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生物鹼：修订间差异

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首个被分离出的生物碱，[[吗啡]]，于1804年由[[罂粟]]中提取<ref>{{cite book |url = http://books.google.com/?id=MtOiLVWBn8cC&pg=PA20 |page=20 |title = Molecular, clinical and environmental toxicology |author=Andreas Luch |publisher=Springer |year=2009 |ISBN = 3-7643-8335-6 }}</ref>。]]
'''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]]及[[蕈類]]的[[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]]和[[氮]]，生物鹼也可以含有[[氧]]，[[硫]]，甚或其他元素，如[[氯]]，[[溴]]，和[[磷]]。[5]


'''生物鹼'''（{{lang-en|alkaloid}}）是一種天然存在的含氮[[鹼性]][[化合物]]。一些[[化學合成|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。<ref name="XimE: alkaloidy">[http://www.xumuk.ru/encyklopedia/119.html Chemical Encyclopedia: alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/119.html |date=20110114014724 }}. xumuk.ru</ref> 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。
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]]、[[罌粟|罂粟]]）、動物（如[[貝殼|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。
古代的毒藥大多為強烈的有毒生物鹼，{{Fact|而犀牛角只要碰到生物鹼就會整個支離破碎|time=2015-02-23T11:09:25+00:00}}，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。

== 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<ref name=":0">{{Cite book|chapter=Preface|title=Alkaloids|url=http://dx.doi.org/10.1016/b978-0-444-59433-4.09990-9|publisher=Elsevier|date=2015|pages=xvii–xviii|first=Tadeusz|last=Aniszewski}}</ref>。[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<ref>{{Cite book|chapter=Industrieroboterperipherie|title=Industrieroboterpraxis|url=http://dx.doi.org/10.1007/978-3-322-88981-2_10|publisher=Vieweg+Teubner Verlag|date=1998|location=Wiesbaden|isbn=978-3-322-88982-9|pages=327–338|first=Stefan|last=Hesse}}</ref>。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[[罌粟|罂粟]]的医疗用途<ref>{{Cite book|chapter=Backmatter|title=Frankfurt – Hesse-Darmstadt|url=http://dx.doi.org/10.1515/9783598440571.bm|publisher=Walter de Gruyter – K. G. Saur|date=2007-06-16|pages=291–304}}</ref>。此外，[[古柯樹|古柯叶]]自古以来就被[[南美洲|南美]]原住民使用。
[[File:Friedrich Wilhelm Adam Sertuerner.jpg|thumb|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[[生物鹼|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<ref name=":0" />。

生物碱的研究始于 19 世纪。

1804年，德国化学家[[弗里德里希·瑟圖納|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“[[嗎啡|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[[约瑟夫·路易·盖-吕萨克|盖-吕萨克]]提出。

法国研究人员[[皮埃尔-约瑟夫·佩尔提埃|皮埃尔-佩尔提埃]]和[[约瑟夫·别奈梅·卡旺图|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[[光谱仪|光谱]]和[[色谱法|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<ref>{{Cite book|chapter=Overview and Introduction|title=Comprehensive Natural Products II|url=http://dx.doi.org/10.1016/b978-008045382-8.00733-4|publisher=Elsevier|date=2010|pages=1–2|first=Tadhg P.|last=Begley}}</ref>。

1886 年，德国化学家[[阿尔贝特·拉登堡|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]]<ref>{{Cite journal |last=Lieberstein |first=Samuel |date=1975-04 |title=Great Soviet Encyclopedia: A Translation of the Third Edition. Vol. 1 |url=http://dx.doi.org/10.2307/127750 |journal=Russian Review |volume=34 |issue=2 |doi=10.2307/127750 |issn=0036-0341}}</ref>。


== 生物鹼的分類 ==
== 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。
⚫
{| Class = "wikitable"

