Vegetables as chemical reagents

Journal of Natural Products

Volumn 70, Issue 3, 2007, Pages 478-492

  Cordell, Geoffrey A ^a   Lemos, Telma L G ^b   Monte, Francisco J Q ^b   De Mattos, Marcos C ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE; ALCOHOL DERIVATIVE; ALKANONE; ATORVASTATIN; BACTERIAL ENZYME; BORNEOL; CINNAMIC ACID DERIVATIVE; CYCLOALKANONE; DEACETYLLANATOSIDE A; DENOPAMINE; DIGITOXIGENIN; DIGITOXIN; ESTER DERIVATIVE; HERBACEOUS AGENT; ISOBORNEOL; LINALOOL; NATURAL PRODUCT; NICOTINAMIDE ADENINE DINUCLEOTIDE; PELITREXOL; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE INHIBITOR; PLANT EXTRACT; PREGNENOLONE; PROGESTERONE; REAGENT; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TALAMPANEL; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL REACTION; CHIRALITY; DRUG INDUSTRY; DRUG MANUFACTURE; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYMOLOGY; METHYLATION; MICROORGANISM; NONHUMAN; ORGANIC CHEMISTRY; PHARMACY; REVIEW; VEGETABLE; YEAST;

CATALYSIS; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; VEGETABLES;

EID: 34247122291     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0680634     Document Type: Review

References (147)

1. Cordell, G. A.; Quinn-Beattie, M. L.; Farnsworth, N. R. Phytother. Res. 2001, 15, 183-205.
2. Prance, G. T.; Beentje, H.; Dransfield, J.; Johns, R. Ann. Missouri Bot. Gard. 2000, 87, 67-71.
3. Rovner, S. Chem. Eng. News 2005, Oct. 10, 44-49.
4. Wink, M. Ed. Functions of Plant Secondary Metabolites and Their Exploitation in Biotechnology; Sheffield Academic Press: Sheffield, 1999; 362 pp.
5. Wink, M. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: Amsterdam, 2000; Vol. 21, pp 3-122.
6. Cordell, G. A. Phytochemistry 2000, 55, 463-480.
7. Cordell, G. A. Phytochem. Rev. 2002, 1, 261-273.
8. Cordell, G. A.; Colvard, M. D. J. Ethnopharmacol. 2005, 100, 5-14.
9. Pasteur, L. C. R. Acad. Sci. 1858, 615.
10. Fischer, E. Ber. Dtsch. Chem. Ges. 1894, 2895.
11. Fischer, E. Ber. Dtsch. Chem. Ges. 1894, 3189.
12. Weid, M.; Ziegler, J.; Kutchan, T. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13957-13962.
13. Carey, J. S; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337-2347.
14. Wells, A. Org. Proc. Res. Dev. 2006, 10, 678-681.
15. Sylvestre, J.; Chautard, H.; Cedrone, F.; Delcourt, M. Org. Proc. Res. Dev. 2006, 10, 562-571.
16. Sharma, S. K.; Husain, M.; Kumar, R.; Samuelson, L. A.; Kumar, J.; Watterson, A. C.; Parmar, V. S. Pure Appl. Chem. 2005, 77, 209-226.
17. Thayer, A. M. Chem. Eng. News 2006, Aug. 14, 15-27.
18. Shaw, N. M.; Robins, K. T.; Kiener, A. Adv. Synth. Catal. 2003, 345, 425-435.
19. Veit, T. Eng. Life Sci. 2004, 4, 508-511.
20. Farnsworth, N. R.; Akerele, O.; Bingel, A. S.; Soejarto, D. D.; Guo, Z. Bull. WHO 1985, 63, 965-81.
21. Cordell, G. A. Rev. Quim. 2003, 17, 1-15.
22. Cordell, G. A. Thai J. Hlth. Res. 2004, 18, 87-105.
23. Cordell, G. A. Rev. Quim. 2004, 19, 33-41.
24. Cordell, G. A.; Colvard, M. D. Arkivoc 2006, vii, 97-115.
25. Reisch, M. S. Chem. Eng. News 2001, Sept. 3, 17-22.
26. Rouhi, A. M. Chem. Eng. News 2002, April 22, 30-33.
27. Anastas, P.; Lankey, R. Chem. Br. 2001, 26-29.
28. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998; p 30.
