生物鹼

生物鹼英語:)是一種天然存在的含氮鹼性化合物。一些人工合成但結構类似的化合物有時也被稱作生物鹼。除了,生物鹼也可以含有等元素。[2] 生物鹼与其它含氮碱性化合物之间的分界并不明确,但氨基酸核苷酸类物质通常不被称作生物碱。

首个被分离出的生物碱,吗啡,于1804年由罂粟中提取[1]

生物鹼在人或動物体内产生藥理反應。雖然大部份的生物鹼對人體有毒,但有些也能入药,起鎮痛或麻醉的作用,以嗎啡可待因尤为重要。生物鹼大都是氨基酸衍生物,嚐起來有苦澀味,是植物(如馬鈴薯蕃茄罂粟)、動物(如貝类)、细菌真菌等多种生命体的次生代谢物。通过对生物体的粗提取物进行酸碱萃取纯化,可以获得大部份的生物鹼。

发现史

自古以来,人类就将含有生物碱的植物用于治疗和娱乐。

例如,早在公元前 2000 年左右,美索不达米亚就已发现药用植物[3]。[30] 荷马(作家)的奥德赛提到了埃及女王送给海伦的礼物,一种带来遗忘的药物。

据信,这份礼物是一种含有鸦片的药物[4]。一本写于公元前一至三世纪的中国室内植物书籍提到了麻黄罂粟的医疗用途[5]。此外,古柯叶自古以来就被南美原住民使用。

德国化学家--弗里德里希·塞图纳第一次从鸦片中分离出吗啡。

含有有毒生物碱(例如乌头碱管箭毒碱)的植物提取物自古以来就被用于毒箭[3]

生物碱的研究始于 19 世纪。

1804年,德国化学家弗里德里希·瑟图纳从鸦片中分离出一种“催眠原理”(拉丁语:principium somniferum),他将其称为“吗啡”,指的是希腊梦神墨菲斯; 在德语和其他一些中欧语言中,这仍然是该药物的名称。 “吗啡”一词在英语和法语中使用,由法国物理学家盖-吕萨克提出。

法国研究人员皮埃尔-佩尔提埃约瑟夫·卡旺图在生物碱发展的早期对化学做出了重大贡献,他们发现了奎宁 (1820年) 和士的宁 (1818年)。

大约在同一时期还发现了其他几种生物碱,包括黄嘌呤(1817年)、阿托品(1819年)、咖啡因(1820年)、可尼碱(1827年)、尼古丁(1828年)、秋水仙碱(1833年)、金雀花碱(1851年)和可卡因(1860年)。

20 世纪光谱色谱方法的出现加速了生物碱化学的发展,到 2008 年已鉴定出超过 12,000 种生物碱[6]

1886 年,德国化学家阿尔伯特·拉登堡首次完成了生物碱的合成。 他通过2-甲基吡啶乙醛反应并用钠还原生成的2-丙烯基吡啶来生产乌头碱[7]

