Antioxidant Activity of Myrtus communis L. and Myrtus nivellei Batt. & Trab. Extracts

68 Pages·2017·0.63 MB·English

medicines
Review
Antioxidant Activity of Myrtus communis L. and
Myrtus nivellei Batt. & Trab. Extracts: A Brief Review
AichaHennia1,MariaGraçaMiguel2,* ID andSaidNemmiche3
1 DepartmentofAgronomy,FacultyofNatureandLifeSciences,UniversityofMostaganem,BP188/227,
Mostaganem27000,Algeria;[email protected]
2 DepartamentodeQuímicaeFarmácia,FaculdadedeCiênciaseTecnologia,UniversidadedoAlgarve,
MeditBio,CampusdeGambelas,8005-139Faro,Portugal
3 DepartmentofBiology,FacultyofNatureandLifeSciences,UniversityofMostaganem,BP188/227,
Mostaganem27000,Algeria;[email protected]
* Correspondence:[email protected];Tel.:[phone]
(cid:1)(cid:2)(cid:3)(cid:1)(cid:4)(cid:5)(cid:6)(cid:7)(cid:8)(cid:1)
(cid:1)(cid:2)(cid:3)(cid:4)(cid:5)(cid:6)(cid:7)
Received:30June2018;Accepted:8August2018;Published:11August2018
Abstract: Myrtus communis L. (myrtle) and Myrtus nivellei Batt. & Trab. (Saharan myrtle) have
been used in folk medicine for alleviating some ailments. M. communis is largely distributed in
the Mediterranean Basin, whereas M. nivellei is confined in specific zones of the central Saharan
mountains. Thechemicalcompositionandantioxidantactivityofberryandleafextractsisolated
from myrtle are deeply documented, whereas those isolated from Saharan myrtle extracts are
less studied. In both species, the major groups of constituents include gallic acid derivatives,
flavonols,flavonolderivatives,andhydroxybenzoicacids. Incolouredberries,anthocyaninsarealso
present. InM.nivelleiextractsarereportedforsomecompoundsnotdescribedinM.communisso
far: 2-hydroxy-1,8-cineole-β-D-glucopyranoside,2-hydroxy-1,8-cineole2-O-α-L-arabinofuranosyl
(1→6)-β-D-glucopyranoside,rugosinA,andrugosinB.Berriesandleavesextractsofbothspecies
had antioxidant activity. Comparative studies of the antioxidant activity between leaf and berry
myrtleextractsrevealedthatleafextractsarebestantioxidants,whichcanbeassignedtothegalloyl
derivatives,flavonols,andflavonolsderivatives,althoughtheratioofthesegroupsofcompounds
mightalsohaveanimportantroleintheantioxidantactivity. Theanthocyaninspresentinmyrtle
berries seem to possess weak antioxidant activity. The antioxidant activity of sample extracts
dependedonvariousfactors: harvestingtime,storage,extractionsolvent,extractiontype,andplant
part used, among other factors. Leaf extracts of myrtle revealed to possess anti-inflammatory
activityinseveralmodelsused. Thispropertyhasbeenattributedeithertotheflavonoidsand/or
hydrolysabletannins,neverthelessnonprenylatedacylphloroglucinols(e.g.,myrtucommuloneand
semimyrtucommulone)havealsorevealedaremarkableroleinthatactivity. Thebiologicalactivities
ofmyrtleextractsfoundsofarmaydirectitsusetowardsforstabilizingcomplexlipidsystems,as
prebioticinfoodformulations,andasnoveltherapeuticforthemanagementofinflammation.
