Comptes Rendus Chimie

Salah Jellali

Patrick Dutournié

Mejdi Jeguirim

Comptes Rendus
Chimie
Guest Editors
Volume 26, Special Issue S1 (2023), p. 1
Online since: 12 June 2024
Part of Special Issue: Materials and Clean Processes for Sustainable Energy and
Environmental Applications
Guest editors: Mejdi Jeguirim (Université de Haute-Alsace, Institut de Sciences des
Matériaux de Mulhouse, France) and Patrick Dutournié (Université de Haute-Alsace,
Institut de Sciences des Matériaux de Mulhouse, France)
https://doi.org/10.5802/crchim.322
This article is licensed under the
Creative Commons Attribution 4.0 International License.
http://creativecommons.org/licenses/by/4.0/
C EN T R E
MER S ENN E
The Comptes Rendus. Chimie are a member of the
Mersenne Center for open scientific publishing
www.centre-mersenne.org — e-ISSN : 1878-1543
Comptes Rendus
Chimie
2023, Vol. 26, Special Issue S1, p. 1
https://doi.org/10.5802/crchim.322
Materials and Clean Processes for Sustainable Energy and Environmental
Applications
Guest Editors
Dr. Mejdi Jeguirim Dr. Patrick Dutournié
Dr. Mejdi Jeguirim is a Professor at the University of
Haute-Alsace (France) in the field of energy, process
engineering, and kinetics modeling. He has coau-
thored more than 200 refereed international journal
papers in his research field and is a member of the
editorial boards for the following international jour-
nals: Energy, Energies, Energy for Sustainable De-
velopment, Biofuels, and the International Journal of
Green Energy.
He is involved as a scientific expert for more than
50 international scientific journals as well as for sev-
eral national and international research programs.
He has received the French National Research Excel-
lence Award for researcher with high-level scientific
activity for the 2009–2012, 2013–2016, 2017–2020,
and 2021–2024 periods. Dr. Jeguirim has appeared
in the World’s Top 2% Scientists ranking established
by Stanford University since 2019.
Dr. Patrick Dutournié is a Professor at the Uni-
versity of Haute-Alsace (France) in the field of en-
ergy and chemical engineering. He dedicates most
of his career to the modeling of heat and mass trans-
fer for different applications (energy storage, ultra-
nanofiltration, etc.). These research topics were per-
formed in the frame of several national and interna-
tional collaborations and he has led several academic
and industrial contracts. He has acted as a PhD advi-
sor for 12 students and has coauthored more than 100
refereed international journal papers in his research
field. He is a member of the editorial board of several
international journals (Membrane Science and Tech-
nology and the American Journal of Environmental
Engineering) and international congresses. He is in-
volved as a scientific expert for several national and
international research programs. He is the leader of
the research team TRM2P (Transfer, Reactivity, Mate-
rials for Clean Processes) of the Institute of Materials
Science in Mulhouse.
ISSN (electronic): 1878-1543 https://comptes-rendus.academie-sciences.fr/chimie/


Materials and clean processes for sustainable energy and environmental applications: Foreword

Christiane Minkosse

Aude Langenfeld

Ahmed Amine Azzaz

Leila El-Bassi

Hanene Akrout

Camélia Matei Ghimbeu

Najat Nassr

Short-term effects of olive-mill-wastes-derived biochars amendment and arbuscular mycorrhizal fungi inoculation on growth of maize (Zea mays) and mycorrhizal colonization

Julius-Alexander Nöpel

Frédéric Ayela

Experimental evidences of radicals production by hydrodynamic cavitation: a short review

Ali Alaaeddine

Vincent Ladmiral

Wassim El Malti

Lolwa Haydar

Sylvain Caillol

Bruno Améduri

Synthesis and characterization of original fluorinated bis-cyclic carbonates and xanthates from a fluorinated epoxide

