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。 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。
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 |
鳥氨酸 或 精氨酸 → 腐胺 → N-甲基腐胺 → N-methyl-Δ1-pyrroline | Cuscohygrine, hygrine, hygroline, stachydrine | |
托烷 類衍生物 |
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 | Atropine, scopolamine, hyoscyamine |
|
可卡因類 原子取代於位置 2, 3 |
Cocaine, ecgonine | ||
吡咯里西啶 類衍生物 |
非酯類 | 鳥氨酸，精氨酸→腐→類精脒→惹卓裂鹼 | Retronecine, heliotridine, laburnine |
| 一元羧酸的複合酯 | Indicine, lindelophin, sarracine | ||
| 大環內二酯 | Platyphylline, trichodesmine | ||
| 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 | Loline, N-formylloline, N-acetylloline | |
哌啶 類衍生物 |
賴氨酸 → 屍胺 → Δ1-piperideine | Sedamine, lobeline, anaferine, piperine | |
| 辛酸 → coniceine → 毒芹碱 | Coniine, coniceine | ||
喹 類衍生物 |
羽扇豆寧 類 | 賴氨酸 → 屍胺 → Δ1-piperideine | Lupinine, nupharidin |
| 金雀花鹼 類 | Cytisine | ||
| 鷹爪豆鹼 類 | Sparteine, lupanine, anahygrine | ||
| 苦參鹼 類 | Matrine, oxymatrine, allomatridine | ||
| 苦豆鹼 類 | Ormosanine, piptantine | ||
吲哚聯啶 類衍生物 |
賴氨酸 → δ-semialdehyde of Α-氨基己二酸 → pipecolic acid → 1 indolizidinone | Swainsonine, castanospermine | |
吡啶 類衍生物 |
吡啶簡單衍生物 | 烟酸 → dihydronicotinic acid → 1,2-dihydropyridine | Trigonelline, ricinine, arecoline |
| 多環芳烴非冷凝吡啶衍生物 | Nicotine, nornicotine, anabasine, anatabine | ||
| 多環芳烴冷凝吡啶衍生物 | Actinidine, gentianine, pediculinine | ||
| Sesquiterpene pyridine derivatives | 烟酸, 異亮氨酸 | Evonine, hippocrateine, triptonine | |
異喹啉 類衍生物及相關生物鹼 |
Simple derivatives of isoquinoline | Tyrosine or 苯丙氨酸 → 多巴胺 or 酪胺 (for alkaloids Amarillis) | Salsoline, lophocerine |
| Derivatives of 1- and 3-isoquinolines | N-methylcoridaldine, noroxyhydrastinine | ||
| Derivatives of 1- and 4-phenyltetrahydroisoquinolines | Cryptostilin | ||
| Derivatives of 5-naftil-isoquinoline | Ancistrocladine | ||
| Derivatives of 1- and 2-benzyl-izoquinolines | Papaverine, laudanosine, sendaverine | ||
| Cularine group | Cularine, yagonine | ||
| Pavines and isopavines | Argemonine, amurensine | ||
| Benzopyrrocolines | Cryptaustoline | ||
| Protoberberines | Berberine, canadine, ophiocarpine, mecambridine, corydaline | ||
| Phthalidisoquinolines | Hydrastine, narcotine (Noscapine) | ||
| Spirobenzylisoquinolines | Fumaricine | ||
| Ipecacuanha alkaloids | Emetine, protoemetine, ipecoside | ||
| Benzophenanthridines | Sanguinarine, oxynitidine, corynoloxine | ||
| Aporphines | Glaucine, coridine, liriodenine | ||
| Proaporphines | Pronuciferine, glaziovine | ||
| Homoaporphines | Kreysiginine, multifloramine | ||
| Homoproaporphines | Bulbocodine | ||
| 嗎啡s | 嗎啡, 可待因, 蒂巴因, 青藤碱 | ||
| Homomorphines | Kreysiginine, androcymbine | ||
| Tropoloisoquinolines | Imerubrine | ||
| Azofluoranthenes | Rufescine, imeluteine | ||
| Amaryllis alkaloids | Lycorine, ambelline, tazettine, galantamine, montanine | ||
| Erythrina alkaloids | Erysodine, erythroidine | ||
| Phenanthrene derivatives | Atherosperminine | ||
| Protopines | Protopine, oxomuramine, corycavidine | ||
| Aristolactam | Doriflavin | ||
噁唑 類衍生物[ |
Tyrosine → tyramine | Annuloline, halfordinol, texaline, texamine | |
異噁唑 類衍生物
 |
Ibotenic acid → Muscimol | Ibotenic acid, Muscimol | |
噻唑 類衍生物 |
1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine | Nostocyclamide, thiostreptone | |
喹唑啉 類衍生物 |
3,4-Dihydro-4-quinazolone derivatives | Anthranilic acid or phenylalanine or ornithine | Febrifugine |
| 1,4-Dihydro-4-quinazolone derivatives | Glycorine, arborine, glycosminine | ||
| Pyrrolidine and piperidine quinazoline derivatives | Vazicine (peganine) | ||
吖啶 類衍生物 |
Anthranilic acid | Rutacridone, acronicine | |
喹啉 類衍生物 |
Simple derivatives of quinoline derivatives of 2 – quinolones and 4-quinolone | Anthranilic acid → 3-carboxyquinoline | Cusparine, echinopsine, evocarpine |
| Tricyclic terpenoids | Flindersine | ||
| Furanoquinoline derivatives | Dictamnine, fagarine, skimmianine | ||
| Quinines | Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon | Quinine, quinidine, cinchonine, cinhonidine | |
吲哚 類衍生物 |
