Rev. bras. farmacogn. vol.27 número4

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w ww.e l s e v i e r . c o m / l o c a t e / b j p

Original

Article

Chemical

composition

of

the

leaf

oil

of

Artabotrys

jollyanus

from

Côte

d’Ivoire

Stéphane

G. Gooré

a,c

,

Zana

A. Ouattara

a

,

Acafou

T. Yapi

b

,

Yves-Alain

Békro

a

,

Ange

Bighelli

c

,

Mathieu

Paoli

c

_,

_Felix

_Tomi

c,∗

a_Laboratoire_de_Chimie_BioOrganique_et_de_Substances_Naturelles,_Université_Nangui_Abrogoua,_Abidjan,_Côte_d’Ivoire b_Laboratoire_de_Chimie_Organique_Biologique,_Université_Félix_Houphouët_Boigny,_Abidjan,_Côte_d’Ivoire

c_Université_de_Corse-Centre_National_de_la_Recherche_{Scientifique,}_Unité_Mixte_de_Recherche_6134,_Equipe_Chimie_et_Biomasse,_Ajaccio,_France

a

r

t

i

c

l

e

i

n

f

o

Articlehistory:

Received29September2016 Accepted3April2017 Availableonline2May2017

Keywords:

7-Hydroxycalamenene Essentialoil Côted’Ivoire

13_C_NMR

Sesquiterpenes

a

b

s

t

r

a

c

t

OneoilsampleisolatedfromleavesofArtabotrysjollyanusPierre,Annonaceae,fromCôted’Ivoirehas beenanalyzedbyGC(RI),GC-MSand13_C_NMR._In_total,_thirty-seven_compounds_accounting_for_96.9%

oftherelativecompositionhavebeenidentified.Thecompositionoftheessentialoilwasdominated bytrans-calamenene(15.7%),␣-copaene(14.8%),␣-cubebene(10.4%),cadina-3,5-diene(10.3%),(E

)-␤-caryophyllene(6.3%)andcadina-1,4-diene (6.1%). 13_C_NMR_spectroscopy_was _very_useful _in_the

identificationoftrans-calamenene,7-hydroxycalamenene,cadina-3,5-dieneandcadina-1,4-diene. More-over,monitoringtheevolutionoftheleafessentialoilcompositionandtheyieldona12-monthperiod (onesamplepermonth)wasachieved.Thetwelveessentialoilsamplesexhibitedachemicalhomogeneity buttheyieldvariedfromsampletosample(0.26–0.60%).

Introduction

Generallydistributedintropicalandsubtropicalregions,mainly intropical Africaand EasternAsia,thegenus Artabotrys, family Annonaceae,containsmorethan100species(Sagenetal.,2003).In Côted’Ivoire,fivespeciesgrowwildindenserainforests,namely ArtabotryshispidusSprague&Hutch.,A.insignisEngler&Diels,A. jollyanusPierre,A. oliganthus Engler&Diels andA. velutinus Sc. Elliot.Theyareeitherclimbingand evergreenshrubs orwoody lianas.

Artabotrysjollyanusisaclimbingshrubwithpersistentelliptic

oblongleaves,15–21cminlength,7–9cmwidth.Thelimbbaseis roundedtocuneateanditsapexacuminate.Flowerpetalsare ellip-tical(25mminlength),groupedindenseaxillaryinflorescences (http://www.plantes-botanique.org).

Ethnomedicinaluses ofspecies ofthegenus Artabotryshave beenreviewed(TanandWiart,2014).Numerouspapersreported onthephytochemistryofthisgenusandhighlightedthepresence ofalkaloidsinA.uncinatus(Lam.)Merr.(Hsiehetal.,1999),A. cras-sifoliusHook.f.&Thomson(Tanetal.,2015),A.hexapetalus(L.f.) Bhandare(Zhouetal.,2015),A.odoratissimusR.Br.(Kabir,2010),or

∗ Correspondingauthor.