29. Luna, H. Rev. Soc. Quim. Mex. 2004, 48, 211-219.
30. Liu, Z.-B.; Weis, R.; Gleider, A. Food Technol. Biotechnol. 2004, 42, 237-249.
31. Deussen, H.-J.; Zundel, M.; Valdois, M.; Lehmann, S. V.; Weil, V.; Hjort, C. M.; Oestergaard, P. R.; Marcussen, E.; Ebdrup, S. Org. Proc. Res. Dev. 2003, 7, 82-88.
32. Elenkov, M. M.; Hauer, B.; Janssen, D. B. Adv. Synth. Catal. 2006, 348, 579-585.
33. Johnson, D. V.; Griengl, H. Adv. Biochem. Eng./Biotechnol. 1999, 65, 31-55.
34. Schmidt, M.; Griengl, H. Top. Curr. Chem. 1999, 200, 193-226.
35. Griengl, H.; Schwab, H.; Fechter, M. Trends Biotechnol. 2000, 18, 252-256.
36. Fechter, M. H.; Greingl, H. Food Technol. Biotechnol. 2004, 42, 287-294.
37. Effenberger, F. Chimia 1999, 53, 3-10.
38. Geyer, R.; Kartnig, T.; Griengl, H.; Steiner, W. Food Technol. Biotechnol. 2001, 39, 161-167.
39. Roda, G.; Riva, S.; Danieli, B.; Griengl, H.; Rinner, U.; Schmidt, M.; Zabelinskaja, A. M. Tetrahedron 2002, 58, 2979-2983.
40. Buhler, H.; Bayer, A.; Effenberger, F. Chemistry (Weinheim) 2000, 6, 2564-2571.
41. Purkartofer, T.; Pabst, T.; van der Broek, C.; Griengl, H.; Maurer, O.; Skranc, W. Org. Proc. Res. Dev. 2006, 10, 618-621.
42. Weis, R.; Poechlauer, P.; Bona, R.; Skranc, W.; Luiten, R.; Wubbolts, M.; Schwab, H.; Glieder, A. J. Mol. Catal. B: Enzym. 2004, 29, 211-218.
43. Greenberg, W.; Weiner, D. P.; Adger, B.; Burk, M. WO 2003-US2177 20030123, 2003; Chem. Abstr. 2003, 139, 129923.
44. Rudroff, F.; Alphand, V.; Furstoss, R.; Mihovilovic, M. D. Org. Proc. Res. Dev. 2006, 10, 599-604.
45. Edegger, K.; Mang, H.; Faber, K.; Gross, J.; Kroutil, W. J. Mol. Catal. A 2006, 251, 66-70.
46. Kroutil, W.; Mang, H.; Edegger, K.; Faber, K. Adv. Synth. Catal. 2004, 346, 125-142.
47. Kroutil, W.; Mang, H.; Edegger, K.; Faber, K. Curr. Opin. Chem. Biol. 2004, 8, 120-126.
48. Jennwein, S.; Schürmann, M.; Wolberg, M.; Hilker, I.; Luiten, R.; Wubbolts, M.; Mink, D. Biotechnol. J. 2006, 1, 537-548.
49. Gröger, H. Chem. Rev. 2003, 103, 2795-2827.
50. Menzel, A.; Werner, H.; Altenbucher, J.; Groger, H. Eng. Life Sci. 2004, 4, 573-576.
51. Gröger, H.; May, O.; Werner, H.; Menzel, A.; Altenbuchner, J. Org. Proc. Res. Dev. 2006, 10, 666-669.
52. Edegger, K.; Stampfer, W.; Seisser, B.; Faber, K.; Mayer, S. F.; Oerhrlein, R.; Hafner, A.; Kroutil, W. Eur. J. Org. Chem. 2006, 1904-1909.
53. van Duersen, R.; Stampfer, W.; Edegger, K.; Faber, K.; Kroutil, W. J. Mol. Catal. B: Enzym. 2004, 31, 159-163.