生物鹼的分類

与大多数其他天然化合物相比,生物碱的特征在于其丰富的结构多样性,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[8]
鳥氨酸精氨酸腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline [9] Cuscohygrine, hygrine, hygroline, stachydrine[8][10]
托烷 類衍生物[11]
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 [9] Atropine, scopolamine, hyoscyamine[8][11][12]
可卡因
原子取代於位置 2, 3
Cocaine, ecgonine [11][13]
吡咯里西啶 類衍生物[14]
鳥氨酸,精氨酸→腐→類精脒→惹卓裂鹼 [9] Retronecine, heliotridine, laburnine [14][15]
一元羧酸的複合酯 Indicine, lindelophin, sarracine [14]
大環內二酯 Platyphylline, trichodesmine[14]
1-氨基吡咯烷類 (lolines) 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 [16][17] Loline, N-formylloline, N-acetylloline[18]
哌啶 類衍生物[19]
賴氨酸屍胺 → Δ1-piperideine [20] Sedamine, lobeline, anaferine, piperine [21][22]
辛酸 → coniceine → 毒芹碱 [23] Coniine, coniceine [23]
類衍生物[24][25]
羽扇豆寧 賴氨酸屍胺 → Δ1-piperideine [26] Lupinine, nupharidin [24]
金雀花鹼 Cytisine [24]
鷹爪豆鹼 Sparteine, lupanine, anahygrine[24]
苦參鹼 Matrine, oxymatrine, allomatridine[24][27][28]
苦豆鹼 Ormosanine, piptantine[24][29]
吲哚聯啶 類衍生物[30]
賴氨酸 → δ-semialdehyde of Α-氨基己二酸pipecolic acid → 1 indolizidinone [31] Swainsonine, castanospermine [32]
吡啶 類衍生物[33][34]
吡啶簡單衍生物 烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [35] Trigonelline, ricinine, arecoline [33][36]
多環芳烴冷凝吡啶衍生物 Nicotine, nornicotine, anabasine, anatabine [33][36]
多環芳烴冷凝吡啶衍生物 Actinidine, gentianine, pediculinine [37]
Sesquiterpene pyridine derivatives 烟酸, 異亮氨酸 [38] Evonine, hippocrateine, triptonine [34][35]
異喹啉 類衍生物及相關生物鹼[39]
Simple derivatives of isoquinoline [40] Tyrosine or 苯丙氨酸多巴胺 or 酪胺 (for alkaloids Amarillis) [41][42] Salsoline, lophocerine [39][40]
Derivatives of 1- and 3-isoquinolines [43] N-methylcoridaldine, noroxyhydrastinine [43]
Derivatives of 1- and 4-phenyltetrahydroisoquinolines [40] Cryptostilin [40][44]
Derivatives of 5-naftil-isoquinoline [45] Ancistrocladine [45]
Derivatives of 1- and 2-benzyl-izoquinolines [46] Papaverine, laudanosine, sendaverine
Cularine group[47] Cularine, yagonine [47]
Pavines and isopavines [48] Argemonine, amurensine [48]
Benzopyrrocolines [49] Cryptaustoline [40]
Protoberberines [40] Berberine, canadine, ophiocarpine, mecambridine, corydaline [50]
Phthalidisoquinolines [40] Hydrastine, narcotine (Noscapine) [51]
Spirobenzylisoquinolines [40] Fumaricine [48]
Ipecacuanha alkaloids[52] Emetine, protoemetine, ipecoside [52]
Benzophenanthridines [40] Sanguinarine, oxynitidine, corynoloxine [53]
Aporphines [40] Glaucine, coridine, liriodenine [54]
Proaporphines [40] Pronuciferine, glaziovine [40][49]
Homoaporphines [55] Kreysiginine, multifloramine [55]
Homoproaporphines [55] Bulbocodine [47]
嗎啡s[56] 嗎啡, 可待因, 蒂巴因, 青藤碱 [57]
Homomorphines [58] Kreysiginine, androcymbine [56]
Tropoloisoquinolines [40] Imerubrine [40]
Azofluoranthenes [40] Rufescine, imeluteine [59]
Amaryllis alkaloids[60] Lycorine, ambelline, tazettine, galantamine, montanine [61]
Erythrina alkaloids[44] Erysodine, erythroidine [44]
Phenanthrene derivatives [40] Atherosperminine [40][50]
Protopines [40] Protopine, oxomuramine, corycavidine [53]
Aristolactam [40] Doriflavin [40]
噁唑 類衍生物[[62]
Tyrosinetyramine [63] Annuloline, halfordinol, texaline, texamine[64]
異噁唑 類衍生物
Ibotenic acidMuscimol Ibotenic acid, Muscimol
噻唑 類衍生物[65]
1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [66] Nostocyclamide, thiostreptone [65][67]
喹唑啉 類衍生物[68]
3,4-Dihydro-4-quinazolone derivatives Anthranilic acid or phenylalanine or ornithine [69] Febrifugine[70]
