We report, for the first time, the remarkable efficacy of uttroside B, a potent saponin from Solanum nigrum Linn, against liver cancer. The compound has been isolated and characterized from the leaves of Solanum nigrum Linn, a plant widely used in traditional medicine and is a rich resource of several anticancer molecules. Uttroside B, that comprises of β-D-glucopyranosyl unit at C-26 of the furostanol and β-lycotetraosyl unit at C-3, is ten times more cytotoxic to the liver cancer cell line, HepG2 (IC50: 0.5 μM) than sorafenib (IC50: 5.8 μM), the only FDA-approved drug for liver cancer. Moreover, it induces cytotoxicity in all liver cancer cell lines, irrespective of their HBV status, while being non-toxic to normal immortalized hepatocytes. It induces apoptosis in HepG2 cells by down-regulating mainly the activation of MAPK and mTOR pathways. The drastic reduction in HepG2-xenograft tumor size achieved by uttroside B in NOD-SCID mice and substantiation of its biological safety through both acute and chronic toxicity studies in Swiss albino mice warrants clinical validation of the molecule against hepatic cancer, for which, the chemotherapeutic armamentarium currently has limited weapons.

An approach to expand the diversity of terpenes to novel polycyclic skeletons with contiguous stereogenic centers is described. An unprecedented 8-oxabicyclo[3.2.1]octane motif was obtained in quantitative yield by photoirradiation of zerumbone in the presence of a catalytic amount of Lewis acid. The vital role of light in the isomerization of double bonds in zerumbone, which ensued cyclization via tertiary carbocation intermediate, emulates a biosynthetic route. Synthetic diversification of the phototransformed product afforded epoxy derivatives with up to seven contiguous stereogenic centers and eight-member ring fused tricyclic motifs. The present work sheds light on the possible role of UV irradiation in the biosynthesis of oxo-bridged tricyclic structures from polyene terpenes.Letter pubs.acs.org/OrgLett

A new spectrophotometric method is proposed for the assay of ranitidine hydrochloride (RNH) in bulk drug and in its dosage forms using ceric ammonium sulphate (CAS) and two dyes, malachite (MAG) green and crystal violet (CV) as reagents. The method involves the addition of a known excess of ceric ammonium sulphate to ranitidine hydrochloride in acid medium, followed by the determination of unreacted CAS by reacting with a fixed amount of malachite green or crystal violet and measuring the absorbance at 615 or 582 nm respectively against the reagent blank. The Beer's law is obeyed in the concentration range of 0.4-8.0 μg/ ml of ranitidine hydrochloride (RNH) for RNH-MAG system and 0.2-1.6μg/ml of ranitidine hydrochloride for RNH-CV system. The molar Absorptivity, Sandell's sensitivity for each system were calculated. The method has been successfully applied to the determination of ranitidine hydrochloride in pure and dosage forms.

The crystal structure of the title compound, C18H17FO4, reported here is a polymorph of the structure first reported by Patil et al. [Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A (2007), 461, 123–130]. It is a chalcone analog and consists of substituted phenyl rings bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between the mean planes of the aromatic rings within the 4-fluoro­phenyl and trimethoxy­phenyl groups is 28.7 (1)° compared to 20.8 (6)° in the published structure. The angles between the mean plane of the prop-2-ene-1-one group and the mean plane of aromatic rings within the 4-fluoro­phenyl and trimethoxy­phenyl groups are 30.3 (4) and 7.4 (7)°, respectively, in contast to 10.7 (3) and 12.36° for the polymorph. While the two 3-meth­oxy groups are in the plane of the trimeth­oxy-substituted ring, the 4-meth­oxy group is in a synclinical [−sc = −78.1 (2)°] or anti­clinical [+ac = 104.0 (4)°] position, compared to a +sc [53.0 (4)°] or −ac [−132.4 (7)°] position. While no classical hydrogen bonds are present, weak inter­molecular C—H⋯π-ring inter­actions are observed which contribute to the stability of the crystal packing. The two polymorphs crystallize in the same space group, P21/c, but have different cell parameters for the a, b and c axes and the β angle. A comparison of the mol­ecular geometries of both polymorphs to a geometry optimized density functional theory (DFT) calculation at the B3-LYP/6–311+G(d,p) level for each structure provides additional support to these observations.

The starting material 3-nitro-2-acetylnaphtho[2,1-b]furan (2) was obtained by nitration of 2-acetylnaphtho[2,1-b] furan (1), under mild condition. The compound 1 was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with chloroacetone, where in both condensation and cyclization took place in single step. The reaction of 3-nitro-2-acetylnaphtho[2,1-b]furan (2) with hydrazine hydrate produced corresponding hydrazone (3) in excellent yield, which on treatment with various aromatic aldehydes under different reaction conditions resulted in the formation of symmetrical azines (4a-e) and unsymmetrical azines (5a-e). All the newly synthesized compounds have been characterized by analytical and spectral studies and were screened for antibacterial antibacterial activity againstBacillus subtilusandAlcaligenes fecaliesand antifungal activity againstAspergillus nidulans, Aspergillus parasiticusandAspergillus terrus. The Second Harmonic Generation (SHG) efficiency of some of the synthesized compounds was measured by powder technique using Nd:YAG laser.

In the crystal structure of the title compound, C21H18F2O3, the cyclo­hexene ring has a slightly distorted sofa conformation; the two benzene rings are inclined by 76.27 (8)° and their planes make dihedral angles of 16.65 (10) and 67.53 (7)° with the approximately planar part of the cyclo­hexenone ring [maximum deviation 0.044 (2) Å, while the sixth atom is displaced by 0.648 (3) Å from this plane]. In the crystal, weak inter­molecular C—H⋯O, C—H⋯F and C—H⋯π inter­actions join mol­ecules into a three-dimensional structure.

New 1,2-dihydropyridine (1,2-DHP)-based fluorophores 1a–1h were designed and synthesized by a one-pot four-component condensation reaction using dienaminodioate, aldehydes, and an in situ-generated hydrazone mediated by trifluoroacetic acid. The photophysical properties of 1,2-DHPs were studied in detail, and a few of them exhibited selective mitochondrial staining ability in HeLa cell lines (cervical cancer cells). A detailed photophysical investigation led to the design of 1,2-DHP 1h as an optimal fluorophore suitable for its potential application as a small molecule probe in the aqueous medium. Also, 1,2-DHP 1h exhibited sixfold enhanced emission intensity than its phosphorylated analogue 1h′ in the long wavelength region (λem ≈ 600 nm), which makes 1,2-DHP 1h′ meet the requirement as a bioprobe for protein tyrosine phosphatases, shown in L6 muscle cell lysate.

In the title compound, C15H10BrClO, the dihedral angle between mean planes of the bromo- and chloro-substituted benzene rings is 46.2 (2)° compared to 45.20 (9)° in the structure with the Cl substituent in the meta position of the aromatic ring. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromo­phenyl and 3-chloro­phenyl rings are 28.7 (5) and 24.2 (4)°, respectively. In the crystal, weak inter­molecular C—H⋯π inter­actions occur.