生物鹼

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第一个单独的生物碱,吗啡,在1804年从鸦片罂粟中分离(罂粟[1]

生物鹼是一種主要包含鹼性氮原子,天然存在於大自然動植物蕈類化合物。一些化學合成但結構與生物鹼相似的化合物有時也被稱作生物鹼。除了,生物鹼也可以含有,甚或其他元素,如,和[2]

很多的生物鹼都對人或動物有藥理反應。生物鹼大都是氨基酸的衍生物,嚐起來有苦澀味。它們常以次生代謝物的形式出現於植物(例如:馬鈴薯蕃茄)、動物(例如:貝殼類)及蕈類。大部份的生物鹼皆能由它們的植物提取液中以酸-鹼萃取獲得。生物鹼的英文為「alkaloid」,這個字由「alkaline」一字衍生而成。原本「alkaloid」泛指一切含有鹼基。 雖然大部份的生物鹼對於人體有毒,但也有些能入藥。主要有鎮痛或麻醉的作用,以嗎啡可待因的作用尤其顯著。

生物碱是被大量的各种生物体产生,包括细菌真菌植物动物。它们可以从通过酸碱萃取这些生物体的粗提物进行纯化。

古代的毒藥大多為強烈的有毒生物鹼,而犀牛角只要碰到生物鹼就會整個支離破碎[3]因此古代的國王或是皇帝都會利用犀牛角來做酒杯,以避免被毒殺。

生物鹼的分類[编辑]