⚫
{| class = "wikitable"
|-
|-
! 類別
! 類別
第15行： 第37行：
!例子
!例子
|-
|-
| colspan="4" style="text-align:center; background:# DADADA;"|''與含氮雜環生物鹼（真正生物鹼）''
| colspan="4" style="text-align:center; background:# DADADA;"|''與含氮雜環生物鹼（真正生物鹼）''
|-
|-
| [[吡咯烷]] 類衍生物<ref name="ref34">[[#Plemenkov|Plemenkov]], p. 224</ref>
| [[吡咯烷]] 類衍生物<ref name="ref34">[[#Plemenkov|Plemenkov]], p. 224</ref>
第21行： 第43行：
|
|
| [[鳥氨酸]] 或 [[精氨酸]] → [[腐胺]] → N-甲基腐胺 → N-methyl-Δ<sup>1</sup>-pyrroline <ref name="ref35">[[#Aniszewski|Aniszewski]], p. 75</ref>
| [[鳥氨酸]] 或 [[精氨酸]] → [[腐胺]] → N-甲基腐胺 → N-methyl-Δ<sup>1</sup>-pyrroline <ref name="ref35">[[#Aniszewski|Aniszewski]], p. 75</ref>
| [[Cuscohygrine]], [[hygrine]], hygroline, stachydrine<ref name="ref34" /><ref>[[#Orekhov|Orekhov]], p. 33</ref>
| {{tsl|en|Cuscohygrine||Cuscohygrine}}, {{tsl|en|hygrine||hygrine}}, hygroline, stachydrine<ref name="ref34" /><ref>[[#Orekhov|Orekhov]], p. 33</ref>
|-
|-
| Rowspan = "2"|[[托烷]] 類衍生物<ref name="ref38">[http://www.xumuk.ru/encyklopedia/2/4609.html Chemical Encyclopedia: Tropan alkaloids]. xumuk.ru</ref>
| Rowspan = "2"|[[托烷]] 類衍生物<ref name="ref38">[http://www.xumuk.ru/encyklopedia/2/4609.html Chemical Encyclopedia: Tropan alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2/4609.html |date=20161024170844 }}. xumuk.ru</ref>
[[File:Tropane numbered.svg|100px|center]]
[[File:Tropane numbered.svg|100px|center]]
| [[阿托品]]類 <br /><small>原子取代於位置 3, 6 或 7 </small>
| [[阿托品]]類 <br /><small>原子取代於位置 3, 6 或 7 </small>
| Rowspan = "2"|鳥氨酸或精氨酸→腐胺→N-甲基腐胺→N-甲基-Δ<sup>1</sup>-吡咯烷酮 <ref name = "ref35 "/>
| Rowspan = "2"|鳥氨酸或精氨酸→腐胺→N-甲基腐胺→N-甲基-Δ<sup>1</sup>-吡咯烷酮 <ref name = "ref35 "/>
| [[Atropine]], [[scopolamine]], [[hyoscyamine]]<ref name="ref34" /><ref name="ref38" /><ref>[[#Hesse|Hesse]], p. 34</ref>
| [[阿托品|Atropine]], [[東莨菪鹼|scopolamine]], [[天仙子胺|hyoscyamine]]<ref name="ref34" /><ref name="ref38" /><ref>[[#Hesse|Hesse]], p. 34</ref>
|-
|-
| [[可卡因]]類 group<br /> <small>原子取代於位置 2, 3 </small>
| [[可卡因]]類 <br /> <small>原子取代於位置 2, 3 </small>
| [[Cocaine]], [[ecgonine]] <ref name="ref38" /><ref>[[#Aniszewski|Aniszewski]], p. 27</ref>
| [[可卡因|Cocaine]], {{tsl|en|ecgonine||ecgonine}} <ref name="ref38" /><ref>[[#Aniszewski|Aniszewski]], p. 27</ref>
|-
|-
| Rowspan = "4"|[[吡咯里西啶]] 類衍生物<ref name="ref45">[http://www.xumuk.ru/encyklopedia/2/3370.html Chemical Encyclopedia: Pyrrolizidine alkaloids]. xumuk.ru</ref>
| Rowspan = "4"|[[吡咯里西啶]] 類衍生物<ref name="ref45">[http://www.xumuk.ru/encyklopedia/2/3370.html Chemical Encyclopedia: Pyrrolizidine alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2/3370.html |date=20160917044956 }}. xumuk.ru</ref>
[[File:Pyrrolizidine.svg|80px|center]]
[[File:Pyrrolizidine.svg|80px|center]]
| 非[[酯]]類
| 非[[酯]]類
| Rowspan = "3"|鳥氨酸，精氨酸→腐→類精脒→惹卓裂鹼 <ref name="ref35" />
| Rowspan = "3"|鳥氨酸，精氨酸→腐→類精脒→惹卓裂鹼 <ref name="ref35" />
| [[Retronecine]], heliotridine, laburnine <ref name="ref45" /><ref>[[#Plemenkov|Plemenkov]], p. 229</ref>
| {{tsl|en|Retronecine||Retronecine}}, heliotridine, laburnine <ref name="ref45" /><ref>[[#Plemenkov|Plemenkov]], p. 229</ref>
|-
|-
| 一元[[羧酸]]的複合酯
| 一元[[羧酸]]的複合酯
第44行： 第66行：
| [[Platyphylline]], trichodesmine<ref name="ref45" />
| [[Platyphylline]], trichodesmine<ref name="ref45" />
|-
|-
| 1-氨基吡咯烷類 ([[Loline alkaloids|lolines]])
| 1-氨基吡咯烷類 ({{tsl|en|Loline alkaloids||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 <ref name="Blankenship">{{cite journal|author=Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL|year= 2005|title=Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids|journal=Chembiochem|volume=6|pages=1016–1022|pmid=15861432|doi=10.1002/cbic.200400327|issue=6}}</ref><ref name="Faulkner et al. 2006">{{cite journal|author=Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL|year= 2006|title=On the sequence of bond formation in loline alkaloid biosynthesis|journal=Chembiochem|volume=7|pages=1078–1088|pmid=16755627|doi=10.1002/cbic.200600066|issue=7}}</ref>
|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 <ref name="Blankenship">{{cite journal|author=Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL|year= 2005|title=Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids|journal=Chembiochem|volume=6|pages=1016–1022|pmid=15861432|doi=10.1002/cbic.200400327|issue=6}}</ref><ref name="Faulkner et al. 2006">{{cite journal|author=Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL|year= 2006|title=On the sequence of bond formation in loline alkaloid biosynthesis|journal=Chembiochem|volume=7|pages=1078–1088|pmid=16755627|doi=10.1002/cbic.200600066|issue=7}}</ref>
|Loline, ''N''-formylloline, ''N''-acetylloline<ref name="Schardl et al. 2007">{{cite journal|author=Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP|year=2007|title=Loline alkaloids: currencies of mutualism|journal = [[Phytochemistry (journal)|Phytochemistry]]|volume=68|pages=980–996|doi=10.1016/j.phytochem.2007.01.010|pmid=17346759|issue=7}}</ref>
|Loline, ''N''-formylloline, ''N''-acetylloline<ref name="Schardl et al. 2007">{{cite journal|author=Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP|year=2007|title=Loline alkaloids: currencies of mutualism|journal = {{tsl|en|Phytochemistry (journal)||Phytochemistry}}|volume=68|pages=980–996|doi=10.1016/j.phytochem.2007.01.010|pmid=17346759|issue=7}}</ref>
|-
|-
| Rowspan = "2"|[[哌啶]] 類衍生物<ref>[[#Plemenkov|Plemenkov]], p. 225</ref>
| Rowspan = "2"|[[哌啶]] 類衍生物<ref>[[#Plemenkov|Plemenkov]], p. 225</ref>
[[File:Piperidin.svg|50px|center]]
[[File:Piperidin.svg|50px|center]]
|
|
| [[Lysine]] → [[cadaverine]] → Δ<sup>1</sup>-piperideine <ref>[[#Aniszewski|Aniszewski]], p. 95</ref>
| [[離胺酸|賴氨酸]] → [[尸胺|屍胺]] → Δ<sup>1</sup>-piperideine <ref>[[#Aniszewski|Aniszewski]], p. 95</ref>
| [[Sedamine]], lobeline, anaferine, [[piperine]] <ref name="ref24" /><ref>[[#Orekhov|Orekhov]], p. 80</ref>
| [[Sedamine]], lobeline, anaferine, [[胡椒碱|piperine]] <ref name="ref24">[[#Hesse|Hesse]], p. 31</ref><ref>[[#Orekhov|Orekhov]], p. 80</ref>
|-
|-
|
|
| [[Caprylic acid|Octanoic acid]] → coniceine → [[coniine]] <ref name="ref25" />
| [[辛酸]] → coniceine → [[毒芹碱]] <ref name="ref25">[[#Dewick|Dewick]], p. 381</ref>
| [[Coniine]], coniceine <ref name="ref25" />
| [[毒芹碱|Coniine]], coniceine <ref name="ref25" />
|-
|-
| Rowspan = "5"|[[喹]] 類衍生物<ref name="ref57">[http://www.xumuk.ru/encyklopedia/2/5011.html Chemical Encyclopedia: Quinolizidine alkaloids]. xumuk.ru</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 93</ref>
| Rowspan = "5"|[[喹]] 類衍生物<ref name="ref57">[http://www.xumuk.ru/encyklopedia/2/5011.html Chemical Encyclopedia: Quinolizidine alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2/5011.html |date=20161024171107 }}. xumuk.ru</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 93</ref>
[[File:Quinolizidine.svg|80px|center]]
[[File:Quinolizidine.svg|80px|center]]
| [[羽扇豆寧]] 類
| [[羽扇豆碱]] 類
| Rowspan = "5"|[[Lysine]] → [[cadaverine]] → Δ<sup>1</sup>-piperideine <ref>[[#Aniszewski|Aniszewski]], p. 98</ref>
| Rowspan = "5"|[[離胺酸|賴氨酸]] → [[尸胺|屍胺]] → Δ<sup>1</sup>-piperideine <ref>[[#Aniszewski|Aniszewski]], p. 98</ref>
| [[Lupinine]], nupharidin <ref name="ref57" />
| {{tsl|en|Lupinine||Lupinine}}, nupharidin <ref name="ref57" />
|-
|-
| [[金雀花鹼]] 類
| [[野靛碱]] 類
| [[Cytisine]] <ref name="ref57" />
| [[野靛碱]] <ref name="ref57" />
|-
|-
| [[鷹爪豆鹼]] 類
| [[司巴丁]] 類
| [[Sparteine]], [[lupanine]], [[anahygrine]]<ref name="ref57" />
| [[司巴丁]], [[lupanine]], [[anahygrine]]<ref name="ref57" />
|-
|-
| [苦參鹼]] 類
| [[苦參鹼]] 類
| Matrine, oxymatrine, allomatridine<ref name="ref57" /><ref>[[#Saxton|Saxton]], Vol. 1, p. 91</ref><ref>{{cite journal|author = Joseph P. Michael|title = Indolizidine and quinolizidine alkaloids|doi = 10.1039/b208137g|journal=Nat. Prod. Rep|year = 2002|volume = 19|pages = 458–475}}</ref>
| Matrine, oxymatrine, allomatridine<ref name="ref57" /><ref>[[#Saxton|Saxton]], Vol. 1, p. 91</ref><ref>{{cite journal|author = Joseph P. Michael|title = Indolizidine and quinolizidine alkaloids|doi = 10.1039/b208137g|journal=Nat. Prod. Rep|year = 2002|volume = 19|pages = 458–475}}</ref>
|-
|-
第76行： 第98行：
| Ormosanine, piptantine<ref name="ref57" /><ref>[[#Saxton|Saxton]], Vol. 1, p. 92</ref>
| Ormosanine, piptantine<ref name="ref57" /><ref>[[#Saxton|Saxton]], Vol. 1, p. 92</ref>
|-
|-
| [吲哚聯啶]] 類衍生物<ref>[[#Dewick|Dewick]], p. 310</ref>
| [[吲哚聯啶]] 類衍生物<ref>[[#Dewick|Dewick]], p. 310</ref>
[[File:Indolizidine.svg|80px|center]]
[[File:Indolizidine.svg|80px|center]]
|
|
| [[Lysine]] → δ-semialdehyde of [[alpha-Aminoadipic acid|α-aminoadipic acid]] → [[pipecolic acid]] → 1 indolizidinone <ref>[[#Aniszewski|Aniszewski]], p. 96</ref>
| [[離胺酸|賴氨酸]] → δ-semialdehyde of [[Α-氨基己二酸]] → {{tsl|en|pipecolic acid||pipecolic acid}} → 1 indolizidinone <ref>[[#Aniszewski|Aniszewski]], p. 96</ref>
| [[Swainsonine]], [[castanospermine]] <ref>[[#Aniszewski|Aniszewski]], p. 97</ref>
| {{tsl|en|Swainsonine||Swainsonine}}, {{tsl|en|castanospermine||castanospermine}} <ref>[[#Aniszewski|Aniszewski]], p. 97</ref>
|-
|-
| Rowspan = "4"|[[吡啶]] 類衍生物<ref name="ref72">[[#Plemenkov|Plemenkov]], p. 227</ref><ref name="ref73">[http://www.xumuk.ru/encyklopedia/2/3336.html Chemical Encyclopedia: pyridine alkaloids]. xumuk.ru</ref>
| Rowspan = "4"|[[吡啶]] 類衍生物<ref name="ref72">[[#Plemenkov|Plemenkov]], p. 227</ref><ref name="ref73">[http://www.xumuk.ru/encyklopedia/2/3336.html Chemical Encyclopedia: pyridine alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2/3336.html |date=20161021214428 }}. xumuk.ru</ref>
[[File:Pyridine.svg|50px|center]]
