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Chemical Compound Review

RoseOx     (4aR)-5,6-dihydroxy-1,1- dimethyl-7-propan...

Synonyms: BSPBio_003259, KBioGR_002116, KBioSS_002115, HMDB02358, MEGxp0_000007, ...
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Disease relevance of AIDS005842


High impact information on AIDS005842


Biological context of AIDS005842

  • We now examine the mechanisms associated with carnosic acid-induced enhancement of cell differentiation (in subline HL60-G) initiated by 1alpha,25(OH)2D3, ATRA, or 12-O-tetradecanoylphorbol-13-acetate (TPA) [6].
  • CONCLUSION: Carnosic acid enhances a program of gene expression consistent with 1alpha,25(OH)2D3-, ATRA-, or TPA-induced monocytic differentiation of HL60-G cells [6].
  • Subcellular localization studies show that carnosic acid protects chloroplasts from oxidative stress in vivo by following a highly regulated compartmentation of oxidation products [7].
  • Furthermore, such combinations of carnosic acid and any of these differentiation inducers synergistically inhibited proliferation and cell cycle progression [8].
  • Substances having inhibitory activity were purified and their chemical structure identified as the diterpenes carnosic acid and carnosol (IC50 values of 33 +/- 3 microM and 57 +/- 4 microM, respectively) [9].

Anatomical context of AIDS005842


Associations of AIDS005842 with other chemical compounds

  • This observation is probably due to the transformation of carnosic acid into carnosol; the analysis of the corresponding ESR spectrum suggests the formation of a keto phenoxy radical exhibiting a great delocalization of the unpaired electron [14].
  • The HPLC analysis of an aged solution of carnosic acid quinone revealed that several antioxidants are produced in the solution [15].
  • The in vitro experiments in rat liver mitochondrial fraction display more effective antioxidant action of alpha-tocopherol in 1 microM concentration than 1 microM carnosic acid by an increase of the time between fast and slow chemiluminescence flashes (p < 0.01) [16].
  • Through bioassay-guided separation using the inhibitory activity against pancreatic lipase activity, 4 abietan-type diterpenes (carnosic acid, carnosol, royleanonic acid, 7-methoxyrosmanol) and a triterpene (oleanolic acid) were isolated from the active fraction [17].
  • 7. Carnosic acid and carnosol reduce cytochrome c but with a rate constant significantly lower than that of O2(-.) [18].

Gene context of AIDS005842

  • Induction of G2/M phase cell cycle arrest by carnosol and carnosic acid is associated with alteration of cyclin A and cyclin B1 levels [13].
  • Carnosol was found to exert its major cell cycle effect after prometaphase, and caused an increase in cyclin B1 protein levels whereas carnosic acid arrested cells prior to prometaphase, and caused a reduction in cyclin A levels [13].
  • We have recently used the plant-derived polyphenolic antioxidant, carnosic acid (CA), to demonstrate an increase in the differentiating action of 1,25D(3) on human leukemia cells under these conditions (M. Danilenko et al., JNCI, 93: 1224-1233, 2001) [19].
  • Radical intermediates and antioxidants: an ESR study of radicals formed on carnosic acid in the presence of oxidized lipids [14].
  • Molar absorptivity (epsilon) of carnosic acid (CA) was determined from 200 to 300 nm, by the proposed method and those values were compared to tert-butyl-hydroxytoluene (BHT) ones for further comparative quantification [20].

Analytical, diagnostic and therapeutic context of AIDS005842

  • Carnosol and carnosic acid were identified in the electrophoregrams of rosemary extracts through their migration times and UV spectra obtained by CZE analysis of pure compounds isolated from a rosemary extract by HPLC fractionation [21].
  • Calculation of the molar absorptivity of polyphenols by using liquid chromatography with diode array detection: the case of carnosic acid [20].
  • Carnosic acid, the polyphenolic diterpene derived from rosemary, is a strong dietary antioxidant that exhibits antimutagenic properties in bacteria and anticarcinogenic activity in various cell and animal models [8].
  • 3. Carnosol and carnosic acid are good scavengers of peroxyl radicals (CCl3O2.) generated by pulse radiolysis, with calculated rate constants of 1-3 x 10(6) M-1 s-1 and 2.7 x 10(7) M-1 s-1 respectively [18].


