Alkaloids, Biosynthesis and Their Applications
Keywords:
alkaloids, synthesis, pharmacological, chromatography, drug, toxic, extraction, metabolism
Abstract
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral[2] and even weakly acidic properties.[3] Some synthetic compounds of similar structure may also be termed alkaloids.[4] In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.[5] Alkaloids are produced by a large variety of organisms including bacteria, fungi, plants, and animals.[6] They can be purified from crude extracts of these organisms by acid-base extraction, or solvent extractions followed by silica-gel column chromatography.[7] Alkaloids have a wide range of pharmacological activities including antimalarial (e.g. quinine), antiasthma (e.g. ephedrine), anticancer (e.g. homoharringtonine),[8] cholinomimetic (e.g. galantamine),[9] vasodilatory (e.g. vincamine), antiarrhythmic (e.g. quinidine), analgesic (e.g. morphine),[10] antibacterial (e.g. chelerythrine),[11] and antihyperglycemic activities (e.g. piperine).[12] [failed verification] Many have found use in traditional or modern medicine, or as starting points for drug discovery. Other alkaloids possess psychotropic (e.g. psilocin) and stimulant activities (e.g. cocaine, caffeine, nicotine, theobromine),[13] and have been used in entheogenic rituals or as recreational drugs. Alkaloids can be toxic too (e.g. atropine, tubocurarine).[14] Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly evoke a bitter taste.[15]
References
1. Andreas Luch (2009). Molecular, clinical and environmental toxicology. Springer. p. 20. ISBN 978-3-7643-8335-0.
2. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "alkaloids". doi:10.1351/goldbook.A00220
3. R. H. F. Manske. The Alkaloids. Chemistry and Physiology. Volume VIII. New York: Academic Press, 1965, p. 673
4. Robert Alan Lewis. Lewis' dictionary of toxicology. CRC Press, 1998, p. 51 ISBN 1-56670-223-2
5. Chemical Encyclopedia: alkaloids. xumuk.ru
6. Roberts, M. F. (Margaret F.); Wink, Michael (1998). Alkaloids: Biochemistry, Ecology, and Medicinal Applications. Boston: Springer US. ISBN 9781475729054. OCLC 851770197.
7. Gonçalves Paterson Fox, Eduardo; Russ Solis, Daniel; Delazari dos Santos, Lucilene; Aparecido dos Santos Pinto, Jose Roberto; Ribeiro da Silva Menegasso, Anally; Cardoso Maciel Costa Silva, Rafael; Sergio Palma, Mario; Correa Bueno, Odair; de Alcântara Machado, Ednildo (April 2013). "A simple, rapid method for the extraction of whole fire ant venom (Insecta: Formicidae: Solenopsis)". Toxicon. 65: 5–8. doi:10.1016/j.toxicon.2012.12.009. hdl:11449/74946. PMID 23333648.
8. Kittakoop P, Mahidol C, Ruchirawat S (2014). "Alkaloids as important scaffolds in therapeutic drugs for the treatments of cancer, tuberculosis, and smoking cessation". Curr Top Med Chem. 14 (2): 239–252. doi:10.2174/1568026613666131216105049. PMID 24359196.
9. Russo P, Frustaci A, Del Bufalo A, Fini M, Cesario A (2013). "Multitarget drugs of plants origin acting on Alzheimer's disease". Curr Med Chem. 20 (13): 1686–93. doi:10.2174/0929867311320130008. PMID 23410167.
10. Raymond S. Sinatra; Jonathan S. Jahr; J. Michael Watkins-Pitchford (2010). The Essence of Analgesia and Analgesics. Cambridge University Press. pp. 82–90. ISBN 978-1139491983.
11. Cushnie TP, Cushnie B, Lamb AJ (2014). "Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities". Int J Antimicrob Agents. 44 (5): 377–386. doi:10.1016/j.ijantimicag.2014.06.001. PMID 25130096.
12. Qiu S, Sun H, Zhang AH, Xu HY, Yan GL, Han Y, Wang XJ (2014). "Natural alkaloids: basic aspects, biological roles, and future perspectives". Chin J Nat Med. 12 (6): 401–406. doi:10.1016/S1875-5364(14)60063-7. PMID 24969519.
13. "Alkaloid". 2007-12-18.
14. Robbers JE, Speedie MK, Tyler VE (1996). "Chapter 9: Alkaloids". Pharmacognosy and Pharmacobiotechnology. Philadelphia: Lippincott, Williams & Wilkins. pp. 143–185. ISBN 978-0683085006.
15. Rhoades, David F (1979). "Evolution of Plant Chemical Defense against Herbivores". In Rosenthal, Gerald A.; Janzen, Daniel H (eds.). Herbivores: Their Interaction with Secondary Plant Metabolites. New York: Academic Press. p. 41. ISBN 978-0-12-597180-5.