Keywords:Anti-inflammatory;berries;leaves;galloylderivatives;flavonolderivatives;anthocyanins;
myrtucommulone
1. Introduction
Myrtaceaeisafamilyofwoodyfloweringplantsthatencompassesaround5500species,classified
in 144 genera, and 17 tribes. Within Myrtaceae, the tribe Myrteae represents half of the family’s
biodiversity with 51 genera and about 2500 species mostly restricted to the Neotropics, though
15 genera and about 450 species are found in other continents, such as Southeast Asia, Northeast
Australia,andthePacificislands,includingNewCaledoniaandNewZealand. ThegenusMyrtus
Medicines2018,5,89;doi:10.3390/medicines5030089 www.mdpi.com/journal/medicines
Medicines2018,5,89 2of68
isthesolefoundinEuropean/NorthernAfrican,Asia,particularlyintheMediterraneanregionof
southernEuropeasfarwestasMacaronesia(MadeiraandtheAzores),theSaharanmountainsandas
fareastaswesternAsia(IranandAfghanistan)[1–3].
TwospeciescanbefoundinthegenusMyrtus:MyrtuscommunisL.andMyrtusnivelleiBatt.&Trab.
ThelatterisendemictothecentralSaharanmountainsgrowinginrockyandsandywadesandgorges,
athighelevations,above1400m. TheformercanbefoundintheMediterraneanBasin,Macaronesia,
Iran,andAfghanistan,particularlyatelevationsnotexceedingc.a. 500ma.s.l.[1]. Bothspeciesare
shrubswithroughbark,oppositeleaves,whiteflowersthatarestar-like(5–9petals),andwhite,purple,
blue,orevenblackberries. Theydifferinthefollowingmorphologicalcharacteristics: theleavesof
M.nivelleiarelinear-lanceolate(4–5cminlength)andnarrower(6–8mm)thantheM.communisones,
whichareovate-lanceolate(2–5cmlong)andwider(10–20mm);thefruitsofM.communisareellipsoid
tosubglobose,pyriform,elongated,orflat(7–9mmlength),whereasthoseofM.nivelleiareglobose
andsmaller(4–5mm)[1,4–6]. M.communisgrowsto0.5–3minheight,whileM.nivelligrowsto1–2m
inheight[1].
Differentparts(berries,branches,andleaves)ofM.communis(myrtle)havebeenusedinfolk
medicinefortreatingdiarrhoea,pepticulcers,haemorrhoids,inflammation,uterinebleeding,headache,
palpitation,leucorrhoea,urethritis,epistaxis,conjunctivitis,excessiveperspiration,andpulmonary
andskindiseases[4,7]. Onlyfewstudieshavereportedasedativeeffectofmyrtle,asaanxiolyticand
musclerelaxantwithoutanticonvulsivantactivity[8,9].
Myrtle leaves have been used for healing wounds or disorders of the digestive and urinary
systemsduetotheirastringent,tonic,andantisepticproperties[4,10]. Fromleavesisalsopossible
toextractessentialoilsthathavebeenusedasanti-septic,anti-catarrhal,andtotreatchestailments,
ulcers,andhemorrhoids[4,10–13].
Althoughtheberriesdecoctionshadbeenusedtobathenewbornswithreddenedskin,andthe
decoctionsofleavesandberriesinsorewashing,themostisusedtoproducethecharacteristicmyrtle
liqueurobtainedbyhydro-alcoholicinfusionoftheberries[4,14,15].
Thebiologicalpropertiesassignedtodiverseorgans(leavesandberries)ofmyrtlecanbedueto
diverse compounds such as volatile compounds or essential oils (terpenoids, particularly α-pinene,
1,8-cineole,geranylacetate,andlinalool),flavonoids(quercetin,catechinandmyricetinderivatives,and
anthocyanins),coumarins,oligomericnonprenylatedacylphloroglucinolcompounds(myrtucommulone
AandBandsemimyrtucommulone),galloyl-glucosides,ellagitannins,galloyl-quinicacids,caffeic,gallic
andellagicacids,fattyacids(linoleic,palmitic,oleic,andstearicacids)indiverseorgans[4]. Table1
showsexamplesofbiologicalpropertiesassignedtoMyrtuscommunis.