与大多数其他类天然化合物相比,生物碱的特征在于很大的结构多样性,和生物碱没有统一分类。

類別 主要結構 主要合成路線 例子
與含氮雜環生物鹼(真正生物鹼)
吡咯烷 類衍生物[4]
Pyrrolidine structure.svg
鳥氨酸精氨酸腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline [5] Cuscohygrine英语Cuscohygrine, hygrine英语hygrine, hygroline, stachydrine[4][6]
托烷 類衍生物[7]
Tropane numbered.svg
阿托品
原子取代於位置 3, 6 或 7
鳥氨酸或精氨酸→腐胺→N-甲基腐胺→N-甲基-Δ1-吡咯烷酮 [5] Atropine, scopolamine, hyoscyamine[4][7][8]
可卡因
原子取代於位置 2, 3
Cocaine, ecgonine英语ecgonine [7][9]
吡咯里西啶 類衍生物[10]
Pyrrolizidine.svg
鳥氨酸,精氨酸→腐→類精脒→惹卓裂鹼 [5] Retronecine英语Retronecine, heliotridine, laburnine [10][11]
一元羧酸的複合酯 Indicine, lindelophin, sarracine [10]
大環內二酯 Platyphylline, trichodesmine[10]
1-氨基吡咯烷類 (lolines英语Loline alkaloids) L-脯氨酸+ L-高絲氨酸→N-(3-氨基-3-羧丙基)脯氨酸→降黑麥草堿 [12][13] Loline, N-formylloline, N-acetylloline[14]
哌啶 類衍生物[15]
Piperidin.svg
賴氨酸屍胺 → Δ1-piperideine [16] Sedamine, lobeline, anaferine, piperine [17][18]
辛酸 → coniceine → 毒芹碱 [19] Coniine, coniceine [19]
類衍生物[20][21]
Quinolizidine.svg
羽扇豆寧 賴氨酸屍胺 → Δ1-piperideine [22] Lupinine英语Lupinine, nupharidin [20]
金雀花鹼 Cytisine英语Cytisine [20]
鷹爪豆鹼 Sparteine英语Sparteine, lupanine, anahygrine[20]
苦參鹼 Matrine, oxymatrine, allomatridine[20][23][24]
苦豆鹼 Ormosanine, piptantine[20][25]
吲哚聯啶 類衍生物[26]
Indolizidine.svg
賴氨酸 → δ-semialdehyde of Α-氨基己二酸pipecolic acid英语pipecolic acid → 1 indolizidinone [27] Swainsonine英语Swainsonine, castanospermine英语castanospermine [28]
吡啶 類衍生物[29][30]
Pyridine.svg
吡啶簡單衍生物 烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [31] Trigonelline英语Trigonelline, ricinine, arecoline英语arecoline [29][32]
多環芳烴冷凝吡啶衍生物 Nicotine, nornicotine英语nornicotine, anabasine英语anabasine, anatabine [29][32]
多環芳烴冷凝吡啶衍生物 Actinidine英语Actinidine, gentianine, pediculinine [33]
Sesquiterpene英语Sesquiterpene pyridine derivatives 烟酸, 異亮氨酸 [34] Evonine, hippocrateine, triptonine [30][31]
異喹啉 類衍生物及相關生物鹼[35]
Isoquinoline numbered.svg
Simple derivatives of isoquinoline [36] Tyrosine or 苯丙氨酸多巴胺 or 酪胺 (for alkaloids Amarillis) [37][38] Salsoline, lophocerine [35][36]
Derivatives of 1- and 3-isoquinolines [39] N-methylcoridaldine, noroxyhydrastinine [39]
Derivatives of 1- and 4-phenyltetrahydroisoquinolines [36] Cryptostilin [36][40]
Derivatives of 5-naftil-isoquinoline [41] Ancistrocladine [41]
Derivatives of 1- and 2-benzyl-izoquinolines [42] Papaverine, laudanosine英语laudanosine, sendaverine
Cularine group[43] Cularine, yagonine [43]
Pavine英语Pavine (molecule)s and isopavines [44] Argemonine, amurensine英语amurensine [44]
Benzopyrrocolines [45] Cryptaustoline [36]
Protoberberines [36] Berberine, canadine英语canadine, ophiocarpine, mecambridine, corydaline [46]
Phthalidisoquinolines [36] Hydrastine, narcotine英语narcotine (Noscapine) [47]
Spirobenzylisoquinolines [36] Fumaricine [44]
Ipecacuanha英语Psychotria ipecacuanha alkaloids[48] Emetine, protoemetine, ipecoside [48]
Benzophenanthridines [36] Sanguinarine, oxynitidine, corynoloxine [49]
Aporphine英语Aporphines [36] Glaucine英语Glaucine, coridine, liriodenine [50]
Proaporphines [36] Pronuciferine, glaziovine [36][45]
Homoaporphines [51] Kreysiginine, multifloramine [51]
Homoproaporphines [51] Bulbocodine [43]
嗎啡s[52] 嗎啡, 可待因, 蒂巴因, 青藤碱 [53]
Homomorphines [54] Kreysiginine, androcymbine [52]
Tropoloisoquinolines [36] Imerubrine [36]
Azofluoranthenes [36] Rufescine, imeluteine [55]
Amaryllis英语Amaryllis alkaloids[56] Lycorine, ambelline, tazettine, galantamine英语galantamine, montanine [57]
Erythrina alkaloids[40] Erysodine, erythroidine [40]
Phenanthrene derivatives [36] Atherosperminine [36][46]
Protopine英语Protopines [36] Protopine英语Protopine, oxomuramine, corycavidine [49]
Aristolactam [36] Doriflavin [36]
噁唑 類衍生物[[58]
Oxazole structure.svg
Tyrosinetyramine [59] Annuloline, halfordinol, texaline, texamine[60]
異噁唑 類衍生物
Isoxazole structure.png
Ibotenic acidMuscimol Ibotenic acid, Muscimol
噻唑 類衍生物[61]
Thiazole structure.svg
1-Deoxy-D-xylulose 5-phosphate英语1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [62] Nostocyclamide, thiostreptone [61][63]
喹唑啉 類衍生物[64]
Quinazoline numbered.svg
3,4-Dihydro-4-quinazolone derivatives Anthranilic acid or phenylalanine or ornithine [65] Febrifugine[66]