E-mail:[email protected](F.Tomi).

polyphenolsinA.hildebrandtiiO.Hffm.(Andriamadioaetal.,2015), A.hexapetalus(Lietal.,1997;Somanawatetal.,2012).Concerning thechemicalcompositionofessentialoilsmorethanfifteenspecies havebeeninvestigated(Hungetal.,2014)andsesquiterpeneswere oftenthemajorcomponents(Menutetal.,1992;Fournieretal., 1999;Thangetal.,2014).Toourknowledgenoinvestigationshave beenundertakentodateonthechemicalcompositionofA.jollyanus essentialoil.

Incontinuationofouron-goingworkrelatedtothe characteriza-tionofaromaticandmedicinalAnnonaceaefromCôted’Ivoire(Yapi etal.,2012,2013,2014;Ouattaraetal.,2011;Ouattaraetal.,2013, 2014)thechemicalcompositionoftheessentialoilisolatedfrom leavesofA.jollyanushasbeeninvestigatedbycombinationof chro-matographic[GC-FID,GC(RI)]andspectroscopictechniques(MS,

13_C_NMR)._Firstly,_we_report_the_detailed_leaf_essential_oil

compo-sitionofaselectedsample.Secondly,thetemporalvariationofleaf oilcompositionwasstudiedbyanalyzingelevenotherleafsamples collectedalongthevegetativecycle.

Materialsandmethods

Plantmaterial

LeavesfromArtabotrysjollyanusPierre,Annonaceae,havebeen harvested(April2014-March2015)intheAdiopodouméforest

http://dx.doi.org/10.1016/j.bjp.2017.04.001

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Adiopodoumé

Abidjan

Fig.1.LocalityofharvestofleavesofA.jollyanusfromCôted’Ivoire.

onAbidjan-Dabou axis(southern Côted’Ivoire, 5◦₁₉′_50.074′′ _N,

4◦₇′_41.109′′_O,_Fig.₁_)._The_plant_species_was_identified_by_M._Assi

Jean,technicianattheHerbariumoftheCentreNationalof Floris-tique(Félix Houphouët-Boigny University, Abidjan-Cocody/Côte d’Ivoire)wherevoucherspecimenwasdepositedwithnumberLAA 7650.

Essentialoilisolation

Essentialoil(EO)sampleswereobtainedbyhydrodistillation fromthefreshleaves(300g)withaClevenger-typeapparatusfor aperiodof3.5h;theessentialoils(S1-S12)weredriedover anhy-droussodiumsulphate(Na2SO4),andthenstoredinafreezeruntil

analysis.Theyields,calculatedonthefreshweightbasis(w/w), werecomprisedbetween0.26%and 0.60%.Alloilsampleswere lightyellowcoloured.

Gaschromatography(GC)analyses

Analyses were performed on a Clarus 500 PerkinElmer (PerkinElmer,Courtaboeuf,France)systemequippedwithaFIDand twofused-silicacapillarycolumns(50m×0.22mm,filmthickness

0.25␮m),BP-1 (polydimethylsiloxane)andBP-20 (polyethylene glycol).The oven temperature wasprogrammed from 60◦_C _to

220◦_C_at₂◦_C/min_and_then_held_isothermal_at₂₂₀◦_C_for₂₀_min;

injectortemperature:250◦_C;_detector_temperature:₂₅₀◦_C;

car-riergas:helium(0.8ml/min);split:1/60;injectedvolume:0.5␮l. Therelativeproportionsoftheoilconstituentswereexpressedas percentagesobtainedbypeak-areanormalization,withoutusing correctionfactors.Retentionindices(RI)weredeterminedrelative totheretentiontimesofaseriesofn-alkanes(C7-C28)withlinear interpolation(TargetCompoundssoftwarefromPerkinElmer).

Gaschromatography–massspectroscopy(GC/MS)analyses

TheessentialoilswereanalyzedwithaPerkin-ElmerTurboMass detector(quadrupole),directlycoupledtoaPerkin-Elmer Autosys-temequippedwithafused-silicacapillarycolumn(50m×0.22mm

i.d.,filmthickness0.25␮m),BP-1(dimethylpolysiloxane).Carrier gas,helium at0.8ml/min;split, 1/60; injectionvolume, 0.5␮l; injectortemperature,250◦_C;_oven_temperature_programmed_from

60◦_C_to₂₂₀◦_C_at₂◦_C/min_and_then_held_isothermal₍₂₀_min);_Ion

sourcetemperature,250◦_C;_energy_ionization,₇₀_eV;_electron

ion-izationmassspectrawereacquiredoverthemassrange40–400Da.

