View source for Chemistry:Aporphine alkaloids

[[File:Aporphine.svg|thumb|right|upright|Chemical structure of [[Chemistry:Aporphine|aporphine]] which forms the core chemical structure of the aporphine alkaloids]]
'''Aporphine alkaloids''' are naturally occurring [[Chemistry:Chemical compound|chemical compound]]s from the group of [[Chemistry:Alkaloid|alkaloid]]s. After the [[Chemistry:Benzylisoquinoline alkaloids|benzylisoquinoline alkaloids]] they are the second largest group of [[Chemistry:Isoquinoline|isoquinoline]] alkaloids.

At least 85 aporphine alkaloids have been isolated from plants of 15 families.  The best known representative is [[Chemistry:Apomorphine|apomorphine]]. The aporphine alkaloids are of interest mainly because of their similarity to [[Biology:Morphine|morphine]].

== Occurrence ==
[[File:Nandina domestica BotGardBln1105Leaves.JPG|thumb|''Nandina domestica'']]
[[File:Komakusa.JPEG|thumb|''[[Biology:Dicentra peregrina|Dicentra peregrina]]'']]
The aporphine alkaloids are most commonly found in plants.  For example, isoboldine can be found in the plants in the genera ''[[Biology:Beilschmiedia|Beilschmiedia]]'', ''[[Biology:Nandina|Nandina]]'' (''[[Biology:Nandina domestica|Nandina domestica]]''), ''[[Biology:Glaucium|Glaucium]]'' (horn poppy), and other plants. As the name suggests, [[Chemistry:Glaucine|glaucine]] was first found in the horn poppy and usually the name of the alkaloids is derived from the plants in which they were first found.

Corydin as a further representative of the aporphine alkaloids is found in ''[[Biology:Corydalis|Corydalis]]'' (larkspurs) ''[[Biology:Dicentra|Dicentra]]'' (heart flowers), and also in the horn poppy.

== Examples ==
<gallery>
Apoglaziovine V2.svg|Apoglaziovine
Apomorphin V2.svg|[[Chemistry:Apomorphine|Apomorphine]]
Bulbocapnin V3.svg|[[Biology:Bulbocapnine|Bulbocapnine]]
Corydin V2.svg|Corydine
Domesticine.svg|[[Chemistry:Domesticine|Domesticine]]
Glaucine V2.svg|[[Chemistry:Glaucine|Glaucine]]
Isoboldin V2.svg|Isoboldine
Isothebain V2.svg|Isothebaine
Nuciferine V2.svg|[[Chemistry:Nuciferine|Nuciferine]]
</gallery>

The aporphine alkaloids differ in their [[Chemistry:Substituent|substituent]]s and their position on the base structure. Furthermore, their stereochemistry is partly different; most often they are (''R'')-configured, but [[Chemistry:Glaucine|glaucine]], [[Biology:Bulbocapnine|bulbocapnine]], and isothebaine, for example, are (''S'')-configured.<ref>{{cite journal | doi = 10.1039/JR9550003252 | title = The Morphine-Thebaine group of alkaloids. Part V. The absolute stereochemistry of the morphine, benzylisoquinoline, aporphine, and tetrahydroberberine alkaloids | year = 1955 | last1 = Bentley | first1 = K. W. | last2 = Cardwell | first2 = H. M. E. | journal = Journal of the Chemical Society (Resumed) | page = 3252 }}</ref>

== Biosynthesis ==
The method by which the central aporphine ring structure is constructed in nature is exemplified by the [[Biology:Biosynthesis|biosynthesis]] of bulbocarpin.  First, [[Chemistry:Reticuline|reticuline]] '''1''' is oxidized, resulting in a mesomery-stabilized diradical with the boundary structures '''2a''' and '''2b'''. Cyclization results in a fourth six-membered ring, corytuberin '''3''', which then [[Chemistry:Dehydration reaction|dehydrates]] to bulbocapnin '''4'''.<ref>{{cite journal | title = Mechanismus der Diphenylverknüpfung bei der Biosynthese von Aporphin-Alkaloiden 3. Mitt.: Untersuchung zur Biosynthese von Alkaloiden | year = 1970 | last1 = Blaschke | first1 = G. | journal = Archiv der Pharmazie | volume = 303 | issue = 4 | pages = 358–363 | doi = 10.1002/ardp.19703030411 | pmid = 5268208 | s2cid = 85841935 }}</ref>

:[[File:Biosynthese Aporphin-Alk. V7b.svg|left|frameless|600px]]{{clear-left}}

== Chemistry ==
[[File:Aporphin-Alk Grundstruktur4b.svg|thumb|130px|[[Chemistry:Stereocenter|Stereocenter]] is marked with a *.]]

The aporphine alkaloids are of particular interest because of their proximity to morphine and [[Chemistry:Benzylisoquinoline alkaloids|benzylisoquinoline alkaloids]]. For example, as the name suggests, [[Biology:Morphine|morphine]] can be used to produce [[Chemistry:Apomorphine|apomorphine]]. This can be done by adding an acid under the influence of heat.

The proaporphin alkaloids and the aporphin alkaloids share a framework isomerism.

The aporphine alkaloids usually have a [[Chemistry:Stereocenter|stereocenter]].

The (''R'')-configured glaucine can be synthesized from (''S'')-glaucine.

== Uses ==
[[Chemistry:Apomorphine|Apomorphine]] lowers blood pressure and is also a powerful emetic. It has been used to treat symptoms of [[Medicine:Parkinson's disease|Parkinson's disease]] because of its stimulating effect on [[Biology:Dopamine receptor|dopamine receptor]]s.<ref>{{cite book | author = Geoffrey A. Cordell | title = Introduction to Alkaloids: A Biogenetic Approach | publisher = John Wiley & Sons | location = Kanada | date = 1981 | isbn = 0-471-03478-9 | pages = 406–408 }}</ref>

[[File:Starr 010520-0081 Cassytha filiformis.jpg|thumb|''Cassytha filiformis'']]
''[[Biology:Cassytha filiformis|Cassytha filiformis]]'', a plant used in African traditional medicine, contains many aporphine alkaloids and that the three main alkaloids actinodaphnin, cassythin, and dicentrin have an ''[[In vitro|in vitro]]'' effect on cancer cells.<ref>{{cite journal | doi = 10.1055/s-2004-818967 | title = Alkaloids from ''Cassytha'' filiformisand Related Aporphines: Antitrypanosomal Activity, Cytotoxicity, and Interaction with DNA and Topoisomerases | journal = Planta Medica | year = 2004 | volume = 70 | issue = 5 | pages = 407–413 | pmid = 15124084 | last1 = Hoet | first1 = S. | last2 = Stévigny | first2 = C. | last3 = Block | first3 = S. | last4 = Opperdoes | first4 = F. | last5 = Colson | first5 = P. | last6 = Baldeyrou | first6 = B. | last7 = Lansiaux | first7 = A. | last8 = Bailly | first8 = C. | last9 = Quetin-Leclercq | first9 = J. }}</ref>

== References ==
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[[Category:Aporphine alkaloids| ]]

{{Sourceattribution|Aporphine alkaloids}}