Nitrile-containing natural products

Abstract

References

1. J. L. Legras, G. Chuzel, A. Arnaud and P. Galzy, World J. Microbiol. Biotechnol., 1990, 6, 83 For the first review of ‘Nitriles in Live Organisms’ see reference 3.
2. P. J. Scheuer, Acc. Chem. Res., 1992, 25, 433.
3. W. Hubel, Dtsch. Apoth. Zeit., 1981, 121, 863.
4. Obtained using references 1–3, and the metabolites included in this review.
5. S. Mahadevan, Ann. Rev. Plant. Physiol., 1973, 24, 69.
6. S. S. Duffy, in Cyanide in Biology, Academic Press, London, 1981, pp. 385–414.
7. B. A. Halkier, H. V. Scheller and B. L. Møller, in Cyanide Compounds in Biology(Ciba Foundation Symposium 140), Wiley, Chichester, 1988, pp. 49–66.
8. P. M. Dewick, Nat. Prod. Rep., 1998, 15, 17.
9. S. Louda and S. Mole, in Herbivores, Their Interactions with Secondary Plant Metabolites, 2nd edn., eds. G. A. Rosenthal and M. R. Berenbaum, Academic Press, San Diego, 1991, vol 1, ch. 4, pp. 124–157.
10. V. Gil and A. J. MacLeod, Phytochemistry, 1980, 19, 2547.
11. M. E. Wall, H. Taylor, P. Perera and M. C. Wani, J. Nat. Prod., 1988, 51, 129.
12. W. C. K. Chiang, D. J. Pusateri and R. E. A. Leitz, J. Agric. Food Chem., 1998, 46, 1018.
13. A. J. MacLeod and G. MacLeod, Phytochemistry, 1977, 16, 907.
14. (a) S. F. Aripova, O. Abdilalimov, E. S. Bagdasarova, M. I. Aizikov, S. Y. Yunusov and A. G. Kurmukov, Chem. Nat. Compd., 1984, 20, 79; (b) A. G. Tolstikov, L. A. Biktimirova, O. V. Tolstikova, V. S. Shmakov, S. F. Aripova, V. N. Odinokov and G. A. Tolstikov, Chem. Nat. Compd., 1991, 27, 225.
15. M. Repcak, J. Imrich, K. Pihlaja and M. Kal'atova, Phytochemistry, 1998, 47, 1219.
16. (a) R. A. Cole, Phytochemistry, 1976, 15, 759; (b) J. T. O. Kirk and C. G. MacDonald, Phytochemistry, 1974, 13, 2611.
17. (a) M. E. Daxenbichler, C. H. VanEtten, W. H. Tallent and I. A. Wolff, Can. J. Chem., 1967, 45, 1971; (b) M. E. Daxenbichler, C. H. VanEtten and I. A. Wolff, Phytochemistry, 1968, 7, 989.
18. M. E. Daxenbichler, C. H. VanEtten and I. A. Wolff, Biochemistry, 1966, 5, 692.
19. M. Lechtenberg, A. Nahrstedt and F. R. Fronczek, Phytochemistry, 1996, 41, 779.
20. H. Pourmohseni, W.-D. Ibenthal, R. Machinek, G. Remberg and V. Wray, Phytochemistry, 1993, 33, 295.
21. A. Nahrstedt, A. Walther and V. Wray, Phytochemistry, 1982, 21, 107.
22. M. Lechtenberg, A. Nahrstedt, V. Wray and F. R. Fronczek, Phytochemistry, 1994, 37, 1039.
23. B. Danieli, G. Palmisano, B. Gabetta and E. M. Martinelli, J. Chem. Soc., Perkin Trans., 1980, 1, 601.
24. T.-S. Kam and K. Yoganathan, Phytochemistry, 1997, 46, 785.
25. T. Arai, K. Takahashi, S. Nakahara and A. Kubo, Experientia, 1980, 36, 1025.
26. (a) T. Hayashi, T. Noto, Y. Nawata, H. Okazaki, M. Sawada and K. Ando, J. Antibiot., 1982, 35, 771; (b) T. Hayashi and Y. Nawata, J. Chem. Soc., Perkin Trans., 1983, 2, 335.
