维基百科
生物鹼
生物鹼（英語：alkaloid）是一種包含氮原子，天然存在的鹼性化合物。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、氮，生物鹼也可以含有氧、硫或其他元素，如氯、溴、磷等。[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。
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[3] | 鳥氨酸 或 精氨酸 → 腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline [4] | Cuscohygrine, hygrine, hygroline, stachydrine[3][5] | |
| 托烷 類衍生物[6] | 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 [4] | Atropine, scopolamine, hyoscyamine[3][6][7] |
| 可卡因類 原子取代於位置 2, 3 | Cocaine, ecgonine [6][8] | ||
| 吡咯里西啶 類衍生物[9] | 非酯類 | 鳥氨酸，精氨酸→腐→類精脒→惹卓裂鹼 [4] | Retronecine, heliotridine, laburnine [9][10] |
| 一元羧酸的複合酯 | Indicine, lindelophin, sarracine [9] | ||
| 大環內二酯 | Platyphylline, trichodesmine[9] | ||
| 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 [11][12] | Loline, N-formylloline, N-acetylloline[13] | |
| 哌啶 類衍生物[14] | 賴氨酸 → 屍胺 → Δ1-piperideine [15] | Sedamine, lobeline, anaferine, piperine [16][17] | |
| 辛酸 → coniceine → 毒芹碱 [18] | Coniine, coniceine [18] | ||
| 喹 類衍生物[19][20] | 羽扇豆寧 類 | 賴氨酸 → 屍胺 → Δ1-piperideine [21] | Lupinine, nupharidin [19] |
| 金雀花鹼 類 | Cytisine [19] | ||
| 鷹爪豆鹼 類 | Sparteine, lupanine, anahygrine[19] | ||
| 苦參鹼 類 | Matrine, oxymatrine, allomatridine[19][22][23] | ||
| 苦豆鹼 類 | Ormosanine, piptantine[19][24] | ||
| 吲哚聯啶 類衍生物[25] | 賴氨酸 → δ-semialdehyde of Α-氨基己二酸 → pipecolic acid → 1 indolizidinone [26] | Swainsonine, castanospermine [27] | |
| 吡啶 類衍生物[28][29] | 吡啶簡單衍生物 | 烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [30] | Trigonelline, ricinine, arecoline [28][31] |
| 多環芳烴非冷凝吡啶衍生物 | Nicotine, nornicotine, anabasine, anatabine [28][31] | ||
| 多環芳烴冷凝吡啶衍生物 | Actinidine, gentianine, pediculinine [32] | ||
| Sesquiterpene pyridine derivatives | 烟酸, 異亮氨酸 [33] | Evonine, hippocrateine, triptonine [29][30] | |
| 異喹啉 類衍生物及相關生物鹼[34] | Simple derivatives of isoquinoline [35] | Tyrosine or 苯丙氨酸 → 多巴胺 or 酪胺 (for alkaloids Amarillis) [36][37] | Salsoline, lophocerine [34][35] |
| Derivatives of 1- and 3-isoquinolines [38] | N-methylcoridaldine, noroxyhydrastinine [38] | ||
| Derivatives of 1- and 4-phenyltetrahydroisoquinolines [35] | Cryptostilin [35][39] | ||
| Derivatives of 5-naftil-isoquinoline [40] | Ancistrocladine [40] | ||
| Derivatives of 1- and 2-benzyl-izoquinolines [41] | Papaverine, laudanosine, sendaverine | ||
| Cularine group[42] | Cularine, yagonine [42] | ||
| Pavines and isopavines [43] | Argemonine, amurensine [43] | ||
| Benzopyrrocolines [44] | Cryptaustoline [35] | ||
| Protoberberines [35] | Berberine, canadine, ophiocarpine, mecambridine, corydaline [45] | ||
| Phthalidisoquinolines [35] | Hydrastine, narcotine (Noscapine) [46] | ||
| Spirobenzylisoquinolines [35] | Fumaricine [43] | ||
| Ipecacuanha alkaloids[47] | Emetine, protoemetine, ipecoside [47] | ||
| Benzophenanthridines [35] | Sanguinarine, oxynitidine, corynoloxine [48] | ||
| Aporphines [35] | Glaucine, coridine, liriodenine [49] | ||
| Proaporphines [35] | Pronuciferine, glaziovine [35][44] | ||
| Homoaporphines [50] | Kreysiginine, multifloramine [50] | ||
| Homoproaporphines [50] | Bulbocodine [42] | ||
| 嗎啡s[51] | 嗎啡, 可待因, 蒂巴因, 青藤碱 [52] | ||
