Naringin inhibits ovarian tumor growth by promoting apoptosis: An in vivo study.

The aim of the present study was to investigate the antitumor activities of naringin in ovarian cancer, and to assess the underlying mechanisms. Ovarian tumor cells were implanted into nude mice to produce ovarian tumors in vivo. The mice were divided into six groups: Control, low dose naringin [0.5 mg/kg, intraperitoneal (i.p.)], middle dose naringin (1 mg/kg, i.p.), high dose naringin (2 mg/kg, i.p.), positive control (cisplatin, 2 mg/kg, i.p.) and a combination of cisplatin and naringin (both 2 mg/kg). Following administration of naringin and/or cisplatin, the tumor size and weight were measured. Apoptosis of tumor cells was detected using a terminal deoxynucleotidyl transferase dUTP nick end labeling assay. Apoptosis-associated gene expression was detected using reverse transcription-polymerase chain reaction and immunohistochemistry. In the range of 0.5-2 mg/kg, naringin dose-dependently inhibited tumor growth, as demonstrated by a decrease in tumor size and weight. Naringin promoted apoptosis of the ovarian tumor cells. Additionally, naringin reduced the expression of B-cell lymphoma (Bcl)-2, Bcl-extra large (Bcl-xL), cyclin D1, c-Myc and survivin, while it increased the expression of caspase-3 and caspase-7. The data demonstrated that naringin inhibited ovarian tumor growth in vivo. Its mechanisms may be associated with caspase-7-, caspase-3-, Bcl-2- and Bcl-xL-mediated apoptosis. Nevertheless, the clinical application of naringin in the treatment of ovarian cancer requires further study.

1-Meth-oxycarbonyl-2-(4-nitro-phen-yl)ethanaminium nitrate.

In the title compound, C(10)H(13)O(4)N(2) (+)·NO(3) (-), the nitro group and the benzene ring are essentially coplanar. The dihedral angle between the benzene ring and the methyl-carboxyl-ate plane is 49.6 (3)°. The crystal structure is stabilized by cation-anion N-H⋯O and N-H⋯N hydrogen bonds, building sheets parallel to (001).

(1S,2S)-2-Carboxy-1-(3-pyridiniometh-yl)pyrrolidin-1-ium dichloride hemihydrate.

In the title mol-ecule, C(11)H(16)N(2)O(2) (2+)·2Cl(-)·0.5H(2)O, all N atoms are protonated. In the crystal structure, the organic cation and Cl(-) ions are linked by N-H⋯Cl and O-H⋯Cl hydrogen bonds, forming a one-dimensional infinite ribbon extending parallel to the (110) plane.

2-Amino-5-(1H-tetra-zol-5-yl)pyridin-1-ium nitrate.

In the cation of the title compound, C(6)H(7)N(6) (+)·NO(3) (-), the pyridine and tetra-zole rings are essentially coplanar, exhibiting a dihedral angle of 6.30 (6)°. In the crystal structure, N-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds form a three-dimensional network.

Diaqua-[5-(2-pyrid-yl)tetra-zolato-κN,N]manganese(II).

The title compound, [Mn(C(6)H(4)N(5))(2)(H(2)O)(2)], was synthesized by the hydro-thermal reaction of Mn(NO(3))(2) with picolino-nitrile in the presence of NaN(3). The Mn atom lies on an inversion centre. The distorted octa-hedral Mn environment contains two planar trans-related N,N'-chelating 5-(2-pyrid-yl)-tetra-zolate ligands in the equatorial plane and two axial water mol-ecules. O-H⋯N hydrogen bonds generate an infinite three-dimensional network.

catena-Poly[zinc(II)-bis-[µ-5-(2-amino-phenyl)tetra-zolato]-κN,N:N;κN:N,N].

The polymeric title compound, [Zn(C(7)H(6)N(5))(2)](n), was synthesized by the hydro-thermal reaction of Zn(NO(3))(2) with 2-amino-benzonitrile in the presence of NaN(3). The zinc(II) metal centre displays a distorted octa-hedral coordination environment provided by N atoms of two bidentate chelating and two monodentate 5-(2-amino-phen-yl)tetra-zolate ligands. These ligands act as bridges, linking adjacent Zn atoms into polymeric criss-crossed chains parallel to the [110] and [10] directions. Intra-chain N-H⋯N hydrogen-bonding inter-actions are observed.

2-Amino-5-cyano-pyridinium chloride.

In the crystal structure of the title compound, C(6)H(6)N(3) (+)·Cl(-), cohesion is maintained by cation-anion N-H⋯Cl and cation-cation N-H⋯N hydrogen bonds, which link the ions into a three-dimensional network.

3-Cyano-anilinium chloride.

In the title salt, C(7)H(7)N(2) (+)·Cl(-), all non-H atoms of the cation are essentially coplanar (r.m.s. deviation = 0.005 Å). In the crystal structure, the organic cations and chloride ions are linked to form a two-dimensional network parallel to the (001) plane by N-H⋯Cl hydrogen bonds.

(S)-1-Methoxy-carbonyl-2-(4-nitro-phen-yl)ethanaminium chloride.

The title compound, C(10)H(13)N(2)O(4) (+)·Cl(-), comprises a Cl(-) anion and a protonated aminium cation. The crystal packing is stabilized by cation-anion N-H⋯Cl hydrogen bonds and N-H⋯O hydrogen bonds, building an infinite two-dimensional network parallel to the (001) plane. The S absolute configuration at the chiral center was deduced from the synthetic pathway and confirmed by the X-ray analysis.

2-Cyano-anilinium nitrate.

In the title compound, C(7)H(7)N(2) (+)·NO(3) (-), all atoms of the cation, with the exception of two H atoms of the NH(3) group, lie on a mirror plane, while the anion lies across this plane with the N and one O atom on the mirror plane. In the crystal structure, the organic cations and NO(3) (-) anions are linked by N-H⋯N and N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100).

2-(2H-Tetra-zol-5-yl)pyridinium chloride.

In the title compound, C(6)H(6)N(5) (+)·Cl(-), the pyridinium and tetra-zole rings are essentially coplanar. The pyridine N atoms are protonated. In the crystal structure, mol-ecules are connected via N-H⋯Cl, C-H⋯Cl, C-H⋯N and N-H⋯N hydrogen bonds into layers that are parallel to the (001) plane. There are two crystallographically independent mol-ecules in the asymmetric unit which are located on mirror planes.

2-Amino-5-(1H-tetra-zol-5-yl)pyridinium chloride.

In the title salt, C(6)H(7)N(6) (+)·Cl(-), there are two organic cations with similar conformations and two chloride anions in the asymmetric unit. The pyridine and tetra-zole rings are essentially coplanar in each cation, with dihedral angles of 4.94 (15) and 5.41 (14)°. The pyridine N atoms are protonated. The crystal packing is stabilized by N-H⋯N and N-H⋯Cl hydrogen bonds, forming an infinite sheets parallel to the (101).