Pierre Braunstein

Comptes Rendus
Chimie
Pierre Braunstein
Editorial January 2023 for Comptes Rendus Chimie
Volume 26 (2023), p. 1-6
Published online: 13 February 2023
https://doi.org/10.5802/crchim.224
This article is licensed under the
Creative Commons Attribution 4.0 International License.
http://creativecommons.org/licenses/by/4.0/
Les Comptes Rendus. Chimie sont membres du
Centre Mersenne pour l’édition scientifique ouverte
www.centre-mersenne.org
e-ISSN : 1878-1543
Comptes Rendus
Chimie
2023, Vol. 26, p. 1-6
https://doi.org/10.5802/crchim.224
Editorial / Éditorial
Editorial January 2023 for Comptes Rendus Chimie
Pierre Braunstein
Established in 1835 by François Arago, a French
mathematician, physicist and astronomer, the
Comptes Rendus de l’Académie des sciences have a
rich and prestigious history, and I am very pleased
to give you an update on the recent developments
that have occurred recently with the Comptes Rendus
Chimie. We still aim at covering the diverse aspects
of chemistry, also at the frontiers with other disci-
plines, by publishing original research and accounts
(short reviews and historic chronicles). Notes (pre-
liminary communications) typically describe novel
and important results, while full papers should pro-
vide a detailed account of new results. In all cases,
the work should be of high general interest or out-
standing specialized interest. Short reviews focusing
on the author(s) research but placed in the context
of the most recent advances in the field are most
welcome. Furthermore, thematic issues coordinated
by one or many guest editor(s) (upon invitation or
spontaneous suggestions) are particularly attractive
because they facilitate gaining an updated overview
on rapidly expanding areas. We are most grateful
to our authors and guest editors because they are
responsible for the success of this journal and its
increasing visibility.
Since 1 January 2020, Comptes Rendus Chimie
have been fully Open Access online worldwide, with
no fee for authors nor readers (“diamond model”)
and this major development has been very well re-
ceived by our authors and readers.
Three such thematic issues covering very diversi-
fied fields, have been published in 2022. These were,
in chronological order:
• Microcrystalline pathologies: Clinical is-
sues and nanochemistry (Guest editors: Do-
minique Bazin, Michel Daudon, Vincent Fro-
chot, Emmanuel Letavernier, Jean-Philippe
Haymanni)
• Sustainable Biomass Resources for Environ-
mental, Agronomic, Biomaterials and Energy
Applications. Part 3 (Guest editors: Mejdi
Jeguirim, Salah Jellali, Besma Khiari)
• Active site engineering in nanostructured
materials for energy, health and environment
(Guest editors: Ioana Fechete, Doina Lutic)
Only submissions considered by the Editorial of-
fice to potentially meet the criteria given above are
sent out to referees. We are fully aware that this pol-
icy can generate frustrations, but this is the only way
to proceed given the number of submissions received
by the Editorial Office. We all know how essential it is
for a journal to be able to rely on high-level scientific
referees with an ethic that lives up to their task and
we also know that these colleagues are being increas-
ingly solicited. We sincerely thank them for their con-
tribution to the success of Comptes Rendus Chimie
and we are particularly grateful to our 15 most active
referees listed in Table 1.
The Académie des sciences has signed “The Decla-
ration on Research Assessment (DORA)” which rec-
ognizes the need to improve the evaluation criteria
applied to researchers as well as to their scientific
production. Therefore, rather than emphasizing the
Impact Factor of our journal, I prefer to highlight the
quality and diversity of the contributions published
ISSN (electronic) : 1878-1543 https://comptes-rendus.academie-sciences.fr/chimie/
2 Pierre Braunstein
Table 1. Our 15 most active referees in 2022
Pierre Grandclaudon (ENSC Lille, France)
Doina Lutic (Alexandru Ioan Cuza University of Iasi, Romania)
Rima Merkache (Université de Strasbourg, France)
Adriana Urda (University of Bucharest, Romania)
Maria Harja (Gheorghe Asachi Technical University of Iasi, Romania)
Salah Jellali (Sultan Qaboos University, Muscat, Oman)
Vincent Rogé (Luxembourg Institute of Science and Technology, Luxembourg)
Elise Bouderlique (Sorbonne Université & Hôpital Tenon, Paris, France)
Monika Jain (Banda University of Agriculture & Technology, Banda, India)
Ioan-Cezar Marcu (University of Bucharest, Romania)
Saliha Haddoum (Ecole Nationale Polytechnique Alger, Algeria)
Ralph Puchta (Friedrich-Alexander-Universität, Erlangen-Nürnberg, Germany)
Vasile Hulea (Université Montpellier, France)
Besma Khiari (National School of Engineers of Carthage, Tunis, Tunisia)
Nawel Outili (University of Constantine 3, Algeria)
Table 2. The 20 articles (published since 1 January 2020) most viewed in 2022
Title Authors
Huiles essentielles et chiralité moléculaire Louisa Aribi-Zouioueche, Françoise Couic-Marinier
Scanning electron microscopy—a powerful imaging
technique for the clinician
D. Bazin, E. Bouderlique, M. Daudon, V. Frochot,