M.nivellei(Saharanmyrtle)leavesininfusionsareusedagainstintestinaldiseases(diarrhoea),
fever,diabetes,andaddedtobarleywafersisemployedagainstblennorrhoea[16–18]. Thecrushed
leavesaddedtooilorbutterointmenthasbeenusedinthetreatmentofdermatosisandforhairand
bodycare[16,17,19]. Thedecoctionofleavesmixedwithgoatmilkandheatedoncharcoalhasbeen
usedforliverdisordersbynomadAlgeriansofTassiliregion[20]. Theleafinfusionisusedinthis
regionasacommonbeverage,insteadofgreentea[20]. Berriesareconsumedeitherfreshordriedto
treatmouthcankersores[19].
ThechemicalcompositionofSaharanmyrtleislessstudiedthanthatofmyrtle.Themainconstituents
reported include volatile essential oils [16,21], phenols (flavonoids, anthocyanins, and tannins),
norterpenoids[19–22].
Thepresentreviewwillfocusontheantioxidantandanti-inflammatoryactivitiesofM.communis
andM.nivelleiinwhichthechemicalcompositionisdiscriminated.
Medicines2018,5,89 3of68
Table1.BiologicalpropertiesattributedtoMyrtuscommunis(antioxidantandanti-inflammatoryactivitiesarenotincluded).
PlantPartUsed Compounds BiologicalProperties References
Antimicrobial
Leaves Notreported Bacterialvaginosis [23]
Leaves Notreported Propionibacteriumacnes [24]
-SpoilagebacteriaPseudomonasaeruginosaIH,PseudomonasaeruginosaCECT118,
PseudomonasaeruginosaCECT110T,PseudomonasfluorescensCECT378andBacillus
subtilisDCM3366
Leavesandberries Notreported -Food-bornepathogenicbacteria,namelyEscherchiacoliK12,ListeriainnocuaCECT [25]
4030,ListeriamonocytogenesCECT4032,EnteroccusfaeciumCECT410,
StaphylococcusaureusMBLA,StaphylococcusaureusCECT976,Staphylococcusaureus
CECT794andProteusvulgarisCECT484
Leaves Notreported OnehundredandtwentystrainsofEscherichiacoliisolatedfromtheurineculture [26]
Streptococcuspneumoniae,Streptococcuspyogenes,Streptococcusagalactiae,
Leaves Notreported Listeriamonocytogenes,Campylobacterjejuni,Staphylococcusaureus, [27]
Micrococcusluteus,Escherichiacoli,Proteusvulgaris,andPseudomonasaeruginosa
Aeromonashydrophilicaisolatedfromfourhundredandfiftysamplesfromthe
Leaves Notreported [28]
intestinesoftheinfectedCyprinuscarpiofish
Ninety-sixP.aeruginosastrainsisolatedfrom400burnpatients(menandwomen)
Leaves Notreported [29]
inIranianhospital
StaphylococcusaureusstrainATCC25923giftofE.Udo
(KuwaitUniversity,Kuwait)
Galloylatednonprenylated S.aureusRN4220containingplasmidpUL5054,whichcarriesthegeneencoding
phloroglucinolglucosides: theMsrAmacrolideeffluxprotein,providedbyJ.Cove
GallomyrtucommuloneA S.aureusXU-212whichpossessestheTetKtetracyclineeffluxprotein,providedby
Leaves [30]
GallomyrtucommuloneB E.Udo
GallomyrtucommuloneC S.aureusSA-1199B,whichoverexpressesthenorAgeneencodingtheNorAMDR
GallomyrtucommuloneD effluxprotein,providedbyG.Kaatz
S.aureusEMRSA-15isanepidemicstrainofMRSAgiftofP.Stapleton,Schoolof
Pharmacy,UniversityofLondon
Medicines2018,5,89 4of68
Table1.Cont.
