Abstract
Liverworts produce a great variety of lipophilic terpenoids, aromatic compounds, and acetogenins. Many of these constituents have characteristic scents, pungency, and bitterness, and display a quite extraordinary array of bioactivities and medicinal properties. These expressions of biological activity are summarized and discussed, and examples are given of the potential of certain lead compounds for structure-activity studies and synthesis.
Conference
International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 25th, Kyoto, Japan, 2006-07-23–2006-07-28
References
1. G. Garnier, L. Bezaniger-Beauquesne, G. Debraux. Ressources Medicinales de la Flore Francaise, Vol. 1, pp. 78-81, Vigot Freres Editeurs, Paris (1969).Search in Google Scholar
2. C. Suire. Rev. Bryol. Lichenol. 41, 105 (1972).10.2307/3638237Search in Google Scholar
3. H. Ding. Zhong guo Yao yun Bao zi Zhi wu., pp. 1-409, Kexue Jishu Chuban She, Shanghai (1982).Search in Google Scholar
4. P. C. Wu. Bryol. Times 13, 5 (1982).Search in Google Scholar
5. (a) H. Ando, A. Matsuo. In Advances in Bryology, Vol. 2, W. Schultze-Motel (Ed.), pp. 133-224, J. Cramer, Vaduz (1984);Search in Google Scholar
5. (b) Y. Asakawa. In Phytochemicals in Human Health Protection, Nutrition, and Plant Defense, J. Romeo (Ed.), pp. 319-342, Kluwer Academic/Plenum Publishers, New York (1999).10.1007/978-1-4615-4689-4_12Search in Google Scholar
6. Y. Asakawa. In Progress in the Chemistry of Organic Natural Products, Vol. 42, W. Herz, H.Grisebach, G. W. Kirby (Eds.), pp. 1-285, Springer, Vienna (1982).Search in Google Scholar
7. Y. Asakawa. In Bryophytes: Their Chemistry and Chemical Taxonomy, D. H. Zinsmeister, R.Mues (Eds.), pp. 369-410, Oxford University Press, Oxford (1990).Search in Google Scholar
8. Y. Asakawa. In Bryophyte Development: Physiology and Biochemistry, R. N. Chopra, S. C. Bhatla (Eds.), pp. 259-287, CRC Press, Boca Raton (1990).Search in Google Scholar
9. Y. Asakawa. In Bioactive Natural Products: Detection, Isolation, and Structural Determination, S. M. Colegate, R. J. Molyneux (Eds.), pp. 319-347, CRC Press, Boca Raton (1993).Search in Google Scholar
10. Y. Asakawa. In Progress in the Chemistry of Organic Natural Products, Vol. 65, W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, Ch. Tamm (Eds.), pp. 1-562, Springer, Vienna (1995).Search in Google Scholar
11. (a) M. Mizutani. Misc. Bryol. Lichenol. 6, 64 (1975);Search in Google Scholar
11. (b) Y. Asakawa. Aroma Res. 15, 204 (2004).10.1155/2004/521892Search in Google Scholar
12. Y. Asakawa, M. Toyota, H. Tanaka, T. Hashimoto, D. Joulain. J. Hattori Bot. Lab. 78, 183 (1995).Search in Google Scholar
13. doi:10.1002/ffj.2730090507, M. Toyota, Y. Asakawa. Flavour Fragr. J. 9, 237 (1994).Search in Google Scholar