13_C_NMR_analyses

13_C_NMR _analysis_were_performed_on_a_Bruker_AVANCE ₄₀₀

FourierTransformspectrometeroperatingat100.63MHzfor13_C,

equippedwitha5mmprobe,indeuteratedchloroform(CDCl3),

withall shiftsreferred to internaltetramethylsilane (TMS).13_C

NMRspectrawererecordedwiththefollowingparameters:pulse width(PW),5␮s(flipangle45◦_);_acquisition_time,_2.7_s_for₁₂₈_K

datatablewithaspectralwidth(SW)of25,000Hz(250ppm); dig-italresolution0.183Hz/pt.Thenumberofaccumulatedscanswas 2500for each sample(about 50mgof essential oilin0.5mlof CDCl3).

Identificationofindividualcomponents

Componentidentificationwasbasedon:(a)comparisonoftheir GCretentionindices(RI)onpolarandapolarcolumnsdetermined relativetotheretentiontimesofaseriesofn-alkaneswithlinear interpolationwiththoseofauthenticcompoundsorliteraturedata; (b)oncomputermatchingwithlaboratory-madeandcommercial massspectrallibraries(Königetal.,2001;Adams,2007;USNational InstituteofStandardsandTechnology,1999);and(c)on compari-sonofthesignalsinthe13_C_NMR_spectra_of_essential_oils_with_those

ofreferencespectracompiledinthelaboratoryspectrallibrarywith thehelpoflaboratory-developedsoftware(Ouattaraetal.,2014). Indeedthe13_C_NMR_spectrum_of_a_molecule_may_be_considered_as

itsfingerprint.Inotherwords,twocompounds,suchas sesquiter-penes,exhibitalwaysenoughchemicalshiftvaluesoftheircarbons sufficientlydifferentiatedtoallowtheiridentification.Therefore, takingintoaccountvariousparameters(thenumberofobserved signals,thenumberofoverlappedsignals,thedifferenceof chemi-calshiftmeasuredinthemixtureandinthereferencespectra)the identificationofanindividualcomponentofacomplexmixtureis possiblewithoutindividualizationofthecompound(Bighelliand Casanova,2010).

Resultsanddiscussion

Detailed analysis of a leaf oilsample (S4) from A. jollyanus hasbeencarriedoutbyGC(RI),GC–MSand13_C_NMR._In_total,₃₇

compounds(12monoterpenes,5.2%and25sesquiterpenes91.7%) that accounted for 96.9% of thewhole composition, have been identifiedinthesample(Table1,Fig.2).Themajorcomponents weresesquiterpenes,particularlysesquiterpenehydrocarbons.It couldbehighlighted that thefivemain componentsaccounted only for 10–16% each: trans-calamenene (15.7%), ␣-copaene (14.8%), ␣-cubebene (10.4%), cadina-3,5-diene (10.3%) and 7-hydroxycalamenene (10.1%). Other sesquiterpenes present at significant levels were (E)-␤-caryophyllene (6.3%), cadina-1,4-diene(6.1%),␤-cubebene(3.1%),␣-humulene(3.0%),␦-cadinene (1.9%)bicyclosesquiphellandrene(1.8%),bicyclogermacrene(1.5%) and spathulenol (1.1%). Finally, the monoterpene fraction was mostlyrepresentedby(Z)-␤-ocimene(3.6%).Theother hydrocar-bonmonoterpeneswerepresentatverylowlevelsnotexceeding 0.5%.