PlantPartUsed Compounds BiologicalProperties References
Escherichiacoli(PTCCNo.1330),Pseudomonasaeruginosa(PTCCNo.1074),
P.fluorescens(PTCCNo.1181),Klebsiellapneumoniae(PTCCNo.1053),
Seeds Notreported Bordetellabronchiseptica(PTCCNo.1025),Staphylococcusaureus(PTCCNo.1112), [31]
S.epidermidis(PTCCNo.1114),Micrococcusluteus(PTCCNo.1170),Bacilluscereus
(PTCCNo.1015),andB.pumilis(PTCCNo.1319)
Hydroxybenzoicacidhexose
Delphinidin-3-O-galactoside
Delphinidin-3-O-glucoside
Quercetinhexoside
Delphinidin-3-O-rhamnoside
Delphinidinrutinoside
Delphinidin-3-(6coumaroyl)-glucoside
EscherichiacoliATCC8739,SalmonellatyphimuriumNCTC6017,Staphylococcus
Petunidin-3-O-glucoside
Berryseeds aureusATCC29213,PseudomonasaeruginosaATCC27853,AeromonashydrophilaEI, [32]
Petunidindiglucoside
andBacilluscereusATCC1247
Petunidinmalonylglucoside
Petunidin-3-O-rutinoside
Isorhamnetin-O-rhamnoside
Malvidin-O-galactoside
Malvidin-O-glucoside
Peonidindiglucoside
Petunidinmethylpentose
Leaves Notreported Streptococcusmutans(PTCC1683) [33]
Gram-positive(ListeriamonocytogenesandBacilluscereus)
Leaves Notreported Gram-negative(EscherichiacoliO157:H7)bacterialstrains [34]
Fungalstrain(Candidaalbicans)
Staphylococcusaureus(ATCC6538),Bacillussubtilis(ATCC6059),Micrococcusflavus
(SBUG16),Escherichiacoli(ATCC11229),Pseudomonasaeruginosa(ATCC27853),
andthreemulti-resistantStaphylococcusstrains(Staphylococcusepidermidis847,
Leavesandberries Notreported [35]
Staphylococcushaemolyticus535,StaphylococcusaureusnorthGerman
epidemicstrain)
Candidamaltosa(SBUG)
Medicines2018,5,89 5of68
Table1.Cont.
PlantPartUsed Compounds BiologicalProperties References
Staphylococcusaureus,Staphylococcusepidermidis,Escherichiacoli,Bacillussubtilis
Leaves Notreported [36]
andSerratiamarcescens
MyrtucommulonesJ-L
Leaves Staphylococcusaureus(ATCC25923) [37]
MyrtucommuloneA
Leaves Notreported Enterococcusfaecalis(ATCC29212) [38]
Leaves Notreported Bacterialvaginosis [39]
Leaves Notreported Pseudomonasaeruginosa [40]
MicrosporumcanisATCC32903,M.gypseumATCC14683,andTrichophyton
Leaves Notreported mentagrophytesATCC1481(var.interdigitale)fromTehranUniversityof [41]
MedicalSciences
Trichophytonmentagrophytes,T.interdigitale,Microsporumcanis,andM.gypseum
Aerialparts Notreported [42]
(10strainofeach)
EscherichiacoliO157:H7,YersiniaenterocoliticaO9,Proteusspp.,and
Leaves Notreported [43]
Klebsiellapneumoniae
Berries Notreported Helicobacterpylori(12clinicalisolates) [44]
Staphylococcusaureus(489samples)isolatedeitherfromhealthycarriers(noseand
Leaves Notreported throat)orclinicalsamplesS.aureususedasreferencestrainsforcomparison: [45]
ATCC25923,ATCC9144,ATCC29737,ATCC12596,andBristolA9596
5-Acetoxy-4-hydroxy-4-isobutyl-2,2,6,6-
tetramethylcyclohexan-1,3-dione
β-Sitosterol
Isomyrtucommulone-B
Leaves Endoperoxide-G-3-hormone PropionibacteriumacnesNRRL(B-4224) [46]
Gallicacid
Myricetin-3-O-α-L-rhamnoside
Myricetin-3-O-β-D-glucoside
Myricetin-3-O-β-D-galactoside-6”-O-gallate(8)
Medicines2018,5,89 6of68
Table1.Cont.