14. doi:10.1016/S0031-9422(96)00722-4, M. Toyota, H. Koyama, Y. Asakawa. Phytochemistry 44, 1261 (1997).Search in Google Scholar
15. doi:10.1039/p19910000435, M. Tori, M. Sono, Y. Nishigaki, K. Nakashima, Y. Asakawa. J. Chem. Soc., Perkin Trans. 1 435 (1991).Search in Google Scholar
16. M. Sono. Ph. D. Thesis, Tokushima Bunri University, p. 110 (1991).Search in Google Scholar
17. doi:10.1016/S0031-9422(96)00723-6, M. Toyota, T. Saito, J. Matsunami, Y. Asakawa. Phytochemistry 44, 1265 (1997).Search in Google Scholar
18. J. D. Connolly. Rev. Latinoamer. Quim. 12, 121 (1982).Search in Google Scholar
19. J. D. Connolly. In Bryophytes: Their Chemistry and Chemical Taxonomy, D. H. Zinsmeister, R.Mues (Eds.), pp. 41-58, Oxford University Press, Oxford (1990).Search in Google Scholar
20. (a) doi:10.1016/0031-9422(90)83066-A, M. Toyota, Y. Asakawa, J.-P. Frahm. Phytochemistry 29, 2334 (1990);Search in Google Scholar
20. (b) D. Joulain, R. Tabacchi. Unpublished results.Search in Google Scholar
21. J. Sporle. Ph. D. Thesis, Universitat des Saarlandes, p. 90 (1990).Search in Google Scholar
22. doi:10.1016/0031-9422(88)80204-8, S. Huneck, J. D. Connolly, A. A. Freer, D. S. Rycroft. Phytochemistry 27, 1405 (1988).Search in Google Scholar
23. (a) doi:10.1016/S0031-9422(00)84508-2, Y. Asakawa, M. Toyota, A. Cheminat. Phytochemistry 25, 2555 (1986);Search in Google Scholar
23. (b) Y. Asakawa. Unpublished results.Search in Google Scholar
24. (a) H. Inoue. Koke no Sekai (World of Bryophytes), p. 178, Idemitsu Ltd., Tokyo (1978);Search in Google Scholar
24. (b) doi:10.1021/np0601298, L.Harinantenaina, S. Takaoka. J. Nat. Prod. 69, 1193 (2006);Search in Google Scholar
24. (c) doi:10.1248/cpb.49.1380, Y. Asakawa, Y. Oiso, J. E. Braggins. Chem. Pharm. Bull. 49, 1380 (2001);Search in Google Scholar
24. (d) doi:10.1002/cbdv.200590079, C. Socolsky, N. Murunga, A. Bardon. Chem. Biodiversity 2, 1105 (2005).Search in Google Scholar
25. T. Hashimoto, Y. Okumura, K. Suzuki, S. Takaoka, Y. Kan, M. Tori, Y. Asakawa. Chem. Pharm. Bull. 43, 2030 (1995).10.1248/cpb.43.2030Search in Google Scholar
26. doi:10.1016/S0031-9422(00)83533-5, Y. Asakawa, L. J. Harrison, M. Toyota. Phytochemistry 24, 261 (1985).Search in Google Scholar
27. doi:10.1016/0031-9422(92)80270-O, K. Ono, T. Sakamoto, Y. Asakawa. Phytochemistry 31, 1249 (1992).Search in Google Scholar
28. doi:10.1002/(SICI)1099-1026(199601)11:1<53::AID-FFJ535>3.0.CO;2-8, K. Ono, T. Sakamoto, H. Tanaka, Y. Asakawa. Flavour Fragr. J. 11, 53 (1995).Search in Google Scholar
29. doi:10.1016/0031-9422(91)83728-4, M. Toyota, A. Ueda, Y. Asakawa. Phytochemistry 30, 567 (1991).Search in Google Scholar
30. T. Hashimoto, H. Tanaka, Y. Asakawa. Chem. Pharm. Bull. 42, 1542 (1994).10.1248/cpb.42.1542Search in Google Scholar