1,4-Dihydro-4-quinazolone derivatives Glycorine, arborine, glycosminine[70]
Pyrrolidine and piperidine quinazoline derivatives Vazicine (peganine) [62]
吖啶 類衍生物[62]
Anthranilic acid [71] Rutacridone, acronicine[72][73]
喹啉 類衍生物[74][75]
Simple derivatives of quinoline derivatives of 2 – quinolones and 4-quinolone Anthranilic acid → 3-carboxyquinoline [76] Cusparine, echinopsine, evocarpine[75][77][78]
Tricyclic terpenoids Flindersine[75][79]
Furanoquinoline derivatives Dictamnine, fagarine, skimmianine[75][80][81]
Quinines Tryptophantryptaminestrictosidine (with secologanin) → korinanteal → cinhoninon [42][76] Quinine, quinidine, cinchonine, cinhonidine [79]
吲哚 類衍生物[57]
異戊二烯吲哚生物鹼
Simple indole derivatives [82] Tryptophantryptamine or 5-hydroxitriptofan [83] Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin [84][85]
Simple derivatives of β-carboline [86] Harman, harmine, harmaline, eleagnine [82]
Pyrroloindole alkaloids [87] Physostigmine (eserine), etheramine, physovenine, eptastigmine[87]
萜類吲哚生物鹼'
Ergot alkaloids[57] Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acidlysergic acid [87] Ergotamine, ergobasine, ergosine[88]
單萜吲哚生物鹼
Corynanthe type alkaloids[83] Tryptophantryptaminestrictosidine (with secologanin) [83] Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine,[89][90] group strychnine and (Strychnine brucine, aquamicine, vomicine [91])
Iboga-type alkaloids[83] Ibogamine, ibogaine, voacangine[83]
Aspidosperma-type alkaloids[83] Vincamine, vinca alkaloids, vincotine, aspidospermine[92][93]
咪唑 類衍生物[62]
Directly from histidine[94] Histamine, pilocarpine, pilosine, stevensine[62][94]
嘌呤 類衍生物[95]
Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthinetheobrominecaffeine [42] Caffeine, theobromine, theophylline, saxitoxin [96][97]
側鏈上含氮原子的生物側鏈鹼
β-苯乙胺 類衍生物[49]
Tyrosine or phenylalaninedioxyphenilalaninedopamineadrenaline and mescaline tyrosinetyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinoneephedrine and pseudoephedrine [38][98][99] Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[38][100]
秋水仙素 類衍生物 [101]
Tyrosine or phenylalaninedopamineautumnalinecolchicine [102] Colchicine, colchamine[101]
毒蕈鹼 [103]
Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[104] Muscarine, allomuscarine, epimuscarine, epiallomuscarine[103]
芐胺[105]
Phenylalanine with valine, leucine or isoleucine[106] Capsaicin, dihydrocapsaicin, nordihydrocapsaicin, vanillylamine[105][107]
多胺生物鹼
腐胺 衍生物[108]
ornithineputrescinespermidinespermine[109] Paucine [108]
亞精胺 衍生物[108]
Lunarine, codonocarpine[108]
精胺 衍生物[108]
Verbascenine, aphelandrine [108]
Peptide (cyclopeptide) alkaloids
Peptide alkaloids with a 13-membered cycle [110][111] Nummularine C type From different amino acids [110] Nummularine C, Nummularine S [110]
Ziziphine type Ziziphine A, sativanine H [110]
Peptide alkaloids with a 14-membered cycle [110][111] Frangulanine type Frangulanine, scutianine J [111]
Scutianine A type Scutianine A [110]
Integerrine type Integerrine, discarine D [111]
Amphibine F type Amphibine F, spinanine A [110]
Amfibine B type Amphibine B, lotusine C [110]
Peptide alkaloids with a 15-membered cycle [111] Mucronine A type Mucronine A [112][111]
Pseudoalkaloids (terpenes and steroids)
Diterpenes [112]
Lycoctonine type Mevalonic acidizopentenilpyrophosfategeranyl pyrophosphate [113][114] Aconitine, delphinine [112][115]
Steroids[116]
Cholesterol, arginine[117] Solasodine, solanidine, veralkamine, batrachotoxin[118]