16. Robert A. Meyers Encyclopedia of Physical Science and Technology – Alkaloids, 3rd edition. ISBN 0-12-227411-3
17. Leland J. Cseke Natural Products from Plants Second Edition. CRC, 2006, p. 30 ISBN 0-8493-2976-0
18. A. William Johnson Invitation to Organic Chemistry, Jones and Bartlett, 1999, p. 433 ISBN 0-7637-0432-6
19. Raj K Bansal A Text Book of Organic Chemistry. 4th Edition, New Age International, 2004, p. 644 ISBN 81-224-1459-1
20. Aniszewski, p. 110
21. Hesse, pp. 1–3
22. Oscar Jacobsen, "Alkaloide" in: Ladenburg, Handwörterbuch der Chemie (Breslau, Germany: Eduard Trewendt, 1882), vol. 1, pp. 213–422.
23. Hesse, p. 5
24. The suffix "ine" is a Greek feminine patronymic suffix and means "daughter of"; hence, for example, "atropine" means "daughter of Atropa" (belladonna): Development of Systematic Names for the Simple Alkanes Archived 2012-03-16 at the Wayback Machine. yale.edu
25. Hesse, p. 7
26. van der Heijden, Robert; Jacobs, Denise I.; Snoeijer, Wim; Hallard, Didier; Verpoorte, Robert (2004). "The Catharanthus alkaloids: Pharmacognosy and biotechnology". Current Medicinal Chemistry. 11 (5): 607–628. doi:10.2174/0929867043455846. PMID 15032608.
27. Cooper, Raymond; Deakin, Jeffrey John (2016). "Africa's gift to the world". Botanical Miracles: Chemistry of Plants That Changed the World. CRC Press. pp. 46–51. ISBN 9781498704304.
28. Raviña, Enrique (2011). "Vinca alkaloids". The evolution of drug discovery: From traditional medicines to modern drugs. John Wiley & Sons. pp. 157–159. ISBN 9783527326693.
29. Aniszewski, p. 182
30. Hesse, p. 338
31. Hesse, p. 304
32. Hesse, p. 350
33. Hesse, pp. 313–316
34. Begley, Natural Products in Plants.
35. Кониин in the Great Soviet Encyclopedia, 1969–1978 (in Russian)
36. Hesse, p. 204
37. Hesse, p. 11
38. Orekhov, p. 6
39. Aniszewski, p. 109
40. Dewick, p. 307
41. Hesse, p. 12
42. Plemenkov, p. 223
43. Aniszewski, p. 108
44. Hesse, p. 84
45. Hesse, p. 31
46. Dewick, p. 381
47. Dimitris C. Gournelif; Gregory G. Laskarisb; Robert Verpoorte (1997). "Cyclopeptide alkaloids". Nat. Prod. Rep. 14 (1): 75–82. doi:10.1039/NP9971400075. PMID 9121730.
48. Aniszewski, p. 11
49. Plemenkov, p. 246
50. Aniszewski, p. 12
51. Dewick, p. 382
52. Hesse, pp. 44, 53
53. Plemenkov, p. 224
54. Aniszewski, p. 75
55. Orekhov, p. 33
56. Chemical Encyclopedia: Tropan alkaloids. xumuk.ru
57. Hesse, p. 34
58. Aniszewski, p. 27
59. Chemical Encyclopedia: Pyrrolizidine alkaloids. xumuk.ru
60. Plemenkov, p. 229
61. Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL (2005). "Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids". ChemBioChem. 6 (6): 1016–1022. doi:10.1002/cbic.200400327. PMID 15861432. S2CID 13461396.
62. Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL (2006). "On the sequence of bond formation in loline alkaloid biosynthesis". ChemBioChem. 7 (7): 1078–1088. doi:10.1002/cbic.200600066. PMID 16755627. S2CID 34409048.
63. Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP (2007). "Loline alkaloids: currencies of mutualism". Phytochemistry. 68 (7): 980–996. doi:10.1016/j.phytochem.2007.01.010. PMID 17346759.
64. Plemenkov, p. 225
65. Aniszewski, p. 95
66. Orekhov, p. 80
67. Chemical Encyclopedia: Quinolizidine alkaloids. xumuk.ru
68. Saxton, Vol. 1, p. 93
69. Aniszewski, p. 98
70. Saxton, Vol. 1, p. 91
71. Joseph P. Michael (2002). "Indolizidine and quinolizidine alkaloids". Nat. Prod. Rep. 19 (5): 458–475. doi:10.1039/b208137g. PMID 14620842.
72. Saxton, Vol. 1, p. 92
73. Dewick, p. 310
74. Aniszewski, p. 96
75. Aniszewski, p. 97
76. Plemenkov, p. 227
77. Chemical Encyclopedia: pyridine alkaloids. xumuk.ru
78. Aniszewski, p. 107
79. Aniszewski, p. 85
80. Plemenkov, p. 228
81. Hesse, p. 36
82. Chemical Encyclopedia: isoquinoline alkaloids. xumuk.ru
83. Aniszewski, pp. 77–78
84. Begley, Alkaloid Biosynthesis
85. Saxton, Vol. 3, p. 122
86. Hesse, p. 54
87. Hesse, p. 37
88. Hesse, p. 38
89. Hesse, p. 46
90. Hesse, p. 50
91. Kenneth W. Bentley (1997). "β-Phenylethylamines and the isoquinoline alkaloids" (PDF). Nat. Prod. Rep. 14 (4): 387–411. doi:10.1039/NP9971400387. PMID 9281839. Archived (PDF) from the original on 2022-10-09.
