Indole alkaloids

Indole as the base of the indole alkaloids

Indole alkaloids form the largest alkaloid group . It has well over 1000 representatives. They are characterized by the indole or indoline (2,3-dihydroindole) basic body. According to their biogenetic origin from tryptophan , almost all of them have a 2-aminoethyl residue in position 3 of the indole ring, which is mostly integrated into one or more rings fused to the indole .

Examples: Ajmaline , Ergotamine , Yohimbine , Reserpine , Strychnine

Some representatives are created by linking two substituted indole bodies. They are known as bis-indole alkaloids.

Occurrence in nature

Indole alkaloids come e.g. B. in the steppe rue ( Peganum harmala L.). This contains harmane alkaloids such as harmine , harmaline and tetrahydroharmine . The calabar bean ( Physostigma venenosum ) contains physostigmine . Some members of the Convolvulaceae plant family , such as B. Ipomoea violacea and Turbina corymbosa contain ergolines and lysergic acid amides . Many monoterpenoid indole alkaloids are found in three families of dicotyledonous plants: Apocynaceae ( Rauvolfia and Catharanthus ), Rubiaceae ( Corynanthe ), and Loganiaceae ( Strychnos ).

Indole alkaloids are also found in mushrooms. Mushrooms containing psilocybin contain derivatives of tryptamine and claviceps contains derivatives of lysergic acid . The skin of several real toads ( bufo ) also contains tryptamine derivatives ( bufotenin ). The skin of Bufo alvarius (a species of toad) contains 5-methoxy- N , N -dimethyltryptamine . Serotonin , an important neurotransmitter in many animal species, can be thought of as a simple indole alkaloid.

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  Rue contains β-carboline alkaloids

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  Ipomoea violacea contains ergoline

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  Alstonia macrophylla contains corynanthe alkaloids

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  Rauwolfia serpentina contains Corynanthe alkaloids

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  Catharanthus roseus contains monoterpenoid indole alkaloids

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  Psilocybe cubensis contains psilocybin and psilocin

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  Ergot contains Ergoline

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  The toad Bufo alvarius contains bufotenin and 5-methoxy- N , N -dimethyltryptamine

Web links

Commons : Indole Alkaloids  - Collection of images, videos, and audio files

Individual evidence

1. ^ Hesse, Alkaloidchemie, Georg Thieme Verlag 1978 ISBN 3-13-381801-5
2. ^ Albert Gossauer: Structure and Reactivity of Biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, pp. 480–482, ISBN 978-3-906390-29-1 .
3. ↑ ^{a b} Waksmundzka-Hajnos, Monika; Sherma, Joseph; Kowalska, Teresa: Thin layer chromatography in phytochemistry . CRC Press, 2008, ISBN 978-1-4200-4677-9 , pp. 625-626.
4. ↑ Tadeusz Aniszewski: Alkaloids - secrets of life . Elsevier, Amsterdam 2007, ISBN 978-0-444-52736-3 , p. 39.
5. ↑ Waksmundzka-Hajnos, Monika; Sherma, Joseph; Kowalska, Teresa : Thin layer chromatography in phytochemistry . CRC Press, 2008, ISBN 978-1-4200-4677-9 , p. 626.
6. ↑ Tadeusz Aniszewski: Alkaloids - secrets of life . Elsevier, Amsterdam 2007, ISBN 978-0-444-52736-3 , pp. 37-39.
7. ↑ Michael E. Peterson, Patricia A. Talcott: Small Animal Toxicology . Saunders, 2005, ISBN 0-7216-0639-3 , p. 1086.
8. ↑ Waksmundzka-Hajnos, Monika; Sherma, Joseph; Kowalska, Teresa : Thin layer chromatography in phytochemistry . CRC Press, 2008, ISBN 978-1-4200-4677-9 , p. 625.