  1. Cooperative antitumor effects of vitamin D(3) derivatives and rosemary preparations in a mouse model of myeloid leukemia. Sharabani, H., Izumchenko, E., Wang, Q., Kreinin, R., Steiner, M., Barvish, Z., Kafka, M., Sharoni, Y., Levy, J., Uskokovic, M., Studzinski, G.P., Danilenko, M. Int. J. Cancer (2006) [Pubmed]
  2. Inhibition of lipid peroxidation and superoxide generation by diterpenoids from Rosmarinus officinalis. Haraguchi, H., Saito, T., Okamura, N., Yagi, A. Planta Med. (1995) [Pubmed]
  3. Antioxidant and antimicrobial activities of rosemary extracts linked to their polyphenol composition. Moreno, S., Scheyer, T., Romano, C.S., Vojnov, A.A. Free Radic. Res. (2006) [Pubmed]
  4. Inhibitory effect of carnosic acid on HIV-1 protease in cell-free assays [corrected]. Paris, A., Strukelj, B., Renko, M., Turk, V., Pukl, M., Umek, A., Korant, B.D. J. Nat. Prod. (1993) [Pubmed]
  5. Oxidation, reduction, and methylation of carnosic acid by Nocardia. Hosny, M., Johnson, H.A., Ueltschy, A.K., Rosazza, J.P. J. Nat. Prod. (2002) [Pubmed]
  6. Carnosic acid and promotion of monocytic differentiation of HL60-G cells initiated by other agents. Danilenko, M., Wang, X., Studzinski, G.P. J. Natl. Cancer Inst. (2001) [Pubmed]
  7. Subcellular compartmentation of the diterpene carnosic acid and its derivatives in the leaves of rosemary. Munné-Bosch, S., Alegre, L. Plant Physiol. (2001) [Pubmed]
  8. Carnosic acid inhibits proliferation and augments differentiation of human leukemic cells induced by 1,25-dihydroxyvitamin D3 and retinoic acid. Steiner, M., Priel, I., Giat, J., Levy, J., Sharoni, Y., Danilenko, M. Nutrition and cancer. (2001) [Pubmed]
  9. Isolation and identification from Salvia officinalis of two diterpenes which inhibit t-butylbicyclophosphoro[35S]thionate binding to chloride channel of rat cerebrocortical membranes in vitro. Rutherford, D.M., Nielsen, M.P., Hansen, S.K., Witt, M.R., Bergendorff, O., Sterner, O. Neurosci. Lett. (1992) [Pubmed]
  10. Photoprotective potential of lycopene, beta-carotene, vitamin E, vitamin C and carnosic acid in UVA-irradiated human skin fibroblasts. Offord, E.A., Gautier, J.C., Avanti, O., Scaletta, C., Runge, F., Krämer, K., Applegate, L.A. Free Radic. Biol. Med. (2002) [Pubmed]
  11. Translational study of vitamin D differentiation therapy of myeloid leukemia: effects of the combination with a p38 MAPK inhibitor and an antioxidant. Wang, Q., Harrison, J.S., Uskokovic, M., Kutner, A., Studzinski, G.P. Leukemia (2005) [Pubmed]
  12. Rosemary (Rosmarinus officinalis) diterpenes affect lipid polymorphism and fluidity in phospholipid membranes. Pérez-Fons, L., Aranda, F.J., Guillén, J., Villalaín, J., Micol, V. Arch. Biochem. Biophys. (2006) [Pubmed]
  13. Induction of G2/M phase cell cycle arrest by carnosol and carnosic acid is associated with alteration of cyclin A and cyclin B1 levels. Visanji, J.M., Thompson, D.G., Padfield, P.J. Cancer Lett. (2006) [Pubmed]
  14. Radical intermediates and antioxidants: an ESR study of radicals formed on carnosic acid in the presence of oxidized lipids. Geoffroy, M., Lambelet, P., Richert, P. Free Radic. Res. (1994) [Pubmed]
  15. Recovery mechanism of the antioxidant activity from carnosic acid quinone, an oxidized sage and rosemary antioxidant. Masuda, T., Inaba, Y., Maekawa, T., Takeda, Y., Tamura, H., Yamaguchi, H. J. Agric. Food Chem. (2002) [Pubmed]
  16. Chemiluminescence determination of the in vivo and in vitro antioxidant activity of RoseOx and carnosic acid. Kuzmenko, A.I., Morozova, R.P., Nikolenko, I.A., Donchenko, G.V., Richheimer, S.L., Bailey, D.T. J. Photochem. Photobiol. B, Biol. (1999) [Pubmed]
  17. Carnosic acid, a new class of lipid absorption inhibitor from sage. Ninomiya, K., Matsuda, H., Shimoda, H., Nishida, N., Kasajima, N., Yoshino, T., Morikawa, T., Yoshikawa, M. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  18. Antioxidant and pro-oxidant properties of active rosemary constituents: carnosol and carnosic acid. Aruoma, O.I., Halliwell, B., Aeschbach, R., Löligers, J. Xenobiotica (1992) [Pubmed]
  19. Carnosic acid potentiates the antioxidant and prodifferentiation effects of 1alpha,25-dihydroxyvitamin D3 in leukemia cells but does not promote elevation of basal levels of intracellular calcium. Danilenko, M., Wang, Q., Wang, X., Levy, J., Sharoni, Y., Studzinski, G.P. Cancer Res. (2003) [Pubmed]
  20. Calculation of the molar absorptivity of polyphenols by using liquid chromatography with diode array detection: the case of carnosic acid. Pelillo, M., Cuvelier, M.E., Biguzzi, B., Gallina Toschi, T., Berset, C., Lercker, G. Journal of chromatography. A. (2004) [Pubmed]
  21. Capillary electrophoretic separation of phenolic diterpenes from rosemary. Sáenz-López, R., Fernández-Zurbano, P., Tena, M.T. Journal of chromatography. A. (2002) [Pubmed]
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