[[File:Pyridine.svg|50px|center]]
| 吡啶簡單衍生物
| 吡啶簡單衍生物
| Rowspan = "3"|[[Nicotinic acid]] → dihydronicotinic acid → 1,2-dihydropyridine <ref name="ref74">[[#Aniszewski|Aniszewski]], p. 107</ref>
| Rowspan = "3"|[[烟酸]] → dihydronicotinic acid → 1,2-dihydropyridine <ref name="ref74">[[#Aniszewski|Aniszewski]], p. 107</ref>
| [[Trigonelline]], ricinine, [[arecoline]] <ref name="ref72" /><ref name="ref76">[[#Aniszewski|Aniszewski]], p. 85</ref>
| {{tsl|en|Trigonelline||Trigonelline}}, ricinine, {{tsl|en|arecoline||arecoline}} <ref name="ref72" /><ref name="ref76">[[#Aniszewski|Aniszewski]], p. 85</ref>
|-
|-
| [[多環芳烴]]非[[冷凝]]吡啶衍生物
| [[多環芳烴]]非[[冷凝]]吡啶衍生物
| [[Nicotine]], [[nornicotine]], [[anabasine]], anatabine <ref name="ref72" /><ref name="ref76" />
| [[尼古丁|Nicotine]], {{tsl|en|nornicotine||nornicotine}}, {{tsl|en|anabasine||anabasine}}, anatabine <ref name="ref72" /><ref name="ref76" />
|-
|-
| 多環芳烴冷凝吡啶衍生物
| 多環芳烴冷凝吡啶衍生物
| [[Actinidine]], gentianine, pediculinine <ref>[[#Plemenkov|Plemenkov]], p. 228</ref>
| {{tsl|en|Actinidine||Actinidine}}, gentianine, pediculinine <ref>[[#Plemenkov|Plemenkov]], p. 228</ref>
|-
|-
| [[Sesquiterpene]] pyridine derivatives
| {{tsl|en|Sesquiterpene||Sesquiterpene}} pyridine derivatives
| [[Nicotinic acid]], [[isoleucine]] <ref name="Aniszewski 110"/>
| [[烟酸]], [[異亮氨酸]] <ref name="Aniszewski 110">[[#Aniszewski|Aniszewski]], p. 110</ref>
| Evonine, hippocrateine, triptonine <ref name="ref73" /><ref name="ref74" />
| Evonine, hippocrateine, triptonine <ref name="ref73" /><ref name="ref74" />
|-
|-
| Rowspan = "26"|[[異喹啉]] 類衍生物及相關生物鹼<ref name="Hesse 36">[[#Hesse|Hesse]], p. 36</ref>
| Rowspan = "26"|[[異喹啉]] 類衍生物及相關生物鹼<ref name="Hesse 36">[[#Hesse|Hesse]], p. 36</ref>
[[File:Isoquinoline numbered.svg|90px|center]]
[[File:Isoquinoline numbered.svg|90px|center]]
| Simple derivatives of isoquinoline <ref name="XimE: izoxinolin">[http://www.xumuk.ru/encyklopedia/1642.html Chemical Encyclopedia: isoquinoline alkaloids]. xumuk.ru</ref>
| Simple derivatives of isoquinoline <ref name="XimE: izoxinolin">[http://www.xumuk.ru/encyklopedia/1642.html Chemical Encyclopedia: isoquinoline alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/1642.html |date=20161024171123 }}. xumuk.ru</ref>
| Rowspan = "26"|[[Tyrosine]] or [[phenylalanine]] → [[dopamine]] or [[tyramine]] (for alkaloids Amarillis) <ref>[[#Aniszewski|Aniszewski]], pp. 77–78</ref><ref name="Begley">[[#Begley|Begley]], Alkaloid Biosynthesis</ref>
| Rowspan = "26"|[[酪氨酸|Tyrosine]] or [[苯丙氨酸]] → [[多巴胺]] or [[酪胺]] (for alkaloids Amarillis) <ref>[[#Aniszewski|Aniszewski]], pp. 77–78</ref><ref name="Begley">[[#Begley|Begley]], Alkaloid Biosynthesis</ref>
| Salsoline, lophocerine <ref name="Hesse 36"/><ref name="XimE: izoxinolin"/>
| Salsoline, lophocerine <ref name="Hesse 36"/><ref name="XimE: izoxinolin"/>
|-
|-
第114行： 第136行：
|-
|-
| Derivatives of 1- and 2-benzyl-izoquinolines <ref>[[#Hesse|Hesse]], p. 38</ref>
| Derivatives of 1- and 2-benzyl-izoquinolines <ref>[[#Hesse|Hesse]], p. 38</ref>
| [[Papaverine]], [[laudanosine]], sendaverine
| [[罂粟碱|Papaverine]], {{tsl|en|laudanosine||laudanosine}}, sendaverine
|-
|-
| [[Cularine]] group<ref name="ref86">[[#Hesse|Hesse]], p. 46</ref>
| [[Cularine]] group<ref name="ref86">[[#Hesse|Hesse]], p. 46</ref>
| Cularine, yagonine <ref name="ref86" />
| Cularine, yagonine <ref name="ref86" />
|-
|-
| [[Pavine (molecule)|Pavine]]s and isopavines <ref name="ref88">[[#Hesse|Hesse]], p. 50</ref>
| {{tsl|en|Pavine (molecule)||Pavine}}s and isopavines <ref name="ref88">[[#Hesse|Hesse]], p. 50</ref>
| Argemonine, [[amurensine]] <ref name="ref88" />
| Argemonine, {{tsl|en|amurensine||amurensine}} <ref name="ref88" />
|-
|-
| Benzopyrrocolines <ref name="ref90">{{cite journal|author = Kenneth W. Bentley|title = β-Phenylethylamines and the isoquinoline alkaloids|doi = 10.1039/NP9971400387|journal=Nat. Prod. Rep|year = 1997|volume = 14|pages = 387–411|pmid = 9281839|issue = 4|url=http://chemistry.mdma.ch/hiveboard/rhodium/pdf/archive/merbst/phenethylamines%20and%20isoquinolines%202001.pdf}}</ref>
| Benzopyrrocolines <ref name="ref90">{{cite journal |author = Kenneth W. Bentley |title = β-Phenylethylamines and the isoquinoline alkaloids |doi = 10.1039/NP9971400387 |journal = Nat. Prod. Rep |year = 1997 |volume = 14 |issue = 4 |pages = 387–411 |PMID = 9281839 |url = http://chemistry.mdma.ch/hiveboard/rhodium/pdf/archive/merbst/phenethylamines%20and%20isoquinolines%202001.pdf |access-date = 2016-04-23 |archive-date = 2014-04-13 |archive-url = https://web.archive.org/web/20140413080855/http://chemistry.mdma.ch/hiveboard/rhodium/pdf/archive/merbst/phenethylamines%20and%20isoquinolines%202001.pdf |dead-url = no }}</ref>
| Cryptaustoline <ref name="XimE: izoxinolin"/>
| Cryptaustoline <ref name="XimE: izoxinolin"/>
|-
|-
| Protoberberines <ref name="XimE: izoxinolin"/>
| Protoberberines <ref name="XimE: izoxinolin"/>
| [[Berberine]], [[canadine]], ophiocarpine, mecambridine, corydaline <ref name="ref91">[[#Hesse|Hesse]], p. 47</ref>
| [[小檗鹼|Berberine]], {{tsl|en|canadine||canadine}}, ophiocarpine, mecambridine, corydaline <ref name="ref91">[[#Hesse|Hesse]], p. 47</ref>
|-
|-
| Phthalidisoquinolines <ref name="XimE: izoxinolin"/>
| Phthalidisoquinolines <ref name="XimE: izoxinolin"/>
| [[Hydrastine]], [[narcotine]] (Noscapine) <ref>[[#Hesse|Hesse]], p. 39</ref>
| [[Hydrastine]], {{tsl|en|narcotine||narcotine}} (Noscapine) <ref>[[#Hesse|Hesse]], p. 39</ref>
|-
|-
| Spirobenzylisoquinolines <ref name="XimE: izoxinolin"/>
| Spirobenzylisoquinolines <ref name="XimE: izoxinolin"/>
| Fumaricine <ref name="ref88" />
| Fumaricine <ref name="ref88" />
|-
|-
| [[Psychotria ipecacuanha|Ipecacuanha]] alkaloids<ref name="ref94">[[#Hesse|Hesse]], p. 41</ref>
| {{tsl|en|Psychotria ipecacuanha||Ipecacuanha}} alkaloids<ref name="ref94">[[#Hesse|Hesse]], p. 41</ref>
| Emetine, protoemetine, ipecoside <ref name="ref94" />
| Emetine, protoemetine, ipecoside <ref name="ref94" />
|-
|-
第140行： 第162行：
| Sanguinarine, oxynitidine, corynoloxine <ref name="ref96">[[#Hesse|Hesse]], p. 49</ref>
| Sanguinarine, oxynitidine, corynoloxine <ref name="ref96">[[#Hesse|Hesse]], p. 49</ref>
|-
|-
| [[Aporphine]]s <ref name="XimE: izoxinolin"/>
| {{tsl|en|Aporphine||Aporphine}}s <ref name="XimE: izoxinolin"/>
| [[Glaucine]], coridine, liriodenine <ref>[[#Hesse|Hesse]], p. 44</ref>
| {{tsl|en|Glaucine||Glaucine}}, coridine, liriodenine <ref>[[#Hesse|Hesse]], p. 44</ref>
|-
|-
| Proaporphines <ref name="XimE: izoxinolin"/>
| Proaporphines <ref name="XimE: izoxinolin"/>
第152行： 第174行：
| Bulbocodine <ref name="ref86" />
| Bulbocodine <ref name="ref86" />
|-
|-
| [[Morphine]]s<ref name="ref103">[[#Hesse|Hesse]], p. 51</ref>
| [[嗎啡]]s<ref name="ref103">[[#Hesse|Hesse]], p. 51</ref>
| [[Morphine]], [[codeine]], [[thebaine]], [[sinomenine]] <ref name="ref104">[[#Plemenkov|Plemenkov]], p. 236</ref>
| [[嗎啡]], [[可待因]], [[蒂巴因]], [[青藤碱]] <ref name="ref104">[[#Plemenkov|Plemenkov]], p. 236</ref>
|-
|-
| Homomorphines <ref>[[#Saxton|Saxton]], Vol. 3, p. 163</ref>
| Homomorphines <ref>[[#Saxton|Saxton]], Vol. 3, p. 163</ref>
第165行： 第187行：
|-
|-
| [[Amaryllis]] alkaloids<ref>[[#Hesse|Hesse]], p. 52</ref>
| [[Amaryllis]] alkaloids<ref>[[#Hesse|Hesse]], p. 52</ref>
| [[Lycorine]], ambelline, tazettine, [[galantamine]], montanine <ref>[[#Hesse|Hesse]], p. 53</ref>
| [[石蒜碱|Lycorine]], ambelline, tazettine, {{tsl|en|galantamine||galantamine}}, montanine <ref>[[#Hesse|Hesse]], p. 53</ref>
|-
|-
| [[Erythrina]] alkaloids<ref name="Hesse 54"/>
| [[刺桐属|Erythrina]] alkaloids<ref name="Hesse 54"/>
| Erysodine, erythroidine <ref name="Hesse 54"/>
| Erysodine, erythroidine <ref name="Hesse 54"/>
|-
|-
| [[Phenanthrene]] derivatives <ref name="XimE: izoxinolin"/>
| [[菲|Phenanthrene]] derivatives <ref name="XimE: izoxinolin"/>
| Atherosperminine <ref name="XimE: izoxinolin"/><ref name="ref91" />
| Atherosperminine <ref name="XimE: izoxinolin" /><ref name="ref91" />
|-
|-
| [[Protopine]]s <ref name="XimE: izoxinolin"/>
| {{tsl|en|Protopine||Protopine}}s <ref name="XimE: izoxinolin"/>
| [[Protopine]], oxomuramine, corycavidine <ref name="ref96" />
| {{tsl|en|Protopine||Protopine}}, oxomuramine, corycavidine <ref name="ref96" />
|-
|-
| Aristolactam <ref name="XimE: izoxinolin"/>
| Aristolactam <ref name="XimE: izoxinolin" />
| Doriflavin <ref name="XimE: izoxinolin"/>
| Doriflavin <ref name="XimE: izoxinolin"/>
|-
|-
第182行： 第204行：
[[File:Oxazole structure.svg|80px|center]]
[[File:Oxazole structure.svg|80px|center]]
|
|
| [[Tyrosine]] → [[tyramine]] <ref>[[#Brossi|Brossi]], Vol. 35, p. 261</ref>
| [[酪氨酸|Tyrosine]] → [[酪胺|tyramine]] <ref>[[#Brossi|Brossi]], Vol. 35, p. 261</ref>
| Annuloline, halfordinol, texaline, texamine<ref>[[#Brossi|Brossi]], Vol. 35, pp. 260–263</ref>
| Annuloline, halfordinol, texaline, texamine<ref>[[#Brossi|Brossi]], Vol. 35, pp. 260–263</ref>
|-
|-
第188行： 第210行：
[[Image:isoxazole structure.png|80px|center]]
[[Image:isoxazole structure.png|80px|center]]
|
|
|[[Ibotenic acid]] → [[Muscimol]]
|[[鹅膏蕈氨酸|Ibotenic acid]] → [[蠅蕈素|Muscimol]]
|Ibotenic acid, Muscimol
|Ibotenic acid, Muscimol
|-
|-
第194行： 第216行：
[[File:Thiazole structure.svg|80px|center]]
[[File:Thiazole structure.svg|80px|center]]
|
|
| [[1-Deoxy-D-xylulose 5-phosphate]] (DOXP), [[tyrosine]], [[cysteine]] <ref>[[#Begley|Begley]], Cofactor Biosynthesis</ref>
| {{tsl|en|1-Deoxy-D-xylulose 5-phosphate||1-Deoxy-D-xylulose 5-phosphate}} (DOXP), [[酪氨酸|tyrosine]], [[半胱氨酸|cysteine]] <ref>[[#Begley|Begley]], Cofactor Biosynthesis</ref>
