Crystal structure of (E)-1-(4-chloro-phen-yl)ethanone O-de-hydro-abietyloxime.

The title compound, C28H34ClNO2 {systematic name: (E)-1-(4-chloro-phen-yl)ethanone O-[(1R,4aS,10aR)-7-isopropyl-1,4a-di-methyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene-1-carbonyl]oxime}, was synthesized from de-hydro-abietic acid. In the de-hydro-abietyl moiety, the central and terminal cyclo-hexane rings display chair and half-chair conformations, respectively, and a trans-ring junction. The C=N bond is in an E conformation and the C-O-N=C torsion angle is 148.1 (5)°. No directional inter-actions except van der Waals contacts occur in the crystal structure.

Crystal structure of (E)-1-(4-meth-oxy-phen-yl)ethanone O-de-hydro-abietyloxime.

In the title compound, C29H37NO3 {systematic name: (E)-1-(4-meth-oxy-phen-yl)ethanone O-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene-1-carbon-yl]oxime}, a new derivative of de-hydro-abietic acid, the two cyclo-hexane rings exhibit a trans-ring junction and are in chair and half-chair conformations. The C=N double bond exhibits an E conformation.

N,N-Di-methyl-dehydro-abietyl-ammonium chloride ethanol monosolvate.

The title compound {systematic name: 1-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenan-thren-1-yl]-N,N-di-methyl-methanaminium chloride ethanol monosolvate}, C22H36N(+)·Cl(-)·C2H6O, was synthesized from dehydroabietylamine by N-methyl-ation with formaldehyde/formic acid and transformation into the hydro-chloride. The de-hydro-abietyl moiety exhibits the usual conformation with the two cyclo-hexane rings in chair and half-chair conformations and a trans-ring junction. The crystal structure is built up from columns of the de-hydro-abietyl moieties stacked along the a axis. These columns are held together by the chloride ions via N-H⋯Cl and C-H⋯Cl inter-actions, which establish a two-dimensional network parallel to (010). The ethanol solvent mol-ecules are located between the columns and anchored via O-H⋯Cl hydrogen bonds.

16-Isopropyl-5,9-dimethyl-tetra-cyclo-[10.2.2.0.0]hexa-dec-15-ene-5,14-dimethanol.

The title compound, C(23)H(38)O(2), a tetra-cyclo-[10.2.2.0(1,10).0(4,9)] hexa-decane structure, crystallized with four independent mol-ecules in the asymmetric unit. In the crystal, these independent mol-ecules are linked by O-H⋯O hydrogen bonds, forming a polymeric chain propagating in [100].

16-Isopropyl-5,9-dimethyl-tetra-cyclo-[10.2.2.0.0]hexa-dec-15-ene-5,13,14-trimethanol ethanol monosolvate.

The title compound, C(24)H(40)O(3)·C(2)H(6)O, is a substituted tetra-cyclo-[10.2.2.0(1,10).0(4,9)]hexa-decane derivative obtained from the reduction of maleopimaric acid which was isolated from a maleic anhydride modified rosin. In the crystal, the triol mol-ecule and the ethanol solvent mol-ecule are linked by hydroxyl O-H⋯O hydrogen bonds, giving a two-dimensional network structure.

Neuropeptide S Attenuates the Alarm Pheromone-Evoked Defensive and Risk Assessment Behaviors Through Activation of Cognate Receptor-Expressing Neurons in the Posterior Medial Amygdala.