J.-P. Haymann, E. Letavernier, F. Tielens, R. Weil
Whitlockite structures in kidney stones indicate
infectious origin: a scanning electron microscopy
and Synchrotron Radiation investigation
D. Bazin, R. J. Papoular, E. Elkaim, R. Weil,
D. Thiaudière, C. Pisapia, B. Ménez, N. S. Hwang,
F. Tielens, M. Livrozet, E. Bouderlique, J.-P. Haymann,
E. Letavernier, L. Hennet, V. Frochot, M. Daudon
Cystinuria and cystinosis are usually related to
L-cystine: is this really the case for cystinosis?
A physicochemical investigation at micrometre and
nanometre scale
D. Bazin, M. Rabant, J. Mathurin, M. Petay,
A. Deniset-Besseau, A. Dazzi, Y. Su, E. P. Hessou,
F. Tielens, F. Borondics, M. Livrozet, E. Bouderlique,
J.-P. Haymann, E. Letavernier, V. Frochot,
M. Daudon
Les noms des éléments nous racontent leur histoire Pierre Avenas
Foreword to Sustainable Biomass Resources for
Environmental, Agronomic, Biomaterials and
Energy Applications 2
Mejdi Jeguirim, Salah Jellali, Besma Khiari
Pathologies related to abnormal deposits in
dermatology: a physico-chemical approach
H. Colboc, P. Moguelet, E. Letavernier, V. Frochot,
J.-F. Bernaudin, R. Weil, S. Rouzière, P. Senet,
C. Bachmeyer, N. Laporte, I. Lucas, V. Descamps,
R. Amode, F. Brunet-Possenti, N. Kluger,
L. Deschamps, A. Dubois, S. Reguer, A. Somogyi,
K. Medjoubi, M. Refregiers, M. Daudon, D. Bazin
(continued on next page)
Pierre Braunstein 3
Table 2. (continued)
Title Authors
Urinary tract infection inducing stones: some
clinical and chemical data
M. Daudon, M. Petay, S. Vimont, A. Deniset,
F. Tielens, J.-P. Haymann, E. Letavernier, V. Frochot,
D. Bazin
XANES spectroscopy for the clinician D. Bazin, S. Reguer, D. Vantelon, J.-P. Haymann,
E. Letavernier, V. Frochot, M. Daudon, E. Esteve,
H. Colboc
The influence of particle(s) size, shape and
distribution on cake filtration mechanics—a short
review
S. S. Haramkar, G. N. Thombre, S. V. Jadhav,
B. N. Thorat
The crucial contribution of X-ray fluorescence
spectroscopy in medicine
D. Bazin, E. Foy, S. Reguer, S. Rouzière, B. Fayard,
H. Colboc, J.-P. Haymann, M. Daudon, C. Mocuta
Randall’s plaque as the origin of idiopathic calcium
oxalate stone formation: an update
E. Van de Perre, D. Bazin, V. Estrade, E. Bouderlique,
K. M. Wissing, M. Daudon, E. Letavernier
Investigations on potential Tunisian biomasses
energetic valorization: thermogravimetric
characterization and kinetic degradation analysis
J. Mabrouki, M. A. Abbassi, B. Khiari, S. Jellali,
M. Jeguirim
Théorie cinétique de l’équilibre chimique Mathieu Lazerges, Sylvain Marque
Investigations on lignite use for lead removal from
aqueous solutions under static and dynamic
conditions: adsorption properties and mechanism
exploration
A. Mlayah, S. Jellali, A. A. Azzaz, M. Jeguirim,
H. Sellalmi, N. Hamdi
Medullary sponge kidney: what kind of stones? M. Daudon, V. Frochot, D. Bazin, J.-P. Haymann,
E. Letavernier
Inflammation plays a critical role in
2,8-dihydroxyadenine nephropathy
E. Bouderlique, E. Tang, J. Perez, H.-K. Ea,
F. Renaudin, A. Coudert, S. Vandermeersch,
D. Bazin, J.-P. Haymann, C. Saint-Jacques,
V. Frochot, M. Daudon, E. Letavernier
Les scénarios énergétiques à l’épreuve du stockage
des énergies intermittentes
Marc Fontecave, Dominique Grand
Pharmaceutical pollutants adsorption onto
activated carbon: isotherm, kinetic investigations
and DFT modeling approaches
M. Kebir, R. Bourzami, N. Nasrallah,
S. E. I. Lebouachera, F. Dergal, R. Ladji, M. Trari,
H. Ben Harharah, A. El Jery, A. A. Azzaz, L. Khezami
Editorial January 2022 for Comptes Rendus Chimie Pierre Braunstein
in Comptes Rendus Chimie, as documented by the
international awareness they have generated, with
most views originating from the USA, France, China
and India. The 20 most viewed and downloaded arti-
cles in 2022 are listed in Tables 2 and 3, respectively.
The most cited articles in 2022 are listed in Table 4.
We wish to congratulate our authors for their suc-
cess and are proud to contribute enhancing the vis-
ibility of their work through a fully Open Access
worldwide journal!
Of course, our authors, guest editors and referees
are responsible for the success of this journal and its
4 Pierre Braunstein
Table 3. The 20 articles (published since 1 January 2020) most downloaded in 2022
Title Authors
Huiles essentielles et chiralité moléculaire Louisa Aribi-Zouioueche, Françoise
Couic-Marinier
Foreword to Sustainable Biomass Resources for Environmental,
Agronomic, Biomaterials and Energy Applications 2
Mejdi Jeguirim, Salah Jellali, Besma Khiari
Optimization of a cationic dye desorption from a
loaded-lignocellulosic biomass: factorial design experiments
and investigation of mechanisms
A. A. Azzaz, S. Jellali, M. Jeguirim, L. Bousselmi,
Z. Bengharez, H. Akrout
Competitive bio-sorption of basic dyes onto petiole palm tree
wastes in single and binary systems
S. Jmai, S. Guiza, S. Jellali, M. Bagane, M. Jeguirim
Investigations on lignite use for lead removal from aqueous
solutions under static and dynamic conditions: adsorption
properties and mechanism exploration
A. Mlayah, S. Jellali, A. A. Azzaz, M. Jeguirim,
H. Sellalmi, N. Hamdi
Investigations on potential Tunisian biomasses energetic