| Nostocyclamide, thiostreptone <ref name="ref114" /><ref>{{cite journal|author = John R. Lewis|title = Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids|journal = Nat. Prod. Rep|year = 2000|volume = 17|pages = 57–84|pmid = 10714899|issue = 1|doi = 10.1039/a809403i}}</ref>
| Nostocyclamide, thiostreptone <ref name="ref114" /><ref>{{cite journal|author = John R. Lewis|title = Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids|journal = Nat. Prod. Rep|year = 2000|volume = 17|pages = 57–84|pmid = 10714899|issue = 1|doi = 10.1039/a809403i}}</ref>
|-
|-
| Rowspan = "3"|[[喹唑啉]] 類衍生物<ref>[http://www.xumuk.ru/encyklopedia/2/5003.html Chemical Encyclopedia: Quinazoline alkaloids]. xumuk.ru</ref>
| Rowspan = "3"|[[喹唑啉]] 類衍生物<ref>[http://www.xumuk.ru/encyklopedia/2/5003.html Chemical Encyclopedia: Quinazoline alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2/5003.html |date=20161024170356 }}. xumuk.ru</ref>
[[File:Quinazoline numbered.svg|90px|center]]
[[File:Quinazoline numbered.svg|90px|center]]
| 3,4-Dihydro-4-quinazolone derivatives
| 3,4-Dihydro-4-quinazolone derivatives
| Rowspan = "3"|[[Anthranilic acid]] or [[phenylalanine]] or [[ornithine]] <ref>[[#Aniszewski|Aniszewski]], p. 106</ref>
| Rowspan = "3"|[[邻氨基苯甲酸|Anthranilic acid]] or [[苯丙氨酸|phenylalanine]] or [[鳥氨酸|ornithine]] <ref>[[#Aniszewski|Aniszewski]], p. 106</ref>
| [[Febrifugine]]<ref name="ref120">[[#Aniszewski|Aniszewski]], p. 105</ref>
| [[常山碱|Febrifugine]]<ref name="ref120">[[#Aniszewski|Aniszewski]], p. 105</ref>
|-
|-
| 1,4-Dihydro-4-quinazolone derivatives
| 1,4-Dihydro-4-quinazolone derivatives
第212行： 第234行：
[[File:Acridine.svg|100px|center]]
[[File:Acridine.svg|100px|center]]
|
|
| [[Anthranilic acid]] <ref>{{cite journal|author = Richard B. Herbert|title = The biosynthesis of plant alkaloids and nitrogenous microbial metabolites|journal=Nat. Prod. Rep|year = 1999|volume = 16|pages = 199–208|doi = 10.1039/a705734b|last2 = Herbert|first2 = Richard B.|last3 = Herbert|first3 = Richard B.}}</ref>
| [[邻氨基苯甲酸|Anthranilic acid]] <ref>{{cite journal|author = Richard B. Herbert|title = The biosynthesis of plant alkaloids and nitrogenous microbial metabolites|journal=Nat. Prod. Rep|year = 1999|volume = 16|pages = 199–208|doi = 10.1039/a705734b|last2 = Herbert|first2 = Richard B.|last3 = Herbert|first3 = Richard B.}}</ref>
| Rutacridone, [[acronicine]]<ref>[[#Plemenkov|Plemenkov]], pp. 231, 246</ref><ref>[[#Hesse|Hesse]], p. 58</ref>
| Rutacridone, [[acronicine]]<ref>[[#Plemenkov|Plemenkov]], pp. 231, 246</ref><ref>[[#Hesse|Hesse]], p. 58</ref>
|-
|-
| Rowspan = "4"|[[喹啉]] 類衍生物<ref>[[#Plemenkov|Plemenkov]], p. 231</ref><ref name="ref126">[http://www.xumuk.ru/encyklopedia/2/5014.html Chemical Encyclopedia: Quinoline alkaloids]. xumuk.ru</ref>
| Rowspan = "4"|[[喹啉]] 類衍生物<ref>[[#Plemenkov|Plemenkov]], p. 231</ref><ref name="ref126">[http://www.xumuk.ru/encyklopedia/2/5014.html Chemical Encyclopedia: Quinoline alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2/5014.html |date=20161024170907 }}. xumuk.ru</ref>
[[File:Quinoline numbered.svg|90px|center]]
[[File:Quinoline numbered.svg|90px|center]]
| Simple derivatives of quinoline derivatives of 2 – [[quinolones]] and 4-quinolone
| Simple derivatives of quinoline derivatives of 2 – [[喹诺酮|quinolones]] and 4-quinolone
| Rowspan = "3"|[[Anthranilic acid]] → 3-carboxyquinoline <ref name="ref127">[[#Aniszewski|Aniszewski]], p. 114</ref>
| Rowspan = "3"|[[邻氨基苯甲酸|Anthranilic acid]] → 3-carboxyquinoline <ref name="ref127">[[#Aniszewski|Aniszewski]], p. 114</ref>
| Cusparine, [[echinopsine]], evocarpine<ref name="ref126" /><ref>[[#Orekhov|Orekhov]], p. 205</ref><ref>[[#Hesse|Hesse]], p. 55</ref>
| Cusparine, [[echinopsine]], evocarpine<ref name="ref126" /><ref>[[#Orekhov|Orekhov]], p. 205</ref><ref>[[#Hesse|Hesse]], p. 55</ref>
|-
|-
第227行： 第249行：
| [[Dictamnine]], fagarine, skimmianine<ref name="ref126" /><ref>[[#Orekhov|Orekhov]], p. 212</ref><ref>[[#Aniszewski|Aniszewski]], p. 118</ref>
| [[Dictamnine]], fagarine, skimmianine<ref name="ref126" /><ref>[[#Orekhov|Orekhov]], p. 212</ref><ref>[[#Aniszewski|Aniszewski]], p. 118</ref>
|-
|-
| [[Quinine]]s
| [[奎寧|Quinine]]s
| [[Tryptophan]] → [[tryptamine]] → [[strictosidine]] (with [[secologanin]]) → korinanteal → [[cinhoninon]] <ref name="Begley"/><ref name = " ref127 "/>
| [[色氨酸|Tryptophan]] → [[色胺|tryptamine]] → {{tsl|en|strictosidine||strictosidine}} (with {{tsl|en|secologanin||secologanin}}) → korinanteal → [[cinhoninon]] <ref name="Begley"/><ref name = " ref127 "/>
| [[Quinine]], [[quinidine]], [[cinchonine]], cinhonidine <ref name="ref131" />
| [[奎寧|Quinine]], [[奎尼丁|quinidine]], [[cinchonine]], cinhonidine <ref name="ref131" />
|-
|-
| Rowspan = "10"|[[吲哚]] 類衍生物<ref name="ref104" />
| Rowspan = "10"|[[吲哚]] 類衍生物<ref name="ref104" />
第237行： 第259行：
|-
|-
| Simple indole derivatives <ref name="ref140">[[#Aniszewski|Aniszewski]], p. 112</ref>
| Simple indole derivatives <ref name="ref140">[[#Aniszewski|Aniszewski]], p. 112</ref>
| Rowspan = "3"|[[Tryptophan]] → [[tryptamine]] or 5-hydroxitriptofan <ref name="ref141">[[#Aniszewski|Aniszewski]], p. 113</ref>
| Rowspan = "3"|[[色氨酸|Tryptophan]] → [[色胺|tryptamine]] or 5-hydroxitriptofan <ref name="ref141">[[#Aniszewski|Aniszewski]], p. 113</ref>
| [[Serotonin]], [[psilocybin]], [[dimethyltryptamine]] (DMT), [[bufotenin]] <ref>[[#Hesse|Hesse]], p. 15</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 467</ref>
| [[血清素|Serotonin]], [[裸盖菇素|psilocybin]], [[二甲基色胺|dimethyltryptamine]] (DMT), [[蟾毒色胺|bufotenin]] <ref>[[#Hesse|Hesse]], p. 15</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 467</ref>
|-
|-
| Simple derivatives of [[beta-carboline|β-carboline]] <ref>[[#Dewick|Dewick]], pp. 349–350</ref>
| Simple derivatives of {{tsl|en|beta-carboline||β-carboline}} <ref>[[#Dewick|Dewick]], pp. 349–350</ref>
| Harman, [[harmine]], [[harmaline]], eleagnine <ref name="ref140" />
| Harman, {{tsl|en|harmine||harmine}}, {{tsl|en|harmaline||harmaline}}, eleagnine <ref name="ref140" />
|-
|-
| Pyrroloindole alkaloids <ref name="ref152">[[#Aniszewski|Aniszewski]], p. 119</ref>
| Pyrroloindole alkaloids <ref name="ref152">[[#Aniszewski|Aniszewski]], p. 119</ref>
| [[Physostigmine]] (eserine), etheramine, physovenine, eptastigmine<ref name="ref152" />
| [[毒扁豆碱|Physostigmine]] (eserine), etheramine, physovenine, eptastigmine<ref name="ref152" />
|-
|-
| colspan="3" style="text-align:center;"|''半[[萜類]]吲哚生物鹼'
| colspan="3" style="text-align:center;"|''半[[萜類]]吲哚生物鹼'
|-
|-
| [[Ergoline|Ergot alkaloids]]<ref name="ref104" />
| [[麥角靈|Ergot alkaloids]]<ref name="ref104" />
| [[Tryptophan]] → chanoclavine → agroclavine → elimoclavine → [[paspalic acid]] → [[lysergic acid]] <ref name="ref152" />
| [[色氨酸|Tryptophan]] → chanoclavine → agroclavine → elimoclavine → [[paspalic acid]] → [[麥角酸|lysergic acid]] <ref name="ref152" />
| [[Ergotamine]], ergobasine, ergosine<ref>[[#Hesse|Hesse]], p. 29</ref>
| [[Ergotamine]], ergobasine, ergosine<ref>[[#Hesse|Hesse]], p. 29</ref>
|-
|-
第255行： 第277行：
|-
|-
| ''Corynanthe'' type alkaloids<ref name="ref141" />
| ''Corynanthe'' type alkaloids<ref name="ref141" />
| Rowspan = "3"|[[Tryptophan]] → [[tryptamine]] → [[strictosidine]] (with [[secologanin]]) <ref name="ref141" />
| Rowspan = "3"|[[色氨酸|Tryptophan]] → [[色胺|tryptamine]] → {{tsl|en|strictosidine||strictosidine}} (with {{tsl|en|secologanin||secologanin}}) <ref name="ref141" />
| Ajmalicine, sarpagine, vobasine, [[ajmaline]], [[yohimbine]], [[reserpine]], [[mitragynine]],<ref>[[#Hesse|Hesse]], pp. 23–26</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 169</ref> group [[strychnine]] and ([[Strychnine]] [[brucine]], aquamicine, [[vomicine]] <ref>[[#Saxton|Saxton]], Vol. 5, p. 210</ref>)
| Ajmalicine, sarpagine, vobasine, [[ajmaline]], [[育亨宾|yohimbine]], [[利血平|reserpine]], {{tsl|en|mitragynine||mitragynine}},<ref>[[#Hesse|Hesse]], pp. 23–26</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 169</ref> group [[番木鳖碱|strychnine]] and ([[番木鳖碱|Strychnine]] {{tsl|en|brucine||brucine}}, aquamicine, [[vomicine]] <ref>[[#Saxton|Saxton]], Vol. 5, p. 210</ref>)
|-
|-
| [[Iboga]]-type alkaloids<ref name="ref141" />
| {{tsl|en|Iboga||Iboga}}-type alkaloids<ref name="ref141" />
| [[Ibogamine]], [[ibogaine]], [[voacangine]]<ref name="ref141" />
| {{tsl|en|Ibogamine||Ibogamine}}, {{tsl|en|ibogaine||ibogaine}}, {{tsl|en|voacangine||voacangine}}<ref name="ref141" />
|-
|-
| [[Aspidosperma]]-type alkaloids<ref name="ref141" />
| [[白堅木屬|Aspidosperma]]-type alkaloids<ref name="ref141" />
| [[Vincamine]], [[vinca alkaloids]], vincotine, aspidospermine<ref>[[#Hesse|Hesse]], pp. 17–18</ref><ref>[[#Dewick|Dewick]], p. 357</ref>
| {{tsl|en|Vincamine||Vincamine}}, {{tsl|en|vinca alkaloids||vinca alkaloids}}, vincotine, aspidospermine<ref>[[#Hesse|Hesse]], pp. 17–18</ref><ref>[[#Dewick|Dewick]], p. 357</ref>
|-
|-
| [[咪唑]] 類衍生物<ref name="Plemenkov 241"/>
| [[咪唑]] 類衍生物<ref name="Plemenkov 241"/>
[[File:Imidazole structure.svg|50px|center]]
[[File:Imidazole structure.svg|50px|center]]
|
|
| Directly from [[histidine]]<ref name="Aniszewski 104">[[#Aniszewski|Aniszewski]], p. 104</ref>
| Directly from [[組氨酸|histidine]]<ref name="Aniszewski 104">[[#Aniszewski|Aniszewski]], p. 104</ref>
| [[Histamine]], pilocarpine, pilosine, stevensine<ref name="Plemenkov 241"/><ref name="Aniszewski 104"/>
| [[組織胺|Histamine]], pilocarpine, pilosine, stevensine<ref name="Plemenkov 241"/><ref name="Aniszewski 104"/>
|-
|-
| [[嘌呤]] 類衍生物<ref>[[#Hesse|Hesse]], p. 72</ref>
| [[嘌呤]] 類衍生物<ref>[[#Hesse|Hesse]], p. 72</ref>
