Fitoterapia100(2015)201–207

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Fitoterapia

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α-GlucosidaseinhibitorsfromtheleavesofEmbeliaribes

PhuHoangDanga,NhanTrungNguyena,HaiXuanNguyena,LuanBaoNguyena,ThoHuuLea,TruongNhatVanDoa,MaoVanCanb,MaiThanhThiNguyena,

ab

FacultyofChemistry,UniversityofScience,VietnamNationalUniversity,HochiminhCity,227NguyenVanCuStreet,District5,HoChiMinhCity,VietnamVietnamMilitaryMedicalUniversity,Vietnam

articleinfoabstract

Anovelandrare1,4-dehydratedceramide,embelamide(1),andanewC-glycoalkaloidwhichisbasedonaβ-carbolineringsystem,1-(2′-deoxy-α-D-ribopyranosyl)-β-carboline(4),wereisolatedfromtheCHCl3solublefractionoftheleavesofEmbeliaribes(Myrsinaceae),togetherwiththirteenknowncompounds(2–3,5–15).Theirstructureswereelucidatedonthebasisofspectroscopicdata.Compounds1,and5–12possessedsignificantα-glucosidaseinhibitoryactivityinaconcentration-dependentmanner,andshowedmorepotentinhibitoryactivity,withIC50valuesrangingfrom1.3to155.0μM,thanthatofapositivecontrolacarbose(IC50,214.5μM).

©2014ElsevierB.V.Allrightsreserved.

Articlehistory:

Received20October2014

Acceptedinrevisedform6December2014Availableonline16December2014Chemicalcompoundsstudiedinthisarticle:p-Nitrophenyl-α-D-glucopyranoside(PubChemCID:92969)

Dimethyldisulfide(PubChemCID:12232)Acarbose(PubChemCID:444254)

Dimethylsulfoxide(PubChemCID:679)Carbondisulfide(PubChemCID:6348)Iodine(PubChemCID:807)Keywords:Embeliaribes

1,4-Dehydratedceramideβ-Carboline

α-Glucosidaseinhibition

1.Introduction

EmbeliaribesBurmf.isawoodyshrubthatbelongstotheMyrsinaceaefamily,whichissparselydistributedinthemoistdeciduousforestsinIndia,Malaysia,SouthChina,Cambodia,andVietnam.InthesouthernpartofVietnam,itisknownas“NguLinhChi”andtraditionallyusedasappetizer,carminative,laxativeandanthelminticfoods[1].Especially,freshfruitsandleavesofE.ribesareusedasdailyvegetablefood/juicefortreatmentofinflammationanddiabetesdiseases[2].Previous-ly,somestudiesonthechemicalconstituentsofsomepartsofE.ribesincludingroots,fruits,seedsandstemshavereported

Correspondingauthor.Tel.:+84907426331;fax:+84838350096.E-mailaddress:nttmai@hcmus.edu.vn(M.T.T.

Nguyen).

anumberofbenzoquinones,benzofurans,benzodioxoles,andresorcinolderivatives[3–5].ThemaincomponentofE.ribes'sleavesisembelin[6],a1,4-benzoquinone,whichhasshownantiproliferativecharacteristic,ananti-nociceptiveandanti-inflammatoryagent,andhasantibacterialpotential[7,8].

OurpreliminaryscreeningstudyalsorevealedthatthemethanolicextractofthestemsofE.ribesexhibitedsignificantα-glucosidaseinhibitoryactivitywithIC50valueof0.1μg/mL[3].Therefore,furtherphytochemicalinvestigationoftheleavesofE.ribesisnecessarytoutilizeitasthemedicinalfoodsforpostprandialhyperglycemialinkedtodiabetesmellitus.Inthisresearch,bioactivity-guidedfractionationofMeOHextractofE.ribes'sleaveswascarriedout;anovelandrare1,4-dehydratedceramide,embelamide(1),andanewC-glycoalkaloid,1-(2′-deoxy-α-D-ribopyranosyl)-β-carboline(4)wereisolatedtogetherwiththirteenknowncompounds(2–3,5–15).Thisstudywasundertakentoisolateandelucidatethe

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0367-326X/©2014ElsevierB.V.Allrightsreserved.