PlantPartUsed Compounds BiologicalProperties References
Bacillussubtilis,Staphylococcusaureus,Escherichiacoli,Saccharomycescerevisiae,
EscherichiacoliB,E.coliCW3747,E.coliK-12,Klebsiellapneumoniae,
Proteusmirabilis,Proteusmorganii,Shigelladysenteriae,S.flexneri,
Leaves MyrtucommuloneA [47]
Salmonellatyphimurium,Pseudomonasfluorescens,Vibriocholerae,Serratia,
Staphylococcusaureus,S.albus,BacillussubtilisW23,B.subtilis16,B.pumilus,
Streptococcusfaecalis,Corynebacteriumdiphtheriae,andC.xerosis
Leaves Notreported Helicobacterpylori [48]
MyrtucomvalonesA–C
Leaves Respiratorysyncytialvirus(RSV) [49]
CallistivimineneJ-N
MyrtucommuloneB-E
UsnoneA
Tectochrysine
2,5-Dihydroxy-4-methoxybenzophenone
(cearoin)
β-Sitosterol
Escherichiacoli,Bacillussubtilis,Shigellaflexneri,Staphylococcusaureus,
Aerialparts Sideroxylin [50]
Pseudomonasaeruginosa,andSalmonellatyphi
Ursolicacid
Corosolicacid
Arjunolicacid
Erythrodiol
Oleanolicacid
Betulin
Semimyrtucommulone StaphylococcusaureusstrainsRN4220(Msr(A)),XU212(Tet(K)),1199-B(Nor(A)),
Leaves [51]
myrtucommuloneA andATCC25923
MyrtucommuninsA-D
6-Methyl-isomyrtucommuloneB
4-MethylmyrtucommuloneB
Escherichiacoli,Staphylococcusaureus(MRSA),Staphylococcusaureus(MSSA),and
Leaves 2-Isobutyryl-4-methylphloroglucinol [52]
Bacillussubtilis
1-O-β-D-glucopyranoside
Chromonederivative,undulatosideA
6’-O-gallate
Medicines2018,5,89 7of68
Table1.Cont.
PlantPartUsed Compounds BiologicalProperties References
Silvernanoparticlessynthesizedusing Escherichiacoli,Bacillussubtilis,Pseudomonasaeruginosa,Staphylococcusaureus
Leaves [53]
MyrtuscommunisL.leafextract methicillin-resistant,Staphylococcusaureus,andEnterococcusfaecalis
Staphylococcusaureus(ATCC25923),Staphylococcusepidermidis(ATCC12228),
Staphylococcusmutans(ATCC31989)andStaphylococcusviridans(ATCC19952),
Pseudomonasaeruginosa(ATCC27853),Escherichiacoli(ATCC25922),
Leaves Beforeandafterencapsulationinliposomes [54]
Enterobactercloacae(ATCC13047)andKlebsiellapneumoniae(ATCC13883),
Candidaalbicans(ATCC10231),Candidatropicalis(ATCC13801)and
Candidaglabrata(ATCC28838),andListeriamonocytogenes
Otherorganisms
Leaves Notreported Anti-Leishmaniatropicaonaninvitromodel [55]
Invivo,anti-PlasmodiumbergheiinfemaleSwissalbinomice,weight18–20g
Aerialparts Notreported [56]
Invitro,chloroquine-sensitivestrain(3D7)ofP.falciparum
Notreported(myrtlewas
obtainedfromalocal Notreported Inducedprogrammedcelldeathinhydatidcystprotoscolices [57]
groceryforherbalplants)
Invitro,anti-chloroquine-resistant(K1)andchloroquine-sensitive(3D7)strainsof
Aerialpart Notreported Plasmodiumfalciparum [58]
Invivo,anti-Plasmodiumbergheiinfectioninadultmalealbinomice
Cytotoxicity
Leaves Notreported CytotoxicactivitiesagainstJ774cells(MouseBALB/cmonocytemacrophage) [55]
Cytotoxicactivitiesagainsturinarybladder5637andhumanbreastcarcinoma
Leavesandberries Notreported [35]
MCF-7celllines
CytotoxicactivitiesagainsthumanhaematologicaltumorcelllineMT-4.
