Phân lập 3 hợp chất Lignan từ lá cây đề (Ficus Religiosal.)

Nghiên cứu phytochemical trên lá của Ficus religiosa dẫn đến sự cô lập của ba lignans. Cấu trúc hóa học của chúng được xác định là (+) - pinoresinol (1), pinoresinol di-0- / 3-Dglucopyranoside (2) và syringaresinol 0- / 3-D-glucopyranoside (3) hy có nghĩa là quang phổ nghiên cứu bao gồm phổ khối NMR và ESI.
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Phân lập 3 hợp chất Lignan từ lá cây đề (Ficus Religiosal.)Tfxp chi Hoa hgc, T. 47 (6), Tr. 758 - 762, 2009PHAN LAP 3 HOP CHAT LIGNAN TLT LA CAY DE{FICUS RELIGIOSA L.)••Den Tda soan 10-6-2009THANH HUONG, TRAN HONG QUANG, CAM THI INH, C H A U V A N MINH,PHAN VAN KIEM, JOELLE QUETIN-LECLERCQ YVAN VANDER HEYDEN^HOANGVien Hod hgc cdc Hgp chdt Thien nhien - Vien Khoa hgc vd Cong nghe Viet Nam Universite Catholique de Louvain, Louvain Drug Research Institute, Analytical chemistry, druganalysis and pharmacognosy unit. Avenue E. Mounier^ Vrije Universiteit Brussel-VUB, Department ofAnalydcal Chemistry andTechnology, LaarheeklaanPharmaceudcalABSTRACTPhytochemical study on the leaves of Ficus religiosa led to the isolation of three lignans.Their chemical structures were determined to be (+)-pinoresinol (1), pinoresinol di-0-/3-Dglucopyranoside (2) and syringaresinol 0-/3-D-glucopyranoside (3) hy means of spectroscopicstudies including NMR and ESI mass spectra. The antioxidant activities of these compounds werescreened using DPPH system. Among them, compounds 1 and 3 exhibited significant scavengingactivines with EC,„ values of 16.90 and 16.93 juM, respectively.I - MODAUcay dl (Ficus religiosa L., hg Moraceae) lamdt loai cay lau nam cd ngudn gdc tir An Do. (!)nudc ta, cay dugc trdng d cac viing ddng bingva vting mii [1]. Vd va la cay dugc sir dungtrong dan gian d Viet Nam dl chira trj cic benheczema, viem da diy, ly va tilu dudng [1, 2]. Lava qua cua nd dugc sir dung trong eac bii thudcdan gian d in Do de chiia tri cic benh vl hd hipvi da lilu [3]. Djch chiet metanol ciia la Ficusreligiosa the hien kha nang khing viem thdngqua lie che sin sinh NO va cic cytokine tilnviem, lie c h i sir bieu hien ciia mARN vi proteincua enzym nitric oxide synthase v i ciia caccytokine d eac dai thue bio khu trii d nao chuot[4].Mdi day chiing tdi da thdng bao kit quiphan lap va xae djnh ciu triic hoi hoc ciia cachgp chit (35,5/?,6/?,7£,9/?)-megastigman-7-en7583,5,6,9-tetrol9-0-/9-D-glucopyranoside [5],(3S,5R,6R,1E,9/?)-megastigman-7-en-3,5,6,9tetrol 9-0-/?-D-glucopyranoside va (3S,1E,9R)3,9-dihydroxy-megastigman-5,7-dien tir li cayFicus religiosa L., [6]. Bai bio nay md ta kitqua phan lap, xac djnh ciu triic hoa hgc cua 3hgp chit lignan va boat tfnh chdng oxy hoa eiiachiing qua md hinh thu dgn gdc tu do DPPH.II - THUC NGHIEM1. Phuofng phap nghien curuDiem chay dugc do tren may Kofler microhotstage. Do quay cue dugc do tren mayPolatronic D Schimidt + Haencb. Phd khdilugng phun mii dien tir (ESI-MS: Electron Spraylonization-Mass Spectra) duac do tren mayAGILENT 1200 LC-MSD Trap. Pho cdnghudng tir nhan (NMR) dugc do tren miy BrukerAM500 FT-NMR Spectrometer.sic ky ldp mdng dugc thuc hien tren ban mdngtrang sin DC-Alufolien 60 F254 (Merck1,05715), RP|8 F254, (Merck). Sic ky cdt dugctiln hanh vdi chit hip phu. Silica gel pha thudngcd cd hat 240 - 430 mesh va Silica gel pha daoODS hoac YMC (30 - 50 i^m, FuJisilisaChemical Ltd.). Sic ky trao ddi ion dugc thuchien qua cdt Dianion HP-20 (Merck).2,5 Hz, H-2, 2), 6,88 (2H, d, J = 8,0 Hz, H-5,5), 6,82 (2H, dd, / = 2,0, 8,0 Hz, H-6, 6), 4,73(2H, d, / = 4,5 Hz, H-7, 7), 4,24 (2H, m, H,-9,9), 3,90 (6H, s, 2 X OCH3), 3,88 (2H, m, Hb-9,9), 3,10 (2H, dd, 7=4,5, 6,5 Hz, H-8, 8).C-NMR (125 MHz, CDQj), 5 (ppm): xembang 1.2. Nguyen lieuLa cay F. religiosa dugc thu hai vao thang 9nam 2007 tai Tam Dao, VTnh Phiic. Ten khoahgc dugc TS Trin Huy Thai, Vien Sinh thai vaTai nguyen Sinh vat, Vien Khoa hgc va Cdngnghe Viet Nam giam djnh. Miu tieu ban dugcluu giir tai Vien Hoa hgc eac Hgp chit Thiennhien, Vien Khoa hgc va Cdng nghe Viet Nam.Nguyen lieu la tuai dugc xir ly diet men va saykhd d nhiet do 60°C.0CH3RjO3. Chiet xuat va phan lapBdt la khd F. religiosa (2 kg) dugc chiltsieu am vdi metanol trong 12 gid, sau khi loaidung mdi dudi ap suit giam, tien hanh chilt phaIdng-ldng vdi 2 loai dung moi nudc:chloroform(1:1). Phin djch chloroform (FKC) dugc sic kytren cot silica gel pha thuan vdi he dung mdigradient n-Hexan:Aceton (90:10-0:100) thudugc 3 phan doan FRCl, FRC2 va FRC3. Phandoan FRC3 dugc tinh e h i tren cot silica gel phathuan, rira giii vdi he dung mdi CHCl3:Aceton(8:1) thu dugc hgp chit 1 (36 mg). Phin djchnudc (FRW) dugc rira giii qua cdt Dianion HP20 vdi he dung mdi gradient nudc-metanol linluat li 100:0, 75:25, 50:50, 25:75 va 0:100 thudugc 3 phan doan FRWl, FRW2 va FRW3.Phan doan FRWl dugc sic ky tren cdt siliga gelpha thuan vdi he dung mdi rira giai liEtOAc:MeOH:H20 (4:1:0.1) thu dugc hgp chat2 (30 mg). Phan doan FRW3 dugc sic ky trencdt silica gel pha dao, rira giai vdi he dung mdiMe0H:H20 (1:1) thu dugc hgp chit 3 (20 mg).4. Hang sd vat ly va du lieu phdHgp chat 1: Dang chit rin miu tring. Diemchay 122°C. [a]o+5l,0 (c=0,l, CHCI3).ESI-MS m/z: 341,0 [M-HjO-t-H]*. H-NMR(500 MHz, CDCI3), 5 (ppm): 6,89 (2H, d, / =R ...