Identificationofsomecomponentsneededspecialattention:

-Calamenenestereoisomers(cisortrans)displayoverlappedpeaks on apolar and polar capillary chromatography columns (RIa: 1509;RIp:1829)andinsufficientlydifferentiatedmassspectra (JoulainandKönig,1998).Therefore,identificationofthecorrect isomerwasachievedby13_C_NMR_analysis,_the_spectra_of_both

compoundsbeingfullydifferentiated(Nakashimaetal.,2002). -Cadina-1,4-diene(6.1%)andcadina-3,5-diene(10.3%)were

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Table1

ChemicalcompositionofArtabotrysjollyanusleafoil.

Componentsa _RIlitb _RIa _RIp _A._jollyanus _{Identification}

1 ␣-Pinene 936 929 1015 0.3 RI,MS

2 Camphene 950 942 1065 tr RI,MS

3 Sabinene 973 964 1123 tr RI,MS

4 ␤-Pinene 978 969 1112 tr RI,MS

5 Myrcene 987 979 1160 0.2 RI,MS

6 Limonene 1025 1019 1201 0.2 RI,MS

7 ␤-Phellandrene 1023 1019 1211 0.4 RI,MS

8 (Z)-␤-Ocimene 1029 1024 1233 3.6 RI,MS,13_C_NMR

9 (E)-␤-Ocimene 1041 1035 1250 0.4 RI,MS,13_C_NMR

10 Terpinolene 1082 1077 1283 tr RI,MS

11 Linalool 1086 1082 1545 tr RI,MS

12 allo-Ocimene 1113 1116 1372 0.1 RI,MS

13 ␣-Cubebene 1355 1348 1456 10.4 RI,MS,13_C_NMR

14 ␣-Copaene 1379 1375 1490 14.8 RI,MS,13_C_NMR

15 ␤-cubebene* 1390 1385 1535 3.1 RI,MS

16 ␤-Elemene* 1389 1385 1587 0.5 RI,MS,13_C_NMR

17 ␣-Gurjunene 1413 1408 1525 0.2 RI,MS

18 (E)-␤-Caryophyllene 1421 1416 1593 6.3 RI,MS,13_C_NMR

19 Cadina-3,5-diene 1448 1444 1627 10.3 RI,MS,13_C_NMR

20 ␣-Humulene 1455 1448 1665 3.0 RI,MS,13_C_NMR

21 allo-Aromadendrene 1462 1456 1640 0.3 RI,MS

22 Cadina-1(6),11-diene - 1466 1655 0.8 RI,MS,13_C_NMR

23 GermacreneD 1479 1474 1704 0.4 RI,MS,13_C_NMR

24 Bicyclosesquiphellandrene 1487 1483 1708 1.8 RI,MS,13_C_NMR

25 4-epi-Cubebol 1490 1485 1883 0.8 RI,MS,13_C_NMR

26 Bicyclogermacrene 1494 1489 1728 1.5 RI,MS,13_C_NMR

27 ␣-Muurolene 1496 1491 1719 0.2 RI,MS

28 Cubebol 1514 1504 1935 0.8 RI,MS,13_C_NMR

29 trans-Calamenene 1517 1509 1829 15.7 RI,MS,13_C_NMR

30 ␦-Cadinene 1520 1513 1751 1.9 RI,MS,13_C_NMR

31 Zonarene 1521 1515 1752 0.4 RI,MS

32 Cadina-1,4-diene 1523 1523 1777 6.1 RI,MS,13_C_NMR

33 Spathulenol 1572 1561 2117 1.1 RI,MS,13_C_NMR

34 Caryophylleneoxide 1578 1567 1976 0.2 RI,MS

35 epi-Cubenol 1623 1612 2058 0.4 RI,MS

36 Cubenol 1630 1628 2051 0.7 RI,MS

37 7-Hydroxycalamenene 1803c ₁₇₇₅ ₂₇₈₃ _10.1 _RI,_MS,13_C_NMR

Total 96.9

Monoterpenehydrocarbons 5.2

Oxygenatedmonoterpenes tr

Sesquiterpeneshydrocarbons 77.7

Oxygenatedsesquiterpenes 14.0

a_Order_of_elution_and_contents_determined_on_the_apolar_column_(BP-1),_except_for_compounds_with_an_asterisk,_percentages_on_polar_column_(BP_20)._RIa,_RIp₌_retention

indicesmeasuredonapolar(BP1)andpolar(BP20)column;tr=tracelevel(<0.05%).

