生物碱
生物碱（英语：alkaloid）是一种天然存在的含氮碱性化合物。一些人工合成但结构类似的化合物有时也被称作生物碱。除了碳、氢、氮，生物碱也可以含有氧、硫、氯、溴、磷等元素。[2] 生物碱与其它含氮碱性化合物之间的分界并不明确，但氨基酸、核苷酸及胺类物质通常不被称作生物碱。
生物碱在人或动物体内产生药理反应。虽然大部分的生物碱对人体有毒，但有些也能入药，起镇痛或麻醉的作用，以吗啡及可待因尤为重要。生物碱大都是氨基酸衍生物，尝起来有苦涩味，是植物（如马铃薯、蕃茄、罂粟）、动物（如贝类）、细菌和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，可以获得大部分的生物碱。
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和罂粟的医疗用途[5]。此外，古柯叶自古以来就被南美原住民使用。
含有有毒生物碱（例如乌头碱和管箭毒碱）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-佩尔提埃和约瑟夫·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 世纪光谱和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-甲基吡啶与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]。
生物碱的分类
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。
| 类别 | 主要结构 | 主要合成路线 | 例子 |
|---|---|---|---|
| 与含氮杂环生物碱（真正生物碱） | |||
吡咯烷 类衍生物[8]
 |
鸟氨酸 或 精氨酸 → 腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline [9] | Cuscohygrine, hygrine, hygroline, stachydrine[8][10] | |
托烷 类衍生物[11]
 |
阿托品类 原子取代于位置 3, 6 或 7 |
鸟氨酸或精氨酸→腐胺→N-甲基腐胺→N-甲基-Δ1-吡咯烷酮 [9] | Atropine, scopolamine, hyoscyamine[8][11][12] |
| 可卡因类 原子取代于位置 2, 3 |
Cocaine, ecgonine [11][13] | ||
吡咯里西啶 类衍生物[14]
 |
非酯类 | 鸟氨酸，精氨酸→腐→类精脒→惹卓裂碱 [9] | Retronecine, heliotridine, laburnine [14][15] |
| 一元羧酸的复合酯 | Indicine, lindelophin, sarracine [14] | ||
| 大环内二酯 | Platyphylline, trichodesmine[14] | ||
| 1-氨基吡咯烷类 (lolines) | L-脯氨酸+ L-高丝氨酸→N-（3-氨基-3-羧丙基）脯氨酸→降黑麦草堿 [16][17] | Loline, N-formylloline, N-acetylloline[18] | |
哌啶 类衍生物[19]
 |
赖氨酸 → 尸胺 → Δ1-piperideine [20] | Sedamine, lobeline, anaferine, piperine [21][22] | |
| 辛酸 → coniceine → 毒芹碱 [23] | Coniine, coniceine [23] | ||
喹 类衍生物[24][25]
 |
羽扇豆碱 类 | 赖氨酸 → 尸胺 → Δ1-piperideine [26] | Lupinine, nupharidin [24] |
| 野靛碱 类 | 野靛碱 [24] | ||
| 司巴丁 类 | 司巴丁, lupanine, anahygrine[24] | ||
| 苦参碱 类 | Matrine, oxymatrine, allomatridine[24][27][28] | ||
| 苦豆碱 类 | Ormosanine, piptantine[24][29] | ||
吲哚联啶 类衍生物[30]
 |
赖氨酸 → δ-semialdehyde of Α-氨基己二酸 → pipecolic acid → 1 indolizidinone [31] | Swainsonine, castanospermine [32] | |
吡啶 类衍生物[33][34]
 |
吡啶简单衍生物 | 烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [35] | Trigonelline, ricinine, arecoline [33][36] |
| 多环芳烃非冷凝吡啶衍生物 | Nicotine, nornicotine, anabasine, anatabine [33][36] | ||
| 多环芳烃冷凝吡啶衍生物 | Actinidine, gentianine, pediculinine [37] | ||
| Sesquiterpene pyridine derivatives | 烟酸, 异亮氨酸 [38] | Evonine, hippocrateine, triptonine [34][35] | |
异喹啉 类衍生物及相关生物碱[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] | ||
| 吗啡s[56] | 吗啡, 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] | ||
𫫇唑 类衍生物[[62]
 |
Tyrosine → tyramine [63] | Annuloline, halfordinol, texaline, texamine[64] | |
异𫫇唑 类衍生物
 |
Ibotenic acid → Muscimol | Ibotenic acid, Muscimol | |
噻唑 类衍生物[65]
 |
1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [66] | Nostocyclamide, thiostreptone [65][67] | |
喹唑啉 类衍生物[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 类衍生物[62]
 |
Anthranilic acid [71] | Rutacridone, acronicine[72][73] | |
喹啉 类衍生物[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 | Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon [42][76] | Quinine, quinidine, cinchonine, cinhonidine [79] | |
吲哚 类衍生物[57]
 |
非异戊二烯吲哚生物碱 | ||
| Simple indole derivatives [82] | Tryptophan → tryptamine 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] | ||
| 半萜类吲哚生物碱' | |||
| Ergot alkaloids[57] | Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid [87] | Ergotamine, ergobasine, ergosine[88] | |
| 单萜吲哚生物碱 | |||
| Corynanthe type alkaloids[83] | Tryptophan → tryptamine → strictosidine (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 类衍生物[62]
 |
Directly from histidine[94] | Histamine, pilocarpine, pilosine, stevensine[62][94] | |
嘌呤 类衍生物[95]
 |
Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine [42] | Caffeine, theobromine, theophylline, saxitoxin [96][97] | |
| 侧链上含氮原子的生物侧链碱 | |||
β-苯乙胺 类衍生物[49]
 |
Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone → ephedrine and pseudoephedrine [38][98][99] | Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[38][100] | |
秋水仙素 类衍生物 [101]
 |
Tyrosine or phenylalanine → dopamine → autumnaline → colchicine [102] | Colchicine, colchamine[101] | |
毒蕈碱 [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] | |
| 多胺生物碱 | |||
腐胺 衍生物[108]
 |
ornithine → putrescine → spermidine → spermine[109] | Paucine [108] | |
亚精胺 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 acid → izopentenilpyrophosfate → geranyl pyrophosphate [113][114] | Aconitine, delphinine [112][115] |
Steroids[116]
 |
Cholesterol, arginine[117] | Solasodine, solanidine, veralkamine, batrachotoxin[118] | |
参考文献
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