27. S. J. Gould, W. He and M. C. Cone, J. Nat. Prod., 1993, 56, 1239.
28. T. Hida, M. Murio, S. Tanida and S. Harada, J. Antibiot., 1994, 47, 917.
29. J.-Y. Su, X.-H. Xu, L.-M. Zeng, M.-Y. Wang, N. Lu, Y. Lu and Q. T. Zhang, Phytochemistry, 1998, 48, 583.
30. P. S. Sarma and G. Padmanaban, Toxic Constituents of Plant Foodstuffs, ed. I. E. Liener, Academic Press, New York and London, 1969, ch. 9.
31. N. Naruse, S. Yamamoto, H. Yamamoto, S. Kondo, S. Masuyoshi, K.-I. Numata, Y. Fukagawa and T. Oki, J. Antibiot., 1993, 46, 685.
32. M. Zeches, T. Ravao, B. Richard, G. Massiot, L. Le Men-Olivier and R. Verpoorte, J. Nat. Prod., 1987, 50, 714.
33. O. Olsen and H. Sorensen, Phytochemistry, 1980, 19, 1783.
34. V. Gil and A. J. MacLeod, Phytochemistry, 1980, 19, 1657.
35. A. Ballester, A. Verwey and J. C. Overeem, Phytochemistry, 1975, 14, 1667.
36. S. Faizi, B. S. Siddiqui, R. Saleem, S. Siddiqui and K. Aftab, J. Nat. Prod., 1994, 57, 1256.
37. Y. Gopichand and F. J. Schmitz, J. Org. Chem., 1980, 45, 5383.
38. G. Cimino, M. Gavagnin, G. Sodano, A. Spinella, G. Strazzullo, F. J. Schmitz and G. Yalamanchili, J. Org. Chem., 1987, 52, 2301.
39. (a) R. Racioppi, M. Gavagnin, G. Strazzullo and G. Sodano, Tetrahedron Lett., 1990, 31, 573; (b) K. Kawamine, R. Takeuchi, M. Miyashita, H. Irie, K. Shimamoto and Y. Ohfune, Chem. Pharm. Bull., 1991, 39, 3170.
40. R. Rajagopal and P. Larsen, Planta, 1972, 103, 45.
41. S. Kosemura, K. Niwa, H. Emori, K. Yokotani-Tomita, K. Hasegawa and S. Yamamura, Tetrahedron Lett., 1997, 38, 8327.
42. S. Tamura, M. Numoto and M. Nagao, Plant Growth Subst., 1970, 127.
43. R. G. Powell, K. L. Mikolajczak, B. W. Zilkowski, H. S. M. Lu, E. K. Mantus and J. Clardy, Experientia, 1991, 47, 304.
44. E. K. Mantus and J. Clardy, Tetrahedron Lett., 1993, 34, 1085.
45. T. Rasmussen, J. Jensen, U. Anthoni, C. Christophersen and P. H. Nielsen, J. Nat. Prod., 1993, 56, 1553.
46. D. B. Stierle and D. J. Faulkner, J. Org. Chem., 1980, 45, 4980.
47. E. E. Conn, in Secondary Plant Products, Encyclopedia of Plant Physiology, 1980, 8, ch. 9, pp. 461–492.
48. R. Eyjolfsson, Fortschr. Chem. Org. Naturst., 1970, 28, 74.
49. (a) A. Nahrstedt, in Cyanide Compounds in Biology(Ciba Foundation Symposium 140), Wiley, Chichester, 1988, pp. 131–144; (b) D. A. Jones, in Cyanide Compounds in Biology(Ciba Foundation Sympo-sium 140), Wiley, Chichester, 1988, pp. 151–159.
50. J. E. Poulton, in Cyanide Compounds in Biology(Ciba Foundation Symposium 140), Wiley, Chichester, 1988, pp. 67–81.
51. J. E. Poulton, Plant Physiol., 1990, 94, 401.
52. K. Thomsen and L. Brimer, Bot. J. Linn. Soc., 1997, 124, 273.
53. D. A. Jones, Phytochemistry, 1998, 47, 155.
54. (a) J. Wilson, Handbook of Clinical Neurology, 1995, 65, 25; (b) T. Shibamoto and L. F. Bjeldanes, in Introduction to Food Toxicology, Academic Press, San Diego, 1993, ch 5.
