*Co esponding au ho : Oua a a Logopho Hyacin he
Copy igh © 2025 Au ho (s) e ain he copy igh o his a icle. This a icle is published unde he e ms o he C ea i e Commons A ibu ion Liscense 4.0.
Isola ion o wo cassane- ype di e penoids om he ba k o E y h ophleum sua eolens
(Guill. & Pe .) B enan (Fabaceae)
Logopho Hyacin he Oua a a 1, *, Richmond Jean-F ançois Kablan 1, Amina a Akoube -Ouayogode 2, Dibi
Jacques Konan 3, Ahmon Land y Claude Kablan 1, N’d i Ma celline Adiko 2 and Obiang Céd ic Sima 4
1 UPR Chemis y, Depa men o Ma hema ics-Physics-Chemis y, Facul y o Biological Sciences, Pele o o GON COULIBALY
Uni e si y, BP 1328 Ko hogo, I o y Coas
2 Labo a o y o Medicinal Sciences, Analy ical Sciences, and Public Heal h, Depa men o Pha maceu ical Sciences, UFR
SPB, Félix Houphouë -Boigny Uni e si y, Cocody (I o y Coas )
3 Labo a o y o Bio-O ganic Chemis y and Na u al Subs ances (LCBOSN), UFR-SFA, NANGUI ABROGOUA Uni e si y, 02 BP
801 Abidjan 02, I o y Coas
4 Labo a o y o Resea ch in Biochemis y (LAREBIO), Facul y o Sciences, Masuku Uni e si y o Science and Technology,
F ance ille, Gabon.
GSC Biological and Pha maceu ical Sciences, 2025, 32(03), 314-321
Publica ion his o y: Recei ed on 21 Augus 2025; e ised on 27 Sep embe 2025; accep ed on 30 Sep embe 2025
A icle DOI: h ps://doi.o g/10.30574/gscbps.2025.32.3.0376
Abs ac
E y h ophleum sua eolens is a plan species used o ea Bu uli ulce in Cô e d'I oi e. This plan is ich in cassane- ype
di e penoids, compounds known o hei mul iple biological ac i i ies. This s udy ocuses on he isola ion, pu i ica ion,
and s uc u al iden i ica ion o wo cassane- ype di e penoids om he e hyl ace a e ex ac o he ba k o
E y h ophleum sua eolens. Two molecules we e isola ed using con en ional pu i ica ion and isola ion me hods, namely
column ch oma og aphy and p epa a i e HPLC. The s uc u al analysis o hese compounds was ca ied ou using one-
dimensional (1D) and wo-dimensional (2D) 1H and 13C Nuclea Magne ic Resonance (NMR), COSY, HMBC, and NOESY.
The molecules we e iden i ied as 3β-ace oxye y h osuamine and 3β-hyd oxy-3-me hylbu anoyloxy-6α-hyd oxy-no -
cassamine. These compounds ha e al eady been isola ed om he oo ba k o his plan , bu his is he i s ime hey
ha e been isola ed om he unk ba k. Bo h compounds belong o he cassane genus, and hei disco e y en iches he
chemis y o E. sua eolens.
Keywo ds: Fabaceae; E y h ophleum sua eolens; Cassane di e penoid; NMR
1. In oduc ion
Cassane- ype di e penoids a e an impo an class o seconda y me aboli es in se e al species o he genus
E y h ophleum as well as in o he Fabaceae. In he genus E y h ophleum, despi e hei high oxici y o humans and
li es ock, many species a e widely used o he apeu ic pu poses in a ious local communi ies [1]. In addi ion, in A ica
and Asia, adi ional medicine p ac i ione s empi ically used decoc ions o lea es o powde ed ba k om species o he
genus E y h phleum o ea a ious condi ions, including ca dio ascula disease, dysen e y, and dia hea (decoc ion o
E. a icanum lea es) [2, 3], blood cance and men al illness (aqueous ex ac o lea es and unk ba k o E. a icanum,
aqueous ex ac o lea es o E. o dii) [4, 5], lung diseases in li es ock (powde om he ba k o E. chlo os achys) [6],
smallpox, con ulsi e diso de s, pain, swelling (ba k o E. i o ense) [7, 8], e e s (powde om he ba k o E. chlo os achys)
[6]. The powde ed ba k o E. couminga is used as a pu ga i e and laxa i e. I was p e iously used as a poison o ishing
and hun ing. Pha maceu ical companies used he ba k o E. couminga as a non-s e oidal ca dioac i e d ug, bu he
p ojec was abandoned due o a sho age o ma e ial [9].