| Homomorphines [53] | Kreysiginine, androcymbine [51] | ||
| Tropoloisoquinolines [35] | Imerubrine [35] | ||
| Azofluoranthenes [35] | Rufescine, imeluteine [54] | ||
| Amaryllis alkaloids[55] | Lycorine, ambelline, tazettine, galantamine, montanine [56] | ||
| Erythrina alkaloids[39] | Erysodine, erythroidine [39] | ||
| Phenanthrene derivatives [35] | Atherosperminine [35][45] | ||
| Protopines [35] | Protopine, oxomuramine, corycavidine [48] | ||
| Aristolactam [35] | Doriflavin [35] | ||
| 噁唑 類衍生物[[57] | Tyrosine → tyramine [58] | Annuloline, halfordinol, texaline, texamine[59] | |
| 異噁唑 類衍生物 | Ibotenic acid → Muscimol | Ibotenic acid, Muscimol | |
| 噻唑 類衍生物[60] | 1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [61] | Nostocyclamide, thiostreptone [60][62] | |
| 喹唑啉 類衍生物[63] | 3,4-Dihydro-4-quinazolone derivatives | Anthranilic acid or phenylalanine or ornithine [64] | Febrifugine[65] |
| 1,4-Dihydro-4-quinazolone derivatives | Glycorine, arborine, glycosminine[65] | ||
| Pyrrolidine and piperidine quinazoline derivatives | Vazicine (peganine) [57] | ||
| 吖啶 類衍生物[57] | Anthranilic acid [66] | Rutacridone, acronicine[67][68] | |
| 喹啉 類衍生物[69][70] | Simple derivatives of quinoline derivatives of 2 – quinolones and 4-quinolone | Anthranilic acid → 3-carboxyquinoline [71] | Cusparine, echinopsine, evocarpine[70][72][73] |
| Tricyclic terpenoids | Flindersine[70][74] | ||
| Furanoquinoline derivatives | Dictamnine, fagarine, skimmianine[70][75][76] | ||
| Quinines | Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon [37][71] | Quinine, quinidine, cinchonine, cinhonidine [74] | |
| 吲哚 類衍生物[52] | 非異戊二烯吲哚生物鹼 | ||
| Simple indole derivatives [77] | Tryptophan → tryptamine or 5-hydroxitriptofan [78] | Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin [79][80] | |
| Simple derivatives of β-carboline [81] | Harman, harmine, harmaline, eleagnine [77] | ||
| Pyrroloindole alkaloids [82] | Physostigmine (eserine), etheramine, physovenine, eptastigmine[82] | ||
| 半萜類吲哚生物鹼' | |||
| Ergot alkaloids[52] | Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid [82] | Ergotamine, ergobasine, ergosine[83] | |
| 單萜吲哚生物鹼 | |||
| Corynanthe type alkaloids[78] | Tryptophan → tryptamine → strictosidine (with secologanin) [78] | Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine,[84][85] group strychnine and (Strychnine brucine, aquamicine, vomicine [86]) | |
| Iboga-type alkaloids[78] | Ibogamine, ibogaine, voacangine[78] | ||
| Aspidosperma-type alkaloids[78] | Vincamine, vinca alkaloids, vincotine, aspidospermine[87][88] | ||
| 咪唑 類衍生物[57] | Directly from histidine[89] | Histamine, pilocarpine, pilosine, stevensine[57][89] | |
| 嘌呤 類衍生物[90] | Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine [37] | Caffeine, theobromine, theophylline, saxitoxin [91][92] | |
| 側鏈上含氮原子的生物側鏈鹼 | |||
| β-苯乙胺 類衍生物[44] | Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone → ephedrine and pseudoephedrine [33][93][94] | Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[33][95] | |
| 秋水仙素 類衍生物 [96] | Tyrosine or phenylalanine → dopamine → autumnaline → colchicine [97] | Colchicine, colchamine[96] | |
