生物鹼
首个被分离出的生物碱,吗啡 ,于1804年由罂粟 中提取[1] 。
生物鹼 (英語:alkaloid )是一種天然存在的含氮鹼性 化合物 。一些人工合成 但結構类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 、氯 、溴 、磷 等元素。[2] 生物鹼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。
生物鹼在人或動物体内产生藥理反應。雖然大部份的生物鹼對人體有毒,但有些也能入药,起鎮痛或麻醉 的作用,以嗎啡 及可待因 尤为重要。生物鹼大都是氨基酸 衍生物,嚐起來有苦澀味,是植物(如馬鈴薯 、蕃茄 、罂粟 )、動物(如貝类 )、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,可以获得大部份的生物鹼。
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。
德国化学家--弗里德里希·塞图纳第一次从鸦片中分离出吗啡。
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] 。
生物鹼的分類
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。
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[8]
鳥氨酸 或 精氨酸 → 腐胺 → N-甲基腐胺 → N-methyl-Δ1 -pyrroline [9]
Cuscohygrine , hygrine , hygroline, stachydrine[8] [10]
托烷 類衍生物[11]
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 [9]
Atropine , scopolamine , hyoscyamine [8] [11] [12]
可卡因 類 原子取代於位置 2, 3
Cocaine , ecgonine [11] [13]
吡咯里西啶 類衍生物[14]
非酯 類
鳥氨酸,精氨酸→腐→類精脒→惹卓裂鹼 [9]
Retronecine , heliotridine, laburnine [14] [15]
一元羧酸 的複合酯
Indicine, lindelophin, sarracine [14]
大環內二酯
Platyphylline , trichodesmine[14]
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 [16] [17]
Loline, N -formylloline, N -acetylloline[18]
哌啶 類衍生物[19]
賴氨酸 → 屍胺 → Δ1 -piperideine [20]
Sedamine , lobeline, anaferine, piperine [21] [22]
辛酸 → coniceine → 毒芹碱 [23]
Coniine , coniceine [23]
喹 類衍生物[24] [25]
羽扇豆寧 類
賴氨酸 → 屍胺 → Δ1 -piperideine [26]
Lupinine , nupharidin [24]
金雀花鹼 類
Cytisine [24]
鷹爪豆鹼 類
Sparteine , lupanine , anahygrine [24]
苦參鹼 類
Matrine, oxymatrine, allomatridine[24] [27] [28]
苦豆鹼 類
Ormosanine, piptantine[24] [29]
吲哚聯啶 類衍生物[30]
賴氨酸 → δ-semialdehyde of Α-氨基己二酸 → pipecolic acid → 1 indolizidinone [31]
Swainsonine , castanospermine [32]
吡啶 類衍生物[33] [34]
吡啶簡單衍生物
烟酸 → dihydronicotinic acid → 1,2-dihydropyridine [35]
Trigonelline , ricinine, arecoline [33] [36]
多環芳烴 非冷凝 吡啶衍生物
Nicotine , nornicotine , anabasine , anatabine [33] [36]
多環芳烴冷凝吡啶衍生物
Actinidine , gentianine, pediculinine [37]
Sesquiterpene pyridine derivatives
烟酸 , 異亮氨酸 [38]
Evonine, hippocrateine, triptonine [34] [35]
異喹啉 類衍生物及相關生物鹼[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]
Pavine s 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]
Aporphine s [40]
Glaucine , coridine, liriodenine [54]
Proaporphines [40]
Pronuciferine, glaziovine [40] [49]
Homoaporphines [55]
Kreysiginine, multifloramine [55]
Homoproaporphines [55]
Bulbocodine [47]
嗎啡 s[56]
嗎啡 , 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]
Protopine s [40]
Protopine , oxomuramine, corycavidine [53]
Aristolactam [40]
Doriflavin [40]
噁唑 類衍生物[[62]
Tyrosine → tyramine [63]
Annuloline, halfordinol, texaline, texamine[64]
異噁唑 類衍生物
Ibotenic acid → Muscimol
Ibotenic acid, Muscimol
噻唑 類衍生物[65]
1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine , cysteine [66]
Nostocyclamide, thiostreptone [65] [67]
喹唑啉 類衍生物[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 類衍生物[62]
Anthranilic acid [71]
Rutacridone, acronicine [72] [73]
喹啉 類衍生物[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]
Quinine s
Tryptophan → tryptamine → strictosidine (with secologanin ) → korinanteal → cinhoninon [42] [76]
Quinine , quinidine , cinchonine , cinhonidine [79]
吲哚 類衍生物[57]
非異戊二烯 吲哚生物鹼
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]
半萜類 吲哚生物鹼'
Ergot alkaloids [57]
Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid [87]
Ergotamine , ergobasine, ergosine[88]
單萜 吲哚生物鹼
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 類衍生物[62]
Directly from histidine [94]
Histamine , pilocarpine, pilosine, stevensine[62] [94]
嘌呤 類衍生物[95]
Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine [42]
Caffeine , theobromine , theophylline , saxitoxin [96] [97]
側鏈上含氮原子的生物側鏈鹼
β-苯乙胺 類衍生物[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 類衍生物 [101]
Tyrosine or phenylalanine → dopamine → autumnaline → colchicine [102]
Colchicine , colchamine[101]
毒蕈鹼 [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]
多胺生物鹼
腐胺 衍生物[108]
ornithine → putrescine → spermidine → spermine [109]
Paucine [108]
亞精胺 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
引用
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来源
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