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315
Species o he genus also ha e a ious biological ac i i ies: cy o oxici y, an imala ial, an ioxidan , and an i-in lamma o y
[10, 11, 12, 13].
E y h ophleum sua eolens, a ee widesp ead in Wes A ica, is used in adi ional medicine [14]. The objec i e o his
s udy is o isola e cassane- ype di e penoids om he ba k o E y h ophleum sua eolens. These molecules will en ich
he knowledge base on cassane di e penoids in his species and may se e as a basis o u he pha macological
in es iga ions.
2. Ma e ial and me hods
2.1. Ma e ial
2.1.1. Plan ma e ial
The ba k o he unk o E y h ophleum sua eolens (Guill. & Pe .) B enan (Fabaceae) was collec ed in Decembe in
Toumodi (Pacobo: 6°09'56.8“N 4°56'26.1”W), a own loca ed in cen al Cô e d'I oi e. I was iden i ied and au hen ica ed
a he Na ional Flo is ic Cen e (CNF) o Félix HOUPHOUËT-BOIGNY Uni e si y (Abidjan, I o y Coas ). A specimen
numbe ed 10 DIBI ES-2014 was deposi ed in he he ba ium o his cen e . The ba k was sc aped om he unk using
a mache e, d ied in he labo a o y away om sunligh , and g ound using an elec ic g inde . The powde ob ained was
used o he ex ac ions.
2.1.2. Chemical ma e ial
The chemical ma e ials consis o dis illed me hanol, ammonium hyd oxide, dichlo ome hane, sul u ic acid, dis illed
e hyl ace a e, o mic acid, ace oni ile, Sephadex® LH 20, and silica gel 60.
2.2. Me hods
2.2.1. Ex ac ion
1 kg o E. sua eolens ba k powde was subjec ed o solid-liquid ex ac ion a oom empe a u e in 10 L o dis illed
me hanol (MeOH) o 24 hou s. This ope a ion was epea ed wice mo e wi h he esidual ma c unde he same
condi ions as be o e. A e il a ion, he a ious solu ions we e e apo a ed using a o a y e apo a o (Ra a apo ,
Sa o ius S edim Bio ech) and hen d ied o yield 48.3 g o c ude ex ac . Nex , 15 g o his me hanolic ex ac was
dissol ed in 50 mL o MeOH, hen alkalized wi h a ew d ops o 25% ammonium hyd oxide (NH4OH), and hen
supplemen ed wi h 100 mL o dichlo ome hane (CH2C12). To he solu ion ob ained, 100 mL o 1% sul u ic acid was
added. The solu ion ob ained was coun e -ex ac ed by liquid-liquid ex ac ion wi h dis illed CH2C12 (100 mL x 4). The
supe na an phase sepa a ed om he dichlo ome hane phase is i s alkalized wi h NH4OH o pH = 10, hen coun e -
ex ac ed wi h dis illed e hyl ace a e (100 mL x 4) o gi e, a e e apo a ion using a o a y e apo a o , he e hyl ace a e
ex ac coded ESA.
2.2.2. P elimina y es : phy ochemical sc eening
The ESA ex ac unde wen phy ochemical sc eening wi h D agendo 's eagen . The es p o ed posi i e, so he ESA
ex ac was used o ac iona ion and pu i ica ion.
2.2.3. Ch oma og aphic me hods
Thin-laye ch oma og aphy (TLC)
Thin-laye ch oma og aphy analyses we e pe o med on aluminum pla es (Silicagel 60 F254, Me ck, Ge many). A e
de elopmen in glass anks, he pla es we e obse ed unde ul a iole ligh (254 nm and 366 nm). The UV lamp used
was manu ac u ed by Vilbe Lou ma (230 V, 50 Hz, F ance).
