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