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[來源請求],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[2]
Pyrrolidine structure.svg
鳥氨酸精氨酸腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline [3] Cuscohygrine英语Cuscohygrine, hygrine英语hygrine, hygroline, stachydrine[2][4]
托烷 類衍生物[5]
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 [3] Atropine, scopolamine, hyoscyamine[2][5][6]
可卡因
原子取代於位置 2, 3
Cocaine, ecgonine英语ecgonine [5][7]
吡咯里西啶 類衍生物[8]
Pyrrolizidine.svg
鳥氨酸,精氨酸→腐→類精脒→惹卓裂鹼 [3] Retronecine英语Retronecine, heliotridine, laburnine [8][9]
一元羧酸的複合酯 Indicine, lindelophin, sarracine [8]
大環內二酯 Platyphylline, trichodesmine[8]
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 [10][11] Loline, N-formylloline, N-acetylloline[12]
哌啶 類衍生物[13]
Piperidin.svg
賴氨酸屍胺 → Δ1-piperideine [14] Sedamine, lobeline, anaferine, piperine [15][16]
辛酸 → coniceine → 毒芹碱 [17] Coniine, coniceine [17]
類衍生物[18][19]
Quinolizidine.svg
羽扇豆寧 賴氨酸屍胺 → Δ1-piperideine [20] Lupinine英语Lupinine, nupharidin [18]
金雀花鹼 Cytisine英语Cytisine [18]
鷹爪豆鹼 Sparteine英语Sparteine, lupanine, anahygrine[18]
苦參鹼 Matrine, oxymatrine, allomatridine[18][21][22]
苦豆鹼 Ormosanine, piptantine[18][23]
吲哚聯啶 類衍生物[24]
Indolizidine.svg
賴氨酸 → δ-semialdehyde of Α-氨基己二酸pipecolic acid英语pipecolic acid → 1 indolizidinone [25] Swainsonine英语Swainsonine, castanospermine英语castanospermine [26]
吡啶 類衍生物[27][28]
Pyridine.svg
吡啶簡單衍生物 烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [29] Trigonelline英语Trigonelline, ricinine, arecoline英语arecoline [27][30]
多環芳烴冷凝吡啶衍生物 Nicotine, nornicotine英语nornicotine, anabasine英语anabasine, anatabine [27][30]
多環芳烴冷凝吡啶衍生物 Actinidine英语Actinidine, gentianine, pediculinine [31]
Sesquiterpene英语Sesquiterpene pyridine derivatives 烟酸, 異亮氨酸 [32] Evonine, hippocrateine, triptonine [28][29]
異喹啉 類衍生物及相關生物鹼[33]
Isoquinoline numbered.svg
Simple derivatives of isoquinoline [34] Tyrosine or 苯丙氨酸多巴胺 or 酪胺 (for alkaloids Amarillis) [35][36] Salsoline, lophocerine [33][34]
Derivatives of 1- and 3-isoquinolines [37] N-methylcoridaldine, noroxyhydrastinine [37]
Derivatives of 1- and 4-phenyltetrahydroisoquinolines [34] Cryptostilin [34][38]
Derivatives of 5-naftil-isoquinoline [39] Ancistrocladine [39]
Derivatives of 1- and 2-benzyl-izoquinolines [40] Papaverine, laudanosine英语laudanosine, sendaverine
Cularine group[41] Cularine, yagonine [41]
Pavine英语Pavine (molecule)s and isopavines [42] Argemonine, amurensine英语amurensine [42]
Benzopyrrocolines [43] Cryptaustoline [34]
Protoberberines [34] Berberine, canadine英语canadine, ophiocarpine, mecambridine, corydaline [44]
Phthalidisoquinolines [34] Hydrastine英语Hydrastine, narcotine英语narcotine (Noscapine) [45]
Spirobenzylisoquinolines [34] Fumaricine [42]
Ipecacuanha英语Psychotria ipecacuanha alkaloids[46] Emetine, protoemetine, ipecoside [46]
Benzophenanthridines [34] Sanguinarine, oxynitidine, corynoloxine [47]
Aporphine英语Aporphines [34] Glaucine英语Glaucine, coridine, liriodenine [48]
Proaporphines [34] Pronuciferine, glaziovine [34][43]
Homoaporphines [49] Kreysiginine, multifloramine [49]
Homoproaporphines [49] Bulbocodine [41]
嗎啡s[50] 嗎啡, 可待因, 蒂巴因, 青藤碱 [51]
Homomorphines [52] Kreysiginine, androcymbine [50]
Tropoloisoquinolines [34] Imerubrine [34]
Azofluoranthenes [34] Rufescine, imeluteine [53]
Amaryllis英语Amaryllis alkaloids[54] Lycorine, ambelline, tazettine, galantamine英语galantamine, montanine [55]
Erythrina alkaloids[38] Erysodine, erythroidine [38]
Phenanthrene derivatives [34] Atherosperminine [34][44]
Protopine英语Protopines [34] Protopine英语Protopine, oxomuramine, corycavidine [47]
Aristolactam [34] Doriflavin [34]
噁唑 類衍生物[[56]
Oxazole structure.svg
Tyrosinetyramine [57] Annuloline, halfordinol, texaline, texamine[58]
異噁唑 類衍生物
Isoxazole structure.png
Ibotenic acidMuscimol Ibotenic acid, Muscimol
噻唑 類衍生物[59]
Thiazole structure.svg
1-Deoxy-D-xylulose 5-phosphate英语1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [60] Nostocyclamide, thiostreptone [59][61]
喹唑啉 類衍生物[62]
Quinazoline numbered.svg
3,4-Dihydro-4-quinazolone derivatives Anthranilic acid or phenylalanine or ornithine [63] Febrifugine[64]
1,4-Dihydro-4-quinazolone derivatives Glycorine, arborine, glycosminine[64]