| 毒蕈鹼 [98] | Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[99] | Muscarine, allomuscarine, epimuscarine, epiallomuscarine[98] | |
| 芐胺[100] | Phenylalanine with valine, leucine or isoleucine[101] | Capsaicin, dihydrocapsaicin, nordihydrocapsaicin, vanillylamine[100][102] | |
| 多胺生物鹼 | |||
| 腐胺 衍生物[103] | ornithine → putrescine → spermidine → spermine[104] | Paucine [103] | |
| 亞精胺 衍生物[103] | Lunarine, codonocarpine[103] | ||
| 精胺 衍生物[103] | Verbascenine, aphelandrine [103] | ||
| Peptide (cyclopeptide) alkaloids | |||
| Peptide alkaloids with a 13-membered cycle [105][106] | Nummularine C type | From different amino acids [105] | Nummularine C, Nummularine S [105] |
| Ziziphine type | Ziziphine A, sativanine H [105] | ||
| Peptide alkaloids with a 14-membered cycle [105][106] | Frangulanine type | Frangulanine, scutianine J [106] | |
| Scutianine A type | Scutianine A [105] | ||
| Integerrine type | Integerrine, discarine D [106] | ||
| Amphibine F type | Amphibine F, spinanine A [105] | ||
| Amfibine B type | Amphibine B, lotusine C [105] | ||
| Peptide alkaloids with a 15-membered cycle [106] | Mucronine A type | Mucronine A [107][106] | |
| Pseudoalkaloids (terpenes and steroids) | |||
| Diterpenes [107] | Lycoctonine type | Mevalonic acid → izopentenilpyrophosfate → geranyl pyrophosphate [108][109] | Aconitine, delphinine [107][110] |
| Steroids[111] | Cholesterol, arginine[112] | Solasodine, solanidine, veralkamine, batrachotoxin[113] | |
参考文献
引用
- ^ Andreas Luch. Molecular, clinical and environmental toxicology. Springer. 2009: 20. ISBN 3-7643-8335-6.
- ^ Chemical Encyclopedia: alkaloids （页面存档备份，存于互联网档案馆）. xumuk.ru
- ^ 3.0 3.1 3.2 Plemenkov, p. 224
- ^ 4.0 4.1 4.2 Aniszewski, p. 75
- ^ Orekhov, p. 33
- ^ 6.0 6.1 6.2 Chemical Encyclopedia: Tropan alkaloids （页面存档备份，存于互联网档案馆）. xumuk.ru
- ^ Hesse, p. 34
- ^ Aniszewski, p. 27
- ^ 9.0 9.1 9.2 9.3 Chemical Encyclopedia: Pyrrolizidine alkaloids （页面存档备份，存于互联网档案馆）. 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
- ^ 18.0 18.1 Dewick, p. 381
- ^ 19.0 19.1 19.2 19.3 19.4 19.5 Chemical Encyclopedia: Quinolizidine alkaloids （页面存档备份，存于互联网档案馆）. 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
- ^ 28.0 28.1 28.2 Plemenkov, p. 227
- ^ 29.0 29.1 Chemical Encyclopedia: pyridine alkaloids （页面存档备份，存于互联网档案馆）. xumuk.ru
- ^ 30.0 30.1 Aniszewski, p. 107
- ^ 31.0 31.1 Aniszewski, p. 85
- ^ Plemenkov, p. 228
- ^ 33.0 33.1 33.2 Aniszewski, p. 110
- ^ 34.0 34.1 Hesse, p. 36
- ^ 35.00 35.01 35.02 35.03 35.04 35.05 35.06 35.07 35.08 35.09 35.10 35.11 35.12 35.13 35.14 35.15 35.16 35.17 35.18 35.19 Chemical Encyclopedia: isoquinoline alkaloids （页面存档备份，存于互联网档案馆）. xumuk.ru
- ^ Aniszewski, pp. 77–78
- ^ 37.0 37.1 37.2 Begley, Alkaloid Biosynthesis
- ^ 38.0 38.1 Saxton, Vol. 3, p. 122
- ^ 39.0 39.1 39.2 Hesse, p. 54
- ^ 40.0 40.1 Hesse, p. 37
- ^ Hesse, p. 38
- ^ 42.0 42.1 42.2 Hesse, p. 46
- ^ 43.0 43.1 43.2 Hesse, p. 50
- ^ 44.0 44.1 44.2 Kenneth W. Bentley. β-Phenylethylamines and the isoquinoline alkaloids (PDF). Nat. Prod. Rep. 1997, 14 (4): 387–411 [2016-04-23]. PMID 9281839. doi:10.1039/NP9971400387. （原始内容 (PDF)于2014-04-13）.