1,4-Dihydro-4-quinazolone derivatives Glycorine, arborine, glycosminine[66]
Pyrrolidine and piperidine quinazoline derivatives Vazicine (peganine) [58]
吖啶 類衍生物[58]
Acridine.svg
Anthranilic acid [67] Rutacridone, acronicine[68][69]
喹啉 類衍生物[70][71]
Quinoline numbered.svg
Simple derivatives of quinoline derivatives of 2 – quinolones and 4-quinolone Anthranilic acid → 3-carboxyquinoline [72] Cusparine, echinopsine, evocarpine[71][73][74]
Tricyclic terpenoids Flindersine[71][75]
Furanoquinoline derivatives Dictamnine, fagarine, skimmianine[71][76][77]
Quinines Tryptophantryptaminestrictosidine英语strictosidine (with secologanin英语secologanin) → korinanteal → cinhoninon [38][72] Quinine, quinidine, cinchonine, cinhonidine [75]
吲哚 類衍生物[53]
Indole numbered.svg
異戊二烯吲哚生物鹼
Simple indole derivatives [78] Tryptophantryptamine or 5-hydroxitriptofan [79] Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin [80][81]
Simple derivatives of β-carboline英语beta-carboline [82] Harman, harmine英语harmine, harmaline英语harmaline, eleagnine [78]
Pyrroloindole alkaloids [83] Physostigmine (eserine), etheramine, physovenine, eptastigmine[83]
萜類吲哚生物鹼'
Ergot alkaloids[53] Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acidlysergic acid [83] Ergotamine, ergobasine, ergosine[84]
單萜吲哚生物鹼
Corynanthe type alkaloids[79] Tryptophantryptaminestrictosidine英语strictosidine (with secologanin英语secologanin) [79] Ajmalicine, sarpagine, vobasine, ajmaline英语ajmaline, yohimbine, reserpine, mitragynine英语mitragynine,[85][86] group strychnine and (Strychnine brucine英语brucine, aquamicine, vomicine [87])
Iboga英语Iboga-type alkaloids[79] Ibogamine英语Ibogamine, ibogaine英语ibogaine, voacangine英语voacangine[79]
Aspidosperma-type alkaloids[79] Vincamine英语Vincamine, vinca alkaloids英语vinca alkaloids, vincotine, aspidospermine[88][89]
咪唑 類衍生物[58]
Imidazole structure.svg
Directly from histidine[90] Histamine, pilocarpine, pilosine, stevensine[58][90]
嘌呤 類衍生物[91]
9H-Purine.svg
Xanthosine英语Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthinetheobrominecaffeine [38] Caffeine, theobromine, theophylline, saxitoxin英语saxitoxin [92][93]
側鏈上含氮原子的生物側鏈鹼
β-苯乙胺 類衍生物[45]
Phenylethylamine numbered.svg
Tyrosine or phenylalaninedioxyphenilalaninedopamineadrenaline and mescaline tyrosinetyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone英语cathinoneephedrine and pseudoephedrine [34][94][95] Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone英语cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[34][96]
秋水仙素 類衍生物 [97]
Colchicine.svg
Tyrosine or phenylalaninedopamineautumnalinecolchicine [98] Colchicine, colchamine[97]
毒蕈鹼 [99]
Muscarine.svg
Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[100] Muscarine, allomuscarine, epimuscarine, epiallomuscarine[99]
芐胺[101]
Benzylamine.svg
Phenylalanine with valine, leucine or isoleucine[102] Capsaicin, dihydrocapsaicin, nordihydrocapsaicin, vanillylamine[101][103]
多胺生物鹼
腐胺 衍生物[104]
Putrescine.svg
ornithineputrescinespermidinespermine[105] Paucine [104]
亞精胺 衍生物[104]
Spermidine.svg
Lunarine, codonocarpine[104]
精胺 衍生物[104]
Spermine.svg
Verbascenine, aphelandrine [104]
Peptide (cyclopeptide) alkaloids
Peptide alkaloids with a 13-membered cycle [106][107] Nummularine C type From different amino acids [106] Nummularine C, Nummularine S [106]
Ziziphine type Ziziphine A, sativanine H [106]
Peptide alkaloids with a 14-membered cycle [106][107] Frangulanine type Frangulanine, scutianine J [107]
Scutianine A type Scutianine A [106]
Integerrine type Integerrine, discarine D [107]
Amphibine F type Amphibine F, spinanine A [106]
Amfibine B type Amphibine B, lotusine C [106]
Peptide alkaloids with a 15-membered cycle [107] Mucronine A type Mucronine A [108][107]
Pseudoalkaloids (terpenes and steroids)
Diterpenes [108]
Isoprene.svg
Lycoctonine type Mevalonic acidizopentenilpyrophosfategeranyl pyrophosphate英语geranyl pyrophosphate [109][110] Aconitine, delphinine英语delphinine [108][111]
Steroids[112]
Cyclopentenophenanthrene.svg
Cholesterol, arginine[113] Solasodine, solanidine英语solanidine, veralkamine, batrachotoxin英语batrachotoxin[114]