[[File:Purin2.svg|90px|center]]
[[File:Purin2.svg|90px|center]]
|
|
| [[Xanthosine]] (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl [[xanthine]] → [[theobromine]] → [[caffeine]] <ref name="Begley"/>
| {{tsl|en|Xanthosine||Xanthosine}} (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl [[黄嘌呤|xanthine]] → [[可可碱|theobromine]] → [[咖啡因|caffeine]] <ref name="Begley"/>
| [[Caffeine]], [[theobromine]], [[theophylline]], [[saxitoxin]] <ref>[[#Hesse|Hesse]], p. 73</ref><ref>[[#Dewick|Dewick]], p. 396</ref>
| [[咖啡因|Caffeine]], [[可可碱|theobromine]], [[茶碱|theophylline]], {{tsl|en|saxitoxin||saxitoxin}} <ref>[[#Hesse|Hesse]], p. 73</ref><ref>[[#Dewick|Dewick]], p. 396</ref>
|-
|-
| colspan="4" style="text-align:center; background:# DADADA;"|''側鏈上含氮原子的生物側鏈鹼''
| colspan="4" style="text-align:center; background:# DADADA;"|''側鏈上含氮原子的生物側鏈鹼''
第281行： 第303行：
[[File:Phenylethylamine numbered.svg|110px|center]]
[[File:Phenylethylamine numbered.svg|110px|center]]
|
|
| [[Tyrosine]] or [[phenylalanine]] → [[dioxyphenilalanine]] → [[dopamine]] → [[adrenaline]] and [[mescaline]] [[tyrosine]] → [[tyramine]] phenylalanine → 1-phenylpropane-1,2-dione → [[cathinone]] → [[ephedrine]] and [[pseudoephedrine]] <ref name="Aniszewski 110"/><ref name="ref31" /><ref>[http://www.plantcyc.org:1555/PLANT/NEW-IMAGE?type=NIL&object=PWY-5883 PlantCyc Pathway: ephedrine biosynthesis] {{wayback|url=http://www.plantcyc.org:1555/PLANT/NEW-IMAGE?type=NIL&object=PWY-5883 |date=20111210040135 }}</ref>
| [[酪氨酸|Tyrosine]] or [[苯丙氨酸|phenylalanine]] → [[dioxyphenilalanine]] → [[多巴胺|dopamine]] → [[肾上腺素|adrenaline]] and [[麦司卡林|mescaline]] [[酪氨酸|tyrosine]] → [[酪胺|tyramine]] phenylalanine → 1-phenylpropane-1,2-dione → {{tsl|en|cathinone||cathinone}} → [[麻黃鹼|ephedrine]] and [[伪麻黄碱|pseudoephedrine]] <ref name="Aniszewski 110"/><ref name="ref31">[[#Dewick|Dewick]], p. 382</ref><ref>[http://www.plantcyc.org:1555/PLANT/NEW-IMAGE?type=NIL&object=PWY-5883 PlantCyc Pathway: ephedrine biosynthesis] {{webarchive|url=https://web.archive.org/web/20111210040135/http://www.plantcyc.org:1555/PLANT/NEW-IMAGE?type=NIL&object=PWY-5883 |date=2011-12-10 }}</ref>
| [[Tyramine]], [[ephedrine]], [[pseudoephedrine]], [[mescaline]], [[cathinone]], [[catecholamines]] ([[adrenaline]], [[noradrenaline]], [[dopamine]])<ref name="Aniszewski 110"/><ref>[[#Hesse|Hesse]], p. 76</ref>
| [[酪胺|Tyramine]], [[麻黃鹼|ephedrine]], [[伪麻黄碱|pseudoephedrine]], [[麦司卡林|mescaline]], {{tsl|en|cathinone||cathinone}}, [[儿茶酚胺|catecholamines]] ([[肾上腺素|adrenaline]], [[去甲肾上腺素|noradrenaline]], [[多巴胺|dopamine]])<ref name="Aniszewski 110"/><ref>[[#Hesse|Hesse]], p. 76</ref>
|-
|-
| [[秋水仙素]] 類衍生物 <ref name="ref179">[http://www.xumuk.ru/encyklopedia/2069.html Chemical Encyclopedia: colchicine alkaloids]. xumuk.ru</ref>
| [[秋水仙素]] 類衍生物 <ref name="ref179">[http://www.xumuk.ru/encyklopedia/2069.html Chemical Encyclopedia: colchicine alkaloids] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2069.html |date=20161024170902 }}. xumuk.ru</ref>
[[File:Colchicine.svg|120px|center]]
[[File:Colchicine.svg|120px|center]]
|
|
| [[Tyrosine]] or [[phenylalanine]] → [[dopamine]] → [[autumnaline]] → [[colchicine]] <ref>[[#Aniszewski|Aniszewski]], p. 77</ref>
| [[酪氨酸|Tyrosine]] or [[苯丙氨酸|phenylalanine]] → [[多巴胺|dopamine]] → [[autumnaline]] → [[秋水仙素|colchicine]] <ref>[[#Aniszewski|Aniszewski]], p. 77</ref>
| [[Colchicine]], colchamine<ref name="ref179" />
| [[秋水仙素|Colchicine]], colchamine<ref name="ref179" />
|-
|-
| [[毒蕈鹼]] <ref name="ref182">[[#Hesse|Hesse]], p. 81</ref>
| [[毒蕈鹼]] <ref name="ref182">[[#Hesse|Hesse]], p. 81</ref>
[[File:Muscarine.svg|100px|center]]
[[File:Muscarine.svg|100px|center]]
|
|
| [[Glutamic acid]] → 3-ketoglutamic acid → muscarine (with [[pyruvic acid]])<ref>[[#Brossi|Brossi]], Vol. 23, p. 376</ref>
| [[穀氨酸|Glutamic acid]] → 3-ketoglutamic acid → muscarine (with [[丙酮酸|pyruvic acid]])<ref>[[#Brossi|Brossi]], Vol. 23, p. 376</ref>
| [[Muscarine]], allomuscarine, epimuscarine, epiallomuscarine<ref name="ref182" />
| [[毒蕈碱|Muscarine]], allomuscarine, epimuscarine, epiallomuscarine<ref name="ref182" />
|-
|-
| [[芐胺]]<ref name="ref185">[[#Hesse|Hesse]], p. 77</ref>
| [[芐胺]]<ref name="ref185">[[#Hesse|Hesse]], p. 77</ref>
[[File:Benzylamine.svg|90px|center]]
[[File:Benzylamine.svg|90px|center]]
|
|
| [[Phenylalanine]] with [[valine]], [[leucine]] or [[isoleucine]]<ref>[[#Brossi|Brossi]], Vol. 23, p. 268</ref>
| [[苯丙氨酸|Phenylalanine]] with [[缬氨酸|valine]], [[亮氨酸|leucine]] or [[異亮氨酸|isoleucine]]<ref>[[#Brossi|Brossi]], Vol. 23, p. 268</ref>
| [[Capsaicin]], [[dihydrocapsaicin]], nordihydrocapsaicin, [[vanillylamine]]<ref name="ref185" /><ref>[[#Brossi|Brossi]], Vol. 23, p. 231</ref>
| [[辣椒素|Capsaicin]], [[dihydrocapsaicin]], nordihydrocapsaicin, [[香兰素胺|vanillylamine]]<ref name="ref185" /><ref>[[#Brossi|Brossi]], Vol. 23, p. 231</ref>
|-
|-
| colspan="4" style="text-align:center; background:# DADADA;"|''多胺生物鹼''
| colspan="4" style="text-align:center; background:# DADADA;"|''多胺生物鹼''
第307行： 第329行：
[[File:Putrescine.svg|90px|center]]
[[File:Putrescine.svg|90px|center]]
|
|
| Rowspan = "3"|[[ornithine]] → [[putrescine]] → [[spermidine]] → [[spermine]]<ref>[http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/spermine.html Spermine Biosynthesis]</ref>
| Rowspan = "3"|[[鳥氨酸|ornithine]] → [[腐胺|putrescine]] → [[亞精胺|spermidine]] → [[精胺|spermine]]<ref>{{Cite web |url=http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/spermine.html |title=Spermine Biosynthesis |access-date=2016-04-23 |archive-date=2016-12-04 |archive-url=https://web.archive.org/web/20161204125102/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/spermine.html |dead-url=no }}</ref>
| Paucine <ref name="ref189" />
| Paucine <ref name="ref189" />
|-
|-
| [[亞精胺] 衍生物<ref name="ref189" />
| [[亞精胺]] 衍生物<ref name="ref189" />
[[File:Spermidine.svg|110px|center]]
[[File:Spermidine.svg|110px|center]]
|
|
第322行： 第344行：
| colspan="4" style="text-align:center; background:# DADADA;"|''Peptide (cyclopeptide) alkaloids''
| colspan="4" style="text-align:center; background:# DADADA;"|''Peptide (cyclopeptide) alkaloids''
|-
|-
| Rowspan = "2"|Peptide alkaloids with a 13-membered cycle <ref name="ref27" /><ref name="ref196">[[#Plemenkov|Plemenkov]], p. 243</ref>
| Rowspan = "2"|Peptide alkaloids with a 13-membered cycle <ref name="ref27">{{cite journal |author1=Dimitris C. Gournelif |author2=Gregory G. Laskarisb |author3=Robert Verpoorte |title = Cyclopeptide alkaloids |doi = 10.1039/NP9971400075 |journal = Nat. Prod. Rep. |year = 1997 |volume = 14 |pages = 75–82 |PMID = 9121730 |issue = 1 }}</ref><ref name="ref196">[[#Plemenkov|Plemenkov]], p. 243</ref>
| Nummularine C type
| Nummularine C type
| Rowspan = "8"|From different amino acids <ref name="ref27" />
| Rowspan = "8"|From different amino acids <ref name="ref27" />
第348行： 第370行：
| Peptide alkaloids with a 15-membered cycle <ref name="ref196" />
| Peptide alkaloids with a 15-membered cycle <ref name="ref196" />
| Mucronine A type
| Mucronine A type
| Mucronine A <ref name="ref23" /><ref name="ref196" />
| Mucronine A <ref name="ref23">[[#Hesse|Hesse]], p. 84</ref><ref name="ref196" />
|-
|-
| colspan="4" style="text-align:center; background:# DADADA;"|''Pseudoalkaloids ([[terpenes]] and [[steroids]])''
| colspan="4" style="text-align:center; background:# DADADA;"|''Pseudoalkaloids ([[萜烯|terpenes]] and [[甾體|steroids]])''
|-
|-
| Diterpenes <ref name="ref23" />
| Diterpenes <ref name="ref23" />
[[File:Isoprene.svg|80px|center]]
[[File:Isoprene.svg|80px|center]]
| Lycoctonine type
| Lycoctonine type
| [[Mevalonic acid]] → [[izopentenilpyrophosfate]] → [[geranyl pyrophosphate]] <ref>[http://www.xumuk.ru/encyklopedia/2/4392.html Chemical Encyclopedia: Terpenes]. xumuk.ru</ref><ref>[[#Begley|Begley]], Natural Products: An Overview</ref>
| [[甲羟戊酸|Mevalonic acid]] → [[izopentenilpyrophosfate]] → {{tsl|en|geranyl pyrophosphate||geranyl pyrophosphate}} <ref>[http://www.xumuk.ru/encyklopedia/2/4392.html Chemical Encyclopedia: Terpenes] {{Wayback|url=http://www.xumuk.ru/encyklopedia/2/4392.html |date=20161002055405 }}. xumuk.ru</ref><ref>[[#Begley|Begley]], Natural Products: An Overview</ref>
| [[Aconitine]], [[delphinine]] <ref name="ref23" /><ref>{{cite journal|author = Atta-ur-Rahman and M. Iqbal Choudhary|title = Diterpenoid and steroidal alkaloids|url = http://www.rsc.org/publishing/journals/NP/article.asp?doi=NP9971400191|journal=Nat. Prod. Rep|year = 1997|volume = 14|pages = 191–203|pmid = 9149410|issue = 2|doi = 10.1039/np9971400191}}</ref>
| [[乌头碱|Aconitine]], {{tsl|en|delphinine||delphinine}} <ref name="ref23" /><ref>{{cite journal |author = Atta-ur-Rahman and M. Iqbal Choudhary |title = Diterpenoid and steroidal alkaloids |url = http://www.rsc.org/publishing/journals/NP/article.asp?doi=NP9971400191 |journal = Nat. Prod. Rep |year = 1997 |volume = 14 |pages = 191–203 |PMID = 9149410 |issue = 2 |doi = 10.1039/np9971400191 }}</ref>
|-
|-
| [[Steroids]]<ref>[[#Hesse|Hesse]], p. 88</ref>
| [[甾體|Steroids]]<ref>[[#Hesse|Hesse]], p. 88</ref>
[[File:Cyclopentenophenanthrene.svg|100px|center]]
[[File:Cyclopentenophenanthrene.svg|100px|center]]
|
|
| [[Cholesterol]], [[arginine]]<ref>[[#Dewick|Dewick]], p. 388</ref>
| [[膽固醇|Cholesterol]], [[精氨酸|arginine]]<ref>[[#Dewick|Dewick]], p. 388</ref>
| Solasodine, [[solanidine]], veralkamine, [[batrachotoxin]]<ref>[[#Plemenkov|Plemenkov]], p. 247</ref>
| Solasodine, {{tsl|en|solanidine||solanidine}}, veralkamine, {{tsl|en|batrachotoxin||batrachotoxin}}<ref>[[#Plemenkov|Plemenkov]], p. 247</ref>
|}
|}


