生物鹼
Multi tool use
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（alkaloids）是一種主要包含鹼性氮原子，天然存在於大自然動植物及蕈類的化合物。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。除了碳，氫和氮，生物鹼也可以含有氧，硫，甚或其他元素，如氯，溴，和磷。[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」泛指一切含有氮的鹼基。
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，以嗎啡及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，植物和动物。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。
目录
1 生物鹼的分類
2 参阅
3 参考资料
4 参考书目
5 外部連結
生物鹼的分類
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]  |
鳥氨酸 或 精氨酸 → 腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline [5] |
Cuscohygrine, hygrine, hygroline, stachydrine[4][6] |
|
托烷 類衍生物[7]  |
阿托品類 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] |
可卡因類 原子取代於位置 2, 3 |
Cocaine, ecgonine [7][9] |
||
吡咯里西啶 類衍生物[10]  |
非酯類 |
鳥氨酸，精氨酸→腐→類精脒→惹卓裂鹼 [5] |
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) |
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]  |
賴氨酸 → 屍胺 → Δ1-piperideine [16] |
Sedamine, lobeline, anaferine, piperine [17][18] |
|
辛酸 → coniceine → 毒芹碱 [19] |
Coniine, coniceine [19] |
||
喹 類衍生物[20][21]  |
羽扇豆寧 類 |
賴氨酸 → 屍胺 → Δ1-piperideine [22] |
Lupinine, nupharidin [20] |
金雀花鹼 類 |
Cytisine [20] |
||
鷹爪豆鹼 類 |
Sparteine, lupanine, anahygrine[20] |
||
苦參鹼 類 |
Matrine, oxymatrine, allomatridine[20][23][24] |
||
苦豆鹼 類 |
Ormosanine, piptantine[20][25] |
||
吲哚聯啶 類衍生物[26]  |
賴氨酸 → δ-semialdehyde of Α-氨基己二酸 → pipecolic acid → 1 indolizidinone [27] |
Swainsonine, castanospermine [28] |
|
吡啶 類衍生物[29][30]  |
吡啶簡單衍生物 |
烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [31] |
Trigonelline, ricinine, arecoline [29][32] |
多環芳烴非冷凝吡啶衍生物 |
Nicotine, nornicotine, anabasine, anatabine [29][32] |
||
| 多環芳烴冷凝吡啶衍生物 |
Actinidine, gentianine, pediculinine [33] |
||
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]  |
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, sendaverine |
||
Cularine group[43] |
Cularine, yagonine [43] |
||
Pavines and isopavines [44] |
Argemonine, amurensine [44] |
||
| Benzopyrrocolines [45] |
Cryptaustoline [36] |
||
| Protoberberines [36] |
Berberine, canadine, ophiocarpine, mecambridine, corydaline [46] |
||
| Phthalidisoquinolines [36] |
Hydrastine, narcotine (Noscapine) [47] |
||
| Spirobenzylisoquinolines [36] |
Fumaricine [44] |
||
Ipecacuanha alkaloids[48] |
Emetine, protoemetine, ipecoside [48] |
||
| Benzophenanthridines [36] |
Sanguinarine, oxynitidine, corynoloxine [49] |
||
Aporphines [36] |
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 alkaloids[56] |
Lycorine, ambelline, tazettine, galantamine, montanine [57] |
||
Erythrina alkaloids[40] |
Erysodine, erythroidine [40] |
||
Phenanthrene derivatives [36] |
Atherosperminine [36][46] |
||
Protopines [36] |
Protopine, oxomuramine, corycavidine [49] |
||
| Aristolactam [36] |
Doriflavin [36] |
||
噁唑 類衍生物[[58]  |
Tyrosine → tyramine [59] |
Annuloline, halfordinol, texaline, texamine[60] |
|
異噁唑 類衍生物  |
Ibotenic acid → Muscimol |
Ibotenic acid, Muscimol |
|
噻唑 類衍生物[61]  |
1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [62] |
Nostocyclamide, thiostreptone [61][63] |
|
喹唑啉 類衍生物[64]  |
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]  |
Anthranilic acid [67] |
Rutacridone, acronicine[68][69] |
|
喹啉 類衍生物[70][71]  |
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 |
Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon [38][72] |
Quinine, quinidine, cinchonine, cinhonidine [75] |