92. Hesse, p. 47
93. Hesse, p. 39
94. Hesse, p. 41
95. Hesse, p. 49
96. Hesse, p. 44
97. Saxton, Vol. 3, p. 164
98. Hesse, p. 51
99. Plemenkov, p. 236
100. Saxton, Vol. 3, p. 163
101. Saxton, Vol. 3, p. 168
102. Hesse, p. 52
103. Hesse, p. 53
104. Plemenkov, p. 241
105. Brossi, Vol. 35, p. 261
106. Brossi, Vol. 35, pp. 260–263
107. Plemenkov, p. 242
108. Begley, Cofactor Biosynthesis
109. John R. Lewis (2000). "Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids". Nat. Prod. Rep. 17 (1): 57–84. doi:10.1039/a809403i. PMID 10714899.
110. Chemical Encyclopedia: Quinazoline alkaloids. xumuk.ru
111. Aniszewski, p. 106
112. Aniszewski, p. 105
113. Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. (1999). "The biosynthesis of plant alkaloids and nitrogenous microbial metabolites". Nat. Prod. Rep. 16 (2): 199–208. doi:10.1039/a705734b.
114. Plemenkov, pp. 231, 246
115. Hesse, p. 58
116. Plemenkov, p. 231
117. Chemical Encyclopedia: Quinoline alkaloids. xumuk.ru
118. Aniszewski, p. 114
119. Orekhov, p. 205
120. Hesse, p. 55
121. Plemenkov, p. 232
122. Orekhov, p. 212
123. Aniszewski, p. 118
124. Aniszewski, p. 112
125. Aniszewski, p. 113
126. Hesse, p. 15
127. Saxton, Vol. 1, p. 467
128. Dewick, pp. 349–350
129. Aniszewski, p. 119
130. Hesse, p. 29
131. Hesse, pp. 23–26
132. Saxton, Vol. 1, p. 169
133. Saxton, Vol. 5, p. 210
134. Keglevich, Péter; Hazai, Laszlo; Kalaus, György; Szántay, Csaba (2012). "Modifications on the basic skeletons of vinblastine and vincristine". Molecules. 17 (5): 5893–5914. doi:10.3390/molecules17055893. PMC 6268133. PMID 22609781.
135. Hesse, pp. 17–18
136. Dewick, p. 357
137. Aniszewski, p. 104
138. Hesse, p. 72
139. Hesse, p. 73
140. Dewick, p. 396
141. PlantCyc Pathway: ephedrine biosynthesis Archived December 10, 2011, at the Wayback Machine
142. Hesse, p. 76
143. Chemical Encyclopedia: colchicine alkaloids. xumuk.ru
144. Aniszewski, p. 77
145. Hesse, p. 81
146. Brossi, Vol. 23, p. 376
147. Hesse, p. 77
148. Brossi, Vol. 23, p. 268
149. Brossi, Vol. 23, p. 231
150. Hesse, p. 82
151. Spermine Biosynthesis
152. Plemenkov, p. 243
153. Chemical Encyclopedia: Terpenes. xumuk.ru
154. Begley, Natural Products: An Overview
155. Atta-ur-Rahman and M. Iqbal Choudhary (1997). "Diterpenoid and steroidal alkaloids". Nat. Prod. Rep. 14 (2): 191–203. doi:10.1039/np9971400191. PMID 9149410.
156. Hesse, p. 88
157. Dewick, p. 388
158. Plemenkov, p. 247
159. Никотин in the Great Soviet Encyclopedia, 1969–1978 (in Russian)
160. Grinkevich, p. 131
161. G. A. Spiller Caffeine, CRC Press, 1997 ISBN 0-8493-2647-8
162. "Caffeine". DrugBank. Retrieved 12 February 2013.
163. "Cocaine". DrugBank. Retrieved 12 February 2013.
164. "Codeine". DrugBank. Retrieved 12 February 2013.
165. "Nicotine". DrugBank. Retrieved 12 February 2013.
166. "Morphine". DrugBank. Retrieved 12 February 2013.
167. "Yohimbine". DrugBank. Archived from the original on 30 January 2013. Retrieved 12 February 2013.
168. Fattorusso, p. 53
169. Thomas Acamovic; Colin S. Stewart; T. W. Pennycott (2004). Poisonous plants and related toxins, Volume 2001. CABI. p. 362. ISBN 978-0-85199-614-1.
170. Aniszewski, p. 13
171. Orekhov, p. 11
172. Hesse, p.4
173. Grinkevich, pp. 122–123
174. Orekhov, p. 12
175. Touchard, Axel; Aili, Samira; Fox, Eduardo; Escoubas, Pierre; Orivel, Jérôme; Nicholson, Graham; Dejean, Alain (2016-01-20). "The Biochemical Toxin Arsenal from Ant Venoms". Toxins. 8 (1): 30. doi:10.3390/toxins8010030. ISSN 2072-6651. PMC 4728552. PMID 26805882.