valorization: thermogravimetric characterization and kinetic
degradation analysis
J. Mabrouki, M. A. Abbassi, B. Khiari, S. Jellali,
M. Jeguirim
Zinc phthalocyanine absorbance in the near-infrared with
application for transparent and colorless dye-sensitized solar
cells
T. Baron, X. Zarate, Y. Hidalgo-Rosa,
M. Zambrano-Angulo, K. Mall-Haidaraly,
R. Pino-Rios, Y. Pellegrin, F. Odobel,
G. Cárdenas-Jirón
The influence of particle(s) size, shape and distribution on cake
filtration mechanics—a short review
S. S. Haramkar, G. N. Thombre, S. V. Jadhav,
B. N. Thorat
Thermal behaviour of impregnated olive stones with
phosphoric acid via TGA-MS
A. Bedoui, S. Souissi-Najar, S. S. Idris,
N. Abd Rahman, A. Ouederni
Les scénarios énergétiques à l’épreuve du stockage des énergies
intermittentes
Marc Fontecave, Dominique Grand
MAPYRO: the French Fellowship of the Pyrrolic Macrocyclic
Ring
Bernard Boitrel, Jean Weiss
Whitlockite structures in kidney stones indicate infectious
origin: a scanning electron microscopy and Synchrotron
Radiation investigation
D. Bazin, R. J. Papoular, E. Elkaim, R. Weil,
D. Thiaudière, C. Pisapia, B. Ménez, N. S. Hwang,
F. Tielens, M. Livrozet, E. Bouderlique,
J.-P. Haymann, E. Letavernier, L. Hennet,
V. Frochot, M. Daudon
Editorial January 2022 for Comptes Rendus Chimie Pierre Braunstein
ORR activity of metalated phenanthroline-strapped porphyrin
adsorbed on carbon nanotubes
M. Hanana, C. Kahlfuss, J. Weiss, R. Cornut,
B. Jousselme, J. A. Wytko, S. Campidelli
Optimal parameters and structural composition of bio-oil and
biochar from intermediate pyrolysis of red algal biomass
H. Bouaik, A. Tabal, A. Barakat, K. El Harfi,
A. Aboulkas
A journey into metal–carbon bond homolysis Rinaldo Poli
Fiat Lux . . . how Alessandro Volta illuminated his scripts E. Barberis, M. Manfredi, E. Marengo,
G. Zilberstein, S. Zilberstein and P. G. Righetti
Théorie cinétique de l’équilibre chimique Mathieu Lazerges, Sylvain Marque
Synthesis of barium alkylbenzene sulfonate and its behavior as
a flow improver for crude oil
Z. Zhou, W. Zhang, F. Zhang, X. Zhang, S. Dong,
J. Zhang, G. Chen
A detailed UV–Vis spectral investigation of six azo dyes derived
from benzoic- and cinnamic acids: experimental and
theoretical insight
L. Matović, J. Lad̄arević, Ž. Vitnik, V. Vitnik, D. Mijin
Pierre Braunstein 5
Table 4. The 15 articles (all years) with the most citations in 2022
Title Authors
Sacrificial electron donor reagents for solar fuel
production
Yann Pellegrin, Fabrice Odobel
Green solvents from ionic liquids and deep eutectic
solvents to natural deep eutectic solvents
H. Vanda, Y. Dai, E. G. Wilson, R. Verpoorte,
Y. H. Choi
Titanium dioxide photocatalysis: present situation
and future approaches
Akira Fujishima, Xintong Zhang
Synthesis, chemistry, physicochemical properties
and industrial applications of amino acid
surfactants: A review
D. B. Tripathy, A. Mishra, J. Clark, T. Farmer
Comprehensive morpho-constitutional analysis of
urinary stones improves etiological diagnosis and
therapeutic strategy of nephrolithiasis
M. Daudon, A. Dessombz, V. Frochot, E. Letavernier,
J.-P. Haymann, P. Jungers, D. Bazin
Some aspects of green solvents Katharina Häckl, Werner Kunz
Removal of fluoride from groundwater using natural
clay (kaolinite): Optimization of adsorption
conditions
N. Nabbou, M. Belhachemi, M. Boumelik,
T. Merzougui, D. Lahcene, Y. Harek, A. A. Zorpas,
M. Jeguirim
Contributions of organic electrosynthesis to green
chemistry
Hans J. Schäfer
Occurrence, fate and removal efficiencies of
pharmaceuticals in wastewater treatment plants
(WWTPs) discharging in the coastal environment of
Algiers
Amine Elmouatezz Bellah Kermia,
Djamila Fouial-Djebbar, Mohamed Trari
Water as a green solvent combined with different
techniques for extraction of essential oil from
lavender flowers
A. Filly, A. S. Fabiano-Tixier, C. Louis, X. Fernandez,
F. Chemat
Hexavalent chromium quantification in solution:
Comparing direct UV–visible spectrometry with
1,5-diphenylcarbazide colorimetry
Arnaud Sanchez-Hachair, Annette Hofmann
Vibrational spectroscopies to investigate
concretions and ectopic calcifications for medical
diagnosis
Michel Daudon, Dominique Bazin
Polymer ageing: physics, chemistry or engineering?
Time to reflect
Jim R.White
Low-cost ceramic membranes: Synthesis,
classifications, and applications
Mansour Issaoui, Lionel Limousy
Structural analysis of spin-crossover materials:
From molecules to materials
Eric Collet, Philippe Guionneau
6 Pierre Braunstein
increasing visibility and we are most grateful to them
for their commitment.
Finally, I would like to warmly thank the members
of the editorial board of Comptes Rendus Chimie,
the editorial and production staff, in particular Julien
Desmarets (scientific secretary), for their support
and cooperation.
The continuing success of Comptes Rendus
Chimie depends on you! We welcome any suggestion
you may have to help us meet your expectations!
I wish you all a happy, scientifically most reward-
ing and successful New Year and look forward to re-
ceiving your manuscripts!
Pierre Braunstein
Editor-in-Chief
Strasbourg
braunstein@unistra.fr


