Studies On Chemical Constituents Of The Seeds Of Prunus Tomentosa And Their Biological Activities

Prunus tomentosa belongs to the Prunus subgenus Lithocerasus in the family Rosaceae,and is widely distributed in China,Korea and Japan.The dried roots,leaves and fruits of P.tomentosa have been used in traditional Chinese medicine to expel wind,drain dampness,treat frostbite and alleviate pains.The fruit is usually eaten fresh or in the form of processed foods such as juice and wine.During the process of manufacturing P.tomentosa drinks,a significant quantity of by-products is generated,such as seeds.These by-products are currently discarded as industrial solid waste or underutilized.Thus,in order to potential utilize the by-products,and provide ideas for P.tomentosa resource depth development,we researched on the chemical composition and biological activity of P.tomentosa seeds.By means of various chromatographic methods such as silica gel,sephadex LH-20,ODS,polyamide column chromatography and semi-preparative HPLC,81 compounds were isolated from the 75%EtOH extract of P.tomentosa seeds.On the basis of analysis of NMR,MS data and measuring of physicochemical characters,the chemical structures of 72 compounds were elucidated as:prustomentoside A(Al),amygdalinamide(A2),?-D-gentiobiosyl-L-(+)-mandelamide(A3),prustomentoside B(A4),benzeneacetic acid methyl ester a-[(6-O-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy]-(S)(A5),prustomentoside C(A6),ethyl amygdalinate(A7),amygadalin(A8),2-?-D-glucopyranosyloxy-2-phenylacetic acid amide(A9),benzyl-O-?-D-xylopyranosyl-(1-6)-?-D-glucopyranoside(A10),phenethanol-?-D-gentiobioside(All),2.6-dimethoxy-p-hydroquinone 1-O-?-D-glucopyranoside(A12),prunustomentosanan A(B1),prunustomentosanan B(B2),prunustomentosanan C(B3),prunustomentosanan D(B4),prunustomentosanan E(B5),prunustomentosanan F(B6),prunustomentosanan G(B7),7R,8S-ficusal(B8),7R,8S-dihydrodehydrodiconiferyl alcohol(B9),7S,8R-dihydrodehydrodiconiferyl alcohol(B10),7R,8S-5-methoxydihydrodehydroconiferyl alcohol(B11),7R,8S-sakuraresinol(B12),7R,8S-dihydrodehydrodiconiferyl alcohol-9-O-?-D-glucoside(B13),7R,8S-glochidioboside(B14),prunustomentosanan H(B15),prunustomentosanan I(B16),prunustomentosanan J(B17),(1R,2S)-rel-1-(4'-hydroxy-3'-methoxyphenyl)-2-[4"-(3-hydroxypropyl)-2",6"-dimethoxyphenoxy]-1,3-propanediol(B18),wikstroemol(B19),erythro-guaiacylglycerol-?-O-4'-sinapyl ether(B20),erythro-(7S,8R)-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphen oxy}-1,3-propanediol(B21),threo-(7R,8R)-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol(B22),erythro-(7S,8R)-guaiacyl-glycerol-?-O-4'-dihydroconiferyl ether(B23),threo-(7R,8R)-guaiacyl-glycerol-?-O-4'-dihydroconiferyl ether(B24),(7S,8R)-4-hydroxy-3,3',5'-trimethoxy-8',9'-dinor-8,4'-oxyneoligna-7,9-diol-7'-aldehyde(B25),(7R,8R)-4-hydroxy-3,3',5'-trimethoxy-8',9'-dinor-8,4'-oxyneoligna-7,9-diol-7'-aldehyde(B26),7',8 '-erythro,7R,8R-1-[4-[(2-hydroxy-2-(4-hydroxyl-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3-methoxyphenyl]-1,2,3-propanetriol(B27),(+)-pinoresinol(B28),5'-(+)-medioresinol(B29),(+)-syringaresinol(B30),lariciresinol(B31),5'-methoxylariciresinol(B32),viadinol D(B33),(7'S,8S,8'R)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one(B34),isotaxiresinol(B35),(7'S,8R,8'R)-isolariciresinol(B36),7S,8R,7'R,8'S-leptolepisol A(B37),7,8-erythro ehletianol C(B38),seslignanoccidentaliol A(B39),prustomenpropanoid A(C1),evofolin B(C2),5'-methoxyevofolin B(C3),1,2-(erythro)-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol(C4),1,2-(threo)-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol(C5),prustomenpropanoid B(C6),p-methoxycinnamic acid(C7),coniferol(C8),threo-3-O-methyl-guaiacylglycerol(C9),erythro-3-O-methyl-guaiacylglycerol(C10),methyl-p-hydroxybenzoate(C11),tomenside D(C12),?-D-(1-O-acetyl-3-O-trans-feruloyl)fructofuranosyl-a-D-2',3',6'-O-triacetyl glucopyranoside(C13),toluene-2,4-dicarbamic acid dimethyl ester(C14),multiflorin A(C15),multinoside A acetate(C16),multiflorin B(C17),multinoside A(C18),afzelin(C19),quercitrin(C20),kaempferol(C21).Of all these compounds,15 compounds(Al,A4,A6,B1,B2,B3,B4,B5,B6,B7,B15,B16,B17,C1,C6)are new compounds,32 compounds were isolated for the first time from genus Prunus tomentosa.The absolute structure of A1-A7 was determined by chemical synthesis and CD spectra(Cotton effect at 220?220 nm)and their CD regularity are summarized.The anti-tumor activities of all the compounds(A1-A11)were evaluated in vitro by an MTT assay.These compounds were inactive for four cell lines used.The antioxidant activities of the neolignans were evaluated using 2,2-diphenyl-1-pikrylhydrazyl(DPPH)and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid)(ABTS)assay,and the results showed that most of the isolates exhibited potent antioxidant activity.Protective effects of some compounds against H2O2-induced injury in HepG2 cell were evaluated,and B7,B11,B16 exhibited remarkable protective activities.