176. Fattorusso, p. XVII
177. Aniszewski, pp. 110–111
178. Hesse, p. 116
179. Grinkevich, p. 132
180. Grinkevich, p. 5
181. Grinkevich, pp. 132–134
182. Grinkevich, pp. 134–136
183. Fox, Eduardo Gonçalves Paterson (2016). "Venom Toxins of Fire Ants". In Gopalakrishnakone, P.; Calvete, Juan J. (eds.). Venom Genomics and Proteomics. Springer Netherlands. pp. 149–167. doi:10.1007/978-94-007-6416-3_38. ISBN 978-94-007-6415-6.
184. Fox, Eduardo G. P.; Xu, Meng; Wang, Lei; Chen, Li; Lu, Yong-Yue (2018-05-01). "Speedy milking of fresh venom from aculeate hymenopterans". Toxicon. 146: 120–123. doi:10.1016/j.toxicon.2018.02.050. ISSN 0041-0101. PMID 29510162.
185. Chen, Jian; Cantrell, Charles L.; Shang, Han-wu; Rojas, Maria G. (2009-04-22). "Piperideine Alkaloids from the Poison Gland of the Red Imported Fire Ant (Hymenoptera: Formicidae)". Journal of Agricultural and Food Chemistry. 57 (8): 3128–3133. doi:10.1021/jf803561y. ISSN 0021-8561. PMID 19326861.
186. Fox, Eduardo G. P.; Xu, Meng; Wang, Lei; Chen, Li; Lu, Yong-Yue (2018-06-01). "Gas-chromatography and UV-spectroscopy of Hymenoptera venoms obtained by trivial centrifugation". Data in Brief. 18: 992–998. doi:10.1016/j.dib.2018.03.101. ISSN 2352-3409. PMC 5996826. PMID 29900266.
187. Plemenkov, p. 253
188. Plemenkov, p. 254
189. Dewick, p. 19
190. Plemenkov, p. 255
191. Dewick, p. 305
192. Hesse, pp. 91–105
193. Hirata, K.; Miyamoto, K.; Miura, Y. (1994). "Catharanthus roseus L. (Periwinkle): Production of Vindoline and Catharanthine in Multiple Shoot Cultures". In Bajaj, Y. P. S. (ed.). Biotechnology in Agriculture and Forestry 26. Medicinal and Aromatic Plants. Vol. VI. Springer-Verlag. pp. 46–55. ISBN 9783540563914.
194. Gansäuer, Andreas; Justicia, José; Fan, Chun-An; Worgull, Dennis; Piestert, Frederik (2007). "Reductive C—C bond formation after epoxide opening via electron transfer". In Krische, Michael J. (ed.). Metal Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents. Topics in Current Chemistry. Vol. 279. Springer Science & Business Media. pp. 25–52. doi:10.1007/128_2007_130. ISBN 9783540728795.
195. Faller, Bryan A.; Pandi, Trailokya N. (2011). "Safety and efficacy of vinorelbine in the treatment of non-small cell lung cancer". Clinical Medicine Insights: Oncology. 5: 131–144. doi:10.4137/CMO.S5074. PMC 3117629. PMID 21695100.
196. Ngo, Quoc Anh; Roussi, Fanny; Cormier, Anthony; Thoret, Sylviane; Knossow, Marcel; Guénard, Daniel; Guéritte, Françoise (2009). "Synthesis and biological evaluation of Vinca alkaloids and phomopsin hybrids". Journal of Medicinal Chemistry. 52 (1): 134–142. doi:10.1021/jm801064y. PMID 19072542.
197. Hardouin, Christophe; Doris, Eric; Rousseau, Bernard; Mioskowski, Charles (2002). "Concise synthesis of anhydrovinblastine from leurosine". Organic Letters. 4 (7): 1151–1153. doi:10.1021/ol025560c. PMID 11922805.
198. Morcillo, Sara P.; Miguel, Delia; Campaña, Araceli G.; Cienfuegos, Luis Álvarez de; Justicia, José; Cuerva, Juan M. (2014). "Recent applications of Cp2TiCl in natural product synthesis". Organic Chemistry Frontiers. 1 (1): 15–33. doi:10.1039/c3qo00024a.
199. Aniszewski, p. 142
200. Hesse, pp. 283–291
201. Aniszewski, pp. 142–143
202. W.E. Conner (2009). Tiger Moths and Woolly Bears—behaviour, ecology, and evolution of the Arctiidae. New York: Oxford University Press. pp. 1–10. ISBN 0195327373.
203. Castells, Eva; Berenbaum, May R. (June 2006). "Laboratory Rearing of Agonopterix alstroemeriana, the Defoliating Poison Hemlock (Conium maculatum L.) Moth, and Effects of Piperidine Alkaloids on Preference and Performance". Environmental Entomology. 35 (3): 607–615. doi:10.1603/0046-225x-35.3.607. S2CID 45478867 – via ResearchGate.
204. Fox, Eduardo G. P.; Wu, Xiaoqing; Wang, Lei; Chen, Li; Lu, Yong-Yue; Xu, Yijuan (2019-02-01). "Queen venom isosolenopsin A delivers rapid incapacitation of fire ant competitors". Toxicon. 158: 77–83. doi:10.1016/j.toxicon.2018.11.428. ISSN 0041-0101. PMID 30529381. S2CID 54481057.
