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.

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.

Crystal structure of 7-isopropyl-1,4a,N-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodeca-hydro-phenanthrene-1-carb-ox-amide.

In the title compound, C26H37NO, a new derivative of di-hydro-abietic acid, the two cyclo-hexene rings adopt half chair conformations, whereas the cyclo-hexane ring has a chair conformation. Each of the methyl groups is in an axial position with respect to the tricyclic hydro-phenanthrene residue. In the crystal packing, methyl-ene-C-H⋯π(phen-yl) inter-actions lead to supra-molecular helical chains along [010]; the amide-H atom does not form a significant inter-molecular inter-action owing to steric pressure.

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.

Tyrosine kinase inhibitory activity of dehydroabietylamine derivatives tested by homogeneous time-resolved fluorescence based high throughput screening model.

Protein tyrosine kinases (PTKs) are attractive targets in searching for therapeutic agents against many diseases. In this study, a series of dehydroabietylamine derivatives were first determined to show PTK inhibitory activity using a high-throughput screening (HTS) method based on homogeneous time-resolved fluorescence (HTRF) technology. The structure-activity relationships of the dehydroabietylamine derivatives were established, and it was found that the compounds with a nitrogen-containing side chain had better inhibitory activity. Further studies showed that the compounds substituted with halogen in the phenyl ring resulted in higher inhibitory activity on the epidermal growth factor receptor (EGFR), and can be a guide to modify the structure of dehydroabietylamine derivatives. Dehydroabietylamine derivatives might be a new class of multi-targeted and effective PTK inhibitors with structure modifications.

Development- and activity-dependent expression of clusterin in the mouse olfactory bulb.

Clusterin, a protein involved in many biological processes, is expressed broadly in the central nervous system, but its functions remain largely unknown. As preparations for elucidating some possible functions, we examined the spatiotemporal expression patterns of clusterin in the mouse olfactory bulb at different developmental stages and under different neuronal activity levels. Our results revealed a dynamic expression of the protein during development. Clusterin signal was seemingly diffuse during the early stages of development, shifted to the cell somas later and then predominantly to the axons of projection neurons in the adult stage, with a transition point at approximately postnatal day 18. The effects of olfactory deficits on the clusterin expression level in an anosmic mouse model were neuron-specific: the signals increased remarkably from faint to strong in olfactory sensory neurons, reduced considerably from moderate/strong to faint in the centrifugal projection neurons, decreased moderately from moderate to faint in the local bulbar projection neurons, and remained intense in long-distance bulbar projection neurons. These results showed that clusterin expression is modulated dynamically during development and by sensory activity. These findings deepen our understanding of this broadly expressed protein.

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.

Syntheses and antibacterial activity of Schiff bases from 16-isopropyl-5, 9-dimethyltetracyclo [10.2.2.0(1, 10).0(4, 9)] hexadec-15-ene-5, 14-dicarboxylic acid.

16-isopropyl-5, 9-dimethyltetracyclo [10.2.2.0(1, 10).0(4, 9)] hexadec-15-ene-5, 14-dicarboxylic acid (1b) was prepared from rosin through a Diels-Alder addition reaction. Then, a group of Schiff bases derived from 1b was synthesised. Their structures were characterised by IR,(1)H-NMR, MS and elemental analysis. The antibacterial activities of these newly synthesised Schiff bases were also investigated. The results show that these compounds possess antibacterial activities against Staphylococcus aureus and Escherichia coli. Among them, compounds 5a, 5b and 5c, exhibit remarkable antibacterial activity against E. coli.

[Progress in activity-dependent structural plasticity of neural circuits in cortex].

Neural circuits of mammalian cerebral cortex have exhibited amazing abilities of structural and functional plasticity in development, learning and memory, neurological and psychiatric diseases. With the new imaging techniques and the application of molecular biology methods, observation neural circuits' structural dynamics within the cortex in vivo at the cellular and synaptic level was possible, so there were many great progresses in the field of the activity-dependent structural plasticity over the past decade. This paper reviewed some of the aspects of the experimental results, focused on the characteristics of dendritic structural plasticity in individual growth and development, rich environment, sensory deprivation, and pathological conditions, as well as learning and memory, especially the dynamics of dendritic spines on morphology and quantity; after that, we introduced axonal structural plasticity, the molecular and cellular mechanisms of structural plasticity, and proposed some future problems to be solved at last.

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.

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].

(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.

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.

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.

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.

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.

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.