参考文献

引用

  1. Andreas Luch. . Springer. 2009: 20. ISBN 3-7643-8335-6.
  2. Chemical Encyclopedia: alkaloids 页面存档备份,存于. xumuk.ru
  3. Aniszewski, Tadeusz. . . Elsevier. 2015: xvii–xviii.
  4. Hesse, Stefan. . . Wiesbaden: Vieweg+Teubner Verlag. 1998: 327–338. ISBN 978-3-322-88982-9.
  5. . . Walter de Gruyter – K. G. Saur. 2007-06-16: 291–304.
  6. Begley, Tadhg P. . . Elsevier. 2010: 1–2.
  7. Lieberstein, Samuel. . Russian Review. 1975-04, 34 (2). ISSN 0036-0341. doi:10.2307/127750.
  8. Plemenkov, p. 224
  9. Aniszewski, p. 75
  10. Orekhov, p. 33
  11. Chemical Encyclopedia: Tropan alkaloids 页面存档备份,存于. xumuk.ru
  12. Hesse, p. 34
  13. Aniszewski, p. 27
  14. Chemical Encyclopedia: Pyrrolizidine alkaloids 页面存档备份,存于. xumuk.ru
  15. Plemenkov, p. 229
  16. Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL. . Chembiochem. 2005, 6 (6): 1016–1022. PMID 15861432. doi:10.1002/cbic.200400327.
  17. Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL. . Chembiochem. 2006, 7 (7): 1078–1088. PMID 16755627. doi:10.1002/cbic.200600066.
  18. Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP. . Phytochemistry. 2007, 68 (7): 980–996. PMID 17346759. doi:10.1016/j.phytochem.2007.01.010.
  19. Plemenkov, p. 225
  20. Aniszewski, p. 95
  21. Hesse, p. 31
  22. Orekhov, p. 80
  23. Dewick, p. 381
  24. Chemical Encyclopedia: Quinolizidine alkaloids 页面存档备份,存于. xumuk.ru
  25. Saxton, Vol. 1, p. 93
  26. Aniszewski, p. 98
  27. Saxton, Vol. 1, p. 91
  28. Joseph P. Michael. . Nat. Prod. Rep. 2002, 19: 458–475. doi:10.1039/b208137g.
  29. Saxton, Vol. 1, p. 92
  30. Dewick, p. 310
  31. Aniszewski, p. 96
  32. Aniszewski, p. 97
  33. Plemenkov, p. 227
  34. Chemical Encyclopedia: pyridine alkaloids 页面存档备份,存于. xumuk.ru
  35. Aniszewski, p. 107
  36. Aniszewski, p. 85
  37. Plemenkov, p. 228
  38. Aniszewski, p. 110
  39. Hesse, p. 36
  40. Chemical Encyclopedia: isoquinoline alkaloids 页面存档备份,存于. xumuk.ru
  41. Aniszewski, pp. 77–78
  42. Begley, Alkaloid Biosynthesis
  43. Saxton, Vol. 3, p. 122
  44. Hesse, p. 54
  45. Hesse, p. 37
  46. Hesse, p. 38
  47. Hesse, p. 46
  48. Hesse, p. 50
  49. Kenneth W. Bentley. (PDF). Nat. Prod. Rep. 1997, 14 (4): 387–411 [2016-04-23]. PMID 9281839. doi:10.1039/NP9971400387. (原始内容存档 (PDF)于2014-04-13).
  50. Hesse, p. 47
  51. Hesse, p. 39
  52. Hesse, p. 41
  53. Hesse, p. 49
  54. Hesse, p. 44
  55. Saxton, Vol. 3, p. 164
  56. Hesse, p. 51
  57. Plemenkov, p. 236
  58. Saxton, Vol. 3, p. 163
  59. Saxton, Vol. 3, p. 168
  60. Hesse, p. 52
  61. Hesse, p. 53
  62. Plemenkov, p. 241
  63. Brossi, Vol. 35, p. 261
  64. Brossi, Vol. 35, pp. 260–263
  65. Plemenkov, p. 242
  66. Begley, Cofactor Biosynthesis
  67. John R. Lewis. . Nat. Prod. Rep. 2000, 17 (1): 57–84. PMID 10714899. doi:10.1039/a809403i.
  68. Chemical Encyclopedia: Quinazoline alkaloids 页面存档备份,存于. xumuk.ru
  69. Aniszewski, p. 106
  70. Aniszewski, p. 105
  71. Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. . Nat. Prod. Rep. 1999, 16: 199–208. doi:10.1039/a705734b.
  72. Plemenkov, pp. 231, 246
  73. Hesse, p. 58
  74. Plemenkov, p. 231
  75. Chemical Encyclopedia: Quinoline alkaloids 页面存档备份,存于. xumuk.ru
  76. Aniszewski, p. 114
  77. Orekhov, p. 205
  78. Hesse, p. 55
  79. Plemenkov, p. 232
  80. Orekhov, p. 212
  81. Aniszewski, p. 118
  82. Aniszewski, p. 112
  83. Aniszewski, p. 113
  84. Hesse, p. 15
  85. Saxton, Vol. 1, p. 467
  86. Dewick, pp. 349–350
  87. Aniszewski, p. 119
  88. Hesse, p. 29
  89. Hesse, pp. 23–26
  90. Saxton, Vol. 1, p. 169
  91. Saxton, Vol. 5, p. 210
  92. Hesse, pp. 17–18
  93. Dewick, p. 357
  94. Aniszewski, p. 104
  95. Hesse, p. 72
  96. Hesse, p. 73
  97. Dewick, p. 396
  98. Dewick, p. 382
  99. PlantCyc Pathway: ephedrine biosynthesis 存檔,存档日期2011-12-10.
  100. Hesse, p. 76
  101. Chemical Encyclopedia: colchicine alkaloids 页面存档备份,存于. xumuk.ru
  102. Aniszewski, p. 77
  103. Hesse, p. 81
  104. Brossi, Vol. 23, p. 376
  105. Hesse, p. 77
  106. Brossi, Vol. 23, p. 268
  107. Brossi, Vol. 23, p. 231
  108. Hesse, p. 82
  109. . [2016-04-23]. (原始内容存档于2016-12-04).
  110. Dimitris C. Gournelif; Gregory G. Laskarisb; Robert Verpoorte. . Nat. Prod. Rep. 1997, 14 (1): 75–82. PMID 9121730. doi:10.1039/NP9971400075.
  111. Plemenkov, p. 243
  112. Hesse, p. 84
  113. Chemical Encyclopedia: Terpenes 页面存档备份,存于. xumuk.ru
  114. Begley, Natural Products: An Overview
  115. Atta-ur-Rahman and M. Iqbal Choudhary. . Nat. Prod. Rep. 1997, 14 (2): 191–203. PMID 9149410. doi:10.1039/np9971400191.
  116. Hesse, p. 88
  117. Dewick, p. 388
  118. Plemenkov, p. 247