205. Hesse, p. 303
206. Hesse, pp. 303–309
207. Hesse, p. 309
208. Dewick, p. 335
209. György Matolcsy, Miklós Nádasy, Viktor Andriska Pesticide chemistry, Elsevier, 2002, pp. 21–22 ISBN 0-444-98903-X
210. Veselovskaya, p. 75
211. Hesse, p. 79
212. Veselovskaya, p. 136
213. Ibogaine: Proceedings from the First International Conference (The Alkaloids Book 56). 1950. p. 8. ISBN 978-0-12-469556-6.
2. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "alkaloids". doi:10.1351/goldbook.A00220
3. R. H. F. Manske. The Alkaloids. Chemistry and Physiology. Volume VIII. New York: Academic Press, 1965, p. 673
4. Robert Alan Lewis. Lewis' dictionary of toxicology. CRC Press, 1998, p. 51 ISBN 1-56670-223-2
5. Chemical Encyclopedia: alkaloids. xumuk.ru
6. Roberts, M. F. (Margaret F.); Wink, Michael (1998). Alkaloids: Biochemistry, Ecology, and Medicinal Applications. Boston: Springer US. ISBN 9781475729054. OCLC 851770197.
7. Gonçalves Paterson Fox, Eduardo; Russ Solis, Daniel; Delazari dos Santos, Lucilene; Aparecido dos Santos Pinto, Jose Roberto; Ribeiro da Silva Menegasso, Anally; Cardoso Maciel Costa Silva, Rafael; Sergio Palma, Mario; Correa Bueno, Odair; de Alcântara Machado, Ednildo (April 2013). "A simple, rapid method for the extraction of whole fire ant venom (Insecta: Formicidae: Solenopsis)". Toxicon. 65: 5–8. doi:10.1016/j.toxicon.2012.12.009. hdl:11449/74946. PMID 23333648.
8. Kittakoop P, Mahidol C, Ruchirawat S (2014). "Alkaloids as important scaffolds in therapeutic drugs for the treatments of cancer, tuberculosis, and smoking cessation". Curr Top Med Chem. 14 (2): 239–252. doi:10.2174/1568026613666131216105049. PMID 24359196.
9. Russo P, Frustaci A, Del Bufalo A, Fini M, Cesario A (2013). "Multitarget drugs of plants origin acting on Alzheimer's disease". Curr Med Chem. 20 (13): 1686–93. doi:10.2174/0929867311320130008. PMID 23410167.
10. Raymond S. Sinatra; Jonathan S. Jahr; J. Michael Watkins-Pitchford (2010). The Essence of Analgesia and Analgesics. Cambridge University Press. pp. 82–90. ISBN 978-1139491983.
11. Cushnie TP, Cushnie B, Lamb AJ (2014). "Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities". Int J Antimicrob Agents. 44 (5): 377–386. doi:10.1016/j.ijantimicag.2014.06.001. PMID 25130096.
12. Qiu S, Sun H, Zhang AH, Xu HY, Yan GL, Han Y, Wang XJ (2014). "Natural alkaloids: basic aspects, biological roles, and future perspectives". Chin J Nat Med. 12 (6): 401–406. doi:10.1016/S1875-5364(14)60063-7. PMID 24969519.
13. "Alkaloid". 2007-12-18.
14. Robbers JE, Speedie MK, Tyler VE (1996). "Chapter 9: Alkaloids". Pharmacognosy and Pharmacobiotechnology. Philadelphia: Lippincott, Williams & Wilkins. pp. 143–185. ISBN 978-0683085006.
15. Rhoades, David F (1979). "Evolution of Plant Chemical Defense against Herbivores". In Rosenthal, Gerald A.; Janzen, Daniel H (eds.). Herbivores: Their Interaction with Secondary Plant Metabolites. New York: Academic Press. p. 41. ISBN 978-0-12-597180-5.
16. Robert A. Meyers Encyclopedia of Physical Science and Technology – Alkaloids, 3rd edition. ISBN 0-12-227411-3
17. Leland J. Cseke Natural Products from Plants Second Edition. CRC, 2006, p. 30 ISBN 0-8493-2976-0
18. A. William Johnson Invitation to Organic Chemistry, Jones and Bartlett, 1999, p. 433 ISBN 0-7637-0432-6
19. Raj K Bansal A Text Book of Organic Chemistry. 4th Edition, New Age International, 2004, p. 644 ISBN 81-224-1459-1
20. Aniszewski, p. 110
21. Hesse, pp. 1–3
22. Oscar Jacobsen, "Alkaloide" in: Ladenburg, Handwörterbuch der Chemie (Breslau, Germany: Eduard Trewendt, 1882), vol. 1, pp. 213–422.
23. Hesse, p. 5
24. The suffix "ine" is a Greek feminine patronymic suffix and means "daughter of"; hence, for example, "atropine" means "daughter of Atropa" (belladonna): Development of Systematic Names for the Simple Alkanes Archived 2012-03-16 at the Wayback Machine. yale.edu
25. Hesse, p. 7
26. van der Heijden, Robert; Jacobs, Denise I.; Snoeijer, Wim; Hallard, Didier; Verpoorte, Robert (2004). "The Catharanthus alkaloids: Pharmacognosy and biotechnology". Current Medicinal Chemistry. 11 (5): 607–628. doi:10.2174/0929867043455846. PMID 15032608.