Editorial January 2023 for Comptes Rendus Chimie

Fanny Mondet

Dominique Beslay

Marianne Cousin

Yves Le Conte

Comptes Rendus
Chimie
Supplementary material to the article available at:
https://doi.org/10.5802/crchim.270
Supplementary material: Impact of temporal
and rearing environment variations on brood
ester pheromone production in the honey bee
Apis mellifera
FannyMondet ∗, a, Dominique Beslaya, Marianne Cousina and Yves Le Contea
a INRAE, UR 406 Abeilles et Environnement, 84914 Avignon, France
E-mail: fanny.mondet@inrae.fr (F. Mondet)
Not yet published
∗Corresponding author.
ISSN (electronic) : 1878-1543 https://comptes-rendus.academie-sciences.fr/chimie/
2 Fanny Mondet et al.
Supplementary Figure S1. Continued on next page.
Fanny Mondet et al. 3
Supplementary Figure S1 (cont.). Temporal evolution of the amount of molecule produced per larva
(last-instar larva) for each of 9 brood ester pheromone compounds (n = 18 for each month). ML, methyl
linoleate; MO, methyl oleate; MP, methyl palmitate; MS, methyl stearate; MLN, methyl linolenate; EO,
ethyl oleate: EP, ethyl palmitate; ES, ethyl stearate; ELN, ethyl linolenate. The EL (ethyl linoleate) temporal
profile could not be analysed because too many samples did not display any amount of this compound.
4 Fanny Mondet et al.
Supplementary Figure S2. Stage and rearing environment variations in brood ester pheromone (BEP)
ethyl/methyl ester ratios.
Supplementary Figure S3. Continued on next page.
Fanny Mondet et al. 5
Supplementary Figure S3. Stage and rearing environment variations of each brood ester pheromone
(BEP) compounds. 5 ≤ n ≤ 15 per stage and rearing condition. Different letters indicate significant
differences between groups. MP, methyl palmitate; MS, methyl stearate; MO, methyl oleate; MLN, methyl
linolenate; EP, ethyl palmitate; ES, ethyl stearate; EO, ethyl oleate. ML (methyl linoleate), ELN (ethyl
linolenate), and EL (ethyl linoleate) profiles could not be analyzed because too many samples did not
display any amount of these compounds.
6 Fanny Mondet et al.
Supplementary Table S1. Statistical test results for temporal variations of each BEP compound (X 2
values of the LMMs, ddl = 6, 115)
Compound Date effect
MP 525.96∗∗∗
MS 141.57∗∗∗
ML 239.83∗∗∗
MO 470.00∗∗∗
MLN 318.20∗∗∗
EP 81.41∗∗∗
ES 63.83∗∗∗
EO 126.50∗∗∗
EL NA
ELN 293.67∗∗∗
Supplementary Table S2. Statistical test results for variations in each BEP compound according to stage
and rearing conditions (F values of the LMs)
Compound Stage effect
Ddl = 8, 113
Rearing effect
Ddl = 1, 113
Stage ∗ rearing
Ddl = 8, 113
MP 38.26∗∗∗ 193.40∗∗∗ 7.37∗∗∗
MS 62.22∗∗∗ 112.12∗∗∗ 15.46∗∗∗
ML NA NA NA
MO 86.09∗∗∗ 256.91∗∗∗ 14.43∗∗∗
MLN 90.15∗∗∗ 14.59∗∗∗ 25.84∗∗∗
EP 14.50∗∗∗ 0.66 0.85
ES 37.71∗∗∗ 0.74 4.04∗∗∗
EO 93.81∗∗∗ 13.48∗∗∗ 3.65∗∗∗
EL NA NA NA
ELN NA NA NA


Impact of temporal and rearing environment variations on brood ester pheromone production in the honey bee Apis mellifera

