Antioxidant cytotoxic antitumor and protective DNAFX抗氧化细胞毒等.docx
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Antioxidant cytotoxic antitumor and protective DNAFX抗氧化细胞毒等.docx
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AntioxidantcytotoxicantitumorandprotectiveDNAFX抗氧化细胞毒等
窗体顶端
窗体底端
PharmacognosyRes.2011Jul-Sep;3(3):
160–165.
doi:
10.4103/0974-8490.85000
PMCID:
PMC3193615
Copyright:
©PharmacognosyResearch
Antioxidant,cytotoxic,antitumor,andprotectiveDNAdamagemetabolitesfromtheredseabrownalgaSargassumsp
Seif-EldinN.Ayyad,SalehT.Ezmirly,SalimA.Basaif,WaliedM.Alarif,1AdelF.Badria,2andFaridA.Badria3
DepartmentofChemistry,FacultyofScience,KingAbdulAzizUniversity,P.O.80203,Jeddah21589,KSA
1DepartmentofMarineChemsitry,FacultyofMarineSciences,KingAbdulazizUniversity,Jeddah21589,P.O.80207,KSA
2TissueEngineeringLab.,FacultyofDentistry,AlexandriaUniversity,Alexandria,Egypt
3DepartmentofPharmacognosy,FacultyofPharmacy,MansouraUniversity,Mansoura35516,Egypt
Addressforcorrespondence:
Dr.Seif-EldinNAyyad,FacultyofSciences,KingAbdulazizUniversity,Jeddah,SaudiArabia.E-mail:
snayyad2@
ReceivedFebruary1,2011;RevisedApril6,2011;AcceptedSeptember16,2011.
Thisisanopen-accessarticledistributedunderthetermsoftheCreativeCommonsAttribution-Noncommercial-ShareAlike3.0Unported,whichpermitsunrestricteduse,distribution,andreproductioninanymedium,providedtheoriginalworkisproperlycited.
Abstract
Background:
Macroalgaecanbeviewedasapotentialantioxidantandanti-inflammatorysourcesowingtotheircapabilityofproducingcompoundsforitsprotectionfromenvironmentalfactorssuchasheat,pollution,stress,oxygenconcentration,andUVradiations.
Objective:
Toisolatemajorcompoundswhicharemainlyresponsibleforthepharmacologicalactivityofbrownalgaunderinvestigation,Sargassumsp.
MaterialsandMethods:
Algalmaterialwasairdried,extractedwithamixtureoforganicsolvents,andfractionatedwithdifferentadsorbents.Thestructuresofobtainedpurecompoundswereelucidatedwithdifferentspectroscopictechniques,andtwopurematerialsweretestedforprotectionofDNAfromdamage,antioxidant,antitumor,andcytotoxicity.
Results:
Fourpurecompoundswereobtained,ofwhichfucosterol
(1)andfucoxanthin(4)weretested;itwasfoundthatfucoxanthinhasstrongantioxidantandcytotoxicityagainstbreastcancer(MCF-7)withIC50=11.5μg/ml.
Conclusion:
Thenaturallyhighlyconjugatedsafecompoundfucoxanthincouldbeusedasantioxidantandasanantitumorcompound.