Neuropeptide S (NPS) acts by activating its cognate receptor (NPSR). High level expression of NPSR in the posterior medial amygdala suggests that NPS-NPSR system should be involved in regulation of social behaviors induced by social pheromones. The present study was undertaken to investigate the effects of central administration of NPS or with NPSR antagonist on the alarm pheromone (AP)-evoked defensive and risk assessment behaviors in mice. Furthermore, H129-H8, a novel high-brightness anterograde multiple trans-synaptic virus, c-Fos and NPSR immunostaining were employed to reveal the involved neurocircuits and targets of NPS action. The mice exposed to AP displayed an enhancement in defensive and risk assessment behaviors. NPS (0.1-1 nmol) intracerebroventricular (i.c.v.) injection significantly attenuated the AP-evoked defensive and risk assessment behaviors. NPSR antagonist [D-Val5]NPS at the dose of 40 nmol completely blocked the effect of 0.5 nmol of NPS which showed the best effective among dose range. The H129-H8-labeled neurons were observed in the bilateral posterodorsal medial amygdala (MePD) and posteroventral medial amygdala (MePV) 72 h after the virus injection into the unilateral olfactory bulb (OB), suggesting that the MePD and MePV receive olfactory information inputs from the OB. The percentage of H129-H8-labeled neurons that also express NPSR were 90.27 ± 3.56% and 91.67 ± 2.46% in the MePD and MePV, respectively. NPS (0.5 nmol, i.c.v.) remarkably increased the number of Fos immunoreactive (-ir) neurons in the MePD and MePV, and the majority of NPS-induced Fos-ir neurons also expressed NPSR. The behavior characteristic of NPS or with [D-Val5]NPS can be better replicated in MePD/MePV local injection within lower dose. The present findings demonstrated that NPS, via selective activation of the neurons bearing NPSR in the posterior medial amygdala, attenuates the AP-evoked defensive and risk assessment behaviors in mice.

N-Morpholino-Δ-dihydro-abietamide.

The title compound, C(24)H(39)NO(2) (systematic name: 4-{[1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,5,6,7,8,9,10,10a-dodeca-hydro-phenanthren-1-yl]carbon-yl}morpholine), has been synthesized from Δ(8)-dihydro-abietic acid. Two cyclo-hexene rings adopt half-chair conformations, whereas the cyclo-hexane and morpholine rings are each in the chair conformation. Two methyl groups are in an axial position with respect to the tricyclic hydro-phenanthrene nuclei.

4-Isopropyl-N-phenyl-cyclo-hexa-1,3-diene-1-carboxamide.

In the crystal structure of the title compound, C(16)H(19)NO, mol-ecules are linked through a pair of N-H⋯O hydrogen bonds, forming chains along the a axis.

(1R,4aS,10aR)-1,4a-Dimethyl-N-[(morpholin-4-yl)carbothio-yl]-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene-1-carboxamide.

In the title compound, C(25)H(36)N(2)O(2)S, the cyclo-hexane and morpholine rings adopt chair conformations. The cyclo-hexene and cyclo-hexane rings form a trans ring junction with the two methyl groups in axial positions. The N-H and C=O bonds in the urea group are anti to each other. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds.

Co-localization of two-color rAAV2-retro confirms the dispersion characteristics of efferent projections of mitral cells in mouse accessory olfactory bulb.

The accessory olfactory bulb (AOB), located at the posterior dorsal aspect of the main olfactory bulb (MOB), is the first brain relay of the accessory olfactory system (AOS), which can parallelly detect and process volatile and nonvolatile social chemosignals and mediate different sexual and social behaviors with the main olfactory system (MOS). However, due to its anatomical location and absence of specific markers, there is a lack of research on the internal and external neural circuits of the AOB. This issue was addressed by single-color labeling and fluorescent double labeling using retrograde rAAVs injected into the bed nucleus of the stria terminalis (BST), anterior cortical amygdalar area (ACo), medial amygdaloid nucleus (MeA), and posteromedial cortical amygdaloid area (PMCo) in mice. We demonstrated the effectiveness of this AOB projection neuron labeling method and showed that the mitral cells of the AOB exhibited efferent projection dispersion characteristics similar to those of the MOB. Moreover, there were significant differences in the number of neurons projected to different brain regions, which indicated that each mitral cell in the AOB could project to a different number of neurons in different cortices. These results provide a circuitry basis to help understand the mechanism by which pheromone information is encoded and decoded in the AOS.

Dehydro-abietic acid.