==参考资料==
== 参考文献 ==
=== 引用 ===
{{reflist}}
{{Reflist|23em}}
⚫
== 参考书目 ==
⚫
{{Commons|Alkaloid}}
⚫
* {{cite book|ref=Aniszewski|author = Aniszewski, Tadeusz |title = Alkaloids – secrets of life|location = Amsterdam|publisher = [[Elsevier]]|year = 2007|isbn = 978-0-444-52736-3}}
⚫
* {{cite book|ref=Begley|author = Begley, Tadhg P. |title = Encyclopedia of Chemical Biology|year = 2009|publisher = Wiley|isbn = 978-0-471-75477-0|doi=10.1002/cbic.200900262}}
⚫
* {{cite book|ref=Brossi|author =Brossi, Arnold |title=The Alkaloids: Chemistry and Pharmacology|publisher= Academic Press|year= 1989}}
⚫
* {{cite book|ref=Dewick|author = Dewick, Paul M |title = Medicinal Natural Products. A Biosynthetic Approach. Second Edition|year = 2002|publisher = Wiley|isbn = 0-471-49640-5}}
⚫
* {{cite book|ref=Fattorusso|author = Fattorusso, E. and Taglialatela-Scafati, O. |title = Modern Alkaloids: Structure, Isolation, Synthesis and Biology|year = 2008|publisher = Wiley-VCH|isbn = 978-3-527-31521-5}}
⚫
* {{cite book|ref=Grinkevich|author = Grinkevich NI Safronich LN|title = The chemical analysis of medicinal plants: Proc. allowance for pharmaceutical universities|location = M|year = 1983}}
⚫
* {{cite book|ref=Hesse|author = Hesse, Manfred |title = Alkaloids: Nature's Curse or Blessing?|year = 2002|publisher = Wiley-VCH|isbn = 978-3-906390-24-6}}
⚫
* {{cite book|ref=Knunyants|author = Knunyants, IL|title = Chemical Encyclopedia|url = http://www.cnshb.ru/AKDiL/0048/base/RA/140004.shtm|publisher = Soviet Encyclopedia|year = 1988}}
⚫
* {{cite book|ref=Orekhov|author = Orekhov, AP|title = Chemistry alkaloids|edition = Acad. 2|location = M.|publisher = USSR|year = 1955}}
⚫
* {{cite book|ref=Plemenkov|author = Plemenkov, VV|title = Introduction to the Chemistry of Natural Compounds|location = Kazan|year = 2001}}
⚫
*{{cite book|ref=Saxton|author =Saxton, J. E. |title=The Alkaloids. A Specialist Periodical Report|place= London|publisher= The Chemical Society|year=1971}}
⚫
* {{cite book|ref=Veselovskaya|author =Veselovskaya, N. B., Kovalenko, A.E |title=Drugs|place=Moscow|publisher= Triada-X|year=2000}}
⚫
* {{cite journal|last=Wink|first=M|title=Mode of action and toxicology of plant toxins and poisonous plants|journal=Mitt. Julius Kühn-Inst.|date=2009|volume=421|pages=93-112|url=http://pub.jki.bund.de/index.php/JKA/article/download/85/74|accessdate=18 March 2014}}