31. doi:10.1016/0031-9422(90)80133-2, F. Nagashima, M. Toyota, Y. Asakawa. Phytochemistry 29, 1619 (1990).Search in Google Scholar
32. D. S. Rycroft. In Bryophytes: Their Chemistry and Chemical Taxonomy, D. H. Zinsmeister, R.Mues (Eds.), pp. 109-119, Oxford University Press, Oxford (1990).Search in Google Scholar
33. (s), 162 (1986); (b) F. Nagashima, H. Tanaka, S. Takaoka, Y. Asakawa. Phytochemistry 45, 555 (1997); (c) M. Toyota, C. Nishimoto, Y. Asakawa. Chem. Pharm. Bull. 46, 542 (1998); (d) A. Bardon, G. B. Motre, N. Kamiya, M. Toyota, Y. Asakawa. Phytochemistry 59, 205 (2002); (e) Y. Asakawa. M. Toyota, M. von Konrat, J. E. Braggins. Phytochemistry 62, 439 (2003); (f) M. von Konrat, J. E. Braggins, Y. Asakawa, M. Toyota. Bryologist (2006). In press.Search in Google Scholar
34. doi:10.1055/s-2006-957484, M. Toyota, K. Tanimura, Y. Asakawa. Planta Med. 64, 462 (1998).Search in Google Scholar
35. (a) doi:10.1351/pac199466102193, Y. Asakawa. Pure Appl. Chem. 66, 2193 (1994);Search in Google Scholar
35. (b) G. A. Cordell, J. M. Pezzuto, Y. Asakawa. Unpublished results.Search in Google Scholar
36. doi:10.1016/0031-9422(93)85107-3, F. Nagasima, Y. Ohi, T. Nagai, M. Tori, Y. Asakawa. S. Huneck. Phytochemistry 33, 1445 (1993).Search in Google Scholar
37. doi:10.1016/0040-4020(96)00889-7, T. Yoshida, T. Hashimoto, S. Takaoka, Y. Kan, M. Tori, Y. Asakawa, J. M. Pezzuto, T.Pengsupaarp, G. A. Cordell. Tetrahedron 52, 14487 (1996).Search in Google Scholar
38. (a) doi:10.1021/np9603378, N. B. Perry, L. M. Foster, S. D. Lorimer, B. C. May, R. T. Weavers, M. Toyota, E. Nakaishi, Y. Asakawa. J. Nat. Prod. 59, 729 (1996);Search in Google Scholar
38. (b) doi:10.1248/cpb.50.808, F. Nagashima, M. Kondoh, T. Uematsu, A.Nishiyama, S. Saito, M. Sato, Y. Asakawa. Chem. Pharm. Bull. 59, 808 (2002);Search in Google Scholar
38. (c) doi:10.1055/s-2003-38888, F.Nagashima, M. Kondoh, M. Kawase, S. Simizu, H. Osada, M. Fujii, M. Watanabe, M. Sato, Y.Asakawa. Planta Med. 69, 377 (2003);Search in Google Scholar
38. (d) doi:10.1248/cpb.51.1189, F. Nagashima, W. Kasai, M. Kondo, M. Fujii, Y.Watanabe, J. E. Braggins, Y. Asakawa. Chem. Pharm. Bull. 51, 1189 (2003);Search in Google Scholar
38. (e) doi:10.1055/s-2004-827202, I. Suzuki, M.Kondoh, F. Nagashima, M. Fujii, Y. Asakawa, Y. Watanabe. Planta Med. 70, 401 (2004);Search in Google Scholar
38. (f) doi:10.1124/jpet.104.069690, M. Kondo, I. Suzuki, M. Sato, F. Nagashima, S. Simizu, M. Handa, M. Fujii, H. Osada, Y.Asakawa, Y. Watanabe. J. Pharmacol. Exp. Ther. 311, 115 (2004);Search in Google Scholar
38. (g) doi:10.1055/s-2004-827202, I. Suzuki, M. Kondoh, M. Harada, N. Koizumi, M. Fujii, Y. Asakawa, Y. Watanabe. Planta Med. 70, 723 (2004);Search in Google Scholar