54. Stampfer, W.; Kosjek, B.; Faber, K.; Kroutil, W. J. Org. Chem. 2002, 68, 402-406.
55. Stampfer, W.; Eddeger, B.; Kosjek, B.; Faber, K.; Kroutil, W. Adv. Synth. Catal. 2004, 346, 57-62.
56. Matsuda, T.; Watanabe, K.; Kamitanaka, T.; Harada, T.; Nakamura, K. Chem. Commun. 2003, 1198-1199.
57. Anderson, B. A.; Hansen, M. M.; Harkness, A. R.; Henry, C. L.; Vicenzi, J. T.; Zmijewski, M. J. J. Am. Chem. Soc. 1995, 117, 12358-9.
58. Toneva, K.; Vlahov, S.; Boneva, S.; Vassilev, S.; Vassilev, K. Dokl. Bulg. Akad. Nauk. 2002, 55, 43-48;
59. Chem. Abstr. 2002, 139, 116329.
60. Negi, M.; Subbaraju, G. V.; Manhas, M. S.; Bose, A. K. Enzyme Microb. Technol. 1993, 15, 483-488.
61. Zhang, B.-L.; Pionnier, S. Chem. - Eur. J. 2003, 9, 3604-3610.
62. Speicher, A.; Roeser, H., Heisel, R. J. Mol. Catal. B: Enzym. 2003, 22, 71-77.
63. Hirata, T.; Hamada, H.; Aoki, T.; Suga, T. Phytochemistry 1982, 21, 2209-2212.
64. Kergomard, A.; Renard, M. F.; Veschambre, H.; Courtois, D.; Petiard, V. Phytochemistry 1988, 27, 407-409.
65. Pollard, D.; Truppo, M.; Pollard, J.; Chen, C.; Moore, J. Tetrahedron: Asymmetry 2006, 17, 554-559.
66. Truppo, M. D.; Kim, J.; Brower, M.; Madin, A.; Sturr, M. G.; Moore, J. C. J. Miol. Catal. B: Enzym. 2006, 38, 158-162.
67. Hu, S.; Martinez, C. A.; Kline, B.; Yazbek, D.; Tao, J.; Kucera, D. J. Org. Process Res. Dev. 2006, 10, 650-654.
68. Hu, S.; Kelly, S.; Lee, S.; Tao, J.; Flahive, E. Org. Lett. 2006, 8, 1653-1655.
69. Thayer, A. M. Chem. Eng. News 2006, Aug. 14, 26-27.
70. Zhu, D.; Rios, B. E.; Rozzell, J. D.; Hua, L. Tetrahedron: Asymmetry 2005, 16, 1541-1546.
71. Zhu, D.; Mukherjee, C.; Rozzell, J. D.; Kambourakis, S.; Hua, L. Tetrahedron 2006, 62, 901-905.
72. Kamal, A.; Damayanthi, Y.; Reddy, B. S. N.; Lakminarayana, B.; Reddy, B. S. P. Chem. Commun. 1997, 1015-1016.
73. Cantello, B. C. C.; Eggleston, D. S.; Haigh, D. ; Haltiwanger, R. C.; Heath, C. M.; Hindley, R. M.; Jennings, K. R.; Sime, J. T.; Woroniecki, S. R. J. Chem. Soc., Perkin Trans. 1 1994, 3319-3324.