Keywords:
Antioxidant,cytotoxicity,fucoxanthin,Sargassumsp
∙ OtherSections▼
oAbstract
oINTRODUCTION
oMATERIALSANDMETHODS
oRESULTSANDDISCUSSION
oREFERENCES
INTRODUCTION
ThegenusSargassumbelongstobrownalgaeofclassPhaeophyceaeintheorderFucales.Numerousspeciesaredistributedthroughoutthetropicalandsubtropicaloceansoftheworld,wheretheygenerallyinhabitshallowwaterandcoralreefs.However,thegenusmaybewellknownforitsplanktonic(free-floating)species.[1]Itwasclearfromtheliteraturesthatmorethan62speciesofthegenusSargassumhasbeeninvestigated,[2]andindicateditsproductivitywithimpressivediversityofnaturalcompounds.Forinstances,thesecondarymetabolitescontaindifferentstructuralclassessuchasplastoquinones,[3–5]chromanols,[6]chromenes,[7,8]steroids,[9]andglycerides.[10]Thepublicationsshowedthat,Sargassummetaboliteshavewiderangeofbiologicalactivities,whichincludeantibiotic,anti-HIV,anticoagulant,anticonvulsant,anti-inflammatory,antineoplastic,andantitumor.[11–14]
Incontinuationofoursearchprogram,whichinterestedintheisolationofsecondarymetabolitesfrommarinesources,especiallymacroalgaecollectedfromRedSea,[15–17]amarinemacroalgae,identifiedasSargassumsp.,collectedfromEl-Shuaibalagoon80kmsouthofJeddah,wasinvestigated.Thetotalextract(Pet.ether:
Chloroform:
Methanol[1:
1:
1])hadbeenfractionatedusingdifferentchromatographictechniquesandaffordedfourmetabolites;fucosterol
(1),saringosterone
(2),saringosterol(3),andfucoxanthin(4).1and4hadbeentestedtowardtheBleomycin-dependentDNAdamage,cytotoxicityagainstHepG2(humanhepatocellularlivercarcinomacellline),WI38(Skincarcinomacellline),Vero(celllinewasinitiatedfromthekidneyofanormaladultAfricangreenmonkey),MCF-7(breastcancercelllines),antitumor,andantioxidantusing2,2‘-azino-bis-3-ethylbenzthiazoline-6-sulfonicacid(ABTS).
∙ OtherSections▼
oAbstract
oINTRODUCTION
oMATERIALSANDMETHODS
oRESULTSANDDISCUSSION
oREFERENCES
MATERIALSANDMETHODS
Apparatusandmaterial
Chromatographicmaterial:
Aluminumoxidetype60-120meshwasusedforcolumnchromatography.Thin-layerchromatography(TLC)silicagelGF254wasusedforTLC.Preparativethin-layerchromatography(PTLC)wasperformedonaluminumoxideplates(20×20cm)of250-mmthickness.Electronimpactmassspectraweredeterminedat70eVonaKratosMS-25instrument.1Dand2DNMR(NuclearMagneticResonance)spectrawererecordedonBrukerAVANCEIIIWM600MHzspectrometersand13CNMRat150MHzChemicalshiftsaregiveninδ(ppm)relativetoTMS(Tetramethylsilane)asinternalstandard.TheInfraRed(IR)spectrawererecordedonaPerkinElmerspectrometermodel100.Thesprayreagentusedis50%-sulfuricacidinmethanolassprayingreagent.Thechromatoplatewasheatedaftersprayingat100to105°Cuntilthespotsattainedmaximumcolorintensity.ThealgawasdescribedasSargassum(FamilySargassaceae)andwascollectedbyhandfromEl-Shuaibalagoon80kmsouthofJeddah,SaudiArabia,intheRedSea,inJune2010.
ExtractionofSargassumsp
Theair-driedalgalmaterial(350g)wasextractedbyequalvolumeofmixtureofPet.ether,chloroform,andmethanol(2×6l,24hoursforeachbatch)atroomtemperature.Theextractwasconcentratedunderreducedpressuretoobtain10gresidue.ThismaterialwaschromatographedonacolumnofSilicagel.
Columnchromatography
Silicagelcolumn(500g,80×2.5cm)wasusedforresolution.Theresidue(10g)washomogenizedwithsmallamountofsilicagel(50g)andpouredontothetopofthecolumnwhichwaspackedinPet.ether(40:
60).Theeluentwereusedsuccessively(Pet.ether-Ether,Pet.ether-Ethylacetate).Fractionswerecollected(50ml);Pet.ether-EthermixtureofincreasingpolaritybydiethyletherandthenethylacetateandfollowedbyTLCusingsilica-gelchromatoplates,appropriatesolventsystemand50%sulfuricacidinmethanolassprayingreagent.Ifthematerialwasnotpure,preparativeTLCwasappliedusingtheappropriatesolventsystemandtheadsorbentaluminumoxideforpurification.
Isolatedcompounds
ThefractionAelutedbyPet.ether-Ether(6:
4)wascollectedandrechromatographedoverPTLCofsilicagelusingPet.Ether-ethylacetate(8:
2)togivethreecompounds:
1,2,and3.ThefractionBelutedbyPet.ether-Ethylacetate(6:
4)wascollectedandrechromatographedonSephadexLH-20usingamixtureofMeOH-CHCl3(9:
1)andthenfinallypurifiedbypreparativeTLCofsilicagelusingchloroformmethanol(9.5:
0.5)toaffordapurecompound4.