55. D. S. Seigler, in Herbivores, Their Interactions with Secondary Plant Metabolites, 2nd edn., eds. G. A. Rosenthal and M. R. Berenbaum, Academic Press, San Diego, 1991, vol. 1, ch. 2., pp. 35-77.
56. A. Nahrstedt, in Biologically Active Natural Products(Annual Proceedings of the Phytochemical Society of Europe 27), eds. K. Hostettmann and P. J. Lea, Clarendon Press, Oxford, 1987, pp. 213–234.
57. H. Prawat, C. Mahidol, S. Ruchirawat, U. Prawat, P. Tuntiwachwuttikul, U. Tooptakong, W. C. Taylor, C. Pakawatchai, B. W. Skelton and A. H. White, Phytochemistry, 1995, 40, 1167.
58. J. Rockenbach, A. Nahrstedt and V. Wray, Phytochemistry, 1992, 31, 567.
59. B. Schwarz, V. Wray and P. Proksch, Phytochemistry, 1996, 42, 633.
60. H. Wada, K. Daidohji and N. Tanaka, Nat. Med., 1997, 51, 69.
61. D. Chassagne and J. Crouzet, Phytochemistry, 1998, 49, 757.
62. N. Nakajima and M. Ubukata, Biosci. Biotechnol. Biochem., 1998, 62, 453.
63. See for example A. Tobari, T. Shimizu, H. Miyamae, A. Nagasawa, M. Kawase and S. Saito, Carbohydr. Res., 1998, 310, 239.
64. The structure of a potential dihydrobenzene precursor was reported but later revised to the known nitriloside menisdurin 49e A. Nahrstedt and V. Wray, Phytochemistry, 1990, 29, 3934.
65. L. R. Simpol, H. Otsuka, K. Ohtani, R. Kasai and K. Yamasaki, Phytochemistry, 1994, 36, 91.
66. A. Murakami, H. Ohigashi, S. Tanaka, M. Hirota, R. Irie, N. Takeda, A. Tatematsu and K. Koshimizu, Phytochemistry, 1993, 32, 1461.
67. A. E. Tih, R. G. Tih, B. L. Sondengam, M. T. Martin and B. Bodo, J. Nat. Prod., 1994, 57, 971.
68. B. B. Messanga, R. Ghogomu, B. L. Sondengram, A. Blond and B. Bodo, Fitoterapia, 1998, 69, 439.
69. (a) C. A. Elliger, A. C. Waiss, Jr. and R. E. Lundin, J. Chem. Soc., Perkin Trans. 1, 1973, 2209; (b) C. A. Elliger, A. C. Waiss, Jr. and R. E. Lundin, J. Org. Chem., 1974, 39, 2930.
70. N. Chida, K. Yamada and S. Ogawa, J. Chem. Soc., Perkin Trans. 1, 1992, 1131.
71. C.-C. Chen, Y.-P. Chen, H.-Y. Hsu, K.-H. Lee, S. Tani and A. T. McPhail, J. Nat. Prod., 1985, 48, 933.
72. D. Dwuma-Badu, W. H. Watson, E. M. Gopalakrishna, T. U. Okarter, J. E. Knapp, P. L. Schiff, Jr. and D. J. Slatkin, Lloydia, 1976, 39, 385.
73. V. Plouvier, Phytochemistry, 1978, 17, 1010.
74. A. Sosa, F. Winternitz, R. Wylde and A. A. Pavia, Phytochemistry, 1977, 16, 707.
75. J. Wu, E. H. Fairchild, J. L. Beal, T. Tomimatsu and R. W. Doskotch, J. Nat. Prod., 1979, 42, 500.
76. K. Ueda, K. Yasutomi and I. Mori, Chem. Lett., 1983, 149.
77. K. Takahashi, S. Matsuzawa and M. Takani, Chem. Pharm. Bull., 1978, 26, 1677.
78. A. Nahrstedt and V. Wray, Phytochemistry, 1990, 29, 3934.
79. T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuo, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang and A. Inada, Chem. Pharm. Bull., 1994, 42, 2251.