|
吲哚 類衍生物[53]  |
非異戊二烯吲哚生物鹼 |
||
| Simple indole derivatives [78] |
Tryptophan → tryptamine or 5-hydroxitriptofan [79] |
Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin [80][81] |
|
| Simple derivatives of β-carboline [82] |
Harman, harmine, harmaline, eleagnine [78] |
||
| Pyrroloindole alkaloids [83] |
Physostigmine (eserine), etheramine, physovenine, eptastigmine[83] |
||
半萜類吲哚生物鹼' | |||
Ergot alkaloids[53] |
Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid [83] |
Ergotamine, ergobasine, ergosine[84] |
|
單萜吲哚生物鹼 | |||
Corynanthe type alkaloids[79] |
Tryptophan → tryptamine → strictosidine (with secologanin) [79] |
Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine,[85][86] group strychnine and (Strychnine brucine, aquamicine, vomicine [87]) |
|
Iboga-type alkaloids[79] |
Ibogamine, ibogaine, voacangine[79] |
||
Aspidosperma-type alkaloids[79] |
Vincamine, vinca alkaloids, vincotine, aspidospermine[88][89] |
||
咪唑 類衍生物[58]  |
Directly from histidine[90] |
Histamine, pilocarpine, pilosine, stevensine[58][90] |
|
嘌呤 類衍生物[91]  |
Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine [38] |
Caffeine, theobromine, theophylline, 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] |
Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone → ephedrine and pseudoephedrine [34][94][95] |
Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[34][96] |
|
秋水仙素 類衍生物 [97]  |
Tyrosine or phenylalanine → dopamine → autumnaline → colchicine [98] |
Colchicine, colchamine[97] |
|
毒蕈鹼 [99]  |
Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[100] |
Muscarine, allomuscarine, epimuscarine, epiallomuscarine[99] |
|
芐胺[101]  |
Phenylalanine with valine, leucine or isoleucine[102] |
Capsaicin, dihydrocapsaicin, nordihydrocapsaicin, vanillylamine[101][103] |
|
多胺生物鹼 | |||
腐胺 衍生物[104]  |
ornithine → putrescine → spermidine → spermine[105] |
Paucine [104] |
|
亞精胺 衍生物[104]  |
Lunarine, codonocarpine[104] |
||
精胺 衍生物[104]  |
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] |
Lycoctonine type |
Mevalonic acid → izopentenilpyrophosfate → geranyl pyrophosphate [109][110] |
Aconitine, delphinine [108][111] |
Steroids[112]  |
Cholesterol, arginine[113] |
Solasodine, solanidine, veralkamine, batrachotoxin[114] |
|
参阅
- 胺
- 鹽基
- 天然产物
- 次级代谢产物
参考资料
^ Andreas Luch. Molecular, clinical and environmental toxicology. Springer. 2009: 20. ISBN 3-7643-8335-6.
^ Chemical Encyclopedia: alkaloids. xumuk.ru
^ 蔡振兴. 犀角九龙杯. 《青岛日报》. 2014.
^ 4.04.14.2 Plemenkov, p. 224
^ 5.05.15.2 Aniszewski, p. 75
^ Orekhov, p. 33
^ 7.07.17.2 Chemical Encyclopedia: Tropan alkaloids. xumuk.ru
^ Hesse, p. 34
^ Aniszewski, p. 27
^ 10.010.110.210.3 Chemical Encyclopedia: Pyrrolizidine alkaloids. xumuk.ru
^ Plemenkov, p. 229
^ 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.
^ 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.
^ Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP. Loline alkaloids: currencies of mutualism. Phytochemistry. 2007, 68 (7): 980–996. PMID 17346759. doi:10.1016/j.phytochem.2007.01.010.
^ Plemenkov, p. 225
^ Aniszewski, p. 95
^ Hesse, p. 31
^ Orekhov, p. 80
^ 19.019.1 Dewick, p. 381
^ 20.020.120.220.320.420.5 Chemical Encyclopedia: Quinolizidine alkaloids. xumuk.ru
^ Saxton, Vol. 1, p. 93
^ Aniszewski, p. 98
^ Saxton, Vol. 1, p. 91
^ Joseph P. Michael. Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep. 2002, 19: 458–475. doi:10.1039/b208137g.