b _Literature_indices_on_a_DB-1₍_{http://massfinder.com}_by_Hochmuth,₂₀₁₇_). c _Indice_on_a_HP-5_column₍_Azevedo_et_al.,₂₀₁₄_).

chemicalshiftswiththosereportedintheliterature(Joulainand König,1998);

-7-Hydroxycalamenene(10.1%). TheMS spectrumof this com-poundwasnotcompiledinMSlibrariesatourdisposalandinour home-madeMSlibrary.Thecompoundwasidentifiedby com-parisonofits13_C_NMR_chemical_shifts_with_those_reported_in_the

literature(Cambieetal.,1990).

ThechemicalcompositionofA.jollyanusleafoildifferedfrom that of Ivoirian A. oliganthus leaf oil, dominated by monoter-penes(␦-3-carene,60.2%,myrcene,10.6%)(Ouattaraetal.,2011).It differedfromthoseofbarkoilsfromGaboneseArtabotrys lastourvil-lensisPell(cyperene,25.9%;cyperenone,11.1%)(Menutetal.,1992) andfromBenineseArtabotrysvelutinus(benzylbenzoate,61.2%; (E)-␤-caryophyllene,9.1%)(Yovoetal.,2016).Itdifferedalsofrom thoseofEOsisolatedfromArtabotrysspeciesgrowninotherareas oftheworld.Forinstance,thecompositionsofVietnamesespecies were mostly dominated by various sesquiterpenes: A. petelotti Merr.leafoil(elemol,19.4%,cis-␤-guaiene,9.2%,␦-cadinene,8.4%);

A. intermedius Hassk. leaf oil (␦-3-carene, 19.1%; ␣-gurjunene;

10.7%;␣-zingiberene,6.3%);A.harmandiiFinet&Gagnep. (spathu-lenol, 17.4%; aromadendrene epoxide, 12.2%; ␥-elemene, 7.1%;

␤-elemene,5.0%; bicyclogermacrene, 5.0%)(Hung et al.,2014);

A.taynguyenensisBanleafoil(valencene,40.1%;␦-selinene,8.8%;

␣-pinene,6.7%;␣-muurolene,5.1%;␣-panasinsene,5.1%)(Thang etal.,2014).ThefloweroilofVietnameseA.hexapetaluscontained mainlycaryophylleneoxide,31.5%;␤-caryophyllene,11.4%; humu-leneepoxide,10.0%and␣-copaene,8.1%(Phanetal.,2007).

The monitoring of the temporal evolution of the yield and the chemical composition of the leaf EO from A. jollyanus has beenachieved over a periodof 12 months,from April2014to March2015(Table2).Yieldsvariedsubstantiallyfrom0.26%to 0.60%(meanvalue=0.40%).Threedomainsmaybedistinguished. Higher yield has been observed in September (0.60%), during thedry period.Acceptableyields(0.39–0.52%,7oilsamplesout of12)occurredintheperiodJune-November andlowestyields (0.26–0.32%,4samplesoutof12)havebeenobtainedinMayon theonehandandduringtheperiodDecember-Marchontheother hand.

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90

80

70

60

50

40

30

20

10

0

15 20 25 30 35 40 45 50 55 60 65 70

1 ₅

6 + 7 8

9

10 12

15

16 +

18

20

17 22

24 26

32 13

19 14

29

33 3536

37

21 23 30 34

Fig.2. Gaschromatogramonapolarcolumn(BP-1)ofleafsampleofArtabotrysjollyanusessentialoil.

Table2

ChemicalcompositionofArtabotrysjollyanusleafoil:maincomponentsoftwelvesamples.