参阅[编辑]

参考资料[编辑]

  1. ^ Andreas Luch. Molecular, clinical and environmental toxicology. Springer. 2009: 20. ISBN 3-7643-8335-6. 
  2. ^ Chemical Encyclopedia: alkaloids. xumuk.ru
  3. ^ 蔡振兴. 犀角九龙杯. 《青岛日报》. 2014. 
  4. ^ 4.0 4.1 4.2 Plemenkov, p. 224
  5. ^ 5.0 5.1 5.2 Aniszewski, p. 75
  6. ^ Orekhov, p. 33
  7. ^ 7.0 7.1 7.2 Chemical Encyclopedia: Tropan alkaloids. xumuk.ru
  8. ^ Hesse, p. 34
  9. ^ Aniszewski, p. 27
  10. ^ 10.0 10.1 10.2 10.3 Chemical Encyclopedia: Pyrrolizidine alkaloids. xumuk.ru
  11. ^ Plemenkov, p. 229
  12. ^ Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL. Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids. Chembiochem. 2005, 6 (6): 1016–1022. PMID 15861432. doi:10.1002/cbic.200400327. 
  13. ^ Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL. On the sequence of bond formation in loline alkaloid biosynthesis. Chembiochem. 2006, 7 (7): 1078–1088. PMID 16755627. doi:10.1002/cbic.200600066. 
  14. ^ Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP. Loline alkaloids: currencies of mutualism. Phytochemistry英语Phytochemistry (journal). 2007, 68 (7): 980–996. PMID 17346759. doi:10.1016/j.phytochem.2007.01.010. 
  15. ^ Plemenkov, p. 225
  16. ^ Aniszewski, p. 95
  17. ^ Hesse, p. 31
  18. ^ Orekhov, p. 80
  19. ^ 19.0 19.1 Dewick, p. 381
  20. ^ 20.0 20.1 20.2 20.3 20.4 20.5 Chemical Encyclopedia: Quinolizidine alkaloids. xumuk.ru
  21. ^ Saxton, Vol. 1, p. 93
  22. ^ Aniszewski, p. 98
  23. ^ Saxton, Vol. 1, p. 91
  24. ^ Joseph P. Michael. Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep. 2002, 19: 458–475. doi:10.1039/b208137g. 
  25. ^ Saxton, Vol. 1, p. 92
  26. ^ Dewick, p. 310
  27. ^ Aniszewski, p. 96
  28. ^ Aniszewski, p. 97
  29. ^ 29.0 29.1 29.2 Plemenkov, p. 227
  30. ^ 30.0 30.1 Chemical Encyclopedia: pyridine alkaloids. xumuk.ru
  31. ^ 31.0 31.1 Aniszewski, p. 107
  32. ^ 32.0 32.1 Aniszewski, p. 85
  33. ^ Plemenkov, p. 228
  34. ^ 34.0 34.1 34.2 Aniszewski, p. 110
  35. ^ 35.0 35.1 Hesse, p. 36
  36. ^ 36.00 36.01 36.02 36.03 36.04 36.05 36.06 36.07 36.08 36.09 36.10 36.11 36.12 36.13 36.14 36.15 36.16 36.17 36.18 36.19 Chemical Encyclopedia: isoquinoline alkaloids. xumuk.ru
  37. ^ Aniszewski, pp. 77–78
  38. ^ 38.0 38.1 38.2 Begley, Alkaloid Biosynthesis
  39. ^ 39.0 39.1 Saxton, Vol. 3, p. 122
  40. ^ 40.0 40.1 40.2 Hesse, p. 54
  41. ^ 41.0 41.1 Hesse, p. 37
  42. ^ Hesse, p. 38
  43. ^ 43.0 43.1 43.2 Hesse, p. 46
  44. ^ 44.0 44.1 44.2 Hesse, p. 50
  45. ^ 45.0 45.1 45.2 Kenneth W. Bentley. β-Phenylethylamines and the isoquinoline alkaloids (PDF). Nat. Prod. Rep. 1997, 14 (4): 387–411. PMID 9281839. doi:10.1039/NP9971400387. 
  46. ^ 46.0 46.1 Hesse, p. 47
  47. ^ Hesse, p. 39
  48. ^ 48.0 48.1 Hesse, p. 41
  49. ^ 49.0 49.1 Hesse, p. 49
  50. ^ Hesse, p. 44
  51. ^ 51.0 51.1 51.2 Saxton, Vol. 3, p. 164
