Biosynthetic Origin of the Methoxy Group in Quinine and Related Alkaloids
Abstract: Quinine is a historically important natural product containing a methoxy group that has been assumed to be incorporated at a late pathway stage. Here we show that the methoxy group in quinine and related alkaloids is introduced onto the starting substrate tryptamine. Feeding studies definitively show that 5‐methoxytryptamine is utilized as a quinine biosynthetic intermediate in planta. We discover the biosynthetic genes that encode the responsible oxidase and methyltransferase, and we use these genes to reconstitute the early steps of the alkaloid biosynthetic pathway in Nicotiana benthamiana to produce a mixture of methoxylated and non‐methoxylated alkaloid intermediates. Importantly, we show that the co‐occurrence of both tryptamine and 5‐methoxytryptamine substrates, along with the substrate promiscuity of downstream pathway enzymes, enable parallel formation of both methoxylated and non‐methoxylated alkaloids.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Biosynthetic Origin of the Methoxy Group in Quinine and Related Alkaloids ; day:22 ; month:11 ; year:2024 ; extent:9
Angewandte Chemie / International edition. International edition ; (22.11.2024) (gesamt 9)
- Creator
- DOI
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10.1002/anie.202418306
- URN
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urn:nbn:de:101:1-2411231308378.755485845832
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:23 AM CEST
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Associated
- Kimbadi Lombe, Blaise
- Zhou, Tingan
- Caputi, Lorenzo
- Ploss, Kerstin
- O'Connor, Sarah E.
Other Objects (12)
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Multiple independent losses of the biosynthetic pathway for two tropane alkaloids in the Solanaceae family
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Darstellung von Methoxy-diflavylenen
Infrarotlaserspektroskopie am Methoxy-Radikal
Biosynthetic Origin of the Methoxy Group in Quinine and Related Alkaloids
Elucidation and metabolic engineering of plant Alkaloid and Terpene biosynthetic pathways
Investigation of benzylisoquinoline alkaloid biosynthetic pathway and its transcriptional regulation in lotus
The Rauvolfia tetraphylla genome suggests multiple distinct biosynthetic routes for yohimbane monoterpene indole alkaloids
Discovery and biosynthetic origin of malleicyprol toxins in human pathogenic bacteria
+/- Dioncophyllacine A, a naphthylisoquinoline alkaloid with a 4-methoxy substituent from the leaves of Triphyophyllum peltatum
Ein neuer Weg zum 7-Methoxy-Mitosen [Methoxy-Mitosen]
Multiple independent losses of the biosynthetic pathway for two tropane alkaloids in the Solanaceae family
Molecular biological and biochemical investigations on the biosynthetic enzymes of prenylated indole alkaloids from fungi
Datura genome reveals duplications of psychoactive alkaloid biosynthetic genes and high mutation rate following tissue culture
Darstellung von Methoxy-diflavylenen
Infrarotlaserspektroskopie am Methoxy-Radikal
Biosynthetic Origin of the Methoxy Group in Quinine and Related Alkaloids
Elucidation and metabolic engineering of plant Alkaloid and Terpene biosynthetic pathways
Investigation of benzylisoquinoline alkaloid biosynthetic pathway and its transcriptional regulation in lotus
The Rauvolfia tetraphylla genome suggests multiple distinct biosynthetic routes for yohimbane monoterpene indole alkaloids
Discovery and biosynthetic origin of malleicyprol toxins in human pathogenic bacteria
+/- Dioncophyllacine A, a naphthylisoquinoline alkaloid with a 4-methoxy substituent from the leaves of Triphyophyllum peltatum
Ein neuer Weg zum 7-Methoxy-Mitosen [Methoxy-Mitosen]
Multiple independent losses of the biosynthetic pathway for two tropane alkaloids in the Solanaceae family
Molecular biological and biochemical investigations on the biosynthetic enzymes of prenylated indole alkaloids from fungi
Datura genome reveals duplications of psychoactive alkaloid biosynthetic genes and high mutation rate following tissue culture
Darstellung von Methoxy-diflavylenen