Sample S1 S2 S3 S4a _S5 _S6 _S7 _S8 _S9 _S10 _S11 _S12

Month Apr May Jun Jul Aug Sept Oct Nov Dec Jan Feb Mar

Components

(Z)-␤-Ocimene 5.5 5.3 5.3 3.6 4.7 3.4 4.6 3.4 5.5 3.5 4.6 2.4

␣-Cubebene 10.7 9.2 10.6 10.4 10.7 11.0 8.8 9.7 14.5 12.9 8.8 10.2

␣-Copaene 14.7 12.4 14.8 14.8 15.7 16.4 12.7 14.3 20.4 18.8 12.3 14.6

␤-Cubebene 2.7 2.1 3.2 3.1 3.1 3.2 2.7 3.1 2.5 1.4 3.2 2.3

(E)-␤-Caryophyllene 8.0 7.9 7.1 6.3 6.6 6.6 6.8 6.7 7.7 7.1 6.5 5.7

Cadina-3,5-diene 7.3 4.6 9.2 10.3 10.2 10.6 9.3 10.8 7.6 8.0 11.0 0.4

␣-Humulene 3.5 3.6 3.2 3.0 3.1 3.0 3.4 3.2 3.2 3.1 3.3 2.9

trans-Calamenene 18.6 22.4 16.4 15.7 16.5 16.3 16.6 16.4 17.8 18.7 14.7 27.6

Cadina-1,4-diene 6.0 5.2 6.0 6.1 5.8 5.8 5.6 6.1 4.5 6.0 6.4 2.9

Spathulenol 1.4 1.9 1.1 1.1 1.0 0.9 1.3 1.1 1.0 0.8 0.8 2.4

7-Hydroxycalamenene 4.8 6.5 7.6 10.1 7.0 7.9 10.4 9.1 1.3 4.9 10.5 10.4

Yield 0.39 0.26 0.48 0.40 0.42 0.60 0.45 0.52 0.28 0.32 0.39 0.32

a_S4_is_previously_described_in_Table₁

␣-copaene(meanvalue=15.2%)displayedmorediversecontents (12.3–12.7%,3samples;14.3–14.8%,5samples;15.7–20.4%,4 sam-ples).The contentof 7-hydroxycalamenene (meanvalue=7.5%) seemedtovarydrasticallyfrom1.3%to10.5%.Infact,thecontents offoursamples(6.5–7.9%)wereveryclosetothemeanvalue,five samplesdisplayedhighercontents(9.1–10.5%),twosamples exhib-itedlowercontents(4.8and4.9%)andthelastsampleaccounted for1.3%only.Finally,thecontentofcadina-3,5-dienevariedfrom 7.3%to11.0%fortensamples,whileitwasonly4.6%foronesample and0.4%forthelastone.Similarly,thecontentofcadina-1,4-diene variedfrom5.2%to6.4%fortensamples,whileitwasonly4.5%and 2.9%forthetwolastones.

Itisnoticeablethatthesumofpercentagesofcadina-1,4-diene, cadina-3,5-diene, trans-calamenene and 7-hydroxy-calamenene were constant in all samples and close to 39%. Indeed,

trans-calamenenemaybeobtainedbydeshydrogenationof

cadina-1,4-dieneandcadina-3,5-diene.Then,7-hydroxy-calamenenewas synthetizedbyhydroxylationoftrans-calamenene.Theseresults areinagreementwiththeproposedpathwayforthebiosynthesis ofthymolfrom␥-terpineneviap-cymene(PouloseandCroteau, 1978).

Conclusion

The chemical composition of A. jollyanus leaf essential oil was reportedfor thefirst time. The essential oilfrom Ivoirian speciesexhibitedoriginalcompositiondominatedbyhydrocarbon sesquiterpenes,mostlytrans-calamenene,␣-copaene,␤-cubebene, cadina-3,5-diene, accompanied by 7-hydroxycalamenene. The compositionoftheEOremaineddominatedbythesame sesquiter-penes during its phenological cycle of the plant, although the contentofsomecomponentsvariedsubstantially.

Authors’contributions

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Conflictsofinterest

Theauthorsdeclarenoconflictsofinterest.

Acknowledgments

TheauthorsaregratefultotheCASES,(NGO)forfinancial sup-port.TheyareindebtedtoDrM.Gibernauforbotanicaladvices.