THE TITLE COMPOUND [SYSTEMATIC NAME: (1R,4aS,10aR)-7-iso-prop-yl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phen-anthrene-1-carboxylic acid], C(20)H(28)O(2), has been isolated from disproportionated rosin which is obtained by isomerizing gum rosin with a Pd-C catalyst.. Two crystallographically independent mol-ecules exist in the asymmetric unit. In each mol-ecule, there are three six-membered rings, which adopt planar, half-chair and chair conformations. The two cyclo-hexane rings form a trans ring junction with the two methyl groups in axial positions. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds.

N-(2-Pyridylmethyleneamino)dehydro-abietylamine.

The title compound {systematic name: 1-[(1R,4aS,10aR)-7-isopropyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthren-1-yl]-N-[(E)-2-pyridylmethyleneamino]methanamine}, C(26)H(33)N(2), has been synthesized from dehydro-abietylamine. The two cyclo-hexane rings form a trans ring junction with classic chair and half-chair conformations, respectively, whereas the benzene and pyridine rings are almost planar, and the dihedral angle between them is 80.4°. The two methyl groups directly attached to the tricyclic nucleus are on the same side of the tricyclic hydro-phenanthrene structure.

16-Isopropyl-5,9-dimethyltetra-cyclo-[10.2.2.0.0]hexa-dec-15-ene-5,14-dicarboxylic acid ethanol hemisolvate.

In the title compound, C(23)H(34)O(4)·0.5C(2)H(6)O, which was isolated from acrylic modified rosin, the endocyclic compound adopts a tetra-cyclo-[10.2.2.01,10.04,9]hexa-decane structure. In the crystal, the components are linked by O-H⋯O and C-H⋯ hydrogen bonds.

N-Benzyl-idenenordehydro-abietylamine.

THE TITLE COMPOUND [SYSTEMATIC NAME: (1R,4aS,10aR,E)-N-benzyl-idene-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthren-1-amine], C(26)H(33)N, has been synthesized from nor-dehydro-abietylamine and benzaldehyde. The two cyclo-hexane rings form a trans ring junction with classic chair and half-chair conformations, respectively, the two methyl groups are on the same side of tricyclic hydro-phenanthrene structure. The dihedral angle between two benzene rings is 44.2 (4)°. The C=N bond is in an E configuration.

15-Hydroxy-ethyl-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-aza-penta-cyclo-[10.5.2.0.0.0]nona-dec-18-ene-5-carboxylic acid.

The title compound, C(26)H(37)NO(5), which was synthesized from monoethano-lamine and maleopimaric acid, consists of two fused and unbridged cyclo-hexane rings. They form a trans ring junction with a chair conformation. The two methyl groups are in axial positions. In the crystal, inter-molecular O-H⋯O hydrogen bonds link adjacent mol-ecules into a layer structure. Two C-H⋯O interactions are also present.

2-Hydr-oxy-6,6-dimethyl-bicyclo-[3.1.1]heptane-2-carboxylic acid.

The title compound, C(10)H(16)O(3), with a bicyclo-[3.1.1]heptane unit, was obtained by oxidation of ß-pinene. The asymmetric unit contains two independent mol-ecules with similar geometry: the six-membered rings in both mol-ecules adopt envelope conformations. In the crystal, the independent mol-ecules exist as O-H⋯O hydrogen-bonded dimers. The dimers are linked into helical chains along the b axis by O-H⋯O hydrogen bonds.

7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodeca-hydro-phenan-threne-1-carboxylic acid.

The title compound, C(20)H(32)O(2), has been isolated from hydrogenated rosin. There are two independent mol-ecules in the asymmetric unit. In each mol-ecule, the cyclo-hexane ring assumes a chair conformation, while the two cyclo-hexene rings adopt half-chair and envelope conformations. Inter-molecular O-H⋯O hydrogen bonding between carboxyl groups links pairs of independent mol-ecules into dimers.

Cohabitation impaired physiology, fitness and sex-related chemosignals in golden hamsters.

