アルカロイド
出典: フリー百科事典『ウィキペディア(Wikipedia)』 (2024/06/27 09:29 UTC 版)
アルカロイド(英: alkaloid)とは、窒素原子を含み、ほとんどの場合塩基性を示す天然由来の有機化合物の総称のこと。一部のアルカロイドには中性[2]や弱酸性[3]を示すものもある。また、似た構造を有する一部の合成化合物もアルカロイドと呼ばれる[4]。アルカロイドは、炭素、水素、窒素の他酸素や硫黄、その他稀に塩素、臭素、リンといった元素を含む[5]。
- ^ Andreas Luch (2009). Molecular, clinical and environmental toxicology. Springer. p. 20. ISBN 3-7643-8335-6
- ^ a b IUPAC. Compendium of Chemical Terminology, 2nd ed. (The "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997) ISBN 0-9678550-9-8 doi:10.1351/goldbook
- ^ R. H. F. Manske. The Alkaloids. Chemistry and Physiology. Volume VIII. – New York: Academic Press, 1965, p. 673
- ^ Robert Alan Lewis. Lewis' dictionary of toxicology. CRC Press, 1998, p. 51 ISBN 1-56670-223-2
- ^ a b c d Chemical Encyclopedia: alkaloids
- ^ a b c Robert A. Meyers Encyclopedia of Physical Science and Technology – Alkaloids, 3rd edition. ISBN 0-12-227411-3
- ^ Leland J. Cseke Natural Products from Plants Second Edition. – CRC, 2006, p. 30 ISBN 0-8493-2976-0
- ^ A. William Johnson Invitation to Organic Chemistry, Jones and Bartlett, 1999, p. 433 ISBN 0-7637-0432-6
- ^ Raj K Bansal A Text Book of Organic Chemistry. 4th Edition, New Age International, 2004, p. 644 ISBN 81-224-1459-1
- ^ a b c d Aniszewski, p. 110
- ^ In the penultimate sentence of his article [W. Meissner (1819) "Über Pflanzenalkalien: II. Über ein neues Pflanzenalkali (Alkaloid)" (On plant alkalis: II. On a new plant alkali (alkaloid)), Journal für Chemie und Physik, vol. 25, pp. 377–381] Meissner wrote "Überhaupt scheint es mir auch angemessen, die bis jetzt bekannten Pflanzenstoffe nicht mit dem Namen Alkalien, sondern Alkaloide zu belegen, da sie doch in manchen Eigenschaften von den Alkalien sehr abweichen, sie würden daher in dem Abschnitt der Pflanzenchemie vor den Pflanzensäuren ihre Stelle finden." (In general, it seems appropriate to me to impose on the known plant substances not the name "alkalis" but "alkaloids", since they differ greatly in some properties from the alkalis; among the chapters of plant chemistry, they would therefore find their place before plant acids [since "Alkaloid" would precede "Säure" (acid)].)
- ^ Hesse, pp. 1–3
- ^ a b Hesse, p. 5
- ^ 接尾辞 "ine" はギリシャ語の女性父称を作る接尾辞であり、「〜の娘」を意味する。すなわち、アトロピンは「Atropa(ベラドンナ)の娘」を意味する。[1]
- ^ Hesse, p. 7
- ^ a b Aniszewski, p. 182
- ^ Hesse, p. 338
- ^ Hesse, p. 350
- ^ Hesse, pp. 313–316
- ^ a b TSB: Coniine
- ^ Hesse, p. 204
- ^ Begley, Natural Products in Plants
- ^ a b Hesse, p. 11
- ^ Orekhov, p. 6
- ^ Aniszewski, p. 109
- ^ a b Dewick, p. 307
- ^ Hesse, p. 12
- ^ a b Plemenkov, p. 223
- ^ Aniszewski, p. 108
- ^ a b c d Hesse, p. 84
- ^ a b c Dewick, p. 381
- ^ a b Hesse, p. 31
- ^ a b c d e f g h i Dimitris C. Gournelif, Gregory G. Laskarisb and Robert Verpoorte (1997). “Cyclopeptide alkaloids”. Nat. Prod. Rep. 14 (1): 75–82. doi:10.1039/NP9971400075. PMID 9121730.