  52. ^ 52.0 52.1 Hesse, p. 51
  53. ^ 53.0 53.1 53.2 Plemenkov, p. 236
  54. ^ Saxton, Vol. 3, p. 163
  55. ^ Saxton, Vol. 3, p. 168
  56. ^ Hesse, p. 52
  57. ^ Hesse, p. 53
  58. ^ 58.0 58.1 58.2 58.3 58.4 Plemenkov, p. 241
  59. ^ Brossi, Vol. 35, p. 261
  60. ^ Brossi, Vol. 35, pp. 260–263
  61. ^ 61.0 61.1 Plemenkov, p. 242
  62. ^ Begley, Cofactor Biosynthesis
  63. ^ John R. Lewis. Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids. Nat. Prod. Rep. 2000, 17 (1): 57–84. PMID 10714899. doi:10.1039/a809403i. 
  64. ^ Chemical Encyclopedia: Quinazoline alkaloids. xumuk.ru
  65. ^ Aniszewski, p. 106
  66. ^ 66.0 66.1 Aniszewski, p. 105
  67. ^ Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. The biosynthesis of plant alkaloids and nitrogenous microbial metabolites. Nat. Prod. Rep. 1999, 16: 199–208. doi:10.1039/a705734b. 
  68. ^ Plemenkov, pp. 231, 246
  69. ^ Hesse, p. 58
  70. ^ Plemenkov, p. 231
  71. ^ 71.0 71.1 71.2 71.3 Chemical Encyclopedia: Quinoline alkaloids. xumuk.ru
  72. ^ 72.0 72.1 Aniszewski, p. 114
  73. ^ Orekhov, p. 205
  74. ^ Hesse, p. 55
  75. ^ 75.0 75.1 Plemenkov, p. 232
  76. ^ Orekhov, p. 212
  77. ^ Aniszewski, p. 118
  78. ^ 78.0 78.1 Aniszewski, p. 112
  79. ^ 79.0 79.1 79.2 79.3 79.4 79.5 Aniszewski, p. 113
  80. ^ Hesse, p. 15
  81. ^ Saxton, Vol. 1, p. 467
  82. ^ Dewick, pp. 349–350
  83. ^ 83.0 83.1 83.2 Aniszewski, p. 119
  84. ^ Hesse, p. 29
  85. ^ Hesse, pp. 23–26
  86. ^ Saxton, Vol. 1, p. 169
  87. ^ Saxton, Vol. 5, p. 210
  88. ^ Hesse, pp. 17–18
  89. ^ Dewick, p. 357
  90. ^ 90.0 90.1 Aniszewski, p. 104
  91. ^ Hesse, p. 72
  92. ^ Hesse, p. 73
  93. ^ Dewick, p. 396
  94. ^ Dewick, p. 382
  95. ^ PlantCyc Pathway: ephedrine biosynthesis 互联网档案馆存檔,存档日期2011-12-10.
  96. ^ Hesse, p. 76
  97. ^ 97.0 97.1 Chemical Encyclopedia: colchicine alkaloids. xumuk.ru
  98. ^ Aniszewski, p. 77
  99. ^ 99.0 99.1 Hesse, p. 81
  100. ^ Brossi, Vol. 23, p. 376
  101. ^ 101.0 101.1 Hesse, p. 77
  102. ^ Brossi, Vol. 23, p. 268
  103. ^ Brossi, Vol. 23, p. 231
  104. ^ 104.0 104.1 104.2 104.3 104.4 104.5 Hesse, p. 82
  105. ^ Spermine Biosynthesis
  106. ^ 106.0 106.1 106.2 106.3 106.4 106.5 106.6 106.7 Dimitris C. Gournelif; Gregory G. Laskarisb; Robert Verpoorte. Cyclopeptide alkaloids. Nat. Prod. Rep. 1997, 14 (1): 75–82. PMID 9121730. doi:10.1039/NP9971400075. 
  107. ^ 107.0 107.1 107.2 107.3 107.4 107.5 Plemenkov, p. 243
  108. ^ 108.0 108.1 108.2 Hesse, p. 84
  109. ^ Chemical Encyclopedia: Terpenes. xumuk.ru
  110. ^ Begley, Natural Products: An Overview
  111. ^ Atta-ur-Rahman and M. Iqbal Choudhary. Diterpenoid and steroidal alkaloids. Nat. Prod. Rep. 1997, 14 (2): 191–203. PMID 9149410. doi:10.1039/np9971400191. 
  112. ^ Hesse, p. 88
  113. ^ Dewick, p. 388
  114. ^ Plemenkov, p. 247

