Cedrone

When cedrene is oxidised by chromic acid, in acetic acid solution, a mixture of two ketones is obtained, of which the principal is a body to which the name cedrone has been assigned. Cedrone has the following characters —... 

By the reduction of cedrone by means of sodium and alcohol, there is formed dihydro-isocedrol, CijH gO, boiling at 148° to 151° C. under a pressure of 9-5 mm. When cedrene is heated at 180° to 210° C. with hydriodic acid and red phosphorus, and the product formed is reduced by sodium and alcohol, a body Cj Hjg is obtained, which Semmler describes by the name dihydro-cedrene It boils at 116° to 122° C. under 12 mm. pressure its specific gravity is 0-9052 at 15° C. 

For some recent reviews on enzyme modification see (a) Reetz, M.T., Evolution in the test-tube as a means to creat selective biocatalysts. Chimia, 2007,61, 100-103 (b) Sylvestre, J., Chautard, H., Cedrone, E. and Delcourt, M., Directed evolution of biocatalysts. Org. Proc. Res. Dev., 2006, 10, 562-571 (c) Hibbert, E.G. and Dalby, P.A., Directed evolution strategies for improved enzymatic performance. Microb. Cell Fact., 2004, 4, 29 (d) Otten, L.G. and Quax, W.J., Directed evolution selecting today s biocatalysts. Biomol. Eng., 2005, 22, 1-9. 

Guidotti M, Giovinazzo R, Cedrone O, Vital M (1998) Investigation on the presence of aromatic hydrocarbons, persistent organochlorine compounds, phthalates and the breathable fraction of atmospheric particulate in the air of Rieti urban area. Ann Chim-Rome 88 419 27... 

The following also gave positive tests Quassisa aitdra, Simaba (= Quassia) cedron (5/6), Q. ferritginea, Simarouba (= Quassia) glauca (1/2). 

Cedrone F, Menez A, Quemeneur E (2000) Tailoring new enzyme functions by rational redesign. Curr Opin Struct Biol 10 405 -10... 

The intramolecular Pauson-Khand reaction has been extensively used as a key step in total synthesis of fairly complex polycyclic natural products. The [2 + 2 + IJcycloaddition was, for example, used in recent syntheses of magellanine (Scheme 269), tecomanine, toward palau amines and styloguanidines (Scheme 270), Sa-hydroxystreptazolone (Scheme 271), ceratopicanol (Scheme 272), 13-deoxyserratine (Scheme 273), ABC-rings of nakadomarin and manzamine (Scheme 274), cedrone (Scheme 275), (-)-dendrobine (Scheme 276), " toward kalmanol (Scheme 277), and (+)-epoxydictymene (Scheme 278). 

Caturelli, E., Squillante, M.M., Andriulli, A., Cedrone, A., Cellerino, C., Pompili, M., Manoja, E.R., Rapaccini, G.L. Hypoechoic lesions in the bright liver a reliable indicator of fatty change. A prospective study. J. Gastroenterol. Hepatol. 1992 7 469-472... 

Cedrone, A., Pompili, M., Sallustio, G., Lorenzelli, G.P., Gasbarrini, G., Rapaccini, G.L. Comparison between color power Doppler ultrasound with echo-enhancer and spiral computed tomography in the evaluation of hepatocellular carcinoma vascularization before and after ablation procedures. Amer. J. Gastroenterol. 2001 96 1854-1859... 

Pompili, M., Rapacdni, G.L., de Luca, F., Caturelll, E., Astone, A., Siena, D.A., Villanl, M.R., Grattagliano, A., Cedrone, A., Gasbarrini, G. Risk factors for intrahepatic recurrence of hepatocellular carcinoma in cirrhotic patients treated by percutaneous ethanol injection. Cancer 1997 79 1501-1508... 

Cabredo-Pinillos, S., Cedron-Fernandez, T. and Saenz-Barrio, C. (2004) Comparison of different extraction methods applied to volatile compounds in wine samples previous to the determination by gas chromatography, Anal. Lett., 37(14), 3063-3084. 

A substrate with the C-C double bond of the 6-alkenyl substituent situated one carbon atom further out from the bicyclohexanone ring system was also examined. The best Lewis acid catalyst was found to be acetyl methanesulfonate which led to the formation of cedrone (17) and epicedrone (18). ... 