Flash ch oma og aphy
We used a de ice wi h an isoc a ic and g adien pumping sys em, wi h a double pis on pump. Ca idges weighing 330
g, 120 g, and 24 g om he G ace Resol ® Silica Flash Silica se ies we e used. These ca idges ha e he ad an age o
e ec i ely eplacing glass columns.
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Silica gel column ch oma og aphy (CC)
Ch oma og aphic column sepa a ions we e pe o med aking in o accoun he mass o he sample ( ac ion o ex ac )
o be ac iona ed and i s ch oma og aphic p o ile (CCM). The diame e and heigh o he column a e de e mined based
on he mass o he sample. Fo e ec i e sepa a ion, he mass o silica in he column is equal o 10 imes he mass o he
sample o be pu i ied [15]. In his s udy, he s a iona y phase used in he a ious CCM sepa a ions was silica gel 60 (40-
63 µm, Ch omagel, Me ck).
F ac iona ion and pu i ica ion o ESA ex ac cons i uen s
The ESA ex ac is ini ially pu i ied using lash ch oma og aphy. Fo 2 g o ESA ex ac , a ca idge con aining 10 g o
silica gel 60 was used. The elu ion sys em consis s o a MeOH/ CH2Cl2 mix u e ollowing an elu ion g adien o 1:99 ( / )
o 50:50 ( / ). The ac ions collec ed a e g ouped acco ding o hei ch oma og aphic p o iles (CCM). A o al o 6
ac ions (F1 o F6) we e collec ed, and each ac ion was hen pu i ied on a ch oma og aphic column using a 1.5 cm
diame e column and Sephadex® LH 20 as he s a iona y phase.
F ac ions F1 o F5 we e pu i ied unde he same condi ions, using a CH2Cl2/MeOH (2:1, / ) mix u e as eluen , ollowing
isoc a ic elu ion, o gi e a single sub ac ion. This ac ion was hen pu i ied by p epa a i e high-pe o mance liquid
ch oma og aphy (HPLC) using he H2O+0.1% me hanoic acid (HCOOH)/ace oni ile (ACN) sys em (85:15 o 50:50, / )
o p o ide compound 1.
F ac ion F6 is pu i ied unde he same condi ions as F1-F5, using he CH2Cl2/MeOH (1:1, / ) mix u e as eluen ,
ollowing isoc a ic elu ion, o gi e a single sub ac ion which is hen pu i ied by p epa a i e HPLC ( e e se phase) wi h
he H2O+0.1% HCOOH/ ACN (85:15 o 50:50, / ) o gi e compound 2.
2.2.4. S uc u al iden i ica ion
The isola ed compounds we e subjec ed o he ollowing spec oscopic echniques:
• 1H and 13C NMR o assign p o on and ca bon signals.
• Two-dimensional expe imen s:
o COSY (Co ela ion Spec oscopy) o iden i y couplings be ween adjacen p o ons.
o HMBC (He e onuclea Mul iple Bond Co ela ion) o long- ange p o on-ca bon co ela ions (2-3
bonds) o loca e subs i uen s and side chains.
o NOESY o es ablish spa ial p oximi ies (in e ac ions ac oss space), which helps de ine ela i e
s e eochemis y (α/β aces, 3β, 6α posi ions, e c.).
• O he spec al da a (exac mass, IR) as needed o con i m unc ional g oups (hyd oxyl, es e , ace oxy) and
molecula o mula.
Fo pu i y con ol, each pu i ied compound was checked by hin-laye ch oma og aphy (TLC) o homogenei y, and by
addi ional spec a o ensu e ha he e was no mix u e.