38. (h) doi:10.1055/s-2005-837830, M.Kondo, I. Suzuki, M. Harada, F. Nagashima, M. Fujii, Y. Asakawa, Y. Watanabe. Planta Med. 71, 275 (2005);Search in Google Scholar
38. (i) doi:10.1016/j.tet.2005.03.010, F. Nagashima, M. Kondoh, M. Fujii, S. Takaoka, Y. Watanabe, Y. Asakawa. Tetrahedron 61, 4531 (2005).Search in Google Scholar
39. doi:10.1007/BF01013481, Y. Asakawa, G. W. Dawson, D. C. Griffith, J.-Y. Lallemand, S. V. Ley, K. Mori, A. Mudd, M.Pezechk-Leclaire, A. J. Picektt, H. Watanabe, C. M. Woodcock, Z. Zong-Ning. J. Chem. Ecol. 14, 1845 (1988).Search in Google Scholar
40. C. Schwartner, W. Bors, C. Michel, U. Franck, S. B. Muller-Jakic, A. Nenninger, Y. Asakawa, H.Wagner. Phytomedicine 2, 113 (1995).10.1016/S0944-7113(11)80055-3Search in Google Scholar
41. doi:10.1016/0031-9422(88)80599-5, T. Hashimoto, M. Tori, Y. Asakawa. Phytochemistry 27, 109 (1998).Search in Google Scholar
42. doi:10.1016/0031-9422(95)00548-X, F. Nagashima, S. Momosaki, Y. Watanabe, M. Toyota, S. Huneck, Y. Asakawa. Phytochemistry 41, 207 (1996).Search in Google Scholar
43. (a) doi:10.1021/np0502589, L. Harinantenaina, N. D. Quang, T. Nishizawa, T. Hashimoto, C. Kohchi, G.-I. Soma, Y.Asakawa. J. Nat. Prod. 68, 1779 (2005);Search in Google Scholar
43. (b) Y. Asakawa, S. Huneck, M. Toyota, T. Takemoto, C. Suire. J. Hattori Bot. Lab. 46, 163 (1979).Search in Google Scholar
44. doi:10.1039/p19910002737, Y. Fukuyama, Y. Asakawa. J. Chem. Soc., Perkin Trans. 1 2737 (1991).Search in Google Scholar
45. Y. Fukuyama, M. Kodama. Food and Food Ingredients J. 45 (1996).Search in Google Scholar
46. Z. Taira, M. Takei, K. Endo, T. Hashimoto, Y. Sakiya, Y. Asakawa. Chem. Pharm. Bull. 42, 52 (1996).10.1248/cpb.42.52Search in Google Scholar
47. doi:10.1007/BF02439448, N. Katsunuma. J. Bone Miner. Metab. 15, 1 (1997).Search in Google Scholar
48. doi:10.1016/0014-5793(93)80144-J, Y. Matsunaga, T. Saibara, H. Kido, N. Katsunuma. FEBS Lett. 324, 325 (1993).Search in Google Scholar
49. T. Hashimoto, H. Irita, M. Yoshida, A. Kikkawa, M. Toyota, H. Koyama, Y. Motoike, Y.Asakawa. J. Hattori Bot. Lab. 84, 309 (1998).Search in Google Scholar
50. doi:10.1016/j.febslet.2005.08.054, N. Tamehiro, Y. Sato, T. Suzuki, T. Hashimoto, Y. Asakawa, S. Yokoyama, T. Kawanishi, Y.Ohno, K. Inoue, T. Nagao, N. Nishimaki-Mogami. FEBS Lett. 579, 5299 (2005).Search in Google Scholar
51. doi:10.1248/cpb.53.256, L. Harinantenaina, Y. Noma, Y. Asakawa. Chem. Pharm. Bull. 53, 256 (2005).Search in Google Scholar
52. T. Hashimoto, K. Shiki, M. Tanaka, S. Takaoka, Y. Asakawa. Heterocycles 49, 315 (1998).10.3987/COM-98-S39Search in Google Scholar
53. doi:10.1016/S0040-4039(03)00236-3, H. Hagihara, F. Takeuchi, T. Hoshi, T. Suzuki, T. Hashimoto, Y. Asakawa. Tetrahedron Lett. 44, 2305 (2003).Search in Google Scholar