参考书目[编辑]

  • Aniszewski, Tadeusz. Alkaloids – secrets of life. Amsterdam: Elsevier. 2007. ISBN 978-0-444-52736-3. 
  • Begley, Tadhg P. Encyclopedia of Chemical Biology. Wiley. 2009. ISBN 978-0-471-75477-0. doi:10.1002/cbic.200900262. 
  • Brossi, Arnold. The Alkaloids: Chemistry and Pharmacology. Academic Press. 1989. 
  • Dewick, Paul M. Medicinal Natural Products. A Biosynthetic Approach. Second Edition. Wiley. 2002. ISBN 0-471-49640-5. 
  • Fattorusso, E. and Taglialatela-Scafati, O. Modern Alkaloids: Structure, Isolation, Synthesis and Biology. Wiley-VCH. 2008. ISBN 978-3-527-31521-5. 
  • Grinkevich NI Safronich LN. The chemical analysis of medicinal plants: Proc. allowance for pharmaceutical universities. M. 1983. 
  • Hesse, Manfred. Alkaloids: Nature's Curse or Blessing?. Wiley-VCH. 2002. ISBN 978-3-906390-24-6. 
  • Knunyants, IL. Chemical Encyclopedia. Soviet Encyclopedia. 1988. 
  • Orekhov, AP. Chemistry alkaloids Acad. 2. M.: USSR. 1955. 
  • Plemenkov, VV. Introduction to the Chemistry of Natural Compounds. Kazan. 2001. 
  • Saxton, J. E. The Alkaloids. A Specialist Periodical Report. London: The Chemical Society. 1971. 
  • Veselovskaya, N. B., Kovalenko, A.E. Drugs. Moscow: Triada-X. 2000. 
  • Wink, M. Mode of action and toxicology of plant toxins and poisonous plants. Mitt. Julius Kühn-Inst. 2009, 421: 93–112 [18 March 2014].