Camosol isolation from rosemary

Hopia, A.I., Huang, S.-W., Schwarz, K., German, J.B. and Frankel, E.N. 1996. Effect of different lipid systems on antioxidant activity of rosemary constituents camosol and camosic acid with and without alpha-xocopherol. J. Agric. Food Chem. 44 2030-2036. Houlihan, C.M., Ho, C.-T. and Chang, S.S. 1984 Elucidation of the chemical structure of a novel antioxidant, rosmaridiphenol, isolated from rosemary. J. Am. Oil Chem. Soc. 61 1036-1039. 

Several phenolic diterpenoids with antioxidant activities were isolated from rosemary leaves. These include camosol, camosic acid, rosmanol, isorosmanol, and epirosmanol. Camosol showed potent antioxidative activity as revealed by scavenging a,a-diphenyl-(3-picrylhydrazyl free radicals and protection of oxidative DNA damage. In chronic inflammation, cytokines induce the production of nitric oxide, which is converted to DNA-damaging and carcinogenic peroxynitrite. Peroxynitrite is a cytotoxicant with... 

When the rosemary extract was administered (i.g.) at lOOmg/kg/day for 5 consecutive days, the number and area of diethylnitrosamine-induced GST placental-form-positive (GST-P) hepatocellular foci were reduced in male F344 rats. A methanol extract of the leaves of rosemary was evaluated for its effects on tumor initiation and promotion in mouse skin carcinogenesis. Topical apphcation of the rosemary extract to mouse skin attenuated the covalent binding of BaP to epidermal DNA and inhibited tumor initiation by BaP and DMBA. Application of rosemary to mouse skin also inhibited TPA-induced ODC activity, inflammation, hyperplasia, and tumor promotion. Likewise, topical application of camosol or ursolic acid isolated from rosemary inhibited TPA-induced ear inflanunation, ODC activity, and tumor promotion. ... 

Camosol and ursolic acid were isolated from rosemary as described (5). Camosic acid and rosmarinic acid were isolated from the ground dried leaves of rosemary, sequentially, by hexane and n-butanol extractions. The final products were purified by column chromatography on silica gel (2). LPS (lipopolysaccharide, Escherichia coli 026 B6), sulfanilamide and naphthyl-ethylenediamine dihydrochloride were purchased from Sigma Chemical Co. (St. Louis, MO). Isotopes were obtained from Amersham (Arlington Heights, IL). RT-PCR reagents were purchased from Promega (Madison, WI). Polynucleotide kinase was purchased from Pharmacia (Piscataway, NJ). 

The antioxidant activity of the four phytochemicals isolated from rosemary were assayed in a DPPH free radical scavenge system. Carnosic acid, camosol and rosmarinic acid showed concentration-dependent scavenging ability. These phytochemicals were more potent than vitamin C and vitamin E. The 50% DPPH... 

Camosol, camosic acid, rosmarinic acid and ursolic acid were isolated from rosemary (/). Their sfructures are shovm in Figure 1. RNase A, proteinase K and propidium iodide were purchased from Sigma (St. Louis, MO). Substrates for caspase-1, Ac-YVAD-AMC casppase-3, Ac-DEVD-AMC caspase-8, Ac-lETD-AMC and caspase-9, Ac-LEHD-AMC were obtained from AnaSpec Inc. (San Jose, CA). DiOC6 (5) and DCFH-DA were obtained from Molecular Probes (Eugene, OR). 

Other abietane derivatives with benzenoid ring C are among the active substances in some well-known medicinal herbs. The parent hydrocarbon (-)-8,l 1,13-abieta-triene occurs in the pine tree Pinus pallasiana (Pinaceae). (+)-Camosolic acid and the 20,7p-lactone (-olide) of its hydroxy-derivative referred to as camosol belong to the bitter substances of the oil of sage from Salvia camosa (Labiatae) and related species. (-)-Rosmanol, a 20,6p-lactone, is an antioxidant isolated from the leaves of rosemary Rosmarinus officinalis (Labiatae), which also contain camosol. 

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