=== 来源 ===
{{ReflistH|33em}}
⚫
* {{cite book |ref = Aniszewski |last = Aniszewski |first = Tadeusz |title = Alkaloids – secrets of life |location = Amsterdam |publisher = [[愛思唯爾|Elsevier]] |year = 2007 |ISBN = 978-0-444-52736-3 }}
⚫
* {{cite book |ref = Begley |last = Begley |first = Tadhg P. |title = Encyclopedia of Chemical Biology |year = 2009|publisher = Wiley |ISBN = 978-0-471-75477-0 |doi = 10.1002/cbic.200900262 }}
⚫
* {{cite book |ref = Brossi |last = Brossi |first = Arnold |title = The Alkaloids: Chemistry and Pharmacology |url = https://archive.org/details/alkaloidschemist0038arno |publisher = Academic Press |year= 1989 }}
⚫
* {{cite book |ref = Dewick |last = Dewick |first = Paul M. |title = Medicinal Natural Products. A Biosynthetic Approach |edition = 2nd |year = 2002 |publisher = Wiley |ISBN = 0-471-49640-5 }}
⚫
* {{cite book |ref = Fattorusso |last1 = Fattorusso |first1 = E. |last2 = Taglialatela-Scafati |first2 = O. |title = Modern Alkaloids: Structure, Isolation, Synthesis and Biology |url = https://archive.org/details/isbn_9783527315215 |year = 2008 |publisher = Wiley-VCH |ISBN = 978-3-527-31521-5 }}
⚫
* {{cite book |ref = Grinkevich |last1 = Grinkevich |first1 = N. I. |last2 = Safronich |first2 = L. N. |title = The chemical analysis of medicinal plants: Proc. allowance for pharmaceutical universities |location = M |year = 1983 }}
⚫
* {{cite book |ref = Hesse |last = Hesse |first = Manfred |title = Alkaloids: Nature's Curse or Blessing? |url = https://archive.org/details/alkaloidsnatures0000hess |year = 2002 |publisher = Wiley-VCH |ISBN = 978-3-906390-24-6 }}
⚫
* {{cite book |ref = Knunyants |last = Knunyants |first = I. L. |title = Chemical Encyclopedia |url = http://www.cnshb.ru/AKDiL/0048/base/RA/140004.shtm |publisher = Soviet Encyclopedia |year = 1988 |access-date = 2014-08-23 |archive-date = 2021-03-07 |archive-url = https://web.archive.org/web/20210307145223/http://www.cnshb.ru/AKDiL/0048/base/RA/140004.shtm |dead-url = no }}
⚫
* {{cite book |ref = Orekhov |last = Orekhov |first = A. P. |title = Chemistry alkaloids |edition = Acad. 2 |location = M. |publisher = USSR |year = 1955 }}
⚫
* {{cite book |ref = Plemenkov |last = Plemenkov |first = V. V. |title = Introduction to the Chemistry of Natural Compounds |location = Kazan |year = 2001 }}
⚫
* {{cite book |ref = Saxton |last = Saxton |first = J. E. |title = The Alkaloids. A Specialist Periodical Report |location = London |publisher = The Chemical Society |year = 1971 }}
⚫
* {{cite book |ref = Veselovskaya |last1 = Veselovskaya |first1 = N. B. |last2 = Kovalenko |first2 = A. E. |title = Drugs |location = Moscow |publisher = Triada-X |year = 2000 }}
⚫
* {{cite journal |last = Wink |first = M. |title = Mode of action and toxicology of plant toxins and poisonous plants |journal = Mitt. Julius Kühn-Inst. |year = 2009 |volume = 421 |pages = 93-112 |url = http://pub.jki.bund.de/index.php/JKA/article/download/85/74 |access-date = 18 March 2014 |archive-date = 2014-03-18 |archive-url = https://web.archive.org/web/20140318213726/http://pub.jki.bund.de/index.php/JKA/article/download/85/74 |dead-url = no }}
{{refend}}