- ^ Aniszewski, p. 11
- ^ Plemenkov, p. 246
- ^ a b Aniszewski, p. 12
- ^ a b Dewick, p. 382
- ^ Hesse, pp. 44, 53
- ^ a b c Plemenkov, p. 224
- ^ a b c Aniszewski, p. 75
- ^ Orekhov, p. 33
- ^ a b c Chemical Encyclopedia: Tropan alkaloids
- ^ Hesse, p. 34
- ^ Aniszewski, p. 27
- ^ a b c d Chemical Encyclopedia: Pyrrolizidine alkaloids
- ^ Plemenkov, p. 229
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Plemenkov, p. 225
- ^ Aniszewski, p. 95
- ^ Orekhov, p. 80
- ^ a b c d e f Chemical Encyclopedia: Quinolizidine alkaloids
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. – London: The Chemical Society, 1971, p. 93
- ^ Aniszewski, p. 98
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. – London: The Chemical Society, 1971, p. 91
- ^ Joseph P. Michael (2002). “Indolizidine and quinolizidine alkaloids”. Nat. Prod. Rep 19: 458–475. doi:10.1039/b208137g.
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. – London: The Chemical Society, 1971, p. 92
- ^ Dewick, p. 310
- ^ Aniszewski, p. 96
- ^ Aniszewski, p. 97
- ^ a b c Plemenkov, p. 227
- ^ a b Chemical Encyclopedia: pyridine alkaloids
- ^ a b Aniszewski, p. 107
- ^ a b Aniszewski, p. 85
- ^ Plemenkov, p. 228
- ^ a b Hesse, p. 36
- ^ a b c d e f g h i j k l m n o p q r s t Chemical Encyclopedia: isoquinoline alkaloids
- ^ Aniszewski, pp. 77–78
- ^ a b c d Begley, Alkaloid Biosynthesis
- ^ a b J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. – London: The Chemical Society, 1973, p. 122
- ^ a b c Hesse, p. 54
- ^ a b Hesse, p. 37
- ^ Hesse, p. 38
- ^ a b c Hesse, p. 46
- ^ a b c Hesse, p. 50
- ^ a b c Kenneth W. Bentley (1997). “β-Phenylethylamines and the isoquinoline alkaloids”. Nat. Prod. Rep 14 (4): 387–411. doi:10.1039/NP9971400387. PMID 9281839.
- ^ a b Hesse, p. 47
- ^ Hesse, p. 39
- ^ a b Hesse, p. 41
- ^ a b Hesse, p. 49
- ^ Hesse, p. 44
- ^ a b c J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. – London: The Chemical Society, 1973, p. 164
- ^ a b Hesse, p. 51
- ^ a b c Plemenkov, p. 236
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. – London: The Chemical Society, 1973, p. 163
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. – London: The Chemical Society, 1973, p. 168
- ^ Hesse, p. 52
- ^ Hesse, p. 53
- ^ a b c d e Plemenkov, p. 241
- ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. – Academic Press, 1989, p. 261
- ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. – Academic Press, 1989, pp. 260–263
- ^ a b Plemenkov, p. 242
- ^ Begley, Cofactor Biosynthesis
- ^ 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 .
- ^ Chemical Encyclopedia: Quinazoline alkaloids
- ^ Aniszewski, p. 106
- ^ a b Aniszewski, p. 105
- ^ Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. (1999). “The biosynthesis of plant alkaloids and nitrogenous microbial metabolites”. Nat. Prod. Rep 16: 199–208. doi:10.1039/a705734b .