74. Vassilev, K.; Toneva, K.; Vlahov, S.; Boneva, S. Dokl. Bulg. Akad. Nauk. 2000, 53, 129-132.
75. Bruyn, J. Koninl. Ned. Acad. Wetenschap. Proc. 1954, 57, 41-45.
76. Reinhard, E.; Alfermann, A. W. Adv. Biochem. Eng. 1980, 16, 49-83.
77. Stohs, S. J.; Staba, E. J. J. Pharm. Sci. 1965, 54, 56-58.
78. Graves, J. M. H.; Smith, W. K. Nature 1967, 214, 1248-1249.
79. Furuya, T.; Hortani, M.; Kawaguchi, K. Phytochemistry 1971, 10, 1013-1017.
80. Hirotani, M.; Furuya, T. Phytochemistry 1974, 13, 2135-2142.
81. Furuya, T.; Hirotani, M.; Shinohara, T. Chem. Pharm. Bull. 1970, 18, 1080-1081.
82. Nawa, H.; Uchibayashi, M.; Kamiya, T.; Yamano, T.; Arai, H.; Abe, M. Nature 1959, 184, 469-470.
83. Alfermann, A. W.; Schuller, I.; Reinhard, E. Planta Med. 1980, 40, 218-223.
84. Suga, T.; Hirata, T.; Hirano, Y.; Ito, T. Chem. Lett. 1976, 1245-1248.
85. Hirata, T.; Aoki, T.; Hirano, Y.; Ito, T.; Suga, T. Bull. Chem. Soc. Jpn. 1981, 3527-3529.
86. Suga, T.; Aoki, T.; Hirata, T.; Lee, Y. S.; Nishimura, O.; Utsumi, M. Chem. Lett. 1980, 229-230.
87. Hirata, T.; Lee, Y. M.; Suga, T. Chem. Lett. 1982, 671-674.
88. Suga, T.; Hamada, T.; Hirata, T. Plant Cell Rep. 1983, 2, 66-68.
89. Suga, T.; Hirata, T.; Hamada, H.; Futatsugi, M. Plant Cell Rep. 1983, 2, 186-188.
90. Takemoto, M.; Matsuoka, Y.; Achiwa, K.; Kutney, J. P. Tetrahedron Lett. 2000, 41, 499-502.
91. Takemoto, M.; Matsuoka, Y.; Tanaka, K.; Achiwa, K.; Stoynov, N.; Kutney, J. P. Heterocycles 2002, 56, 227-234.
92. Chai, W.; Hayashida, Y.; Sakamaki, H.; Horiuchi, C. A. J. Mol. Catal. B: Enzym. 2004, 27, 55-60.
93. Bouwmeester, H. J.; De Kraker, J.-W.; Schurink, M.; Bino, R. J.; De Groot, A.; Franssen, M. C. R. WO 2002-NL591 20020917, 2002; Chem. Abstr. 2003, 138, 270406.
94. Lima, A. W. O.; Nascimento, V. B.; Pedrotti, J. J.; Angnes, L. Anal. Chim. Acta 1997, 354, 325-331.
95. Signori, C. A.; Fatibello Filho, O. Quim. Nova 1994, 17, 38-42.
96. Jaminet, F. J. Pharm. Berg. 1950, 5, 191-199.
97. Finkle, B.; Lewis, J. C.; Corse, J. W.; Lundin, R. E. J. Biol. Chem. 1962, 237, 2926-2931.
98. Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 2001, 49, 639-641.
99. Takemoto, M.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 2925-2928.
100. Takemoto, M.; Achiwa, K. Phytochemistry 1998, 49, 1627-1629.
101. Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 577-580.
102. Takemoto, M.; Moriyasu, Y.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 1458-1461.
103. Takemoto, M.; Yamamoto, Y.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 419-422.
104. Naoshima, Y.; Akakabe, Y.; Watanabe, F. Agric Biol. Chem. 1989, 53, 545-547.
105. Naoshima, Y.; Akakabe, Y. J. Org. Chem. 1989, 54, 4237-4239.
106. Naoshima, Y.; Akakabe, Y. Phytochemistry 1991, 30, 3595-3597.
107. Akakabe, Y.; Naoshima, Y. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1993, 35, 202-209.
108. Akakabe, Y.; Takahashi, M.; Kamezawa, M.; Kikuchi, K.; Tachibana, H.; Otani, T.; Naoshima, Y. J. Chem. Soc., Perkin Trans. 1 1995, 1295-1298.
