生物鹼

生物鹼（英語：）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]

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]。

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，据传说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。

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]

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