MyrtucommulonesJ-L Cytotoxicactivitiesagainstagainstsolidtumorcelllines(HepG2orhumanliver
Leaves [37]
MyrtucommuloneA cancer,DU145orhumanprostatecancercelllines),andagainst“normal”human
tissuecells(CRL7065)
CytotoxicactivitiesagainstU-937(humanlung(lymphoblast),K-562(human
Leaves MyrtucommuloneA blood(chronicmyelogenousleukemia),leukemiccelllineKBM-5,andMEG-01 [59]
(humanbonemarrow)celllines
Medicines2018,5,89 8of68
Table1.Cont.
PlantPartUsed Compounds BiologicalProperties References
CytotoxicactivitiesagainstMCF7(breastadenocarcinoma),HepG2
Aerialpart Notreported (hepatocellularcarcinoma),WEHI(fibrosarcoma),andMDBK(normal [58]
kidneycells)
L20B(celllineamousecell-linegeneticallyengineeredtoexpresshuman
Notreported Notreported poliovirusreceptor,CD155celllines),RD(rhabdomyosarcom),andVero(African [60]
greenmonkeykidney)
Notreported MyrtucommuloneA MitochondriallysatesfromleukemicHL-60cells [61]
Jurkat-A3cells,caspase-8-deficientJurkatcells,FADDdeficientJurkatcells,PC-3
(androgen-independentprostatecarcinoma),LNCaP(androgen-dependent
prostatecarcinoma),H9(cutaneousT-celllymphoma),DLD-1(colorectal
Myrtucommulone
Leaves adenocarcinoma),HL-60(acutepromyelocyticleukaemia),Jurkat(acuteT-cell [62]
Semi-myrtucommulone
leukaemia)andJurkatDD3(mutatedinCD95),KFR(rhabdomyosarcoma)and
UKF-NB-3(neuroblastoma)cells,monoMac6(MM6,acutemonocyticleukaemia)
cells,andhumanperipheralbloodmononuclearcells(PBMC)
MouseBreastcancercellline4T1,mouseembryonicfibroblasts,andhuman
Notreported Myrtucommulone [63]
dermalfibroblasts(hDFs)
MyrtucomvalonesA–C
Leaves Humanlarynxepidermoidcarcinomacells(HEp-2)cells [49]
CallistivimineneJ-N
Myricetin-3-O-galactoside
Leaves HumanchronicmyelogenousleukemiacelllineK562 [64]
Myricetin-3-O-rhamnoside
Leaves 3,5-O-Di-galloylquinicacid HumanchronicmyelogenousleukemiaCMLcelllineK562 [65]
Genotoxicity/mutagenicity
ProtectiveeffectagainstgenotoxicityontheSOSreponseinducedbyAflatoxinB1
Leaves Notreported [66]
(AFB1)andNifuroxazideinEscherichiacoliPQ37
ProtectiveeffectagainstthemutagenicityinducedbyaflatoxinB1(AFB1)in
Leaves Notreported SalmonellatyphimuriumTA100andTA98assaysystems,andagainstthe [67]
mutagenicityinducedbysodiumazideinTA100andTA1535assaysystem
Medicines2018,5,89 9of68
Table1.Cont.
