Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins

Quinolizidine alkaloids (QAs) are synthesized by the genus <i>Lupinus</i> as a defense against herbivores. Synthesis of QAs in lupins is species- and organ-specific. Knowledge about their biosynthesis and their corresponding pathways are still fragmentary, in part because lupins of comme...

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Main Authors: Astrid Ramírez-Betancourt, Arianna Michelle Hernández-Sánchez, Guadalupe Salcedo-Morales, Elsa Ventura-Zapata, Norma Robledo, Michael Wink, Kalina Bermúdez-Torres
Format: Article
Language:English
Published: MDPI AG 2021-08-01
Series:Diversity
Subjects:
Online Access:https://www.mdpi.com/1424-2818/13/8/375
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spelling doaj-88b4abd316134ae483f539ffdf260d3a2021-08-26T13:40:54ZengMDPI AGDiversity1424-28182021-08-011337537510.3390/d13080375Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican LupinsAstrid Ramírez-Betancourt0Arianna Michelle Hernández-Sánchez1Guadalupe Salcedo-Morales2Elsa Ventura-Zapata3Norma Robledo4Michael Wink5Kalina Bermúdez-Torres6Departamento de Biotecnología, Centro de Desarrollo de Productos Bióticos, Instituto Politécnico Nacional, CeProBi 8, Yautepec Morelos 62731, MexicoDepartamento de Biotecnología, Centro de Desarrollo de Productos Bióticos, Instituto Politécnico Nacional, CeProBi 8, Yautepec Morelos 62731, MexicoDepartamento de Biotecnología, Centro de Desarrollo de Productos Bióticos, Instituto Politécnico Nacional, CeProBi 8, Yautepec Morelos 62731, MexicoDepartamento de Biotecnología, Centro de Desarrollo de Productos Bióticos, Instituto Politécnico Nacional, CeProBi 8, Yautepec Morelos 62731, MexicoDepartamento de Biotecnología, Centro de Desarrollo de Productos Bióticos, Instituto Politécnico Nacional, CeProBi 8, Yautepec Morelos 62731, MexicoDepartment of Biology, Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, INF 364, 69120 Heidelberg, GermanyDepartamento de Biotecnología, Centro de Desarrollo de Productos Bióticos, Instituto Politécnico Nacional, CeProBi 8, Yautepec Morelos 62731, MexicoQuinolizidine alkaloids (QAs) are synthesized by the genus <i>Lupinus</i> as a defense against herbivores. Synthesis of QAs in lupins is species- and organ-specific. Knowledge about their biosynthesis and their corresponding pathways are still fragmentary, in part because lupins of commercial importance were mainly investigated, representing a small sample of the chemodiversity of the genus. Here, we explore the use of three Mexican lupins: <i>Lupinus aschenbornii</i>, <i>Lupinus montanus,</i> and <i>Lupinus bilineatus</i> as a model to study the physiology of QA biosynthesis. The corresponding QA patterns cover widely and narrowly distributed tetracyclic QAs. Quinolizidine alkaloid patterns of seeds and plantlets at different developmental stages were determined by GLC–MS and compared to identify the onset of de novo QA synthesis and to gain insight into specific and common biosynthesis trends. Onset of de novo QA biosynthesis occurred after the metabolization of seed QA during germination and was species-specific, as expected. A common QA pattern, from which the diversity of QA observed in these species is generated, was not found; however, lupanine and 3β-lupanine were found in the three specieswhile sparteine was not found in <i>Lupinus bilineatus</i>, suggesting that this simplest tetracyclic QA is not the precursor of more complex QAs. Similar patterns of metabolization and biosynthesis of structurally related QAs were observed, suggesting a common regulation.https://www.mdpi.com/1424-2818/13/8/375chemodiversitylysinesecondary metabolismFabaceaegermination
collection DOAJ
language English
format Article
sources DOAJ
author Astrid Ramírez-Betancourt
Arianna Michelle Hernández-Sánchez
Guadalupe Salcedo-Morales
Elsa Ventura-Zapata
Norma Robledo
Michael Wink
Kalina Bermúdez-Torres
spellingShingle Astrid Ramírez-Betancourt
Arianna Michelle Hernández-Sánchez
Guadalupe Salcedo-Morales
Elsa Ventura-Zapata
Norma Robledo
Michael Wink
Kalina Bermúdez-Torres
Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins
Diversity
chemodiversity
lysine
secondary metabolism
Fabaceae
germination
author_facet Astrid Ramírez-Betancourt
Arianna Michelle Hernández-Sánchez
Guadalupe Salcedo-Morales
Elsa Ventura-Zapata
Norma Robledo
Michael Wink
Kalina Bermúdez-Torres
author_sort Astrid Ramírez-Betancourt
title Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins
title_short Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins
title_full Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins
title_fullStr Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins
title_full_unstemmed Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins
title_sort unraveling the biosynthesis of quinolizidine alkaloids using the genetic and chemical diversity of mexican lupins
publisher MDPI AG
series Diversity
issn 1424-2818
publishDate 2021-08-01
description Quinolizidine alkaloids (QAs) are synthesized by the genus <i>Lupinus</i> as a defense against herbivores. Synthesis of QAs in lupins is species- and organ-specific. Knowledge about their biosynthesis and their corresponding pathways are still fragmentary, in part because lupins of commercial importance were mainly investigated, representing a small sample of the chemodiversity of the genus. Here, we explore the use of three Mexican lupins: <i>Lupinus aschenbornii</i>, <i>Lupinus montanus,</i> and <i>Lupinus bilineatus</i> as a model to study the physiology of QA biosynthesis. The corresponding QA patterns cover widely and narrowly distributed tetracyclic QAs. Quinolizidine alkaloid patterns of seeds and plantlets at different developmental stages were determined by GLC–MS and compared to identify the onset of de novo QA synthesis and to gain insight into specific and common biosynthesis trends. Onset of de novo QA biosynthesis occurred after the metabolization of seed QA during germination and was species-specific, as expected. A common QA pattern, from which the diversity of QA observed in these species is generated, was not found; however, lupanine and 3β-lupanine were found in the three specieswhile sparteine was not found in <i>Lupinus bilineatus</i>, suggesting that this simplest tetracyclic QA is not the precursor of more complex QAs. Similar patterns of metabolization and biosynthesis of structurally related QAs were observed, suggesting a common regulation.
topic chemodiversity
lysine
secondary metabolism
Fabaceae
germination
url https://www.mdpi.com/1424-2818/13/8/375
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