A. Picarelli, M. Greco, F. Di Giovambattista, A. Ramazzotti, C. Cedrone, E. Coarzziari, and A. Torsoli. Quantitative determination of faecal fat, nitrogen and water by means of a spectrophotometric technique near infrared reflectance analysis (NIRA). Assessment of its accuracy and reproducibility compared with chemical methods. Clin. Chim. Acta 234 147 (1995). 

Vitali, M., Guidotti, M., Giovinazzo, R., and Cedrone, O. (1998). Determination of pesticide residues in wine by SPME and GC/MS for consumer risk assessment, Food Addit. Contain., 15(3), 280-287. 

Two almost simultaneous communications reported the successful syntheses of a-cedrene (123) and cedrol (124). Both syntheses were modelled along a proposed biogenetic scheme, and as such the penultimate goal was the generation of the cation (125) which should, and did, undergo a smooth acid-catalysed cyclisa-tion to a-cedrene. The two pathways to this cation differed in several respects yet practically coincided at the key spiro-dienone ester (126, R = Me and R = Et ). Whereas Crandall and Lawton completed the synthesis by formic acid treatment of the alcohol (127), Corey et al. found that similar treatment of the diol (128) also yielded a-cedrene, albeit in lower yield. Alternatively, the ene-diol (129) was converted into a-cedrene in better yield by formic acid treatment, thermolysis of the derived formates and subsequent lithium-ethylamine reduction of the diene (130). Finally, cedrol (124) was obtained by boron trifluoride cyclisation of the enol-acetate (131), followed by methyl-lithium treatment of the intermediate cedrone. 

Cedrin. 3a,5,5a,9b-Tetrahydro-4,S-dihydroxy-9-methoxy-3,5a-dimethylnaphiho[l,2-b]furan-2,8(3H,4H)-dtone. C SH 06 mol wt 294.29. C 61.21%, H 6.17%. O 32.62%. From seeds of Sintaba cedron Planch., Simorouba-ceae Lewy, Compt. Rend. 32, 510 (1851) Stieren, Arch. Pharm. 23, 398 (1885). Structure Krebs, Ruber, Arzneimit-tel-Forsch. 10, 500 (I960). 

Only nine quassinoids possessing the C19 basic skeleton were isolated until 1985 samaderins B (11), C (12), D (13), an 3,4-dihydrosamaderin B (14) from the stem and leaves of Samadera indica, cedronin (15) and cedronolin (16) isolated from the fruits of Simaba cedron, eurycomalactone (17) and 5,6-dehydroeurycomalactone (18) from Eurycoma longifolia Jack, and shinjulactone B (19) isolated from Ailanthus altissima Swingle [1],... 

Cedronolactone B (29) and cedronolactone C (30), isolated from wood of Simaba cedron were shown, exhibited in vitro cytotoxicity (IC50 6.5 and 49 pg/mL) against P-388 lymphocytic leukemia cells [19]. 

Cedronin (224) was isolated from Simaba cedron, a species popularly believed in South America to have antimalarial properties. It was examined for in vitro and in vivo antimalarial activities and for cytotoxicity against KB cells. Experimental results showed that cedronin was active against chloroquine-sensitive and resistant strain, with an ICso of 0.25 pg/mL (0.65 pmol/mL). It was also found to be active in vivo against P. vinkei with an IC50 of 1,8 mg/Kg (4.7 riM/Kg) in the classic 4-day test. Cedronin (224) show a rather low cytotoxicity against KB cells (ICjo= 4 pg/mL, 10.4 pM) however its toxic/therapeutic ratio (10/1.8) remains lower than chloroquine (225) (10/0.5) [99]. 

Zamorano-Ponce, E., J. Fernandez, G. Vargas, P. Rivera, and M. A. Carballo. 2004. Protective activity of cedron Aloysio triphylla) infusion over genetic damage induced by cisplatin evaluated by the comet assay technique. Toxicol. Lett. 152(l) 85-90. Zamorano-Ponce, E., C. Morales, D. Ramos, et al. 2006. Anti-genotoxic effect of Aloysio triphylla infusion against acrylamide-induced DNA damage as shown by the comet assay technique. Mutat. Res. 603(2) 145-150. 

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