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...
Main Authors: | , , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2021-08-01
|
Series: | Diversity |
Subjects: | |
Online Access: | https://www.mdpi.com/1424-2818/13/8/375 |
id |
doaj-88b4abd316134ae483f539ffdf260d3a |
---|---|
record_format |
Article |
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 |
work_keys_str_mv |
AT astridramirezbetancourt unravelingthebiosynthesisofquinolizidinealkaloidsusingthegeneticandchemicaldiversityofmexicanlupins AT ariannamichellehernandezsanchez unravelingthebiosynthesisofquinolizidinealkaloidsusingthegeneticandchemicaldiversityofmexicanlupins AT guadalupesalcedomorales unravelingthebiosynthesisofquinolizidinealkaloidsusingthegeneticandchemicaldiversityofmexicanlupins AT elsaventurazapata unravelingthebiosynthesisofquinolizidinealkaloidsusingthegeneticandchemicaldiversityofmexicanlupins AT normarobledo unravelingthebiosynthesisofquinolizidinealkaloidsusingthegeneticandchemicaldiversityofmexicanlupins AT michaelwink unravelingthebiosynthesisofquinolizidinealkaloidsusingthegeneticandchemicaldiversityofmexicanlupins AT kalinabermudeztorres unravelingthebiosynthesisofquinolizidinealkaloidsusingthegeneticandchemicaldiversityofmexicanlupins |
_version_ |
1721193930847944704 |