References

Adams,R.P.,2007.IdentificationofEssentialOilComponentsbyGas Chromatogra-phy/MassSpectrometry,4thed.AlluredPubl.Corp.,CarolStream,IL,USA. Andriamadioa,J.H.,Rasoanaivo,L.H.,Benedec,D.,Vlase,L.,Gheldiu,A.M.,Duma,

M.,Toiu,A.,Raharisololalao,A.,Oniga,I.,2015.HPLC/MSanalysisof polyphe-nols,antioxidantandantimicrobialactivitiesofArtabotryshildebrandtiiOHffm. extracts.Nat.Prod.Res.29,2188–2196.

Azevedo,M.M.B.,Almeida,C.A.,Chaves,F.C.M.,Campos-Talaki,G.M.,Rozental,S., Bizzo,H.R.,Alviano,C.S.,Alviano,D.S.,2014.Effectsof7-hydroxycalamene isolatedfromCrotoncajucaraessentialoilofgrowth,lipidcontentand ultra-structuralanalysisaspectsofRhizotusoryzae.PlantaMed.80,550–556. Bighelli,A.,Casanova,J.,2010.Essentialoil-bearinggrasses,thegenusCymbopogon.

A.Akhilaed.CRCPress,BocaRaton,FL,USA.

Cambie,R.C.,Lal,A.R.,Ahmad,F.,1990.SesquiterpenesfromHeritieraornithocephala. Phytochemistry29,2329–2331.

Fournier,G.,Leboeuf,M.,Cavé,A.,1999.Annonaceaeessentialoils:areview.J.Essent. OilRes.11,131–142.

Hsieh,T.J.,Chen,C.Y.,Kuo,R.Y.,Chang,F.R.,Wu,Y.C.,1999.Twonewalkaloidsfrom Artabotrysuncinatus.J.Nat.Prod.62,1192–1193.

Hung,N.H.,Dai,D.N.,Dung,D.M.,Giang,T.T.B.,Thang,T.D.,Ogunwande,I.A.,2014. ChemicalcompositionofessentialoilsofArtabotryspetelotiiMerr.,Artabotrys intermediusHassk.,andArtabotrysharmandiiFinet&Gagnep.(Annonaceae)from Vietnam.J.Essent.OilBear.Pl.17,1105–1111.

Hochmuth,D.,http://massfinder.com/wiki/TerpenoidsLibrary.TerpenoidsLibrary Website.

http://www.plantes-botanique.org,accessedAug2016.

Joulain,D.,König,W.A.,1998.Theatlasofspectradataofsesquiterpene hydrocar-bons.E.B.-VerlagHamburg.

Kabir,K.E.,2010.LarvicidaleffectofanalkaloidalfractionofArtabotrysodoratissimus (Annonaceae)barkagainstthefilarialmosquitoCulexquinquefasciatus(Diptera: Culicidae).Int.J.Trop.InsectSci.30,167–169.

König,W.A.,Hochmuth,D.H.,Joulain,D.,2001.Terpenoidsandrelatedconstituents ofessentialoils,LibraryofMassfinder2.1.UniversityofHamburg.

Li,T.M.,Li,W.K.,Yu,J.G.,1997.FlavonoidsfromArtabotryshexapetalus. Phytochem-istry45,831–833.

Menut,C.,Lamaty,G.,Bessiere,J.-M.,Mve-Mba,C.E.,Affane-Nguema,J.-P.,1992. AromaticplantsoftropicalcentralAfrica,VI.TheessentialoilofArtabotrys lastourvillensisPell,fromGabon.J.Essent.Oil.Res.4,305–307.

Nakashima,K.,Imoto,M.,Sono,M.,Tori,M.,Nagashima,F.,Asakawa,Y.,2002.Total synthesisof(−)-(7S,10R)-calameneneand(-)-(7S,10R)-2-hydroxycalamenene byuseofaring-closingmetathesisreaction.Acomparisonofthecis-and trans-isomers.Molecules7,517–527.

Ouattara,Z.A.,Boti,J.B.,Ahibo,A.C.,Tomi,F.,Bighelli,A.,2011.Artabotrysoliganthus Engl.&DielsfromIvoryCoast:compositionofleaf,stembarkandfruitoils.J. Essent.OilBear.Pl.14,95–100.