3. Resul s
3.1. S uc u al elucida ion o compound 1
Compound 1, soluble in me hanol, was ob ained as an amo phous solid. I s IR spec um shows ce ain cha ac e is ic
bands, such as hose a ʋmax 1735, 1721, and 1594 cm-1, which indica e he p esence o h ee es e unc ions, and he
band a ʋmax 1669 cm-1, which sugges s he p esence o a ke one unc ion. The hyd oxyl and amine g oups gi e b oad
abso p ion bands cen e ed a ʋmax 3342 and 3323 cm-1. The mass o his compound was de e mined using he HRESI-
QTOF-SM+ me hod. The HRESI-QTOF-SM+ mass spec um shows he peak o he pseudomolecula ion [M+H]+ a m/z
494.2713, co esponding o a molecula mass o 493.2635 g/mol. This alue is consis en wi h he molecula o mula
C26H39NO8 (calcula ed mass 493.2676). The agmen a ion pa e n o his molecule is ypical o di e penoid cassanes
and esembles hose o 3β-hyd oxy-3-me hyl-bu anoyloxy)-no -e y h osuamine and 3β-hyd oxy-3-me hyl-
bu anoyloxy-6α-hyd oxy-no -cassamine [11]. The di e ence wi h hese compounds is he loss o he ace a e agmen
(CH3-COO-; m/z 59 g/mol) in he o m o ace ic acid (CH3-COOH) obse ed a m/z 60 g/mol. The 1H and 13C NMR spec a
o compound 1, pe o med in deu e a ed me hanol, con i m he link be ween his compound and hose o 3β-hyd oxy-
3-me hyl-bu anoyloxy)-no -e y h osuamine and 3β-hyd oxy-3-me hyl-bu anoyloxy-6α-hyd oxy-no -cassamine [11].
Indeed, he e is a e y s ong esemblance be ween he spec a o hese h ee molecules. Howe e , on he p o on
spec um o compound 1, a single is obse ed a H 2.00 ppm, whe eas on hose o 3β-hyd oxy-3-me hyl-bu anoyloxy)-
GSC Biological and Pha maceu ical Sciences, 2025, 32(03), 314-321
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no -e y h osuamine and 3β-hyd oxy-3-me hyl-bu anoyloxy-6α-hyd oxy-no -cassamine, his single esona es a H
2.49 (s, 2H) and 2.45 (s, 2H) ppm, espec i ely. The HSQC spec um indica es ha he p o on a H 2.00 ppm (s, 3H) is
ca ied by he ca bon a δC 20.8 ppm. Also, he HMBC spec um da a allowed he ace oxy g oup (CH3COO) o be ixed in
he C-3 posi ion on he ca bon chain. Indeed, he ca bon a δC 172.1 ppm (C=O) co ela es in 2JCH wi h he p o on a H
2.00 ppm, and in 3JCH wi h he p o on a H 4.72 ppm (HC-OH; C-3). We also obse e co ela ions in 3JCH be ween he
ca bon a δC 77.0 ppm (HC-OH) and he p o ons a H 1.96 ppm (H-9) and 2.81 ppm (H-14). We can he e o e deduce
ha he seconda y alcohol a δC 77.0 ppm is in posi ion C-7. The ca bon o he ke one unc ion obse ed a δC 209.6 ppm
(C=O, ke one) co ela es in 2JCH wi h he p o ons a δH 2.75 ppm (H-5) and H 4.05 ppm (H-7). We can also deduce ha
he ke one unc ion is in posi ion C-6. Acco ding o he NOESY spec um, he p o on in posi ion (H-7) sees p o ons H-3,
H-5, H-9, and H-18, which a e behind he plane. Compa ing ou spec a wi h hose o his compound allowed us o
iden i y compound 1 as 3β-ace oxye y h osuamine (Figu e 1).
Table I p o ides in o ma ion on 1H and 13C NMR chemical shi s, COSY, NOESY, and HMBC co ela ions.
