Disease relevance of decalin

• Non-aromatic Croatian naphthalane (NAN), shown to be efficace in the treatment of psoriasis vulgaris, was studied in order to improve our understanding of its constituents, which may be potentially responsible for its bioactivity [1].
• These changes were time and dose dependent and were identical to the renal toxicity that has been reported to occur in male rats following 90 days of continuous exposure to decalin by inhalation [2].
• Decalin (in corn oil vehicle) was administered at doses of 0, 0.1, 0.5, 1.0 or 2.0 g/kg body weight to male rats, and 0, 1.0, 1.5, 1.75 or 2.0 g/kg to female rats [3].
• Two bacterial strains, Pseudomonas aeruginosa K1 and Rhodococcus equi P1, were used to degrade cyclo-alkanes (such as decalin) by a co-oxidation mechanism [4].
• This triad of lesions (hyaline droplet accumulation, granular cast formation and chronic nephrosis) lends specificity to the decalin response and establishes a potential mechanistic relationship with other chemicals that induce these effects [5].

Psychiatry related information on decalin

• Three naturally occurring ajugarins and seven semisynthetic derivatives of them, possessing different functionalities in the decalin part, together with two natural furoneoclerodane diterpenes, have been assessed as feeding behavior modifying agents of larvae of the generalist Spodoptera exigua and a specialist like Leptinotarsa decemlineata [6].

High impact information on decalin

• 19-Nor-trans-decalin-1,25(OH)2-vitamin D3 (19-nor-TD-vitamin D), characterized by the presence of a trans-fused decalin CD-ring system, was 10-fold more potent than the parent compound and was a potent activator of the genomic signal transduction pathway [7].
• The Diels-Alder adduct is transformed into the natural product via a three-step sequence including selective hydrogenation, base-catalyzed epimerization of the cis- into the trans-decalin system and O-demethylation [8].
• We demonstrate that LovD has broad substrate specificity towards the acyl carrier, the acyl substrate, and the decalin acyl acceptor [9].
• The X-ray structure of AS suggested that the steric bulk of residue 92 was central in binding of FPP to the active site of AS in a quasi-cyclic conformation, thereby facilitating attack of C1 by the C10-C11 double bond to produce the cis-fused Decalin S-germacrene A [10].
• The membrane protein cytochrome b5 was found not to bind at the decalin/water interface, indicating that interaction with lipid is required for its adherence to biological membranes [11].

Biological context of decalin

• Efficient construction of the functionalized trans-decalin core (11) is achieved through intramolecular Diels-Alder cyclization followed by diastereoselective epoxidation and aziridination [12].
• In this project, 13-week and two-year inhalation studies of decalin were conducted consecutively in both sexes of F344/N rats [13].
• The hydroxylation of cis-decalin afforded cis-9-decalol and cis-decalin-9,10-diol, exclusively, thus, excluding a long-lived radicals mechanism [14].
• Mice were more efficient in eliminating decalin than rats at lower exposure concentrations, but nonlinear elimination kinetics were more noticeable at 400 ppm [15].
• Sex differences in blood decalin elimination were observed in rats; females had a consistently higher AUC infinity at all exposure concentrations [15].

Anatomical context of decalin

• These observations are consistent with excessive accumulation of alpha2u-globulin occurring in protein droplets in renal proximal tubule epithelial cells as a result of decreased catabolic activity due to formation of ligand-protein complexs with Decalin and its metabolite(s) [16].
• It was concluded that the carcinogenic effect on the renal cortical epithelium of male rats exposed to decalin was related to increased turnover of this epithelium, resulting from the cytotoxic effects of alpha2u-globulin accumulation in the renal cortical tubular cell cytoplasm [13].
• Characterization of spontaneous and decalin-induced hyaline droplets in kidneys of adult male rats [17].
• Decalin exposure increased the size and significantly (p less than 0.01) reduced the acid phosphatase stain intensity of individual lysosomes [18].
• In stark contrast, the NCI-Black-Reiter strain, which does not produce measurable quantities of alpha 2u-globulin, neither forms hyaline droplets nor accumulates any filtered protein in its kidney cortex either spontaneously or after exposure to decalin [19].

Associations of decalin with other chemical compounds

• In an effort to determine the surface appearance of the hydrophobic ring binding region of the norepinephrine N-methyltransferase active site, we employed some trans-decalin analogues of 1-(aminomethyl)cycloundecanol (1), a potent NMT inhibitor [20].
• Administration of decalin to male rats as either the cis or trans isomer revealed that more cis -decalone is produced per unit dose as compared to trans-decalone, and that more trans-decalin accumulated in the kidney (as alpha2u-globulin-ligand complexes) compared to cis-decalin [15].
• Decalin induces a nephrotoxic response unique to the male rat, but the primary response associated with decalin exposure--hyaline droplet formation within the cytoplasm of the epithelial cells of the proximal convoluted tubule--was not recognized in the kidneys of d-limonene-exposed male rats [21].
• Coprophilin, a decalin pentanedienoic acid methyl ester, was isolated from an unidentified fungus by bioassay guided separation [22].
• The depletion-induced phase separation in a mixture of colloidal particles (PMMA-latex) and nonadsorbing polymers [poly(styrene)] in a solvent (mixture of tetralin, cis-decalin, and carbon tetrachloride) was investigated in real space with confocal scanning laser microscopy in the initial, intermediate, and final stage [23].

Gene context of decalin

• Applicability of the LC-ESI/MS method was demonstrated by determination of alpha2u-globulin in both urine and kidney samples collected from male Fischer 344/N rats dosed intravenously with cis-Decalin at concentrations of 0, 2.5, 5.0, 10, and 20 mg/kg [16].
• A strategic [2,3]-Wittig rearrangement was employed for establishing the stereogenic center at C9 and an exo-methylene function at C8 present in the decalin portion [24].
• Synthesis of the C7-C15 trans decalin portion of the natural antibiotic tetrodecamycin [25].
• In the presence of an inert atmosphere and an antioxidant, 5 g of material were methodically dissolved in decahydronaphthalene over the temperature range, 80-191 degrees C. Initially, intrinsic viscosities were measured in decalin at 135 degrees C by single point capillary viscometry [26].
• Dose-related hyaline droplet formation associated with renal accumulation of a specific protein alpha 2u-globulin) is considered the primary response in the morphogenesis of decalin-induced nephrotoxicity in the male rat and was present to a maximal degree in all decalin- and d-limonene-treated groups by day 6 [27].

Analytical, diagnostic and therapeutic context of decalin

• Decalin exposure caused increases in kidney weight, urinalysis parameters (protein, AST, LDH), kidney alpha2u-globulin concentration, and proximal convoluted renal tubular cell proliferation in males [13].
• Adsorption of polyethylene standards from decalin on liquid chromatography column packings [28].

References