Marc Gibernau

Arianna Amadori

Adrienne Godschalx

Jérôme Albre

Félix Tomi

Paolo Marcia

Emmanuele Farris

Comptes Rendus
Chimie
Supplementary material to the article available at:
https://doi.org/10.5802/crchim.236
Supplementary material: Mediterranean island
endemic Arum pictum emits isomyocorene as a
major component of floral scent
Marc Gibernau ∗, a, Arianna Amadori b, Adrienne Godschalxa, c, Jérôme Albrea,
Félix Tomi a, Paolo Marciad and Emmanuele Farris b, e
a CNRS-University of Corsica Pascal Paoli, UMR 6134 SPE, Projet Phytochimie &
Écologie chimique, Route des Sanguinaires - Vignola, 20000 Ajaccio, France
b Department of Chemical, Physical, Mathematical and Natural Sciences, University
of Sassari, via Piandanna 4 – 07100 Sassari, Italy
c Lower Columbia College, 1600 Maple St, Longview, WA 98632, USA
d Department of Veterinary, University of Sassari, via Piandanna 4 – 07100 Sassari,
Italy
e NBFC, National Biodiversity Future Center, Palermo 90133, Italy
E-mails: gibernau_m@univ-corse.fr (M. Gibernau), ariannaamadori81@gmail.com
(A. Amadori), adrienne.godschalx@gmail.com (A. Godschalx), albrej@gmail.com
(J. Albre), tomi_f@univ-corse.fr (F. Tomi), pmarcia@uniss.it (P. Marcia), emfa@uniss.it
(E. Farris)
Not yet published
∗Corresponding author.
ISSN (electronic) : 1878-1543 https://comptes-rendus.academie-sciences.fr/chimie/
2 Marc Gibernau et al.
Mass spectra of the 4 unidentified compounds from Table 2 with the “wrong” best mass library match.
Unknown 1 (mass library best match: cis- β-ocimene)
Unknown 2 (mass library best match: Rothrochene)
Unknown 3 (mass library best match: artemisia ketone)
Marc Gibernau et al. 3
Unknown 4 (mass library best match: citronellyl formate)
NMR proton and carbon chemical shift values for isomyocorene comparing our results with published ones.
4 Marc Gibernau et al.
NMR data for the identification of isomyocorene or 2,6-dimethyl-1,3,7-octatriene
1H spectrum (CDCl3)
Marc Gibernau et al. 5
13C spectrum (CDCl3)
6 Marc Gibernau et al.
COSY
Marc Gibernau et al. 7
HSQC
8 Marc Gibernau et al.
HMBC


Mediterranean island endemic Arum pictum emits isomyocorene as a major component of floral scent

Jérôme Dejeu

Eric Defrancq

Chemical Biology of G-quadruplex and i-motif DNA: use of topologically constrained DNA

Alexandra Magro

Felipe Ramon-Portugal

David Touboul

Isabel Borges

Jean-Louis Hemptinne

First report of fatty acid-derived alkaloids produced by species of the ladybird genus Scymnus (Coccinellidae: Coleoptera)