Table 1 1H and 13C NMR chemical shi (1D and 2D) o compound 1 (MeOD)
N° a om
13C (δ, ppm)
1H (δ, ppm ; m ; J, Hz)
COSY
HMBC
NOESY
1
37,2
1,51 ; 1H ; m
1,85 ; 1H ; m
H-2α
H-2β
C-3 ; C-9 ; C-20
-
-
-
2
24,9
1,69; 1H; m
2,21 ; 1H ; m
H-1α ; H-3α
H-1β ; H-3β
-
-
-
-
3
80,3
4,72 ; 1H ; dd (12,4 ;3,03)
H-2α
C-1 ; C-19 ; C25
-
4
43,3
-
-
-
-
5
65,0
2,75 ; 1H ; s
-
C-6; C9, C-19; C18 C-20
H-18
6
209,6
-
-
-
-
7
77,0
4,05 ; 1H ; d (11,4)
-
C-8; C14, C-6
H-17
8
52,1
1,84 ; 1H ; m
H-9
-
H-20
9
47,1
1,96 ; 1H ; m
H-8
C-20
-
10
37,2
-
-
-
-
11
27,7
1,12 ; 1H ; m
1,93 ; 1H ; m
H-12α
H-12β
-
C-12; C13
-
-
12
24,8
2,11 ; 1H ; m
3,31 ; 1H ; m
H-11α
H-11β
C-11; C-15
C-16
-
-
13
167,4
-
-
-
-
14
41,9
2,81 ; 1H ; m
H-17
C-8; C-15
H-15
15
113,1
5,81 ; 1H ; s
-
C-12; C-13; C-16
H-14
16
169,7
-
-
-
-
17
14,9
1,21 ; 3H ; d (6,8)
H-14
C-8; C-13
H-7
18
25,7
1,18 ; 3H; s
-
C-19; C-5; C-5; C-10
H-5
19
174,8
-
-
-
-
20
14,9
0,96; 3H; s
-
C-1; C-5; C-9; C-10
H-8
21
60,2
4,33 ; 2H ; m
H-22
C-16
-
22
49,6
3,28 ; 2H ; m
H-21
C-23
-
23
33,8
2,71 ; 3H ; s
-
C-21
-
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24
52,0
3,70 ; 3H ; s
-
C-19
-
26
172,1
-
-
-
-
26
20,8
2,00 ; 3H ; s
-
C-25
-
Figu e 1 S uc u e o 3β-acé oxyé y h osuamine
3.2. S uc u al elucida ion o compound 2
Compound 2 was ob ained as an amo phous solid, soluble in me hanol. I s IR spec um also indica es he p esence o
ca bonyl g oups (es e , ke one, and amide) as e idenced by abso p ion bands obse ed a ʋmax 3343, 3321, 1733, 1713,
1706, and 1670 cm⁻¹. The molecula mass o his compound was de e mined using high- esolu ion elec osp ay
ioniza ion in posi i e mode (HRESI-QTOF-SM+). The HRESI-QTOF-SM+ mass spec um shows he pseudo-molecula ion
[M+H]+ peak a m/z 552.3177, gi ing a molecula mass o 551.3099 g/mol. This alue co esponds o he molecula
o mula C29H45NO9 (calcula ed mass 551.3094).
The agmen a ion pa e n o compound 2 sugges s ha i is a cassane- ype di e penoid [16]. Some agmen s a e also
compa able o hose o 6α-hyd oxy-no cassamine [17]. Speci ically, he ion [(M+H)-75]+ obse ed a m/z 478.2111
co esponds o he loss o HO-CH2-CH2-NHCH3; he ion [(M+H)-75-118]+ obse ed a 360.1566 co esponds o he loss
o HO-CH2-CH2-NHCH3; he ion [(M+H)-75-118-60]+ obse ed a 300.1415 co esponds o he loss o CH3O-CO; and he
ion [(M+H)-31]+ obse ed a m/z 522.2316 co esponds o he loss o CH3-NH2 (Figu e 2).
Figu e 2 ESI-MS/MS mass spec um o 3β-hyd oxy-3-me hyl-bu anoyloxy-6α-hyd oxy-no -cassamine
GSC Biological and Pha maceu ical Sciences, 2025, 32(03), 314-321
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The agmen ha di e en ia es 6α-hyd oxy-no cassamine om compound 2 is he 3-hyd oxy-3-me hylbu anoa e
g oup (HO-C(CH3)2-CH2-COO-), which cap u es a p o on o o m 3-hyd oxy-3-me hylbu anoic acid (Figu e 3),
co esponding o he loss o a mass uni o 118 g/mol.
