. No. 5455045, Appl. No. 61656, 13 May 1993, Publ. 3 Oct. 1995; Ref. Zh. Khim., 16, O151P (1997).

    Google Scholar 

  35. E. P. Serebryakov and A. G. Nigmatov, Khim.-Farm. Zh., No. 2, 104 (1990).

  36. K. C. Nicolaou and D. Hepworth, Angew. Chem. Intl. Ed. Engl., 37, No. 6, 839 (1998); Ref. Zh. Khim., 23, E279 (1998).

    CAS  Google Scholar 

  37. A. Sendl, J. L. Chen, S. D. Jolad, C. Stoddart, E. Rozhon, M. Kernan, W. Nanakorn, and M. Balick, J. Nat. Prod., 59, No. 8, 808 (1996); Ref. Zh. Khim., 6, E207 (1998).

    Article  CAS  PubMed  Google Scholar 

  38. G. A. Kuznetsova, Natural Coumarins and Furocoumarins [in Russian], Nauka, Leningrad (1967).

    Google Scholar 

  39. V. P. Georgievskii, N. F. Komissarenko, and S. E. Dmitruk, Biologically Active Substances from Medicinal Plants [in Russian], Nauka, Novosibirsk (1990).

    Google Scholar 

  40. T. Suga, Jpn. Pat. No. 63-057590, Appl. No. 202597, 28 Aug. 1986, Publ. 12 Mar. 1988; Ref. Zh. Khim., 6, O352P (1989).

  41. C. Ito, H. Ohta, H. T.-W. Tan, and H. Furukawa, Chem. Pharm. Bull., 44, No. 12, 2231 (1996); Ref. Zh. Khim., 16, E63 (1997).

    CAS  Google Scholar 

  42. D. Lamnaouer, O. Fraigui, M. T. Martin, and B. Bodo, Phytochemistry, 30, No. 7, 2383 (1991); Ref. Zh. Khim., 24, E277 (1991).

    Article  CAS  Google Scholar 

  43. M. Amoros, C. M. Simoes, L. Girre, F. Sauvager, and M. Cormier, J. Nat. Prod., 55, No. 12, 1732 (1992).

    Article  CAS  PubMed  Google Scholar 

  44. M. Abou-Karam and W. T. Shier, J. Nat. Prod., 55, No. 10, 1525 (1992).

    CAS  PubMed  Google Scholar 

  45. M. Iinuma, M. Sato, H. Tsuchiya, and S. Fujiwara, US Pat. No. 5399723, Appl. No. 55966, 30 Apr. 1993, Publ. 21 Mar. 1995; Ref. Zh. Khim., 4, O136P (1997).

    Google Scholar 

  46. G. B. Russell, Aust. J. Chem., 50, No. 4, 333 (1997); Ref. Zh. Khim., 3, E200 (1998).

    CAS  Google Scholar 

  47. W.-J. Tsai, W.-C. Hsin, and C.-C. Chen, J. Nat. Prod., 59, No. 7, 671 (1996); Ref. Zh. Khim., 8, E191 (1997).

    CAS  PubMed  Google Scholar 

  48. S. A. Achmad, E. H. Hakim, L. D. Juliawaty, L. S. Makmur, N. Aimi, and E. L. Ghisalberti, J. Nat. Prod., 59, No. 9, 878 (1996); Ref. Zh. Khim., 10, E212 (1997).

    Article  CAS  Google Scholar 

  49. Y. Shirataki, T. Tsuzuku, I. Yokoe, R. T. Hirano, and M. Komatsu, Chem. Pharm. Bull., 38, No. 6, 1712 (1990); Ref. Zh. Khim., 1, E283 (1991).

    CAS  Google Scholar 

  50. T. Fukai, Y.-H. Pei, T. Nomura, C.-Q. Xu, L.-J. Wu, and Y.-J. Chen, Heterocycles, 43, No. 2, 425 (1996); Ref. Zh. Khim., 21, E224 (1996).

    CAS  Google Scholar 

  51. Y. Inamori, K. Baba, H. Tsujibo, M. Taniguchi, K. Nakata, and M. Kozawa, Chem. Pharm. Bull., 39, No. 6, 1604 (1991); Ref. Zh. Khim., 8, O348 (1992).

    CAS  PubMed  Google Scholar 

  52. M. Iinuma, M. Ohyama, Y. Kawasaka, and T. Tanaka, Phytochemistry, 39, No. 3, 667 (1995); Ref. Zh. Khim., 8, E183 (1996).

