Benzylisoquinoline alkaloids

Benzylisoquinoline, basic structure of the benzylisoquinoline alkaloids

Netzannone fruit ( Annona reticulata )

Flower and fruit of the opium poppy

The benzyl (tetrahydro) isoquinoline alkaloids are natural substances of the isoquinoline alkaloid type, which are derived from benzylisoquinoline .

Occurrence

Benzylisoquinoline alkaloids are u. a. Formed in the plant families of the poppy family , annone family and laurel family . Well-known representatives are found primarily in poppy plants or the opium obtained from them, but also in Christopher's herbs . For example, the reticulin was isolated from the Netzannone .

Well-known representatives

More than 2500 biologically active derivatives of the benzylisoquinoline alkaloids are known. Due to their structure, the substances can be divided into numerous subgroups: the aporphines, the phthalidisoquinoline alkaloids , the morphinans , the protoberberine alkaloids and the pavins.

Papaverine is one of the known individual substances in this group of substances . Further representatives are u. a. Reticulin and laudanosine .

Papaverine

(+) - reticulin

(+) - laudanosine

properties

Papaverine has vasodilating and muscle relaxing properties. Laudanosine acts as a tetanic poison .

biosynthesis

The biosynthesis of the benzylisoquinoline alkaloids has been studied intensively. It begins with the amino acid tyrosine , which is converted into dopamine through hydroxylation and decarboxylation and into 4-hydroxyphenylacetaldehyde through oxidative deamination . These two compounds are linked in a condensation reaction catalyzed by the enzyme norcoclaurine synthase to form the benzylisoquinoline backbone.

The benzylisoquinoline from this reaction can have different substituents ; reticulin is an important intermediate.

Individual evidence

↑ ^a ^b ^c Entry on benzyl (tetrahydro) isoquinoline alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on May 22, 2020.
^ Hermann Hager: Hager's Handbook of Pharmaceutical Practice: Volume 2: Methods , 1133 pages, Verlag Springer (1991), ISBN 978-3-540-52459-5 , p. 35 ( limited preview in the Google book search).
↑ ^a ^b Eberhard Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 62 .
↑ Bettina Ruff: Chemical and biochemical methods for the stereoselective synthesis of complex natural substances , 199 pages, Verlag Logos Berlin (2012), ISBN 978-3-8325-3121-8 , p. 8 ( limited preview in the Google book search).
↑ ^a ^b Jennifer M. Finefield, David H. Sherman, Martin Kreitman, Robert M. Williams: Enantiomeric Natural Products: Occurrence and Biogenesis. In: Angewandte Chemie. 124, 2012, pp. 4886-4920, doi: 10.1002 / anie.201107204 .
^ ^A ^b Yang-Chang Wu: New Research and Development on the Formosan Annonaceous Plants . In: Studies in Natural Products Chemistry . tape 33 , 2007, p. 957-1023 , doi : 10.1016 / s1572-5995 (06) 80044-x (English).

[Römpp-1] Entry on benzyl (tetrahydro) isoquinoline alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on May 22, 2020.

[2] Hermann Hager: Hager's Handbook of Pharmaceutical Practice: Volume 2: Methods , 1133 pages, Verlag Springer (1991), ISBN 978-3-540-52459-5 , p. 35 ( limited preview in the Google book search).

[Alkaloide-3] Eberhard Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 62 .

[4] Bettina Ruff: Chemical and biochemical methods for the stereoselective synthesis of complex natural substances , 199 pages, Verlag Logos Berlin (2012), ISBN 978-3-8325-3121-8 , p. 8 ( limited preview in the Google book search).

[angew-5] Jennifer M. Finefield, David H. Sherman, Martin Kreitman, Robert M. Williams: Enantiomeric Natural Products: Occurrence and Biogenesis. In: Angewandte Chemie. 124, 2012, pp. 4886-4920, doi: 10.1002 / anie.201107204 .

[Wu-6] A ^b Yang-Chang Wu: New Research and Development on the Formosan Annonaceous Plants . In: Studies in Natural Products Chemistry . tape 33 , 2007, p. 957-1023 , doi : 10.1016 / s1572-5995 (06) 80044-x (English).