Figu e 3 Con e sion o he 3-hyd oxy-3-me hylbu anoa e ion o 3-hyd oxy-3-me hylbu anoic acid
The posi ioning o he 3-hyd oxy-3-me hylbu anoa e g oup on he ca bon skele on o compound 2 was de e mined
based on co ela ions obse ed in he HMBC spec um. In his spec um, he ca bonyl a δC 172.5 ppm shows a 3JCH
co ela ion wi h he p o on a δH 4.64 ppm (H-3), allowing i o be assigned o ca bon C-3 o he basic cassane- ype
di e penoid skele on. Rega ding he s e eochemical a angemen o his molecule, he NOESY spec um shows ha he
H-3 p o on is posi ioned behind he plane, as i co ela es wi h H-5, H-9, H-17, and H-18, which a e also behind he
plane. F om his, i is deduced ha he 3-hyd oxy-3-me hylbu anoic acid g oup (Figu e 3) is o ien ed in on o he
molecula plane. Based on he analyses abo e, compound 2 was o mally iden i ied as 3β-hyd oxy-3-
me hylbu anoyloxy-6α-hyd oxy-no -cassamine (Figu e 4). This molecule has p e iously been isola ed om he oo
ba k o E y h ophleum sua eolens [18]; howe e , his is he i s ime i has been iden i ied in he unk ba k o his plan .
Figu e 4 S uc u e de la 3β-hyd oxy-3-mé hyl-bu anoyloxy-6α-hyd oxy-no -cassamine
We ha e hus p oposed a agmen a ion scheme wi h he majo agmen s obse ed a m/z 553.3247, 522.2316,
478.2111, 360.1566, and 300.1415 (Figu e 5).
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Figu e 5 F agmen a ion pa e n o 3β-hyd oxy-3-me hyl-bu anoyloxy-6α-hyd oxy-no -cassamine
4. Discussion
The s uc u es isola ed in his s udy, namely 3β-ace oxy-e y h osuamine and 3β-hyd oxy-3-me hylbu anoyloxy-6α-
hyd oxy-no -cassamine, a e cassane- ype di e penoids wi h an amine unc ion. Bo h molecules ha e p e iously been
epo ed om he oo ba k o E. sua eolens. Se e al cassane- ype di e penoids wi h an amine unc ion, such as 6α-
hyd oxy-no -cassamine o 8,9-dehyd o-no -cassamine [1], show simila i ies wi h compound 2 isola ed in his s udy (3β-
hyd oxy-3-me hylbu anoyloxy-6α-hyd oxy-no -cassamine), pa icula ly ega ding he no -cassamine skele on.
Likewise, he wo k o Konan e al. [11] epo ed new cassane- ype amine de i a i es bea ing “3-hyd oxy-3-
me hylbu anoyloxy” g oups, which u he links compound 2 om ou s udy o hese cases.
Al hough nume ous cassane di e penoids ha e been desc ibed, hese wo compounds exhibi pa icula subs i u ions:
an ace oxy g oup in he i s case, and a 3-me hylbu anoyloxy g oup plus a 6α-hyd oxy g oup in he second. These
modi ica ions can s ongly in luence pola i y, chemical s abili y, and po en ially biological p ope ies (a ini y, ac i i y,
oxici y). These compounds could be good candida es o biological ac i i y s udies (an ioxidan , an i-in lamma o y,
cy o oxic). Indeed, some cassane- ype di e penoids wi h amide o hyd oxyl unc ions om E. sua eolens epo ed by
Konan e al. [11] ha e shown signi ican an ioxidan capaci ies. I would be in e es ing o e alua e he compounds
isola ed in his s udy in simila es s, o o he s, o assess he in luence o hese speci ic subs i u ions (ace oxy s. hyd oxy
+ bulky es e ) on ac i i y.
5. Conclusion
This s udy allowed he isola ion om he unk ba k o E y h ophleum sua eolens o wo cassane- ype di e penoids
newly cha ac e ized in he con ex o unk ba k: 3β-ace oxy-e y h osuamine and 3β-hyd oxy-3-me hylbu anoyloxy-
6α-hyd oxy-no -cassamine. These molecules en ich he chemical epe oi e o he species, pa icula ly ega ding
es e i ied and hyd oxyla ed subs i uen s. Thei disco e y pa es he way o u u e biological in es iga ions o explo e
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321
hei pha macological po en ial. Fo u u e s udies, i is ecommended o e alua e hei biological ac i i y and, i
possible, o syn hesize de i a i es o es ablish s uc u e-ac i i y ela ionships.
Compliance wi h e hical s anda ds
Disclosu e o con lic o in e es
Au ho s decla e ha he e a e no con lic s o in e es .
Re e ences
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