Studies On The Chemical Constituents And Bioactivities Of The Seeds Of Prunus Davidiana And The Leaves Of Morus Alba

Prunus davidiana (Carr.) Franch belongs to to the family Rosaceae and the genus Prunus. Prunus davidiana (Carr.) Franch grow wildly in China. The seeds of Prunus davidiana (Carr.) Franch, persicae semen, have been used in traditional Chinese medicine to treat cardiovascular, cerebrovascular, and gynecological diseases. Previous phytochemical studies on persicae semen have led to the isolation and identification of cyanogenic glycosides, glycerides, sterols, and emulsins. The Morus alba L. tree belongs to to the family Moraceae and the genus Morus. Morus alba L. grow wildly in China. Its leaves have been used to treat cold, cough, hypertension, and diabetes and as functional foods. Previous phytochemical studies on Morus alba L. have led to the isolation and identification of benzofuran derivatives, flavones, and stilbenes.The seeds of Prunus davidiana and the leaves of Morus alba were investigated on their chemical constituents systematically by various kinds of chromatographic methods. The sructures of isolates were elucidated on the basis of spectroscopic analysis and chemical evidence. Some of them were assayed for their bioactivities.32compounds were obtained from ethanolic extract of the seeds of Prunus davidiana. These compounds were identified as follows:Prupersin A (1), Prupersin (2), Prupersin B (3), Prupersin C (4), Prupersin D (5), Prupersin E (6), ethyl amygdalinate (7),4-hydroxymethyl-2-methoxyphenyl6-O-benzoyl-β-D-glucopyranoside (8), benzyl-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside (9), Amygadalin (10),(7R)-mandelic acid7-O-β-D-glucopyranoside (11), benzoic acid4-O-β-D-glucopyranoside (12), Benzyl-β-D-glucopyranoside (13), vanilloloside (14),1’-O-vanilloyl-β-D-glucoside (15), androsin (16),2-β-D-glucopyranos-yloxy-2-phenylacetic acid amide (17), prunasin和sambunigrin (18), R-mandelamide (19),(-)-secoisolariciresinol4-O-β-D-glucopyranoside (20), dihydro dehydrodiconiferyl alcoh-ol4-O-β-D-glucopyranosides (21), sucrose (22), uridine (23), adenosine (24), enthyl β-D-glucopyranoside (25), ethyl a-D-fructofuranoside (26), glycerol (27), oleic acid (28), linoleic acid (29), ergosterol peroxide (30), P-sitosterol (31), β-daucosterol (32)。Among the isolated thirty two compounds, there were nineteen aromatic glucosides (1-19), two lignans (20-21), two fatty acid (28-29), two nucleosides (23-24) and seven other components. Five compounds (1-5) were new compounds.70compounds were obtained from ethanolic extract of leaves of Morus alba. These compounds were identified as follows:2"-(1"’-hydroxy-isopropyl)-2H-furan-(4",5":8,7)- flavane (1),2’-hydroxy-4’-methoxyl-2H-(’",2"-dimethyl-3"-hydroxy)-pyran-(’",6":8,7)-flavane (2),(2R)-4’-hydroxy-2’-methoxyl-8-(2’"-hydro-xylethyl)-flavane-2’-O-β-D-glucopyranoside (3),2-methoxyl-4-allylbenzene-1-O-β-D-[6’-O-[3"-hydroxy-3"-methyl-glutaryl]]glucopyranoside (4),(-)-conicaoside (5), Moralsin (6), benzyl2-O-[β-D-apiofuranosyl(1→6)-β-D-glucopyranosyl]-2,6-dihydroxybenzoate (7),2,4,4-trimethyl-2-oxazoline (8), ethyl (16R)-hydroxyl-9-oxo-(10E,12E,14E)-octadecatrienoate (9),(25)-1-O-hexadeca-noyl glycerol (10),(3E,5E,10Z)-7-hydroxy-6,10-dimethyl-pentadecatrien-2,14-dione (11),(3R)-hydroxy-β-ionone (12),(6S,7E,9S)9-hydroxy-megastigma-4,7-dien-3-one (13), dehydrovomifol (14),(35,9R)-3-hydroxy-7,8-didehydro-β-ionol9-O-β-D-gluco pyranoside (15),(6R,9R)-3-oxo-a-ionol9-O-β-D-glucopyranoside (16),(E)-6-[9-(β-D-glucopyranosyloxy)butylidene]-1,1,5-trimethyl-4-cyclohexen-3-one (17),(Z)-6-[9-(β-D-glucopyranosyloxy)butylidene]-1,1,5-trimethyl-4-cyclohexen-3-one (18),(6S,9S)-3-oxo-a-ionol9-O-β-D-glucopyranoside (19), blumenol C9-O-β-D-glucopyranoside (20), icariside B1(21),(35)-O-β-D-glucopyranosyl-6-[3-oxo-(25)-butenylidenyl]-1,1,5-tri methylcyclohexan-(5R)-ol (22), icariside B2(23),(6S,9R)-roseoside (24),(E)-4-((1S,3R,4R)-1-hydroxy-4,5,5-trimethyl-7-oxabicyclo[4.1.0] heptan-1-yl)but-1-en-3-o-ne (25), Morusin (26), kaempferol-3-O-β-D-glucopyranoside (27), kaempferol-3-O-(6"-O-acetyl)-β-D-glucopyranoside (28), kaempferol (29), quercetin (30), quercetin-3-O-(6"-acetyl)-β-D-glucopyranoside (31), quercetin-3-O-β-D-glucopyranoside (32), rutin (33), kaempferol-3,7-di-O-β-D-glucopyranoside (34), quercetin-3,7-di-O-β-D-glucopyranoside (35),(25)-7-methoxyl-8-hydroxyethyl-4’-hydrolflavane-2’-O-β-D-glucopyrano-side(36),(25)-7-hydroxyl-8-hydroxyethyl-4’-methoxylflavane-2’-O-β-D-glucopyrano-side(37),7-Hydroxycoumarin (38), scopoletin (39), scoparone (40), skimmin (41), scopolin (42), cichoriin (43),5-hydroxycoumarin-7-O-β-D-glucopyranoside (44),(+)-Pinoresinol (45), Syringaresinol-β-D-glucoside (46),5,5’-Dimethoxylariciresinol4’-O-β-D-glucopyran-oside (47), Indigoticoside A (48), n-dotriacotane (49), n-dotfiacontanol (50),(9R)-hydroxyl-(10E,12Z,15Z)-octadecatrienoic acid (51),(2E)-dodecenedioic acid (52),2,5-Dihydro-5-oxo-5-furanoctanoic acid(53),1-glyceryl linolenate (54), Dehydrodiconiferyl alcohol9’-O-β-D-glucopyranoside(55), ursolic acid (56), aurantiamide acetate (57),5-hydroxymethyl-2-furancarboxaldehyde (58), lolide (59),1H-indole-3-carboxaldehyde (60), syringaresinol (61), trans-caffeic acid (62), eugenylglucoside (63), benzyl-β-D-glucopyranoside (64), phenethyl-8-O-β-D-glucopyranoside (65), Mulberroside F (66), ergosterol peroxide (67),(6R,9S)-Vomifoliol-9-O-β-apiofuranosyl-(1"→6’)-O-β-gluco-pyranoside (68),4-O-Feruloylquinic acid (69), Eucommin A (70)。Among the isolated seventy compounds, there were fifteen flavones (1-3,26-37), fifteen ionone derivatives (12-25,68), eight ligans (5,45-48,55,61,70), seven coumarin derivatives (5,45-48,55,61), six fatty acid (9,10,49-54) and seventeen other components. Eight compounds (1-4,6,7,9,11) were new compounds.By the model of inhibiting the production of lipid peroxide induced by Fe2+-Cys system in the liver microsomal, sixteen compounds from persicae semen were evaluated for their antioxidant activities and ten compounds1-5,7,10,15,19,29exhibited moderate activities.Compounds28and29from persicae semen showed moderate inhibitory effects on nitric oxide production in LPS-induced macrophages at10-5M.For antidiabetic bioactivities, compounds11,31, and51from the leaves of Morus alba possesed obvious inhibition agaist aldose reductase, with IC50values of4.33×10-6μM,4.33-10-7μM, and6.0×10-6μM, respectively.The anti-tumor activities of all the compounds were evaluated in vitro. All compounds from persicae semen were inactive for all cell lines used (IC50>10μM is defined as "inactive"). Compound67from the leaves of Morus alba showed cytotoxicit yagainst HELA (human cervical carcinoma) cell lines.Compound2from the leaves of Morus alba exhibited neuroprotective activity on PC12cell damage induced by serum at a concentration of10-5M. Compounds9,51, and67exhibited neuroprotective activity on PC12cell damage induced by nicouline at a concentration of10-5M.