== 外部連結 ==
⚫
* {{Commons-inline|Alkaloid}}

⚫
== 参见 ==
{{Portal|化学|植物}}
* [[胺]]
* [[鹽基]]
* [[天然产物]]
* [[次级代谢产物]]

{{-}}
{{生物碱}}
{{生物碱}}


{{Authority control}}
{{Authority control}}

[[Category:生物碱|*]]
[[Category:生物碱| ]]

2024年7月10日 (三) 15:12的最新版本

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

[编辑]

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

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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（英语：Cuscohygrine）, hygrine（英语：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（英语：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（英语：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（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 [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]
羽扇豆碱 類 賴氨酸 → 屍胺 → Δ1-piperideine [26] Lupinine（英语：Lupinine）, nupharidin [24]
野靛碱 類 野靛碱 [24]
司巴丁 類 司巴丁, 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（英语：pipecolic acid） → 1 indolizidinone [31] Swainsonine（英语：Swainsonine）, castanospermine（英语：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（英语：Trigonelline）, ricinine, arecoline（英语：arecoline） [33][36]
多環芳烴非冷凝吡啶衍生物 Nicotine, nornicotine（英语：nornicotine）, anabasine（英语：anabasine）, anatabine [33][36]
多環芳烴冷凝吡啶衍生物 Actinidine（英语：Actinidine）, gentianine, pediculinine [37]
Sesquiterpene（英语：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（英语：laudanosine）, sendaverine
Cularine group[47] Cularine, yagonine [47]
Pavine（英语：Pavine (molecule)）s and isopavines [48] Argemonine, amurensine（英语：amurensine） [48]
Benzopyrrocolines [49] Cryptaustoline [40]
Protoberberines [40] Berberine, canadine（英语：canadine）, ophiocarpine, mecambridine, corydaline [50]
Phthalidisoquinolines [40] Hydrastine, narcotine（英语：narcotine） (Noscapine) [51]
Spirobenzylisoquinolines [40] Fumaricine [48]
Ipecacuanha（英语：Psychotria ipecacuanha） alkaloids[52] Emetine, protoemetine, ipecoside [52]
Benzophenanthridines [40] Sanguinarine, oxynitidine, corynoloxine [53]
Aporphine（英语：Aporphine）s [40] Glaucine（英语：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（英语：galantamine）, montanine [61]
Erythrina alkaloids[44] Erysodine, erythroidine [44]
Phenanthrene derivatives [40] Atherosperminine [40][50]
Protopine（英语：Protopine）s [40] Protopine（英语：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（英语：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]
Quinines Tryptophan → tryptamine → strictosidine（英语：strictosidine） (with secologanin（英语：secologanin）) → korinanteal → cinhoninon [42][76] Quinine, quinidine, cinchonine, cinhonidine [79]
吲哚 類衍生物[57]
参见：indole alkaloids
 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（英语：beta-carboline） [86] Harman, harmine（英语：harmine）, harmaline（英语：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（英语：strictosidine） (with secologanin（英语：secologanin）) [83] Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine（英语：mitragynine）,[89][90] group strychnine and (Strychnine brucine（英语：brucine）, aquamicine, vomicine [91])
Iboga（英语：Iboga）-type alkaloids[83] Ibogamine（英语：Ibogamine）, ibogaine（英语：ibogaine）, voacangine（英语：voacangine）[83]
Aspidosperma-type alkaloids[83] Vincamine（英语：Vincamine）, vinca alkaloids（英语：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（英语：Xanthosine） (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine [42] Caffeine, theobromine, theophylline, saxitoxin（英语：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（英语：cathinone） → ephedrine and pseudoephedrine [38][98][99] Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone（英语：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（英语：geranyl pyrophosphate） [113][114] Aconitine, delphinine（英语：delphinine） [112][115]
Steroids[116]
Cholesterol, arginine[117] Solasodine, solanidine（英语：solanidine）, veralkamine, batrachotoxin（英语：batrachotoxin）[118]

参考文献

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引用

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来源

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外部連結

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参见

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吲哚：
苯乙胺：
嘌呤：
哌啶：
吡咯：
喹啉：
异喹啉：
莨菪烷：
萜类：
甜菜碱：
糖类
酯質
核酸
蛋白質
其他
 
各地
其他
检索自“https://zh.wikipedia.org/w/index.php?title=生物鹼&oldid=83357770”