80. M. Yogo, S. Ishiguro, H. Murata and H. Furukawa, Chem. Pharm. Bull., 1990, 38, 225.
81. M. Oda, A. Yamamuro and T. Watabe, Chem. Lett., 1979, 1427 and references therein.
82. D. S. Seigler and C. S. Butterfield, Phytochemistry, 1976, 15, 842.
83. A. J. J. van den Berg, S. F. A. J. Horsten, J. J. Kettenes-van den Bosch, B. H. Kroes and R. P. Labadie, Phytochemistry, 1995, 40, 597.
84. (a) M. Yoshikawa, H. Shimada, H. Shimoda, N. Murakami, J. Yamahara and H. Matsuda, Chem. Pharm. Bull., 1996, 44, 2086; (b) M. Yoshikawa, H. Shimada, H. Shimoda, H. Matsuda, J. Yamahara and N. Murakami, Chem. Pharm. Bull., 1995, 43, 1245.
85. M. Yoshikawa, H. Shimada, S. Horikawa, T. Murakami, H. Shimoda, J. Yamahara and H. Matsuda, Chem. Pharm. Bull., 1997, 45, 1498.
86. S. D. Fang, X. Q. Yan, C. F. Li, Z. Y. Fan, X. R. Xu and J. S. Xu, Acta Chim. Sinica, 1982, 40, 273.
87. R. Nishida, M. Rothschild and R. Mummery, Phytochemistry, 1994, 36, 37.
88. R. Nishida and M. Rothschild, Experientia, 1995, 51, 267.
89. W. K. Swenson, J. E. Dunn and E. E. Conn, Phytochemistry, 1987, 26, 1835.
90. J. R. Aldrich, S. P. Carroll, W. R. Lusby, M. J. Thompson, J. P. Kochansky and R. M. Waters, J. Chem. Ecol., 1990, 16, 199.
91. J. C. Braekman, D. Daloze and J. M. Pasteels, Biochem. System. Ecol., 1982, 10, 355.
92. K. L. Mikolajczak, Prog. Chem. Fats Other Lipids, 1977, 15, 97.
93. M. G. Ettlinger, J. W. Jaroszewski, S. R. Jensen, B. J. Nielsen and F. Nartey, J. Chem. Soc. Chem. Commun., 1977, 952.
94. M. Ettlinger and R. Eyjolfsson, J. Chem. Soc. Chem. Commun., 1972, 572.
95. (a) Y. Kato, N. Fusetani, S. Matsunaga and K. Hashimoto, J. Am. Chem. Soc., 1986, 108, 2780; (b) Y. Kato, N. Fusetani, S. Matsunaga and K. Hashimoto, J. Org. Chem., 1988, 53, 3930; (c) A. Okada, K. Watanabe, K. Umeda and M. Miyakado, Agric. Biol. Chem., 1991, 55, 2765.
96. S. Matsunaga, H. Fujiki, D. Sakata and N. Fusetani, Tetrahedron, 1991, 47, 2999.
97. E. J. Dumdei, J. W. Blunt, M. H. G. Munro and L. K. Pannell, J. Org. Chem., 1997, 62, 2636.
98. H. Ishihara, B. L. Martin, D. L. Brautigan, H. Kiraki, H. Ozaki, Y. Kato, N. Fusetani, S. Watabe, K. Hashimoto, D. Uemura and D. J. Hartshorne, Biochem. Biophys. Res. Commun., 1989, 159, 871.
99. (a) A. B. Smith III, G. K. Friestad, J. J.-W. Duan, J. Barbosa, K. G. Hull, M. Iwashima, Y. Qiu, P. G. Spoors, E. Bertounesque and B. A. Salvatore, J. Org. Chem., 1998, 63, 7596; (b) P. M. Pihko and A. M. P. Koskinen, J. Org. Chem., 1998, 63, 92; (c) N. Tanimoto, S. W. Gerritz, A. Sawabe, T. Noda, S. A. Filla and S. Masamune, Angew. Chem., Int. Ed. Engl., 1994, 33, 673; (d) D. A. Evans, J. R. Gage and J. L. Leighton, J. Am. Chem. Soc., 1992, 114, 9434 and references therein..