- ^ Plemenkov, pp. 231, 246
- ^ Hesse, p. 58
- ^ Plemenkov, p. 231
- ^ a b c d Chemical Encyclopedia: Quinoline alkaloids
- ^ a b Aniszewski, p. 114
- ^ Orekhov, p. 205
- ^ Hesse, p. 55
- ^ a b Plemenkov, p. 232
- ^ Orekhov, p. 212
- ^ Aniszewski, p. 118
- ^ a b Aniszewski, p. 112
- ^ a b c d e f Aniszewski, p. 113
- ^ Hesse, p. 15
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. – London: The Chemical Society, 1971, p. 467
- ^ Dewick, p. 349-350
- ^ a b c Aniszewski, p. 119
- ^ Hesse, p. 29
- ^ Hesse, pp. 23–26
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. – London: The Chemical Society, 1971, p. 169
- ^ J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 5. – London: The Chemical Society, 1975, p. 210
- ^ Hesse, pp. 17–18
- ^ Dewick, p. 357
- ^ a b Aniszewski, p. 104
- ^ Hesse, p. 72
- ^ Hesse, p. 73
- ^ Dewick, p. 396
- ^ PlantCyc Pathway: ephedrine biosynthesis
- ^ Hesse, p. 76
- ^ a b Chemical Encyclopedia: colchicine alkaloids
- ^ Aniszewski, p. 77
- ^ a b Hesse, p. 81
- ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. – Academic Press, 1984, p. 376
- ^ a b Hesse, p. 77
- ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. – Academic Press, 1984, p. 268
- ^ Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. – Academic Press, 1984, p. 231
- ^ a b c d e f Hesse, p. 82
- ^ Spermine Biosynthesis
- ^ a b c d e f Plemenkov, p. 243
- ^ Chemical Encyclopedia: Terpenes
- ^ Begley, Natural Products: An Overview
- ^ 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 .
- ^ Hesse, p. 88
- ^ Dewick, p. 388
- ^ Plemenkov, p. 247
- ^ TSB: Nicotine
- ^ a b c Grinkevich, p. 131
- ^ a b G. A. Spiller Caffeine, CRC Press, 1997 ISBN 0-8493-2647-8
- ^ Fattorusso, p. 53
- ^ Thomas Acamovic, Colin S. Stewart, T. W. Pennycott (2004). Poisonous plants and related toxins, Volume 2001. CABI. p. 362. ISBN 0-85199-614-0
- ^ Fattorusso, p. XVII
- ^ Aniszewski, p. 13
- ^ Orekhov, p. 11
- ^ Hesse, p.4
- ^ Grinkevich, pp. 122–123
- ^ Orekhov, p. 12
- ^ Aniszewski, pp. 110–111
- ^ a b c d Hesse, p. 116
- ^ a b Grinkevich, p. 132
- ^ Grinkevich, p. 5
- ^ Grinkevich, pp. 132–134
- ^ Grinkevich, pp. 134–136
- ^ a b c Plemenkov, p. 253
- ^ Plemenkov, p. 254
- ^ a b Dewick, p. 19
- ^ Plemenkov, p. 255
- ^ Dewick, p. 305
- ^ Hesse, pp. 91–105
- ^ Aniszewski, p. 142
- ^ Hesse, pp. 283–291
- ^ Aniszewski, pp. 142–143
- ^ Hesse, p. 303
- ^ Hesse, pp. 303–309
- ^ Hesse, p. 309
- ^ Dewick, p. 335
- ^ György Matolcsy, Miklós Nádasy, Viktor Andriska Pesticide chemistry, Elsevier, 2002, pp. 21–22 ISBN 0-444-98903-X
- ^ Veselovskaya, p. 75
- ^ Hesse, p. 79
- ^ Veselovskaya, p. 136
- ^ Geoffrey A. Cordell The Alkaloids: Chemistry and Biology. Volume 56, Elsevier, 2001, p. 8
- ^ Veselovskaya, p. 6
- ^ Veselovskaya, pp. 51–52
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