Ouattara,Z.A.,Boti,J.B.,Ahibo,A.C.,Tomi,F.,Casanova,J.,Bighelli,A.,2013. Com-binedanalysisoftherootbarkoilofCleistopholisglaucabychromatographic andspectroscopictechniques.Nat.Prod.Commun.8,1773–1776.

Ouattara,Z.A.,Boti,J.B.,Ahibo,A.C.,Sutour,S.,Casanova,J.,Tomi,F.,Bighelli,A.,2014. Thekeyroleof13_C_NMR_analysis_in_the_{identification}_of_individual_components ofPolyalthialongifolialeafoil.Flav.Fragr.J.29,371–379.

Phan,G.M.,Phan,S.T.,König,W.A.,2007.Chemicalcompositionoftheflower essen-tialoilofArtabotryshexapetalus(L.f.)BhandareofVietnam.J.Essent.OilRes.19, 523–524.

Poulose,A.J.,Croteau,R.,1978.Biosynthesisofaromaticsmonoterpenes-Conversion of␥-terpinenetop-cymeneandthymolinThymusvulgarisL.Arch.Biochem. Biophys.187,307–314.

Sagen,A.L.,Sahpaz,S.,Mavi,S.,Hostettmann,K.,2003.Isoquinolinealkaloidsfrom ArtabotrysBrachypetalus.Biochem.Syst.Ecol.31,1447–1449.

Somanawat,J.,Talangsri,N.,Deepolngam,S.,Kaewamatawong,R.,2012.Flavonoid andmegastigmaneglycosidesfromArtabotryshexapetalusleaves.Biochem.Syst. Ecol.44,124–127.

Tan,K.K.,Wiart,C.,2014.Botanicaldescriptions,ethnomedicinalandnon-medicinal usesofthegenusArtabotrysR.BR.Int.J.Curr.Pharm.Res.6,34–40.

Tan,K.K.,Khoo,T.J.,Rajagopal,M.,Wiart,C.,2015.Antibacterialalkaloidsfrom ArtabotryscrassifoliusHook.f.&Thomson.Nat.Prod.Res.29,2346–2349. Thang,T.D.,Dai,D.N.,Thanh,B.V.,Dung,D.M.,Ogunwande,I.A.,2014.Studyonthe

chemicalconstituentsofessentialoilsoftwoAnnonaceaeplantsfromVietnam: MiliusasinensisandArtabotrystaynguyenensis.Am.J.Essent.Oil.Nat.Prod.1, 24–28.

USNationalInstituteofStandardsandTechnology,1999.PCVersion1.7ofthe NIST/EPA/NIHMassSpectraLibrary,Norwalk,CT,USA.

Yapi,A.T.,Boti,J.B.,Attioua,B.K.,Ahibo,C.A.,Bighelli,A.,Casanova,J.,Tomi,F.,2012. ThreenewnaturalcompoundsfromtherootbarkessentialoilfromXylopia aethiopica.Phytochem.Anal.23,651–656.

Yapi,A.T.,Boti,J.B.,Ahibo,C.A.,Bighelli,A.,Casanova,J.,Tomi,F.,2013.Combined analysisofXylopiarubescensOliv.leafoilbyGC-FID,GC-MSand13CNMR: structureelucidationofnewcompounds.FlavourFrag.J.28,373–379. Yapi,A.T.,Boti,J.B.,Tonzibo,Z.F.,Ahibo,C.A.,Bighelli,A.,Casanova,J.,Tomi,F.,2014.

ChemicalVariabilityofXylopiaquintasiiEngler&DielsLeafOilfromCôted’Ivoire. Chem.Biodivers.11,332–339.

Yovo,M.,Alitonou,G.A.,Yedomonhan,H.,Tchobo,F.,Dedome,O.,Sessou,P.,Avlessi, F.,Menu,C.,Sohounhloué,D.,2016.Firstreportonchemicalcompositionand antimicrobialactivityofArtabotrysvelutinusScott-Elliotextractsagainstsome clinicalstrainsinBenin.Am.J.Appl.Chem.4,71–76.