非異戊二烯吲哚生物鹼 | ||
| Simple indole derivatives | Tryptophan → tryptamine or 5-hydroxitriptofan | Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin | |
| Simple derivatives of β-carboline | Harman, harmine, harmaline, eleagnine | ||
| Pyrroloindole alkaloids | Physostigmine (eserine), etheramine, physovenine, eptastigmine | ||
| 半萜類吲哚生物鹼' | |||
| Ergot alkaloids | Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid | Ergotamine, ergobasine, ergosine | |
| 單萜吲哚生物鹼 | |||
| Corynanthe type alkaloids | Tryptophan → tryptamine → strictosidine (with secologanin) | Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine, group strychnine and (Strychnine brucine, aquamicine, vomicine ) | |
| Iboga-type alkaloids | Ibogamine, ibogaine, voacangine | ||
| Aspidosperma-type alkaloids | Vincamine, vinca alkaloids, vincotine, aspidospermine | ||
咪唑 類衍生物 |
Directly from histidine | Histamine, pilocarpine, pilosine, stevensine | |
嘌呤 類衍生物 |
Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine | Caffeine, theobromine, theophylline, saxitoxin | |
| 側鏈上含氮原子的生物側鏈鹼 | |||
β-苯乙胺 類衍生物 |
Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone → ephedrine and pseudoephedrine | Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine) | |
秋水仙素 類衍生物  |
Tyrosine or phenylalanine → dopamine → autumnaline → colchicine | Colchicine, colchamine | |
毒蕈鹼  |
Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid) | Muscarine, allomuscarine, epimuscarine, epiallomuscarine | |
芐胺 |
Phenylalanine with valine, leucine or isoleucine | Capsaicin, dihydrocapsaicin, nordihydrocapsaicin, vanillylamine | |
| 多胺生物鹼 | |||
腐胺 衍生物 |
ornithine → putrescine → spermidine → spermine | Paucine | |
亞精胺 衍生物 |
Lunarine, codonocarpine | ||
精胺 衍生物 |
Verbascenine, aphelandrine | ||
| Peptide (cyclopeptide) alkaloids | |||
| Peptide alkaloids with a 13-membered cycle | Nummularine C type | From different amino acids | Nummularine C, Nummularine S |
| Ziziphine type | Ziziphine A, sativanine H | ||
| Peptide alkaloids with a 14-membered cycle | Frangulanine type | Frangulanine, scutianine J | |
| Scutianine A type | Scutianine A | ||
| Integerrine type | Integerrine, discarine D | ||
| Amphibine F type | Amphibine F, spinanine A | ||
| Amfibine B type | Amphibine B, lotusine C | ||
| Peptide alkaloids with a 15-membered cycle | Mucronine A type | Mucronine A | |
| Pseudoalkaloids (terpenes and steroids) | |||
Diterpenes  |
Lycoctonine type | Mevalonic acid → izopentenilpyrophosfate → geranyl pyrophosphate | Aconitine, delphinine |
Steroids |
Cholesterol, arginine | Solasodine, solanidine, veralkamine, batrachotoxin | |
引用
来源
- Aniszewski, Tadeusz. Alkaloids – secrets of life. Amsterdam: Elsevier. 2007. ISBN 978-0-444-52736-3.
- Begley, Tadhg P. Encyclopedia of Chemical Biology. Wiley. 2009. ISBN 978-0-471-75477-0. doi:10.1002/cbic.200900262.
- Brossi, Arnold. The Alkaloids: Chemistry and Pharmacology. Academic Press. 1989.
- Dewick, Paul M. Medicinal Natural Products. A Biosynthetic Approach 2nd. Wiley. 2002. ISBN 0-471-49640-5.
- Fattorusso, E.; Taglialatela-Scafati, O. Modern Alkaloids: Structure, Isolation, Synthesis and Biology. Wiley-VCH. 2008. ISBN 978-3-527-31521-5.
- Grinkevich, N. I.; Safronich, L. N. The chemical analysis of medicinal plants: Proc. allowance for pharmaceutical universities. M. 1983.
- Hesse, Manfred. Alkaloids: Nature's Curse or Blessing?. Wiley-VCH. 2002. ISBN 978-3-906390-24-6.
- Knunyants, I. L. Chemical Encyclopedia. Soviet Encyclopedia. 1988 [2014-08-23]. （原始内容存档于2021-03-07）.
- Orekhov, A. P. Chemistry alkaloids Acad. 2. M.: USSR. 1955.
- Plemenkov, V. V. Introduction to the Chemistry of Natural Compounds. Kazan. 2001.
- Saxton, J. E. The Alkaloids. A Specialist Periodical Report. London: The Chemical Society. 1971.
- Veselovskaya, N. B.; Kovalenko, A. E. Drugs. Moscow: Triada-X. 2000.
- Wink, M. Mode of action and toxicology of plant toxins and poisonous plants. Mitt. Julius Kühn-Inst. 2009, 421: 93–112 [18 March 2014]. （原始内容存档于2014-03-18）.
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