Margot Lefèvre

Lielou Lantigner

Laura Andolfo

Corinne Vanucci-Bacqué

Eric Benoist

Charlène Esmieu

Florence Bedos-Belval

Christelle Hureau

Comptes Rendus
Chimie
Supplementary material to the article available at:
https://doi.org/10.5802/crchim.255
Supplementary material: Reduced Schiff-base
derivatives to stop reactive oxygen species
production by the Cu(Aβ) species:
a structure–activity relationship
Margot Lefèvre a, Lielou Lantignera, Laura Andolfoa, b, Corinne Vanucci-Bacqué b,
Eric Benoist b, Charlène Esmieu a, Florence Bedos-Belval ∗, b
and Christelle Hureau ∗, a
a LCC-CNRS, Université de Toulouse, CNRS, Toulouse, France
b LSPCMIB, CNRS UMR 5068, Université Toulouse III-Paul Sabatier, 118 route de
Narbonne, 31062 Toulouse cedex 9, France
E-mails: margot.lefevre@lcc-toulouse.fr (M. Lefèvre), lielou.lantigner@lcc-toulouse.fr
(L. Lantigner), laura.andolfo21@gmail.com (L. Andolfo),
corinne.bacque@univ-tlse3.fr (C. Vanucci-Bacqué), eric.benoist@univ-tlse3.fr
(E. Benoist), charlene.esmieu@lcc-toulouse.fr (C. Esmieu),
florence.bedos@univ-tlse3.fr (F. Bedos-Belval), christelle.hureau@lcc-toulouse.fr
(C. Hureau)
Not yet published
∗Corresponding authors.
ISSN (electronic) : 1878-1543 https://comptes-rendus.academie-sciences.fr/chimie/
2 Margot Lefèvre et al.
1. Synthesis
Supplementary Scheme S1. Synthetic routes to the ligands L .
2. Experimental section
2.1. Chemicals
All the chemicals were purchased from Sigma-
Aldrich unless otherwise specified. All of the solu-
tions were prepared using ultrapure water (18.2 MΩ).
Stock solutions of metallic salts and peptides were
prepared by dissolving the salts or the peptides
in ultrapure water; the concentrations were de-
termined using UV–vis absorption spectroscopy.
A stock solution of Zn(II) ions was prepared at
100 mM using monohydrated ZnSO4•H2O salt. A
stock solution of Cu(II) was prepared at 100 mM
using hydrated CuSO4•5H2O salt. The concentra-
tion of the Cu(II) stock solution was determined
using UV–vis (λ = 800 nm corrected at 400 nm)
while considering a molar extinction coefficient
of 12 M−1·cm−1. A stock solution of HEPES buffer
(sodium salt of 2-[4-(2-hydroxyethyl)piperazin-1-
yl]ethanesulfonic acid) was prepared at 500 mM
and the pH was adjusted to 7.4 using concentrated
sodium hydroxide. All pH values are given with a
±0.1 pH unit error. The stock solution of sodium
ascorbate were prepared at 5 mM every day due
to its auto-oxidation in solution. The Aβ1–16 (DAE-
FRHDSGYEVHHQK) peptide was purchased from
Genecust (purity > 95%). A stock solution and its
concentration was determined using UV–vis ab-
sorption spectroscopy with Tyr10 absorption con-
sidered as free tyrosine (in acidic condition, ε276–
ε360 = 1410 M−1·cm−1). Stock solutions of ligands
were prepared and concentration was determined by
a Cu(II) titration followed by UV–vis absorption spec-
troscopy (see Figure S1 as a matter of example). The
stock solutions of ligands and peptide were stored at
−20 °C.
Margot Lefèvre et al. 3
2.2. Synthesis of the ligands
All experiments were carried out in methanol or
ethanol purchased from VWR chemicals without
further purifications. NMR spectra were recorded on
Brucker Avance 300 MHz spectrometers. 1H NMR
spectra were referenced to residual protonated sol-
vents (δH = 4.79 ppm for D2O). Reactions were
monitored by TLC on silica gel Alugram® Xtra SIL
G/UV254.
All the ligands but SL′ were obtained accord-
ing to reported protocols. Using similar proce-
dures to those reported previously, the ligands
L [1], L′ [2] on the one hand and ligands SL [3]
and SL′ [4] on the other hand were synthesized in
two steps from 2-hydroxybenzaldehyde or 4-formyl-
3-hydroxybenzenesulfonic acid [5], respectively.
To that end, the required aldehydes were condensed
on ethylene diamine or rac(1,2)-cyclohexanediamine
to yield the corresponding diimine intermediates.
Diamines L, L′ and SL were readily obtained us-
ing NaBH4 as reductive agent. However, PtO2 cat-
alytic hydrogenation was required to obtain pure
ligand SL′ . Subsequent N-methylation of com-
pounds L and L′ was achieved by reductive ami-
nation with an excess of formaldehyde to form the
intermediate imine, followed by reduction in the
presence of NaBH4 to give diimines LMe [1] and
L′Me [6].
Their characterization by 1H NMR spectroscopy
correspond to the one described in the literature.
Ligand SL′ was obtained according to an alterna-
tive protocol:
A mixture of 4-formyl-3-hydroxybenzenesulfonic
acid (424 mg, 2.1 mmol) and (±)-trans-1,2-
diaminocyclohexane (115 mg, 1 mmol) was refluxed
in EtOH for 20 h. The reaction mixture is cooled to
room temperature, and the precipitated diimine was
collected by filtration (322 mg, 68% yield) and used
in the next step without further purification.
The latter diimine (70 mg, 0.14 mmol) was sus-
pended in absolute EtOH (11 mL), PtO2 was added
(10 mg) and the reaction mixture was subjected to
catalytic hydrogenation at 5 atm for 24 h and room
temperature. Filtration and concentration under vac-
uum yielded the expected ligand SL′ (55 mg, 80%
yield) as a white solid [4].
1H NMR (300 MHz, D2O): δ = 7.60 (m; 4H); 6.81
(d, J ′ = 9.2 Hz; 2H); 4.11 (d; J = 13.4 Hz; 2H); 3.94
Supplementary Figure S1. UV–vis spectra cor-
responding to the titration of CuII into a solu-
tion of ligand L. Inset: Absorbance at 600 nm
versus number of CuII equiv. added. [hepes]
50 mM, pH 7.4, T = 25 °C, [L] is approx. 500µM;
1 equiv. of CuII = 500 µM.
(d; J = 13.4 Hz; 2H; H6′ ); 2.70 (m; 2H); 2.24 (m; 2H);
1.77 (m; 2H); 1.28 (m; 4H).
HR-MS: (DCI-CH4) calculated for C20H27N2O8S2
[MH]+ = 487.1209; found: 487.1206 m/z.
2.2.1. UV–visible spectroscopy
Titration and UV–vis kinetic data from the ascor-
bate consumption experiments were recorded with
a Hewlett Packard Agilent 8453 or 8454 spectropho-
tometer at a controlled temperature of 25 °C in a 1 cm
path length quartz cuvette with 800 rpm stirring.
2.2.2. CuII titration
