生物鹼

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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]

生物鹼是一種主要包含鹼性氮原子,天然存在於大自然動植物蕈類化合物。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,生物鹼也可以含有,甚或其他元素,如,和。[5]

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[2]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[编辑]

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]
Pyrrolidine structure.svg
鳥氨酸精氨酸腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline [4] Cuscohygrine英语Cuscohygrine, hygrine英语hygrine, hygroline, stachydrine[3][5]
托烷 類衍生物[6]
Tropane numbered.svg
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 [4] Atropine, scopolamine, hyoscyamine[3][6][7]
可卡因
原子取代於位置 2, 3
Cocaine, ecgonine英语ecgonine [6][8]
吡咯里西啶 類衍生物[9]
Pyrrolizidine.svg
鳥氨酸,精氨酸→腐→類精脒→惹卓裂鹼 [4] Retronecine英语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英语Loline alkaloids) 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]
Piperidin.svg
賴氨酸屍胺 → Δ1-piperideine [15] Sedamine, lobeline, anaferine, piperine [16][17]
辛酸 → coniceine → 毒芹碱 [18] Coniine, coniceine [18]
類衍生物[19][20]
Quinolizidine.svg
羽扇豆寧 賴氨酸屍胺 → Δ1-piperideine [21] Lupinine英语Lupinine, nupharidin [19]
金雀花鹼 Cytisine英语Cytisine [19]
鷹爪豆鹼 Sparteine英语Sparteine, lupanine, anahygrine[19]
苦參鹼 Matrine, oxymatrine, allomatridine[19][22][23]
苦豆鹼 Ormosanine, piptantine[19][24]
吲哚聯啶 類衍生物[25]
Indolizidine.svg
賴氨酸 → δ-semialdehyde of Α-氨基己二酸pipecolic acid英语pipecolic acid → 1 indolizidinone [26] Swainsonine英语Swainsonine, castanospermine英语castanospermine [27]
吡啶 類衍生物[28][29]
Pyridine.svg
吡啶簡單衍生物 烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [30] Trigonelline英语Trigonelline, ricinine, arecoline英语arecoline [28][31]
多環芳烴冷凝吡啶衍生物 Nicotine, nornicotine英语nornicotine, anabasine英语anabasine, anatabine [28][31]
多環芳烴冷凝吡啶衍生物 Actinidine英语Actinidine, gentianine, pediculinine [32]
Sesquiterpene英语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]
Isoquinoline numbered.svg
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英语laudanosine, sendaverine
Cularine group[42] Cularine, yagonine [42]
Pavine英语Pavine (molecule)s and isopavines [43] Argemonine, amurensine英语amurensine [43]
Benzopyrrocolines [44] Cryptaustoline [35]
Protoberberines [35] Berberine, canadine英语canadine, ophiocarpine, mecambridine, corydaline [45]
Phthalidisoquinolines [35] Hydrastine英语Hydrastine, narcotine英语narcotine (Noscapine) [46]
Spirobenzylisoquinolines [35] Fumaricine [43]
Ipecacuanha英语Psychotria ipecacuanha alkaloids[47] Emetine, protoemetine, ipecoside [47]
Benzophenanthridines [35] Sanguinarine, oxynitidine, corynoloxine [48]
Aporphine英语Aporphines [35] Glaucine英语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英语Amaryllis alkaloids[55] Lycorine, ambelline, tazettine, galantamine英语galantamine, montanine [56]
Erythrina alkaloids[39] Erysodine, erythroidine [39]
Phenanthrene derivatives [35] Atherosperminine [35][45]
Protopine英语Protopines [35] Protopine英语Protopine, oxomuramine, corycavidine [48]
Aristolactam [35] Doriflavin [35]
噁唑 類衍生物[[57]
Oxazole structure.svg
Tyrosinetyramine [58] Annuloline, halfordinol, texaline, texamine[59]
異噁唑 類衍生物
Isoxazole structure.png
Ibotenic acidMuscimol Ibotenic acid, Muscimol
噻唑 類衍生物[60]
Thiazole structure.svg
1-Deoxy-D-xylulose 5-phosphate英语1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [61] Nostocyclamide, thiostreptone [60][62]