27. Cooper, Raymond; Deakin, Jeffrey John (2016). "Africa's gift to the world". Botanical Miracles: Chemistry of Plants That Changed the World. CRC Press. pp. 46–51. ISBN 9781498704304.
28. Raviña, Enrique (2011). "Vinca alkaloids". The evolution of drug discovery: From traditional medicines to modern drugs. John Wiley & Sons. pp. 157–159. ISBN 9783527326693.
29. Aniszewski, p. 182
30. Hesse, p. 338
31. Hesse, p. 304
32. Hesse, p. 350
33. Hesse, pp. 313–316
34. Begley, Natural Products in Plants.
35. Кониин in the Great Soviet Encyclopedia, 1969–1978 (in Russian)
36. Hesse, p. 204
37. Hesse, p. 11
38. Orekhov, p. 6
39. Aniszewski, p. 109
40. Dewick, p. 307
41. Hesse, p. 12
42. Plemenkov, p. 223
43. Aniszewski, p. 108
44. Hesse, p. 84
45. Hesse, p. 31
46. Dewick, p. 381
47. Dimitris C. Gournelif; Gregory G. Laskarisb; Robert Verpoorte (1997). "Cyclopeptide alkaloids". Nat. Prod. Rep. 14 (1): 75–82. doi:10.1039/NP9971400075. PMID 9121730.
48. Aniszewski, p. 11
49. Plemenkov, p. 246
50. Aniszewski, p. 12
51. Dewick, p. 382
52. Hesse, pp. 44, 53
53. Plemenkov, p. 224
54. Aniszewski, p. 75
55. Orekhov, p. 33
56. Chemical Encyclopedia: Tropan alkaloids. xumuk.ru
57. Hesse, p. 34
58. Aniszewski, p. 27
59. Chemical Encyclopedia: Pyrrolizidine alkaloids. xumuk.ru
60. Plemenkov, p. 229
61. Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL (2005). "Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids". ChemBioChem. 6 (6): 1016–1022. doi:10.1002/cbic.200400327. PMID 15861432. S2CID 13461396.
62. Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL (2006). "On the sequence of bond formation in loline alkaloid biosynthesis". ChemBioChem. 7 (7): 1078–1088. doi:10.1002/cbic.200600066. PMID 16755627. S2CID 34409048.
63. Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP (2007). "Loline alkaloids: currencies of mutualism". Phytochemistry. 68 (7): 980–996. doi:10.1016/j.phytochem.2007.01.010. PMID 17346759.
64. Plemenkov, p. 225
65. Aniszewski, p. 95
66. Orekhov, p. 80
67. Chemical Encyclopedia: Quinolizidine alkaloids. xumuk.ru
68. Saxton, Vol. 1, p. 93
69. Aniszewski, p. 98
70. Saxton, Vol. 1, p. 91
71. Joseph P. Michael (2002). "Indolizidine and quinolizidine alkaloids". Nat. Prod. Rep. 19 (5): 458–475. doi:10.1039/b208137g. PMID 14620842.
72. Saxton, Vol. 1, p. 92
73. Dewick, p. 310
74. Aniszewski, p. 96
75. Aniszewski, p. 97
76. Plemenkov, p. 227
77. Chemical Encyclopedia: pyridine alkaloids. xumuk.ru
78. Aniszewski, p. 107
79. Aniszewski, p. 85
80. Plemenkov, p. 228
81. Hesse, p. 36
82. Chemical Encyclopedia: isoquinoline alkaloids. xumuk.ru
83. Aniszewski, pp. 77–78
84. Begley, Alkaloid Biosynthesis
85. Saxton, Vol. 3, p. 122
86. Hesse, p. 54
87. Hesse, p. 37
88. Hesse, p. 38
89. Hesse, p. 46
90. Hesse, p. 50
91. Kenneth W. Bentley (1997). "β-Phenylethylamines and the isoquinoline alkaloids" (PDF). Nat. Prod. Rep. 14 (4): 387–411. doi:10.1039/NP9971400387. PMID 9281839. Archived (PDF) from the original on 2022-10-09.
92. Hesse, p. 47
93. Hesse, p. 39
94. Hesse, p. 41
95. Hesse, p. 49
96. Hesse, p. 44
97. Saxton, Vol. 3, p. 164
98. Hesse, p. 51
99. Plemenkov, p. 236
100. Saxton, Vol. 3, p. 163
101. Saxton, Vol. 3, p. 168
102. Hesse, p. 52
103. Hesse, p. 53
104. Plemenkov, p. 241
105. Brossi, Vol. 35, p. 261
106. Brossi, Vol. 35, pp. 260–263
107. Plemenkov, p. 242
108. Begley, Cofactor Biosynthesis
109. John R. Lewis (2000). "Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids". Nat. Prod. Rep. 17 (1): 57–84. doi:10.1039/a809403i. PMID 10714899.