The concentrations of ligands stock solutions
were determined via CuII titration with a solution
of known concentration using the d−d and LMCT
transition absorption of the formed complex (see for
example Figure S1 for the titration of ligand L). All
the ligands were titrated at about 500 µM (based on
weighting) with the addition of an increasing amount
of a CuII stock solution. For competition experiment,
CuII and Aβ were added to the cuvette to preform
CuII(Aβ) complex and L was added after.
4 Margot Lefèvre et al.
Supplementary Figure S2. CuII removal from CuII(Aβ) by L followed by UV–vis. Each panel contains
spectra of CuII(Aβ) (black curves), CuII (L) (L in pink, LMe in blue, L′ in green, SL in light pink, SL′ in light
green and SLMe in light green), and spectra of the addition of L to CuII(Aβ) with mixing for 5 min (thick
curves). Experimental conditions: [CuII] = 500 µM, [L] = [Aβ] = 500 µM, [HEPES] = 100 mM, pH 7.4,
T = 25 °C.
Margot Lefèvre et al. 5
Supplementary Figure S3. CuII removal from CuII (Aβ) and CuII ZnII(Aβ) by L followed by X-band EPR.
Each panel contains spectra of CuII(Aβ) (black curves), CuII(L ) and of the addition of L to CuII(Aβ)
(thick curve) and CuII ZnII(Aβ) (doted curve) and mixing for 5 min. Experimental conditions: [65CuII] =
480 µM, [L , Aβ] = 500 µM, or [65CuII] = [Zn] = 180 µM, [L , Aβ] = 200 µM [HEPES] = 50 mM, pH 7.4,
10% of glycerol as cryoprotectant, T = 120 K, ν ≈ 9.5 GHz, mod. ampl. = 5 G, microwave power: 5 mW.
6 Margot Lefèvre et al.
Supplementary Figure S4. CuII removal from
CuII(Aβ) and CuII by L′Me monitored by UV–
vis. Experimental conditions: [L′Me] = [Cu(II)] =
[Zn(II)] = [Aβ] 500 µM, [HEPES] = 100 mM, pH
7.4, T = 25 °C. Cu(II)Aβ was pre-formed in the
cuvette and then, L′Me was added at 500 s in red:
absorbance at 392 nm and in black at 620 nm.
2.2.3. ROS experiment
The ROS production was determined using an
ascorbate consumption assay monitored via UV–vis
spectroscopy. The decrease in the absorption band at
λmax = 265 nm of the Asc (ε= 14,500 M−1·cm−1, cor-
rected at 800 nm for the background absorption) was
plotted as a function of time.
The samples were prepared from stock solutions
at 1 mM and mixed in situ in the UV–vis cuvette at a
final concentration of 12 µM for L , Aβ1-16, and ZnII
and 10 µM for CuII in HEPES at pH 7.4. Ascorbate
was added to obtain 100 µM as the final concentra-
tion. The final volume was adjusted with ultrapure
water to 2 mL. The ROS experiments were performed
following three different procedures: (i) starting from
Cu(II) with 300 s incubation time where CuII/ZnII, Aβ
and L were added at 30, 60 and 120 s respectively;
(ii) with long enough incubation time to reach the
thermodynamic equilibrium where CuII + Aβ + L
or CuII + Aβ + ZnII + L mixtures were prepared
out of the cuvette, in Eppendorf tubes, and incu-
bated at 25 °C with stirring. These experiments are
Supplementary Figure S5. Continued on next
page.
Margot Lefèvre et al. 7
Supplementary Figure S5. (cont.) Ascorbate
consumption induced by Cu(Aβ). Starting from
Cu(II) (in presence of increasing Zn stoichiom-
etry, A, B and C) and with Ascorbate added 300 s
after mixing of the others chemicals. [L ]= [Aβ]
= [ZnII] = 0, 12 and 120 µM, [CuII] = 10 µM,
[Asc] = 100µM, [HEPES] = 100 mM, pH 7.4, T =
25 °C. The arrows indicate the time at which the
different components are added into the cu-
vette.
called “A” in the main text. Third, (iii) with the lig-
and added in the course of Asc consumption (ex-
periment called “B”) where ascorbate was first intro-
duced into the cuvette, then, either CuII + Aβ + L
or CuII + Aβ + ZnII + L was added. Ascorbate, Aβ,
and/or ZnII and CuII were added at 30, 120, and 240 s,
respectively. When the absorbance reached about 1.1
in O.D., L was added. These experiments were run
under aerobic conditions.
2.2.4. EPR
Electron paramagnetic resonance (EPR) spectra
were recorded using an Elexsys E-500 Bruker spec-
trometer operating at a microwave frequency of
approximatively 9.5 GHz. The spectra were recorded
using a microwave power of 5 mW, a magnetic field
range of 2400 to 3700 G, and a modulation amplitude
of 5 G. The experiments were carried out at 120 K us-
ing a liquid nitrogen cryostat. EPR samples were pre-
pared in Eppendorf tubes from a 10 mM 65CuII and
Aβ stock solution and diluted to 480 µM and 500 µM
respectively in 50 mM of HEPES buffer (pH 7.4) with
Supplementary Figure S6. Ascorbate con-
sumption induced by Cu(Aβ) and effect of
pre-incubation of L′Me (times are given in
the figure). [L′Me] = [Aβ] = 12 µM, [CuII] =
10 µM, [Asc] = 100 µM, [HEPES] = 100 mM,
pH 7.4, T = 25 °C. Ascorbate was added at
30 s (after having taken the starting spectrum
corresponding to the incubated mixture).
the addition of 500 µM of ligands. Experiment with
ZnII were conducted at 200 µM to limit precipitation.
As a cryoprotectant, 10% glycerol was added. The
final volume was adjusted to 200 µL using ultrapure
water. The mixture was then transferred into a EPR
quartz tube and frozen in liquid nitrogen.
8 Margot Lefèvre et al.
Supplementary Figure S7. Ascorbate consumption induced by Cu,Zn(Aβ) with ZnII 10 eq and effect of
pre-incubation of L (left: 1 h of CuZn(Aβ) +L incubation and right: 24 h of CuZn(Aβ) +L incubation).
[L ] = [Aβ] = 12 µM, [ZnII] = 120 µM, [CuII] = 10 µM, [Asc] = 100 µM, [HEPES] = 100 mM, pH 7.4,
T = 25 °C. Ascorbate was added at 30 s (after having taken the starting spectrum corresponding to the
incubated mixture). Solutions of ligands L and Cu, Zn(Aβ) were pre-incubated at room temperature,
with agitation and at experimental concentrations.
Supplementary Scheme S2. Scheme of the ligands from Ref. [7]. Charges are omitted for simplicity.
References
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Reduced Schiff-base derivatives to stop reactive oxygen species production by the Cu(A$\beta $) species: a structure–activity relationship

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