喹唑啉 類衍生物[63]
Quinazoline numbered.svg
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]
Acridine.svg
Anthranilic acid [66] Rutacridone, acronicine[67][68]
喹啉 類衍生物[69][70]
Quinoline numbered.svg
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 Tryptophantryptaminestrictosidine英语strictosidine (with secologanin英语secologanin) → korinanteal → cinhoninon [37][71] Quinine, quinidine, cinchonine英语cinchonine, cinhonidine [74]
吲哚 類衍生物[52]
Indole numbered.svg
異戊二烯吲哚生物鹼
Simple indole derivatives [77] Tryptophantryptamine or 5-hydroxitriptofan [78] Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin [79][80]
Simple derivatives of β-carboline英语beta-carboline [81] Harman, harmine英语harmine, harmaline英语harmaline, eleagnine [77]
Pyrroloindole alkaloids [82] Physostigmine (eserine), etheramine, physovenine, eptastigmine[82]
萜類吲哚生物鹼'
Ergot alkaloids[52] Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acidlysergic acid [82] Ergotamine英语Ergotamine, ergobasine, ergosine[83]
單萜吲哚生物鹼
Corynanthe type alkaloids[78] Tryptophantryptaminestrictosidine英语strictosidine (with secologanin英语secologanin) [78] Ajmalicine, sarpagine, vobasine, ajmaline英语ajmaline, yohimbine, reserpine, mitragynine英语mitragynine,[84][85] group strychnine and (Strychnine brucine英语brucine, aquamicine, vomicine [86])
Iboga英语Iboga-type alkaloids[78] Ibogamine英语Ibogamine, ibogaine英语ibogaine, voacangine英语voacangine[78]
Aspidosperma-type alkaloids[78] Vincamine英语Vincamine, vinca alkaloids英语vinca alkaloids, vincotine, aspidospermine[87][88]
咪唑 類衍生物[57]
Imidazole structure.svg
Directly from histidine[89] Histamine, pilocarpine, pilosine, stevensine[57][89]
嘌呤 類衍生物[90]
9H-Purine.svg
Xanthosine英语Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthinetheobrominecaffeine [37] Caffeine, theobromine, theophylline, saxitoxin英语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]
Phenylethylamine numbered.svg
Tyrosine or phenylalaninedioxyphenilalaninedopamineadrenaline and mescaline tyrosinetyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone英语cathinoneephedrine and pseudoephedrine [33][93][94] Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone英语cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[33][95]
秋水仙素 類衍生物 [96]
Colchicine.svg
Tyrosine or phenylalaninedopamineautumnalinecolchicine [97] Colchicine, colchamine[96]
毒蕈鹼 [98]
Muscarine.svg
Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[99] Muscarine, allomuscarine, epimuscarine, epiallomuscarine[98]
芐胺[100]
Benzylamine.svg
Phenylalanine with valine, leucine or isoleucine[101] Capsaicin, dihydrocapsaicin英语dihydrocapsaicin, nordihydrocapsaicin, vanillylamine英语vanillylamine[100][102]
多胺生物鹼
腐胺 衍生物[103]
Putrescine.svg
ornithineputrescinespermidinespermine[104] Paucine [103]
亞精胺 衍生物[103]
Spermidine.svg
Lunarine, codonocarpine[103]
精胺 衍生物[103]
Spermine.svg
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]
Isoprene.svg
Lycoctonine type Mevalonic acidizopentenilpyrophosfategeranyl pyrophosphate英语geranyl pyrophosphate [108][109] Aconitine, delphinine英语delphinine [107][110]
Steroids[111]
Cyclopentenophenanthrene.svg
Cholesterol, arginine[112] Solasodine, solanidine英语solanidine, veralkamine, batrachotoxin英语batrachotoxin[113]

参阅[编辑]

参考资料[编辑]

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参考书目[编辑]

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