- ^ 45.0 45.1 Hesse, p. 47
- ^ Hesse, p. 39
- ^ 47.0 47.1 Hesse, p. 41
- ^ 48.0 48.1 Hesse, p. 49
- ^ Hesse, p. 44
- ^ 50.0 50.1 50.2 Saxton, Vol. 3, p. 164
- ^ 51.0 51.1 Hesse, p. 51
- ^ 52.0 52.1 52.2 Plemenkov, p. 236
- ^ Saxton, Vol. 3, p. 163
- ^ Saxton, Vol. 3, p. 168
- ^ Hesse, p. 52
- ^ Hesse, p. 53
- ^ 57.0 57.1 57.2 57.3 57.4 Plemenkov, p. 241
- ^ Brossi, Vol. 35, p. 261
- ^ Brossi, Vol. 35, pp. 260–263
- ^ 60.0 60.1 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 （页面存档备份，存于互联网档案馆）. xumuk.ru
- ^ Aniszewski, p. 106
- ^ 65.0 65.1 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
- ^ 70.0 70.1 70.2 70.3 Chemical Encyclopedia: Quinoline alkaloids （页面存档备份，存于互联网档案馆）. xumuk.ru
- ^ 71.0 71.1 Aniszewski, p. 114
- ^ Orekhov, p. 205
- ^ Hesse, p. 55
- ^ 74.0 74.1 Plemenkov, p. 232
- ^ Orekhov, p. 212
- ^ Aniszewski, p. 118
- ^ 77.0 77.1 Aniszewski, p. 112
- ^ 78.0 78.1 78.2 78.3 78.4 78.5 Aniszewski, p. 113
- ^ Hesse, p. 15
- ^ Saxton, Vol. 1, p. 467
- ^ Dewick, pp. 349–350
- ^ 82.0 82.1 82.2 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
- ^ 89.0 89.1 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，存档日期2011-12-10.
- ^ Hesse, p. 76
- ^ 96.0 96.1 Chemical Encyclopedia: colchicine alkaloids （页面存档备份，存于互联网档案馆）. xumuk.ru
- ^ Aniszewski, p. 77
- ^ 98.0 98.1 Hesse, p. 81
- ^ Brossi, Vol. 23, p. 376
- ^ 100.0 100.1 Hesse, p. 77
- ^ Brossi, Vol. 23, p. 268
- ^ Brossi, Vol. 23, p. 231
- ^ 103.0 103.1 103.2 103.3 103.4 103.5 Hesse, p. 82
- ^ Spermine Biosynthesis. [2016-04-23]. （原始内容于2016-12-04）.
- ^ 105.0 105.1 105.2 105.3 105.4 105.5 105.6 105.7 Dimitris C. Gournelif; Gregory G. Laskarisb; Robert Verpoorte. Cyclopeptide alkaloids. Nat. Prod. Rep. 1997, 14 (1): 75–82. PMID 9121730. doi:10.1039/NP9971400075.
- ^ 106.0 106.1 106.2 106.3 106.4 106.5 Plemenkov, p. 243
- ^ 107.0 107.1 107.2 Hesse, p. 84
- ^ Chemical Encyclopedia: Terpenes （页面存档备份，存于互联网档案馆）. 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
来源
- 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 2nd. Wiley. 2002. ISBN 0-471-49640-5.
- Fattorusso, E.; Taglialatela-Scafati, O. Modern Alkaloids: Structure, Isolation, Synthesis and Biology. Wiley-VCH. 2008. ISBN 978-3-527-31521-5.
- Grinkevich, N. I.; Safronich, L. N. 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, I. L. Chemical Encyclopedia. Soviet Encyclopedia. 1988 [2014-08-23]. （原始内容于2021-03-07）.
- Orekhov, A. P. Chemistry alkaloids Acad. 2. M.: USSR. 1955.
- Plemenkov, V. V. 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]. （原始内容于2014-03-18）.
外部連結
- 维基共享资源上的相關多媒體資源：生物鹼