54. doi:10.1021/jo060477e, H. Hagihara, F. Takeuchi, M. Kudou, T. Hoshi, T. Suzuki, T. Hashimoto, Y. Asakawa. J. Org. Chem. 71, 4619 (2006).Search in Google Scholar
55. doi:10.1248/cpb.50.1390, M. Toyota, T. Shimomura, H. Ishii, Y. Asakawa. Chem. Pharm. Bull. 50, 1390 (2002).Search in Google Scholar
56. T. Hashimoto, S. Takaoka, M. Tanaka, Y. Asakawa. Heterocycles 59, 645 (2003).10.3987/COM-02-S67Search in Google Scholar
57. R. Lu, C. Paul, Basar, S. W. A. Konig, T. Hashimoto, Y. Asakawa. Phytochemistry 63, 5817 (2003).10.1016/S0031-9422(03)00188-2Search in Google Scholar
58. F. Nagashima, N. Matsumura, Y. Ashigaki, Y. Asakawa. J. Hattori Bot. Lab. 94, 197 (2003).Search in Google Scholar
59. doi:10.1016/j.phytochem.2003.08.022, F. Nagashima, M. Murakami, S. Takaoka, Y. Asakawa. Phytochemistry 64, 1319 (2003).Search in Google Scholar
60. doi:10.1016/j.bse.2004.04.009, L. Harinantenaina, Y. Asakawa. Biochem. Syst. Ecol. 32, 1073 (2004).Search in Google Scholar
61. doi:10.1248/cpb.52.481, M. Toyota, I. Omatsu, J. E. Braggins, Y. Asakawa. Chem. Pharm. Bull. 52, 481 (2004).Search in Google Scholar
62. doi:10.1248/cpb.52.556, F. Nagashima, T. Sekiguchi, Y. Asakawa. Chem. Pharm. Bull. 52, 556 (2004).Search in Google Scholar
63. doi:10.1248/cpb.52.949, F. Nagashima, M. Murakami, S. Takaoka, Y. Asakawa. Chem. Pharm. Bull. 52, 949 (2004).Search in Google Scholar
64. doi:10.1248/cpb.52.1382, L. Harinantenaina, Y. Asakawa. Chem. Pharm. Bull. 52, 1382 (2004).Search in Google Scholar
65. doi:10.1021/np030074z, G. V. Mitre, N. Kamiya, A. Bardon, Y. Asakawa. J. Nat. Prod. 67, 31 (2004).Search in Google Scholar
66. doi:10.1016/j.phytochem.2005.03.003, H. Tesso, W. A. Konig, Y. Asakawa. Phytochemistry 66, 941 (2005).Search in Google Scholar
67. doi:10.1016/j.phytochem.2005.05.012, F. Nagashima, K. Kishi, Y. Hamada, S. Takaoka, Y. Asakawa. Phytochemistry 66, 1662 (2005).Search in Google Scholar
68. doi:10.1080/14786410512331328722, F. Nagashima, T. Sekiguchi, Y. Asakawa. Nat. Prod. Rec. 19, 679 (2005).Search in Google Scholar
69. doi:10.1248/cpb.53.515, L. Harinantenaina, R. Kurata, Y. Asakawa. Chem. Pharm. Bull. 53, 515 (2005).Search in Google Scholar
70. doi:10.1248/cpb.54.902, F. Nagashima, Y. Kuba, Y. Asakawa. Chem. Pharm. Bull. 54, 902 (2006).Search in Google Scholar
71. doi:10.1248/cpb.54.1046, L. Harinantenaina, Y. Takahara, T. Nishizawa, C. Kohchi, G.-I. Soma, Y. Asakawa. Chem. Pharm. Bull. 54, 1046 (2006).Search in Google Scholar
72. doi:10.1248/cpb.54.996, M. Furusawa, T. Hashimoto, Y. Noma, Y. Asakawa. Chem. Pharm. Bull. 54, 996 (2006).Search in Google Scholar
73. M. Toyota, I. Omatsu, J. Braggins, Y. Asakawa. J. Oleo Sci. 55, 579 (2006).10.5650/jos.55.579Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston