生物鹼

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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。[5]

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。

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[來源請求],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]

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

参考资料[编辑]

  1. ^ 1.0 1.1 1.2 Plemenkov, p. 224
  2. ^ 2.0 2.1 2.2 Aniszewski, p. 75
  3. ^ Orekhov, p. 33
  4. ^ 4.0 4.1 4.2 Chemical Encyclopedia: Tropan alkaloids. xumuk.ru
  5. ^ Hesse, p. 34
  6. ^ Aniszewski, p. 27
  7. ^ 7.0 7.1 7.2 7.3 Chemical Encyclopedia: Pyrrolizidine alkaloids. xumuk.ru
  8. ^ Plemenkov, p. 229
  9. ^ 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. doi:10.1002/cbic.200400327. PMID 15861432. 
  10. ^ 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. doi:10.1002/cbic.200600066. PMID 16755627. 
  11. ^ 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. doi:10.1016/j.phytochem.2007.01.010. PMID 17346759. 
  12. ^ Plemenkov, p. 225
  13. ^ Aniszewski, p. 95
  14. ^ 引用错误:没有为名为ref24的参考文献提供内容
  15. ^ Orekhov, p. 80
  16. ^ 16.0 16.1 引用错误:没有为名为ref25的参考文献提供内容
  17. ^ 17.0 17.1 17.2 17.3 17.4 17.5 Chemical Encyclopedia: Quinolizidine alkaloids. xumuk.ru
  18. ^ Saxton, Vol. 1, p. 93
  19. ^ Aniszewski, p. 98
  20. ^ Saxton, Vol. 1, p. 91
  21. ^ Joseph P. Michael. Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep. 2002, 19: 458–475. doi:10.1039/b208137g. 
  22. ^ Saxton, Vol. 1, p. 92
  23. ^ Dewick, p. 310
  24. ^ Aniszewski, p. 96
  25. ^ Aniszewski, p. 97
  26. ^ 26.0 26.1 26.2 Plemenkov, p. 227
  27. ^ 27.0 27.1 Chemical Encyclopedia: pyridine alkaloids. xumuk.ru
  28. ^ 28.0 28.1 Aniszewski, p. 107
  29. ^ 29.0 29.1 Aniszewski, p. 85
  30. ^ Plemenkov, p. 228
  31. ^ 31.0 31.1 31.2 引用错误:没有为名为Aniszewski_110的参考文献提供内容
  32. ^ 32.0 32.1 Hesse, p. 36
  33. ^ 33.00 33.01 33.02 33.03 33.04 33.05 33.06 33.07 33.08 33.09 33.10 33.11 33.12 33.13 33.14 33.15 33.16 33.17 33.18 33.19 Chemical Encyclopedia: isoquinoline alkaloids. xumuk.ru
  34. ^ Aniszewski, pp. 77–78
  35. ^ 35.0 35.1 35.2 Begley, Alkaloid Biosynthesis
  36. ^ 36.0 36.1 Saxton, Vol. 3, p. 122
  37. ^ 37.0 37.1 37.2 Hesse, p. 54
  38. ^ 38.0 38.1 Hesse, p. 37
  39. ^ Hesse, p. 38
  40. ^ 40.0 40.1 40.2 Hesse, p. 46
  41. ^ 41.0 41.1 41.2 Hesse, p. 50
  42. ^ 42.0 42.1 42.2 Kenneth W. Bentley. β-Phenylethylamines and the isoquinoline alkaloids (PDF). Nat. Prod. Rep. 1997, 14 (4): 387–411. doi:10.1039/NP9971400387. PMID 9281839. 
  43. ^ 43.0 43.1 Hesse, p. 47
  44. ^ Hesse, p. 39
  45. ^ 45.0 45.1 Hesse, p. 41
  46. ^ 46.0 46.1 Hesse, p. 49
  47. ^ Hesse, p. 44
  48. ^ 48.0 48.1 48.2 Saxton, Vol. 3, p. 164
  49. ^ 49.0 49.1 Hesse, p. 51
  50. ^ 50.0 50.1 50.2 Plemenkov, p. 236
  51. ^ Saxton, Vol. 3, p. 163
  52. ^ Saxton, Vol. 3, p. 168
  53. ^ Hesse, p. 52
  54. ^ Hesse, p. 53
  55. ^ 55.0 55.1 55.2 55.3 55.4 Plemenkov, p. 241
  56. ^ Brossi, Vol. 35, p. 261
  57. ^ Brossi, Vol. 35, pp. 260–263
  58. ^ 58.0 58.1 Plemenkov, p. 242
  59. ^ Begley, Cofactor Biosynthesis
  60. ^ John R. Lewis. Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids. Nat. Prod. Rep. 2000, 17 (1): 57–84. doi:10.1039/a809403i. PMID 10714899. 
  61. ^ Chemical Encyclopedia: Quinazoline alkaloids. xumuk.ru
  62. ^ Aniszewski, p. 106
  63. ^ 63.0 63.1 Aniszewski, p. 105
  64. ^ 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. 
  65. ^ Plemenkov, pp. 231, 246
  66. ^ Hesse, p. 58
  67. ^ Plemenkov, p. 231
  68. ^ 68.0 68.1 68.2 68.3 Chemical Encyclopedia: Quinoline alkaloids. xumuk.ru
  69. ^ 69.0 69.1 Aniszewski, p. 114
  70. ^ Orekhov, p. 205
  71. ^ Hesse, p. 55
  72. ^ 72.0 72.1 Plemenkov, p. 232
  73. ^ Orekhov, p. 212
  74. ^ Aniszewski, p. 118
  75. ^ 75.0 75.1 Aniszewski, p. 112
  76. ^ 76.0 76.1 76.2 76.3 76.4 76.5 Aniszewski, p. 113
  77. ^ Hesse, p. 15
  78. ^ Saxton, Vol. 1, p. 467
  79. ^ Dewick, pp. 349–350
  80. ^ 80.0 80.1 80.2 Aniszewski, p. 119
  81. ^ Hesse, p. 29
  82. ^ Hesse, pp. 23–26
  83. ^ Saxton, Vol. 1, p. 169
  84. ^ Saxton, Vol. 5, p. 210
  85. ^ Hesse, pp. 17–18
  86. ^ Dewick, p. 357
  87. ^ 87.0 87.1 Aniszewski, p. 104
  88. ^ Hesse, p. 72
  89. ^ Hesse, p. 73
  90. ^ Dewick, p. 396
  91. ^ 引用错误:没有为名为ref31的参考文献提供内容
  92. ^ PlantCyc Pathway: ephedrine biosynthesis 页面存档备份,存于互联网档案馆
  93. ^ Hesse, p. 76
  94. ^ 94.0 94.1 Chemical Encyclopedia: colchicine alkaloids. xumuk.ru
  95. ^ Aniszewski, p. 77
  96. ^ 96.0 96.1 Hesse, p. 81
  97. ^ Brossi, Vol. 23, p. 376
  98. ^ 98.0 98.1 Hesse, p. 77
  99. ^ Brossi, Vol. 23, p. 268
  100. ^ Brossi, Vol. 23, p. 231
  101. ^ 101.0 101.1 101.2 101.3 101.4 101.5 Hesse, p. 82
  102. ^ Spermine Biosynthesis
  103. ^ 103.0 103.1 103.2 103.3 103.4 103.5 103.6 103.7 引用错误:没有为名为ref27的参考文献提供内容
  104. ^ 104.0 104.1 104.2 104.3 104.4 104.5 Plemenkov, p. 243
  105. ^ 105.0 105.1 105.2 引用错误:没有为名为ref23的参考文献提供内容
  106. ^ Chemical Encyclopedia: Terpenes. xumuk.ru
  107. ^ Begley, Natural Products: An Overview
  108. ^ Atta-ur-Rahman and M. Iqbal Choudhary. Diterpenoid and steroidal alkaloids. Nat. Prod. Rep. 1997, 14 (2): 191–203. doi:10.1039/np9971400191. PMID 9149410. 
  109. ^ Hesse, p. 88
  110. ^ Dewick, p. 388
  111. ^ 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. doi:10.1002/cbic.200900262. ISBN 978-0-471-75477-0. 
  • 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].