来源

  • Aniszewski, Tadeusz. . Amsterdam: Elsevier. 2007. ISBN 978-0-444-52736-3.
  • Begley, Tadhg P. . Wiley. 2009. ISBN 978-0-471-75477-0. doi:10.1002/cbic.200900262.
  • Brossi, Arnold. . Academic Press. 1989.
  • Dewick, Paul M. 2nd. Wiley. 2002. ISBN 0-471-49640-5.
  • Fattorusso, E.; Taglialatela-Scafati, O. . Wiley-VCH. 2008. ISBN 978-3-527-31521-5.
  • Grinkevich, N. I.; Safronich, L. N. . M. 1983.
  • Hesse, Manfred. . Wiley-VCH. 2002. ISBN 978-3-906390-24-6.
  • Knunyants, I. L. . Soviet Encyclopedia. 1988 [2014-08-23]. (原始内容存档于2021-03-07).
  • Orekhov, A. P. Acad. 2. M.: USSR. 1955.
  • Plemenkov, V. V. . Kazan. 2001.
  • Saxton, J. E. . London: The Chemical Society. 1971.
  • Veselovskaya, N. B.; Kovalenko, A. E. . Moscow: Triada-X. 2000.
  • Wink, M. . Mitt. Julius Kühn-Inst. 2009, 421: 93–112 [18 March 2014]. (原始内容存档于2014-03-18).

外部連結

参见

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.