110. Chemical Encyclopedia: Quinazoline alkaloids. xumuk.ru
111. Aniszewski, p. 106
112. Aniszewski, p. 105
113. Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. (1999). "The biosynthesis of plant alkaloids and nitrogenous microbial metabolites". Nat. Prod. Rep. 16 (2): 199–208. doi:10.1039/a705734b.
114. Plemenkov, pp. 231, 246
115. Hesse, p. 58
116. Plemenkov, p. 231
117. Chemical Encyclopedia: Quinoline alkaloids. xumuk.ru
118. Aniszewski, p. 114
119. Orekhov, p. 205
120. Hesse, p. 55
121. Plemenkov, p. 232
122. Orekhov, p. 212
123. Aniszewski, p. 118
124. Aniszewski, p. 112
125. Aniszewski, p. 113
126. Hesse, p. 15
127. Saxton, Vol. 1, p. 467
128. Dewick, pp. 349–350
129. Aniszewski, p. 119
130. Hesse, p. 29
131. Hesse, pp. 23–26
132. Saxton, Vol. 1, p. 169
133. Saxton, Vol. 5, p. 210
134. Keglevich, Péter; Hazai, Laszlo; Kalaus, György; Szántay, Csaba (2012). "Modifications on the basic skeletons of vinblastine and vincristine". Molecules. 17 (5): 5893–5914. doi:10.3390/molecules17055893. PMC 6268133. PMID 22609781.
135. Hesse, pp. 17–18
136. Dewick, p. 357
137. Aniszewski, p. 104
138. Hesse, p. 72
139. Hesse, p. 73
140. Dewick, p. 396
141. PlantCyc Pathway: ephedrine biosynthesis Archived December 10, 2011, at the Wayback Machine
142. Hesse, p. 76
143. Chemical Encyclopedia: colchicine alkaloids. xumuk.ru
144. Aniszewski, p. 77
145. Hesse, p. 81
146. Brossi, Vol. 23, p. 376
147. Hesse, p. 77
148. Brossi, Vol. 23, p. 268
149. Brossi, Vol. 23, p. 231
150. Hesse, p. 82
151. Spermine Biosynthesis
152. Plemenkov, p. 243
153. Chemical Encyclopedia: Terpenes. xumuk.ru
154. Begley, Natural Products: An Overview
155. Atta-ur-Rahman and M. Iqbal Choudhary (1997). "Diterpenoid and steroidal alkaloids". Nat. Prod. Rep. 14 (2): 191–203. doi:10.1039/np9971400191. PMID 9149410.
156. Hesse, p. 88
157. Dewick, p. 388
158. Plemenkov, p. 247
159. Никотин in the Great Soviet Encyclopedia, 1969–1978 (in Russian)
160. Grinkevich, p. 131
161. G. A. Spiller Caffeine, CRC Press, 1997 ISBN 0-8493-2647-8
162. "Caffeine". DrugBank. Retrieved 12 February 2013.
163. "Cocaine". DrugBank. Retrieved 12 February 2013.
164. "Codeine". DrugBank. Retrieved 12 February 2013.
165. "Nicotine". DrugBank. Retrieved 12 February 2013.
166. "Morphine". DrugBank. Retrieved 12 February 2013.
167. "Yohimbine". DrugBank. Archived from the original on 30 January 2013. Retrieved 12 February 2013.
168. Fattorusso, p. 53
169. Thomas Acamovic; Colin S. Stewart; T. W. Pennycott (2004). Poisonous plants and related toxins, Volume 2001. CABI. p. 362. ISBN 978-0-85199-614-1.
170. Aniszewski, p. 13
171. Orekhov, p. 11
172. Hesse, p.4
173. Grinkevich, pp. 122–123
174. Orekhov, p. 12
175. Touchard, Axel; Aili, Samira; Fox, Eduardo; Escoubas, Pierre; Orivel, Jérôme; Nicholson, Graham; Dejean, Alain (2016-01-20). "The Biochemical Toxin Arsenal from Ant Venoms". Toxins. 8 (1): 30. doi:10.3390/toxins8010030. ISSN 2072-6651. PMC 4728552. PMID 26805882.
176. Fattorusso, p. XVII
177. Aniszewski, pp. 110–111
178. Hesse, p. 116
179. Grinkevich, p. 132
180. Grinkevich, p. 5
181. Grinkevich, pp. 132–134
182. Grinkevich, pp. 134–136
183. Fox, Eduardo Gonçalves Paterson (2016). "Venom Toxins of Fire Ants". In Gopalakrishnakone, P.; Calvete, Juan J. (eds.). Venom Genomics and Proteomics. Springer Netherlands. pp. 149–167. doi:10.1007/978-94-007-6416-3_38. ISBN 978-94-007-6415-6.
184. Fox, Eduardo G. P.; Xu, Meng; Wang, Lei; Chen, Li; Lu, Yong-Yue (2018-05-01). "Speedy milking of fresh venom from aculeate hymenopterans". Toxicon. 146: 120–123. doi:10.1016/j.toxicon.2018.02.050. ISSN 0041-0101. PMID 29510162.