    Article  CAS  Google Scholar 

  53. M. Iinuma, M. Ohyama, and T. Tanaka, Phytochemistry, 38, No. 2, 539 (1995); Ref. Zh. Khim., 22, E205 (1995).

    CAS  Google Scholar 

  54. K. Shinya, K. Furihata, Y. Teshima, Y. Hayakawa, and H. Seto, J. Org. Chem., 58, No. 15, 4170 (1993).

    Article  CAS  Google Scholar 

  55. K. Shinya, K. Furihata, Y. Hayakawa, H. Seto, Y. Kato, and J. Clardy, Tetrahedron Lett., 32, No. 7, 943 (1991).

    CAS  Google Scholar 

  56. V. P. Pathak and R. N. Khanna, Curr. Sci., 48, No. 17, 770 (1979); Ref. Zh. Khim., 10, E147 (1980).

    CAS  Google Scholar 

  57. N. Kihara and M. Tashiro, Chem. Express, 5, No. 9, 641 (1990); Ref. Zh. Khim., 8, E41 (1991).

    CAS  Google Scholar 

  58. M. Reuman and A. I. Meyers, Tetrahedron, 41, No. 5, 837 (1985).

    Article  CAS  Google Scholar 

  59. A. P. Phadnis, B. Sinha, S. A. Patwardhan, G. D. Hebbalkar, and R. N. Sharma, Indian J. Chem., Sect. A, 29, No. 3, 291 (1990); Ref. Zh. Khim., 15, E33 (1990).

    Google Scholar 

  60. H. Shirahama, Jpn. Pat. No. 01-226843, Appl. No. 63-54490, 8 Mar. 1988, Publ. 11 Sep. 1989; Ref. Zh. Khim., 24, O98P (1990).

  61. A. Sato, T. Shindo, K. Hasegawa, and S. Ushiyama, Jpn. Pat. No. 02-290826, Appl. No. 1-111294, 28 Apr. 1989, Publ. 30 Nov. 1990; Ref. Zh. Khim., 7, O125P (1993).

    Google Scholar 

  62. S. Takanashi and K. Mori, Liebigs Ann., No. 6, 1081 (1997); Ref. Zh. Khim., 22, E255 (1998).

  63. L. Jaenicke and F. J. Marner, Liebigs Ann., No. 7, 1343 (1995); Ref. Zh. Khim., 24, E470 (1995).

  64. R. Nanba, M. Isozaki, I. Endo, and Y. Yomo, Jpn. Pat. No. 02-240037, Appl. No. 64-60236, 13 Mar. 1989, Publ. 25 Sep. 1990; Ref. Zh. Khim., 10, O138P (1993).

    Google Scholar 

  65. O. S. Kukovinets, E. T. Yamansarova, A. G. Kukovinets, R. A. Zainullin, F. Z. Galin, R. V. Kunakova, V. V. Zorin, and G. A. Tolstikov, Zh. Org. Khim., 37, No. 2, 259 (2001).

    Google Scholar 

  66. O. S. Kukovinets, E. T. Yamansarova, R. A. Zainullin, F. Z. Galin, R. V. Kunakova, L. A. Tyurina, M. I. Abdullin, A. L. Lukmanova, A. M. Kolbin, and S. V. Nikolaeva, Bashk. Khim. Zh., 7, No. 6, 25 (2000).

    Google Scholar 

  67. O. S. Kukovinets, T. A. Valiev, R. A. Zainullin, E. T. Yamansarova, and A. G. Kukovinets, in: Abstracts of Papers of the Jubilee Scientific-Practical Conference, UTIS, Ufa (1996), p. 65.

    Google Scholar 

  68. O. S. Kukovinets, R. A. Zainullin, V. I. Roshchin, G. A. Tolstikov, V. N. Odinokov, et al., USSR Pat. No. 1399302, Publ. 30 May 1988, Byull. Izobr., No. 20.

  69. O. S. Kukovinets, R. A. Zainullin, V. N. Odinokov, M. I. Kislitsyn, V. I. Roshchin, F. Z. Galin, and G. A. Tolstikov, Zh. Org. Khim., 37, No. 2, 248 (2001).

    Google Scholar 

  70. S. Torii, K. Uneyama, I. Kawahara, and M. Kuyama, Chem. Lett., 455 (1978).

  71. S. Torii, K. Uneyama, and M. Kuyama, Jpn. Pat. No. 53-105470, Appl. No. 52-20471, 25 Feb. 1977, Publ. 13 Sep. 1978; Ref. Zh. Khim., 2, R492P (1980).

  72. M. Nishizawa, H. Yakenaka, H. Nishide, and Y. Hayashi, Tetrahedron Lett., 24, No. 25, 2581 (1983).

    Article  CAS  Google Scholar 

  73. M. Prashad, F. G. Kathawala, and T. Scallen, J. Med. Chem., 36, No. 10, 1501 (1993).

    Article  CAS  PubMed  Google Scholar 

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  1. Bashkir State University, 450074, Ufa, ul. Mingazheva, 100

    O. S. Kukovinets, R. A. Zainullin & M. I. Kislitsyn

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  1. O. S. Kukovinets
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 3–13, January–February, 2006.

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Kukovinets, O.S., Zainullin, R.A. & Kislitsyn, M.I. Natural arylterpenes and their biological activity. Chem Nat Compd 42, 1–15 (2006). https://doi.org/10.1007/s10600-006-0025-6

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