PlantPartUsed Compounds BiologicalProperties References
ProtectiveeffectagainstonthemutagenicityinducedbyaflatoxinB1in
Leaves Notreported [68]
SalmonellatyphimuriumTA100orTA98
Myricetin-3-O-galactoside ProtectiveeffectagainstthemutagenicityinducedbyaflatoxinB1in
Leaves [64]
Myricetin-3-O-rhamnoside EscherichiacoliPQ37strain
Leaves 3,5-O-Di-galloylquinicacid InhibitoryeffectagainstH O -inducedgenotoxicity,usingthecometassay [65]
2 2
Gastrointestinalsystem
Hydroxybenzoicacidhexose
Delphinidin-3-O-galactoside
Delphinidin-3-O-glucoside
Quercetinhexoside
Delphinidin-3-O-rhamnoside
Delphinidinrutinoside
Delphinidin-3-(6coumaroyl)-glucoside
Petunidin-3-O-glucoside
Berryseeds Anti-diarrhoealinadultmaleWistarratsaftercastoroiladministration [32]
Petunidindiglucoside
Petunidinmalonylglucoside
Petunidin-3-O-rutinoside
Isorhamnetin-O-rhamnoside
Malvidin-O-galactoside
Malvidin-O-glucoside
Peonidindiglucoside
Petunidinmethylpentose
Anti-diarrhoealinSwissalbinomiceofeithersexweighing20–30gandaged
Leaves Notreported [69]
6–8weeks,aftercastoroiladministration
Protectiveeffectongastriculceragainstethanol,indomethacin,andpyloric
Berries Notreported [70]
ligationinducedmodelsinalbinoratsofWistarstrainweighing150–200g
ProtectiveeffectonoralulcerrecoveryprocessinwhiteSpraque–Dawleyrats
Stemsandseeds Notreported weighing250–300gafterpunchtocreateawoundinthehardpalateinthe [71]
oralcavity
Medicines2018,5,89 10of68
Table1.Cont.
PlantPartUsed Compounds BiologicalProperties References
Palmiticacid
Stearicacid
Oleicacid ProtectiveeffectonpepticulceragainstethanolinducedinadultmaleWistarrats
Berryseeds [72]
Linoleicacid (weighing220–240g)
Linolelaidic(trans,trans-C18:2)
Arachidicacid
Hydroxybenzoicacidhexose
Delphinidin-3-O-galactoside
Delphinidin-3-O-glucoside
Quercetinhexoside
Delphinidin-3-O-rhamnoside
Delphinidinrutinoside
Delphinidin-3-(6coumaroyl)-glucoside
Petunidin-3-O-glucoside Protectiveeffectonaceticacid-inducedulcerativecolitisinadultmaleWistarrats
Berryseeds [73]
Petunidindiglucoside (weighing220–240g)
Petunidinmalonylglucoside
Petunidin-3-O-rutinoside
Isorhamnetin-O-rhamnoside
Malvidin-O-galactoside
Malvidin-O-glucoside
Peonidindiglucoside
Petunidinmethylpentose
Protectiveeffectonaceticacid-inducedulcerativecolitisinWistaralbinorats
Leaves Notreported [74]
(weighing250–300g)
ProtectiveeffectonliverinjuryandfibrosisoccurringinWistaralbinorats
Leaves Notreported [75]
(weighing250–300g)withbiliaryobstructionbydoubleligatureswithsuturesilk
Decreaseofrefluxanddyspepticscoresascomparedwiththebaseline,in
Berries Notreported [76]
double-blindrandomizedcontrolledclinicaltrialinadultagedfrom18to60years
Decreaseoftherecurrenceofsymptomsinrefluxpatientsafterthediscontinuance
Berries Notreported ofprotonpumpinhibitors,inoutpatient,double-blind,randomized,parallel [77]
treatmentgroupsstudy
Decreaseoftherecurrentaphthousstomatitisinrandomized,doubleblind,
Leaves Notreported [78]
controlledbefore–afterclinicaltrial