185. Chen, Jian; Cantrell, Charles L.; Shang, Han-wu; Rojas, Maria G. (2009-04-22). "Piperideine Alkaloids from the Poison Gland of the Red Imported Fire Ant (Hymenoptera: Formicidae)". Journal of Agricultural and Food Chemistry. 57 (8): 3128–3133. doi:10.1021/jf803561y. ISSN 0021-8561. PMID 19326861.
186. Fox, Eduardo G. P.; Xu, Meng; Wang, Lei; Chen, Li; Lu, Yong-Yue (2018-06-01). "Gas-chromatography and UV-spectroscopy of Hymenoptera venoms obtained by trivial centrifugation". Data in Brief. 18: 992–998. doi:10.1016/j.dib.2018.03.101. ISSN 2352-3409. PMC 5996826. PMID 29900266.
187. Plemenkov, p. 253
188. Plemenkov, p. 254
189. Dewick, p. 19
190. Plemenkov, p. 255
191. Dewick, p. 305
192. Hesse, pp. 91–105
193. Hirata, K.; Miyamoto, K.; Miura, Y. (1994). "Catharanthus roseus L. (Periwinkle): Production of Vindoline and Catharanthine in Multiple Shoot Cultures". In Bajaj, Y. P. S. (ed.). Biotechnology in Agriculture and Forestry 26. Medicinal and Aromatic Plants. Vol. VI. Springer-Verlag. pp. 46–55. ISBN 9783540563914.
194. Gansäuer, Andreas; Justicia, José; Fan, Chun-An; Worgull, Dennis; Piestert, Frederik (2007). "Reductive C—C bond formation after epoxide opening via electron transfer". In Krische, Michael J. (ed.). Metal Catalyzed Reductive C—C Bond Formation: A Departure from Preformed Organometallic Reagents. Topics in Current Chemistry. Vol. 279. Springer Science & Business Media. pp. 25–52. doi:10.1007/128_2007_130. ISBN 9783540728795.
195. Faller, Bryan A.; Pandi, Trailokya N. (2011). "Safety and efficacy of vinorelbine in the treatment of non-small cell lung cancer". Clinical Medicine Insights: Oncology. 5: 131–144. doi:10.4137/CMO.S5074. PMC 3117629. PMID 21695100.
196. Ngo, Quoc Anh; Roussi, Fanny; Cormier, Anthony; Thoret, Sylviane; Knossow, Marcel; Guénard, Daniel; Guéritte, Françoise (2009). "Synthesis and biological evaluation of Vinca alkaloids and phomopsin hybrids". Journal of Medicinal Chemistry. 52 (1): 134–142. doi:10.1021/jm801064y. PMID 19072542.
197. Hardouin, Christophe; Doris, Eric; Rousseau, Bernard; Mioskowski, Charles (2002). "Concise synthesis of anhydrovinblastine from leurosine". Organic Letters. 4 (7): 1151–1153. doi:10.1021/ol025560c. PMID 11922805.
198. Morcillo, Sara P.; Miguel, Delia; Campaña, Araceli G.; Cienfuegos, Luis Álvarez de; Justicia, José; Cuerva, Juan M. (2014). "Recent applications of Cp2TiCl in natural product synthesis". Organic Chemistry Frontiers. 1 (1): 15–33. doi:10.1039/c3qo00024a.
199. Aniszewski, p. 142
200. Hesse, pp. 283–291
201. Aniszewski, pp. 142–143
202. W.E. Conner (2009). Tiger Moths and Woolly Bears—behaviour, ecology, and evolution of the Arctiidae. New York: Oxford University Press. pp. 1–10. ISBN 0195327373.
203. Castells, Eva; Berenbaum, May R. (June 2006). "Laboratory Rearing of Agonopterix alstroemeriana, the Defoliating Poison Hemlock (Conium maculatum L.) Moth, and Effects of Piperidine Alkaloids on Preference and Performance". Environmental Entomology. 35 (3): 607–615. doi:10.1603/0046-225x-35.3.607. S2CID 45478867 – via ResearchGate.
204. Fox, Eduardo G. P.; Wu, Xiaoqing; Wang, Lei; Chen, Li; Lu, Yong-Yue; Xu, Yijuan (2019-02-01). "Queen venom isosolenopsin A delivers rapid incapacitation of fire ant competitors". Toxicon. 158: 77–83. doi:10.1016/j.toxicon.2018.11.428. ISSN 0041-0101. PMID 30529381. S2CID 54481057.
205. Hesse, p. 303
206. Hesse, pp. 303–309
207. Hesse, p. 309
208. Dewick, p. 335
209. György Matolcsy, Miklós Nádasy, Viktor Andriska Pesticide chemistry, Elsevier, 2002, pp. 21–22 ISBN 0-444-98903-X
210. Veselovskaya, p. 75
211. Hesse, p. 79
212. Veselovskaya, p. 136
213. Ibogaine: Proceedings from the First International Conference (The Alkaloids Book 56). 1950. p. 8. ISBN 978-0-12-469556-6.
Published
2023-05-03
How to Cite
Tyagi, R., Kalani, R., & Pareek, C. (2023). Alkaloids, Biosynthesis and Their Applications. International Journal on Orange Technologies, 5(5), 1-16. Retrieved from https://journals.researchparks.org/index.php/IJOT/article/view/4328
Section
Articles
.png)