109. Akakabe, Y.; Naoshima, Y. Phytochemistry 1993, 32, 1189-1191.
110. Baskar, B.; Ganesh, S.; Lokeswari, T. S.; Chadha, A. J. Mol. Catal. B Enzym. 2004, 27, 13-17.
111. Chadha, A.; Manohar, M.; Soundarajan, T.; Lokeswari, T. S. Tetrahedron: Asymmetry 1996, 7, 1571-1572.
112. Hamada, H.; Umeda, N.; Otsuka, N.; Kawabe, S. Plant Cell Rep. 1988, 7, 493-494.
113. Galun, E.; Aviv, D.; Dantes, A.; Freeman, A. Planta Med. 1985, 51, 511-514.
114. Aviv, D.; Galun, E. Planta Med. 1978, 33, 70-77.
115. Aviv, D.; Krochmal, E.; Dantes, A.; Galun, E. Planta Med. 1981, 42, 236-243.
116. Aviv, D.; Krochmal, E.; Dantes, A.; Galun, E. Planta Med. 1983, 47, 7-10.
117. Galun, E.; Aviv, D.; Dantes, A.; Freeman, A. Planta Med. 1983, 49, 9-13.
118. Suga, T.; Hirata, T.; Hamada, H. Bull. Chem. Soc. Jpn. 1986, 59, 2865-2867.
119. Suga, T.; Hamada, H.; Hirata, T. Chem. Lett. 1987, 471-474.
120. Suga, T.; Hamada, H.; Hirata, T.; Izumi, S. Chem. Lett. 1987, 903-906.
121. Hamada, H. Bull. Chem. Soc. Jpn. 1988, 61, 869-878.
122. Mukherjee, K. D. Lipid Biotechnol. 2002, 399-415.
123. Gardner, H. W.; Grechkin, A. N. Lipid Biotechnol. 2002, 157-182.
124. Giri, A.; Dhingra, V.; Giri, C. C.; Singh, A.; Ward, O. P.; Narasu, M. L. Biotechnol. Adv. 2001, 19, 175-199.
125. Robins, R. J.; Walton, N. J. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 43, pp 115-187.
126. Baldassarre, F.; Bertoni, G. Chiappe, C; Marioni, F. J. Mol. Catal. B: Enzym. 2000, 11, 55-58.
127. Marioni, F.; Chiappe, C. Ital. Pat. 199907192001; Chem. Abstr. 2004, 140, 217083.
128. Yadav, J. S.; Thirupathi Reddy, P.; Nanda, S.; Bhaskar Rao, A. Tetrahedrom Asymmetry 2000, 3381-3385.
129. Yadav, J. S.; Nanda, S.; Thirupathi, Reddy, P.; Bhaskar Rao, A. J. Org. Chem. 2002, 67, 3900-3903.
130. Comasseto, J. V.; Omori, A. T.; Porto, A. L.; Andrade, L. H. Tetrahedron Lett. 2004, 45, 473-476.
131. Andrade, L. H.; Utsunomiya, R. S.; Omori, A. T.; Porto, A. L. M., Comasseto, J. V. J. Mol. Catal. B: Enzym. 2006, 38, 84-90.
132. Sousa, J. S. N.; Machado, L. L.; de Mattos, M. C.; Solange, S.; Lemos, T. L. G.; Cordell, G. A. Phytochemistry 2006, 67, 1637-1643.
133. Nitschke, M.; Haddad, R.; Costa, G. N.; Gilioli, R.; Meurer, E. C.; Gatti, M. S. V.; Eberlin, M. N.; Hoehr, N. F.; Pastore, G. N. Food Sci. Biotechnol. 2004, 13, 591-596.
134. Nitschke, M. Pastore, G. M. Appl. Biochem. Biotechnol. 2004, 112, 163-172.
135. Suga, T.; Hirata, T.; Izumi, S. Phytochemistry 1986, 25, 2791-2792.
136. Mironowicz, A.; Jarosz, B.; Siewinski, A. Acta Soc. Bot. Pol. 1995, 64, 281-285.
137. Mironowicz, A. Phytochemistry 1998, 47, 1531-1534.
138. Mironowicz, A.; Kromer, K.; Pawlowicz, P.; Siewinski, A. Acta Soc. Bot. Pol. 1994, 63, 43-48.
139. Pawlowicz, P.; Siewinski, A. Phytochemistry 1987, 26, 1001-1004.
140. Mironowicz, A.; Kukulczanka, K.; Siewinski, A. Acta Soc. Bot. Pol. 1993, 62, 21-23.
141. Mironowicz, A. Acta Soc. Bot. Pol. 1997, 66, 325-328.
142. Mironowicz, A.; Kromer, K. Collect. Czech. Chem. Commun. 1998, 63, 1655-1662.
143. Maczka, W. K.; Mironowicz, A. Tetrahedron: Asymmetry 2002, 13, 2299-2302.
144. Ma̧czka, W. K.; Mironowicz, A. Tetrahedron: Asymmetry 2004, 15, 1965-1967.
145. Kumaraswarmy, G.; Ramesh, S. Green Chem. 2003, 5, 306-308.
146. Nagaoka, H. Biotechnol. Progr. 2004, 20, 128-133.
147. Wilson, E. O. The Diversity of Life; Penguin Press: London, 1992; p 275.