^ Saxton, Vol. 1, p. 92
^ Dewick, p. 310
^ Aniszewski, p. 96
^ Aniszewski, p. 97
^ 29.029.129.2 Plemenkov, p. 227
^ 30.030.1 Chemical Encyclopedia: pyridine alkaloids. xumuk.ru
^ 31.031.1 Aniszewski, p. 107
^ 32.032.1 Aniszewski, p. 85
^ Plemenkov, p. 228
^ 34.034.134.2 Aniszewski, p. 110
^ 35.035.1 Hesse, p. 36
^ 36.0036.0136.0236.0336.0436.0536.0636.0736.0836.0936.1036.1136.1236.1336.1436.1536.1636.1736.1836.19 Chemical Encyclopedia: isoquinoline alkaloids. xumuk.ru
^ Aniszewski, pp. 77–78
^ 38.038.138.2 Begley, Alkaloid Biosynthesis
^ 39.039.1 Saxton, Vol. 3, p. 122
^ 40.040.140.2 Hesse, p. 54
^ 41.041.1 Hesse, p. 37
^ Hesse, p. 38
^ 43.043.143.2 Hesse, p. 46
^ 44.044.144.2 Hesse, p. 50
^ 45.045.145.2 Kenneth W. Bentley. β-Phenylethylamines and the isoquinoline alkaloids (PDF). Nat. Prod. Rep. 1997, 14 (4): 387–411. PMID 9281839. doi:10.1039/NP9971400387.
^ 46.046.1 Hesse, p. 47
^ Hesse, p. 39
^ 48.048.1 Hesse, p. 41
^ 49.049.1 Hesse, p. 49
^ Hesse, p. 44
^ 51.051.151.2 Saxton, Vol. 3, p. 164
^ 52.052.1 Hesse, p. 51
^ 53.053.153.2 Plemenkov, p. 236
^ Saxton, Vol. 3, p. 163
^ Saxton, Vol. 3, p. 168
^ Hesse, p. 52
^ Hesse, p. 53
^ 58.058.158.258.358.4 Plemenkov, p. 241
^ Brossi, Vol. 35, p. 261
^ Brossi, Vol. 35, pp. 260–263
^ 61.061.1 Plemenkov, p. 242
^ Begley, Cofactor Biosynthesis
^ 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.
^ Chemical Encyclopedia: Quinazoline alkaloids. xumuk.ru
^ Aniszewski, p. 106
^ 66.066.1 Aniszewski, p. 105
^ 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.
^ Plemenkov, pp. 231, 246
^ Hesse, p. 58
^ Plemenkov, p. 231
^ 71.071.171.271.3 Chemical Encyclopedia: Quinoline alkaloids. xumuk.ru
^ 72.072.1 Aniszewski, p. 114
^ Orekhov, p. 205
^ Hesse, p. 55
^ 75.075.1 Plemenkov, p. 232
^ Orekhov, p. 212
^ Aniszewski, p. 118
^ 78.078.1 Aniszewski, p. 112
^ 79.079.179.279.379.479.5 Aniszewski, p. 113
^ Hesse, p. 15
^ Saxton, Vol. 1, p. 467
^ Dewick, pp. 349–350
^ 83.083.183.2 Aniszewski, p. 119
^ Hesse, p. 29
^ Hesse, pp. 23–26
^ Saxton, Vol. 1, p. 169
^ Saxton, Vol. 5, p. 210
^ Hesse, pp. 17–18
^ Dewick, p. 357
^ 90.090.1 Aniszewski, p. 104
^ Hesse, p. 72
^ Hesse, p. 73
^ Dewick, p. 396
^ Dewick, p. 382
^ PlantCyc Pathway: ephedrine biosynthesis 互联网档案馆的存檔，存档日期2011-12-10.
^ Hesse, p. 76
^ 97.097.1 Chemical Encyclopedia: colchicine alkaloids. xumuk.ru
^ Aniszewski, p. 77
^ 99.099.1 Hesse, p. 81
^ Brossi, Vol. 23, p. 376
^ 101.0101.1 Hesse, p. 77
^ Brossi, Vol. 23, p. 268
^ Brossi, Vol. 23, p. 231
^ 104.0104.1104.2104.3104.4104.5 Hesse, p. 82
^ Spermine Biosynthesis
^ 106.0106.1106.2106.3106.4106.5106.6106.7 Dimitris C. Gournelif; Gregory G. Laskarisb; Robert Verpoorte. Cyclopeptide alkaloids. Nat. Prod. Rep. 1997, 14 (1): 75–82. PMID 9121730. doi:10.1039/NP9971400075.
^ 107.0107.1107.2107.3107.4107.5 Plemenkov, p. 243
^ 108.0108.1108.2 Hesse, p. 84
^ Chemical Encyclopedia: Terpenes. xumuk.ru
^ Begley, Natural Products: An Overview
^ 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.
^ Hesse, p. 88
^ Dewick, p. 388
^ Plemenkov, p. 247
参考书目
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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].
外部連結
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维基共享资源中相关的多媒体资源：生物鹼 |
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