AIMTo study the benzophenones in the roots of Securidaca inappendiculata Hassk.

METHODSColumn chromatography (including silica gel and Sephadex LH-20) was used to isolate benzophenones whose structures were elucidated by HREI-MS, NMR (1D and 2D) methods.

RESULTSA new benzophenone was isolated and identified as 2-methoxy-3,4-methylenedioxy-benzophenone (I), along with a known compound 4-hydroxy-2,6-dimethoxy-benzophenone (II).

CONCLUSIONCompound I is a new one named as securiphenone B, compound II was isolated from the genus for the first time.

Benzophenones ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Securidaca ; chemistry

Seven acylated triterpene saponins were isolated from the roots of Securidaca inappendiculata by means of various chromatographic techniques such as silica gel, MPLC, preparative HPLC, and semi-preparative HPLC. Their chemical structures were identified as securioside A(1), securioside B(2), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3)]-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3) ] -4-O-[(E/Z)-3, 4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3/4), 3-O-β-D-glucopyranosyl presenegenin 28-O-α-L-arabinopyranosyl-(1-->3)-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(5), polygalasa- ponin XLV(6), and polygalasaponin XLVI (7) on the basis of spectroscopic data analysis and physicochemical properties. Among them, compounds 5-7 were isolated from the plants in genus Securidaca for the first time and compounds 3, 3/4 were isolated from the species for the first time. The cytotoxicity assay showed that compounds 2, 3/4, 5 have moderate cytotoxic activities against Lewis lung carcinoma LLC cells with IC50 values of 41.10, 38.17, and 48.92 µmol · L(-1), respectively; compound 2 exhibited moderate cytotoxic activities against human breast cancer MCF-7 cells with an IC50 value of 47.93 µmol · L(-1).
Antineoplastic Agents, Phytogenic ; isolation & purification ; pharmacology ; Humans ; MCF-7 Cells ; Plant Roots ; chemistry ; Saponins ; chemistry ; isolation & purification ; pharmacology ; Securidaca ; chemistry

OBJECTIVETo study the antioxidant constituents from the roots of Securidaca inappendiculata.

METHODThe bioassay-guided isolation of antioxidant constituents was carried out by the column chromatographic techniques. The combination of IR, MS, NMR and 2D-NMR spectroscopics methods was used to identify their structures.

RESULTTwo new xanthones, 1, 2, 5-trihydroxy-6, 8-dimethoxy-9H-xanthen-9-one(1), 1, 5-dihydroxy-2, 6, 8-trimethoxy-9H-xanthen-9-one (2), along with seven known ones, 3, 8-dihydroxy-1, 4-dimethoxy-9H-xanthen-9-one(3), 4, 6-dihydroxy-1, 5, 7-trimethoxy-9H-xanthen-9-one(4), 7-hydroxy-1, 2, 3, 8-tetramethoxy-9H-xanthen- 9-one(5), 1, 7-dihydroxy-9H-xanthen-9-one(6), 4-hydroxy-3, 7-dimethoxy-9H-xanthen-9-one(7), 1,7-dimethoxy-9H-xanthen-9-one(8) and aucuparin(9), were isolated from the roots of S. inappendiculata.

CONCLUSIONCompounds 1 and 2 were new xanthones, and compound 3 was isolated as a natural product for the first time, and compounds 4 and 6 were isolated for the first time from this genus. The antioxidant activities of all compounds were evaluated by ABTS, FRAP and DPPH assays respectively. Compound 9 showed significant activity by the ABTS and FRAP assays. Compound 1 showed significant activity with IC50 value of 0.31 mg x L(-1) in DPPH assay. Scavenging capacity of all compounds determined by all assays were well correlated between ABTS and FRAP assay (r = 0.9555).

Antioxidants ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Securidaca ; chemistry ; Spectrometry, Mass, Electrospray Ionization ; Spectrophotometry, Infrared ; Xanthones ; chemistry

OBJECTIVETo study the chemical constituents of Securidaca inappendiculata.

METHODColumn chromatographic techniques were applied to isolate constituents. A combination of MS and NMR spectroscopy was used to identify structures of constituents.

RESULTSeven compounds were isolated from the CHCl3 fraction and their structures were elucidated as 3, 4-dihydroxybezoic acid (1), 3-hydroxy-4-methoxylbenzoic acid (2), coniferaldehyde (3), 7-hydroxy-1, 2, 3, 8-tetrame thoxyxanthone (4), 1, 3, 8-trihydroxy-4-methoxyxanthone (5), 1, 3, 8-trihydroxy-2-methoxyxanth-one (6), 1, 3, 6-trihydroxy-2,7-dimethoxyxanthone (7).

CONCLUSIONCompounds 1-6 were isolated for the first time from the genus. The antioxidant activities of compounds 3-6 were assayed by the method of DPPH and compound 3 showed the IC50 value of 4.14 microg x mL(-1).

Antioxidants ; analysis ; pharmacology ; Drugs, Chinese Herbal ; chemistry ; Inhibitory Concentration 50 ; Magnetic Resonance Spectroscopy ; Rhizome ; chemistry ; Securidaca ; chemistry ; Spectrometry, Mass, Electrospray Ionization

AIMTo investigate the chemical constituents of Securidaca inappendiculata.

METHODSCompounds were isolated by silica gel column chromatography and Medium Pressure Liquid Chromatography, respectively. Structures of the compounds were elucidated by chemical evidence and spectral (UV, IR, MS, 1HNMR and 13CNMR) analysis.

RESULTSEight compounds (1-8) were isolated and identified. Seven of them (2-7) are known compounds: oleanolic acid, p-hydroxytruxinic acid, p-coumaric acid, ethyl p-methoxycinnamate, uridine, beta-sitosterol and daucosterol. One (1) is a new hemiterpenoic acid glycoside, named securiterpenoside.

CONCLUSIONA new hemiterpenoic acid glycoside, named securiterpenoside, was isolated from Securidaca inappendiculata Hassk. Seven known compounds were isolated from genus Securidaca for the first time.

Butyrates ; chemistry ; isolation & purification ; Coumaric Acids ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Oleanolic Acid ; chemistry ; isolation & purification ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Securidaca ; chemistry