Pyrrolidine and piperidine quinazoline derivatives Vazicine (peganine) [56]
吖啶 類衍生物[56]
Acridine.svg
Anthranilic acid [65] Rutacridone, acronicine[66][67]
喹啉 類衍生物[68][69]
Quinoline numbered.svg
Simple derivatives of quinoline derivatives of 2 – quinolones and 4-quinolone Anthranilic acid → 3-carboxyquinoline [70] Cusparine, echinopsine, evocarpine[69][71][72]
Tricyclic terpenoids Flindersine[69][73]
Furanoquinoline derivatives Dictamnine, fagarine, skimmianine[69][74][75]
Quinines Tryptophantryptaminestrictosidine英语strictosidine (with secologanin英语secologanin) → korinanteal → cinhoninon [36][70] Quinine, quinidine, cinchonine英语cinchonine, cinhonidine [73]
吲哚 類衍生物[51]
Indole numbered.svg
異戊二烯吲哚生物鹼
Simple indole derivatives [76] Tryptophantryptamine or 5-hydroxitriptofan [77] Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin [78][79]
Simple derivatives of β-carboline英语beta-carboline [80] Harman, harmine英语harmine, harmaline英语harmaline, eleagnine [76]
Pyrroloindole alkaloids [81] Physostigmine (eserine), etheramine, physovenine, eptastigmine[81]
萜類吲哚生物鹼'
Ergot alkaloids[51] Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acidlysergic acid [81] Ergotamine英语Ergotamine, ergobasine, ergosine[82]
單萜吲哚生物鹼
Corynanthe type alkaloids[77] Tryptophantryptaminestrictosidine英语strictosidine (with secologanin英语secologanin) [77] Ajmalicine, sarpagine, vobasine, ajmaline英语ajmaline, yohimbine, reserpine, mitragynine英语mitragynine,[83][84] group strychnine and (Strychnine brucine英语brucine, aquamicine, vomicine [85])
Iboga英语Iboga-type alkaloids[77] Ibogamine英语Ibogamine, ibogaine英语ibogaine, voacangine英语voacangine[77]
Aspidosperma-type alkaloids[77] Vincamine英语Vincamine, vinca alkaloids英语vinca alkaloids, vincotine, aspidospermine[86][87]
咪唑 類衍生物[56]
Imidazole structure.svg
Directly from histidine[88] Histamine, pilocarpine, pilosine, stevensine[56][88]
嘌呤 類衍生物[89]
9H-Purine.svg
Xanthosine英语Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthinetheobrominecaffeine [36] Caffeine, theobromine, theophylline, saxitoxin英语saxitoxin [90][91]
側鏈上含氮原子的生物側鏈鹼
β-苯乙胺 類衍生物[43]
Phenylethylamine numbered.svg
Tyrosine or phenylalaninedioxyphenilalaninedopamineadrenaline and mescaline tyrosinetyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone英语cathinoneephedrine and pseudoephedrine [32][92][93] Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone英语cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[32][94]
秋水仙素 類衍生物 [95]
Colchicine.svg
Tyrosine or phenylalaninedopamineautumnalinecolchicine [96] Colchicine, colchamine[95]
毒蕈鹼 [97]
Muscarine.svg
Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[98] Muscarine, allomuscarine, epimuscarine, epiallomuscarine[97]
芐胺[99]
Benzylamine.svg
Phenylalanine with valine, leucine or isoleucine[100] Capsaicin, dihydrocapsaicin英语dihydrocapsaicin, nordihydrocapsaicin, vanillylamine英语vanillylamine[99][101]
多胺生物鹼
腐胺 衍生物[102]
Putrescine.svg
ornithineputrescinespermidinespermine[103] Paucine [102]
亞精胺 衍生物[102]
Spermidine.svg
Lunarine, codonocarpine[102]
精胺 衍生物[102]
Spermine.svg
Verbascenine, aphelandrine [102]
Peptide (cyclopeptide) alkaloids
Peptide alkaloids with a 13-membered cycle [104][105] Nummularine C type From different amino acids [104] Nummularine C, Nummularine S [104]
Ziziphine type Ziziphine A, sativanine H [104]
Peptide alkaloids with a 14-membered cycle [104][105] Frangulanine type Frangulanine, scutianine J [105]
Scutianine A type Scutianine A [104]
Integerrine type Integerrine, discarine D [105]
Amphibine F type Amphibine F, spinanine A [104]
Amfibine B type Amphibine B, lotusine C [104]
Peptide alkaloids with a 15-membered cycle [105] Mucronine A type Mucronine A [106][105]
Pseudoalkaloids (terpenes and steroids)
Diterpenes [106]
Isoprene.svg
Lycoctonine type Mevalonic acidizopentenilpyrophosfategeranyl pyrophosphate英语geranyl pyrophosphate [107][108] Aconitine, delphinine英语delphinine [106][109]
Steroids[110]
Cyclopentenophenanthrene.svg
Cholesterol, arginine[111] Solasodine, solanidine英语solanidine, veralkamine, batrachotoxin英语batrachotoxin[112]

参阅[编辑]

参考资料[编辑]

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参考书目[编辑]

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