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Complementary biophysical tools to investigate the membrane activities of essential oils

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(1)

Complementary biophysical tools to

investigate the membrane activities of

essential oils

Magali Deleu and Laurence Lins

(2)

Fields of use of essential oils

 « Historical applications »

 Flavoring / preservative agent in food

 Fragrance in cosmetics

 Aromatherapy / massage

 Human and animal health

 …

 Recent trends in agronomy: bio-based pesticide or biopesticide

 Antimicrobial agent

 Antifungal agent

 Insecticide

(3)

Essential oils as bio-herbicides

Conventional herbicides - resistance

- impact on environment - impact of human health

high demand for bio-based herbicides Development of a bio-herbicide based

on essential oils Cinnamon EO Java Citronella EO

(4)

Bio-herbicide based on essential oils

0% 20% 40% 60% 80% 100% C i n n a m o n E O 3 % C i t r o n e l l a E O 3 % P e l a r g o n i c a c i d G l y p h o s a t e B l a n c k N o n t r e a t e d

Herbicidal activity after 7 days (A. thaliana)

Citronellol Citronellal

Cinnamaldehyde

(5)

Bio-herbicide based on essential oils

 Action modes of Eos as herbicide in the literature:

 waxy cuticular layer removal

 disruption of microtubule polymerization

 cellular respiration decrease

 mitosis inhibition

 ion leakage and membrane depolarization

 oxidative damages

 chlorophyll content decrease

Membrane damage to E. Coli and S. aureus by

cinnamaldehyde(Shen et al, Food control,2015)

?

 detailed molecular mechanisms ?????? small amphiphilic molecules

 Could interact with the plant plasma membrane?

(6)

Plant plasma membrane

6

Adapted from Encyclopædia Britannica, Inc

Sterols

Palmitoyl linoleoyl Phosphatidylcholine

(PLPC)

β-Sitosterol Glycosyl inositol phosphoceramides (GIPC)

Glycerolipids Sphingolipids

Model membranes PLPC/sito 80/20

with 10% CitO, CitA or CIN

(7)

In silico approaches

7

?

In vitro biophysical tools

Molecular dynamics simulations Isothermal titration calorimetry (ITC) [mol bioactive]

[liposomes]

Permeability

?

h h

8-hydroxypyrene-1,3,6 trisulfonic acid

Lipid fusion

?

h h Dequenching Octadecylrhodamine B - R18 Dequenching Lipid Permeability

(8)

MD simulations

Evolution of a molecular system with time

Based on Newton

𝐹 = 𝑚 𝑎

Give insight into the inter- and intramolecular interactions

8

(9)

The EO molecules can insert into a model PPM

9

CIN CitA CitO

Polar heads

Hydrophobic tails

(10)

CIN, CitA et CitO have a different behavior

10

CIN CitA CitO

 Insertion CIN less deeper than CitO/CitA  CIN can get out of the membrane

(11)

Isothermal Titration Calorimetry (ITC)

Full thermodynamical characterization of the interaction

(∆G, ∆H, ∆S, K

D

)

11

[bioactive mol]

[liposomes]

(12)

CitA et CitO interact with the membrane but not CIN

12

0.0307 0.0147 non quantifiable 0.000 0.005 0.010 0.015 0.020 0.025 0.030 0.035 0.040

Citronellal Citronellol Cinnamaldehyde

K

(mM

(13)

K for PLPC/sito liposomes similar for CitA and CitO

Interaction is entropy driven (hydrophobic)

13

compound K (mM-1) ∆H DW→D (kj.mol-1) T∆SDW→D (kj.mol-1) ∆GDW →D (kj.mol-1) Citronellal 0.0307 ±0.004 5.13 ±0.64 21.62 ±0.34 -16.53 ±0.93 Citronellol 0.0147 ±0.006 5.05 ±0.52 23.28 ±0.50 -18.47 ±0.46

(14)

14

0 1 2 3 4 5 L eakag e (% ) CitA CitO CIN

Permeability

?

h h

8-hydroxypyrene-1,3,6 trisulfonic acid

Lipid fusion

?

h h

Dequenching

Octadecylrhodamine B - R18

Dequenching

Fluorescence assays

(15)

15

How is the membrane activity of EO

components related to their herbicidal effects

?

CitO/CitA

no membrane permeabilization/effects of sterol: Metabolism perturbation via interaction with lipid

domains (signalling platform) ?

Signalling pathways modified

GCPR(phenylpropanoid receptors)

CIN

no direct interaction with the lipid membrane: Interaction with membrane receptors ?

(16)

Conclusions

Promising herbicide activities

More than one action mode

Many work to be done …

 More in depth action mode studies: biophysics, molecular biology (proteomics,

metabolomics,…)

 Formulation

(17)

Thank you for your attention

IUPP Lab

Simon Dal Maso Caroline De Clerck Pr Haissam Jijakli LCMN Lab Manon Genva Pr ML Fauconnier LBMI Lab Berenice Foncoux Yoann Laurin

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