quinolizidine alkaloids in lupinus · (wink & hartman, 1982 ; wink & witte, 1983; lee et...
TRANSCRIPT
Quinolizidine alkaloids in Lupinus:
when and how are they synthesized?
ILC, Cochabamba Bolivia, March 2019
Biotechnology DepartmentCentre for Development of BioticProducts, National Polytechnic InstituteMorelos, Mexico
Astrid P. Ramírez Betancourt Arianna M. Hernández Sánchez Macdiel E. Acevedo Quiroz Guadalupe Salcedo Morales Kalina Bermúdez Torres
QA as defense in Lupinus
pollinationdefense against
herbivoresallelopathic
effect antimicrobial
Lupinine Sparteine Lupanine
13a-Hydroxylupanine 13a-Tigloiloxilupanine
Quinolizidine
Quinolizidine alkaloids
(Wink & Hartman, 1982 ; Wink & Witte, 1983; Lee et al., 2007; Bunsupa et al. 2012)
Diiminium cation
L-Lysine Cadaverine
Epilupinine
Lupinine
Matrine
Biosynthesis of QA in photosynthetic tissues
LDC: Lysine decarboxylase
QA biosynthesis and transport
PhloemXylem
Flowers Seeds
Light-regulated
RootsEpidermal
cells
L-Lysine Cadaverine
Lupinine
Epilupinine
Matrine
Multiflorine
LDC
p-Coumaroyl-CoA
o
p-Feruloyl-CoA CoA-SH
ECT/EFT-LCT/LFT
p-Coumaroyllupinine
Feruloyllupinine
13a-Hidroxymultiflorine
13a-HidroxylupanineSparteine Lupanine
Diiminium Cation
Tigloyl-CoA CoA-SH
Tigloyl-CoA CoA-SH
13a-Tigloyloxilupanine
13a-Tigloyloximultiflorine
HMT/HLT
HMT/HLT
Feruloylepilupinine
p-CoumaroylepilupininePiperideine
CAO
Okada et al., 2005; Bunsupa et al., 2012; Yang et al., 2017
Biosynthesis route?
de novo QA biosynthesis
Wink and Witte, 1985
L. aschenbornii
L. bilineatus
L. montanus
Mexican lupins
Sparteine
Nutaline
Multiflorine
Lupanine
Sparteine
Multiflorine
Lupanine
Aphyllidine
Aphylline
Angustifoline
Isolupanine
Nutaline
Lupanine
Oxilupanine
QA biosynthesis
QA used as N source
QA biosynthesis onset and QA diversification, when and how?
L. aschenbornii L. bilineatus L. montanus
Bermúdez-Torres et al 2015
L. montanus
L. aschenbornii
L. billineatus
m. a.
s.
l.
Altitudinal distribution of Lupinus
species in the Iztaccihuatl-Popocatepetl
Seed collection
Seeds were obtained from
the seed bank of CEPROBI
Mexican lupins development
Grown in agrolite-native soil (10%) at 20 °C, 60% RH and 16/8 h photoperiod
Developmental stages: 1- Germination, 2- Hypocotyl elongation, 3- First leaf emergence,
4- Second leaf emergence
Mexican lupins development
L. aschenbornii
L. bilineatus
L. montanus
Germination
Hypocotyl
elongation
First leaf
emergenceSecond leaf
emergencen
QA content along seedling development
0
100
200
300
400
500
Seeds 1 2 3 4
Lupinus aschenbornii Lupinus bilineatus Lupinus montanus
1- Germination, 2- Hypocotyl elongation, 3- First leaf emergence, 4- Second leaf
emergence
QA
co
nte
nt
(mg
/g)
StageNumber of QA
L. aschenbornii L. bilineatus L. montanusSeed 23 27 6
1 44 35 282 49 35 273 47 35 274 45 36 28
Conclusions
L. aschenbornii, L. montanus and L. bilineatus sedllingdevelopment differs on the onset time of eachdevelopmental stage as well as in its duration.
Quinolizidine alkaloids seem to be used as a source of N during germination of L. aschenbornii, L. bilineatus and L. montanus seeds.
The onset of QA biosynthesis seems to occur after L. aschenbornii, L. montanus and L. bilineatus the second leafemergence.
Number of QA increases during germination and is highlyspecific.
Acknowledgments
Ignacio ReglaMacdiel E. Acevedo QuirozJesús Arnoldo Sánchez LópezEstela GonzálezNorma Robledo
Thank you!
Posters: Health Benefits, Non Food Uses, Biochemistry and Biotechnology