100. S. Matsunaga, T. Wakimoto and N. Fusetani, J. Org. Chem., 1997, 62, 2640.
101. S. Matsunaga, T. Wakimoto, N. Fusetani and M. Suganuma, Tetrahedron Lett., 1997, 38, 3763.
102. H. Takahashi, K. Nozawa and K.-i. Kawai, Chem. Pharm. Bull., 1996, 44, 2227.
103. M. Ishida, T. Hamasaki and Y. Hatsuda, Agr. Biol. Chem., 1975, 39, 2181.
104. See, for example: T. Morino, M. Nishimoto, N. Itou and T. Nishikiori, J. Antibiot., 1994, 47, 1546.
105. C. Rüchardt, M. Meier, K. Haaf, J. Pakusch, E. K. A. Wolber and B. Müller, Angew. Chem., Int. Ed. Engl., 1991, 30, 893.
106. M. T. Hamann, P. J. Scheuer and M. Kelly-Borges, J. Org. Chem., 1993, 58, 6565.
107. J. K. Zjawiony, P. Bartyzel and M. T. Hamann, J. Nat. Prod., 1998, 61, 1502.
108. K. Shin-ya, K. Furihata, Y. Teshima, Y. Hayakawa and H. Seto, J. Org. Chem., 1993, 58, 4170.
109. W. Toshiaki, K. Reina, F. Yasuhiro, N. Yasuaki, Y. Yumi, W. Yoshio and O. Kazuhiko, Jpn. Kokai Tokkyo Koho JP 08173176 A2 9, July 1996; Chem. Abstr., 1996, 125, 193565u.
110. (a) N. Haddad, M. Grishko and A. Brik, Tetrahedron Lett., 1997, 38, 6075; (b) N. Haddad, A. Brik and M. Grishko, Tetrahedron Lett., 1997, 38, 6079.
111. (a) J. Berger, L. M. Jampolsky and M. W. Goldberg, Arch. Biochem., 1949, 22, 476; (b) W. Keller-Schierlein, Helv. Chem. Acta, 1967, 50, 731; (c) R. Hutter, K. Poralla, H. G. Zachau and H. Zahneer, Biochem. Z., 1966, 344, 190; (d) H. Maher and R. H. Evans, J. Antibiot., 1987, 40, 1455 and 1988, 41, C-1.
112. S. K. Singh, S. Gurusiddaiah and J. W. Whalen, Antimicrob. Agents Chemother., 1985, 27, 239.
113. U. Huber, R. E. Moore and G. M. L. Patterson, J. Nat. Prod., 1998, 61, 1304.
114. G.-i. Nonaka, M. Hayashi, T. Tanaka, R. Saijo and I. Nishioka, Chem. Pharm. Bull., 1990, 38, 861.
115. E. R. H. Jones, V. Thaller and J. L. Turner, J. Chem. Soc., Perkin Trans. 1, 1975, 424.
116. S. D. Sastry and G. R. Waller, Phytochemistry, 1972, 11, 2241.
117. K. Yakushijin, S. Sugiyama, Y. Mori, H. Murata and H. Furukawa, Phytochemistry, 1980, 19, 161.
118. X.-F. Cheng, Z.-M. Meng and Z.-L. Chen, Phytochemistry, 1998, 49, 2193.
119. H. Hikino, M. Tamada and K.-Y. Yen, Planta Med., 1978, 33, 385.
120. S. N. Ganguly, Phytochemistry, 1970, 9, 1667.
121. R. Mukherjee and A. Chatterjee, Tetrahedron, 1966, 22, 1461.
122. (a) L. Skursky, D. Burleson and G. R. Waller, J. Biol. Chem., 1969, 244, 3238; (b) H. J. Lee and G. R. Waller, Phytochemistry, 1972, 11, 965.
123. G. M. Konig, A. D. Wright and A. Linden, Planta Med., 1998, 64, 443.
124. Y. Kato, N. Fusetani, S. Matsunaga and K. Hashimoto, Tetrahedron Lett., 1985, 26, 3483.
125. K. Ohkuma, J. Antibiot., 1961, 14, 343.
126. N. G. Bisset, A. K. Choudhury and M. D. Walker, Phytochemistry, 1974, 13, 255.
127. S. J. Gould, Chem. Rev., 1997, 97, 2499.
128. S. Tsukamoto, H. Kato, H. Hirota and N. Fusetani, J. Org. Chem., 1996, 61, 2936.
129. W. E. Conner, T. H. Jones, J. Eisner and J. Meinwald, Experientia, 1977, 33, 206.