This study investigated the impact of long-term paternal presence (cohabitation) on several physiological parameters such as body weight, adrenal weight, cortisol of parents, and the survival of pups compared with brief daily encounters (isolation) of male-female pairs in golden hamsters (Mesocricetus auratus). We showed that females were affected more by cohabitation as evidenced by increased body and adrenal weights, elevated cortisol concentrations, and heavier uteri and spleens as compared with cohabiting male and isolated females. Furthermore, we found that tetradecanoic and hexadecanoic acids of the flank glands were sexually dimorphic, for which they were putative female pheromones. These two compounds were suppressed in females and elevated in males by cohabitation, suggesting that cohabitation impaired sex chemosignals. Overall, we concluded that housing females and males together had deleterious effects on adults and the survival of their pups in the golden hamster.

Cytotoxic effects and pro-apoptotic mechanism of TBIDOM, a novel dehydroabietylamine derivative, on human hepatocellular carcinoma SMMC-7721 cells.

We have investigated the antiproliferative effects of TBIDOM (N-(4-(2,2,2-trifluoroethyl) benzylidene) (7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl) meth-anamine) and have explored its possible mechanisms on human hepatocellular carcinoma SMMC-7721 cells. The proliferative status of cells treated with TBIDOM was measured by the colorimetric MTT assay. Cellular apoptosis was analysed using Hoechst 33342 staining and flow cytometry. Reduction of mitochondrial membrane potential (Delta psi(m)) was also detected by flow cytometry. Western blotting assay was used to evaluate the release of cytochrome c and expression of p53, Bcl-2 and Bax proteins. It was shown that TBIDOM displayed a significant inhibitory effect on growth of SMMC-7721 cells in a dose- and time-dependent manner. Hoechst 33342 staining and flow cytometry analysis showed an increase of apoptosis rate and decrease of mitochondrial membrane potential after SMMC-7721 cells were exposed to TBIDOM for 24 h. Pretreatment of SMMC-7721 cells with TBIDOM significantly induced a decrease of Bcl-2 protein expression and an increase of caspase-3 activity and Bax protein expression. The results indicated that TBIDOM could effectively inhibit proliferation by induction of apoptosis and could be a promising candidate in the development of a novel class of antitumour agent.

[Protective effects of glutamine on the intestinal mucosal barrier in young rabbits under hemorrhagic shock].

OBJECTIVE: Glutamine (Gln) is now considered as conditionally essential amino acid with many biological activities. This study aimed to investigate whether it has protective effects on the intestinal mucosal barrier in young rabbits under hemorrhagic shock. METHODS: Eighteen young rabbits aged 26 +/- 3 days were randomly assigned into 3 groups: Control (no treatment), Low-dose Gln (L-Gln, 0.5 g/kg daily) and High-dose Gln (H-Gln, 1.0 g/kg daily) treatment groups. Gln was administered by gastric tube daily for 7 days and then hemorrhagic shock was induced by blood withdrawing from femoral artery. Plasma levels of diamine oxidase (DAO) and serum levels of interleukin-8 (IL-8) were measured before shock, and at 2, 6 and 24 hrs after resuscitation. Ileum tissues located approximately 5 cm away from the ileocecal valve was removed for histological examination, lymphocyte distribution, polymorphonuclear (PMN) count and assessing the height, width and surface area of the villi. RESULTS: Plasma levels of DAO and serum levels of IL-8 at 6 and 24 hrs after resuscitation in the L-Gln and the H-Gln groups decreased significantly compared with those of the Control group. L-Gln and H-Gln also resulted in a decrease in the PMN counts and the lymphocyte percentage in the ileum compared with the Control group. Exfoliation and atrophy of villous epithelial cells occurred and the height and surface area of villous were reduced in the Control group. The ileum morphology of the two Gln treatment groups was found to be nearly normal. There were no differences between the L-Gln and the H-Gln groups. CONCLUSIONS: Gln within a therapeutic dose has protective effects on intestinal mucosal barrier in young rabbits under hemorrhagic shock.