Fucosterol
(1),(24E)-Stigmasta-5,24(28)-diene-3β-ol:
whitesolid(30mg,0.008%drywt)m.p.133-135°C.IR(cm-1):
3480(OH),1945(C=C-H),1640(C=C),1370(gem.Di-Me);EI-MSm/z:
412[M,C29H48O]+,397[M-CH3]+,379[M-CH3-H2O]+,314(100)[M-C6H10O]+.1HNMR(CDCl3)δ(ppm)0.86-0.88(d,J=6.6Hz,6H,Me-26andMe-27),0.91(d,J=6.6Hz,3H,Me-21),0.68(s,3H,Me-18),1.00(s,3H,Me-19),1.59(d,J=6.6Hz,3H,Me-29),3.53(m,H,H-3),5.35(m,H,H-6),5.11(q,H,H-28),2.22(sep,J=6.6Hz,H,H-25).13CNMR(CDCl3)δ(ppm)(39.75,C-1),(35.20,C-2),(71.80,C-3),(42.33,C-4),(140.74,C-5),(121.70,C-6),(36.14,C-7),(35.78,C-8),(50.10,C-9),(39.72,C-10),(28.23,C-11),(42.28,C-12),(42.30,C-13),(56.74,C-14),(31.64,C-15),(34.78,C-16),(56.72,C-17),(11.85,C-18),(19.40,C-19),(39.50,C-20),(24.32,C-21),(37.23,C-22),(31.90,C-23),(146.00,C-24),(33.90,C-25),(22.50,C-26),(22.23,C-27),(115.94,C-28),(18.90,C-29).
Saringosterone
(2),24-vinylcholest-4-ene-3-one:
acolorlessoil(10mg,0.003%drywt).IR(cm-1):
3420(OH),1675(C=O),1630(C=C);EIMSm/z(rel.int.):
426(12)[M,C29H46O2]+,383(21)[M+-C3H7],313(30),271(35),269(100).HREIMS:
m/z426.3413(calcd.426.3349)C29H46O2;1H-NMR(CDCl3)δ5.76(dd,J=17,12Hz,H,H-28),5.73(brs,H,H-4),5.27(d,J=12Hz,H,H-29),5.15(d,J=17Hz,H,H-29),1.16(s,3H,Me-19),0.95(d,J=6.5Hz,3H,Me-21),0.86(d,J=7.0Hz,3H,Me-26),0.84(d,J=7.0Hz,3H,Me-27),0.72(s,3H,Me-18).13C-NMRδ(36.54,C-1),(34.65,C-2),(200.35,C-3),(124.43,C-4),(172.35,C-5),(33.64,C-6),(32.65,C-7),(36.32,C-8),(54.41,C-9),(39.25,C-10),(21.65,C-11),(40.22,C-12),(43.08,C-13),(56.26,C-14),(24.85,C-15),(28.86,C-16),(56.55,C-17),(12.63,C-18),(17.34,C-19),(36.84,C-20),(18.35,C-21),(32.54,C-22),(28.95,C-23),(89.76,C-24),(29.05,C-25),(19.46,C-26),(18.07,C-27),(137.78,C-28),(117.12,C-29).
Saringosterol(3),24-vinylcholest-5-ene-3β,24-diol,saringosterol:
colorlessoil(5mg,0.001%drywt.).IR(cm-1):
3445(OH),1644(C=C);EIMSm/z(rel.int.):
428(12)[M,C29H48O2]+,410(6)[M+-H2O],314(40),273(20),271(100),255(28),228(22),213(40),145(64).1HNMR(CDCl3)d5.73(dd,J=17,12Hz,H,H-28),5.34(brs,H,H-6),5.28(d,J=12Hz,H,H-29),5.17(d,J=17Hz,H,H-29),3.53(m,H,H-3),1.02(s,3H,Me-19),0.97(d,J=6.6Hz,3H,Me-21),0.88(d,J=6.6Hz,3H,Me-26],0.86(d,J=6.6Hz,3H,Me-27),0.67(s,3H,Me-18],13C-NMRd(37.17,C-1),(32.54,C-2),(72.43,C-3),(37.94,C-4),(141.43,C-5),(122.31,C-6),(32.35,C-7),(36.84,C-8),(50.74,C-9),(37.93,C-10),(21.75,C-11
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