cas 121927-71-7, 2H-10,4a-(Epoxymethano)phenanthrene-5,6,12-trione,1,3,4,9,10,10a-hexahydro-9-hydroxy-1,1-dimethyl-7-(1-methylethyl)-,(4aR,9S,10S,10aS)-

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Recovery of antioxidant activity from carnosol quinone: Antioxidants obtained from a water-promoted conversion of carnosol quinone
Carnosol is one of the main antioxidants in sage and rosemary. Although carnosol quinone is the antioxidation product of carnosol and has a very weak antioxidant activity, its treatment in water-containing solvent restored its strong antioxidant activity. HPLC analysis of the water-stimulated recovery reaction of the antioxidant activity revealed that the strong activity was due to the reproduced carnosol. The analysis also showed that an almost equal amount of quinone derivatives of rosmanol (rosmanol quinone) was produced in the reaction along with the carnosol. The rosmanol was formed by the addition of 1 equiv of water and the following isomerization from carnosol quinone in the water-containing solvent. The formed rosmanol was also found to be oxidized by the remaining carnosol quinone to produce rosmanol quinone. At the same time, carnosol quinone was reduced to afford carnosol. This redox phenomenon is an important part of the mechanism for the recovery of the antioxidant activity from carnosol quinone under the water-containing conditions.
Masuda, Toshiya,Kirikihira, Takuya,Takeda, Yoshio
p. 6831 - 6834
(2005)
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Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities
The known diterpenes rosmanoi (3), rosmaquinone (4), 7-methoxyrosmanol (5), 7-ethoxyrosmanol (6), galdosol (7), and epirosmanol (8) have been obtained by partial synthesis from carnosol (2), an abundant natural product present in Salvia species. The physical and spectroscopic data of these semisynthetic diterpenes were identical to those of authentic natural samples and with data reported in the literature. These abietane diterpenes have very interesting biological activities and are present in the genus Salvia in low quantities; thus, the semisynthetic approach described here represents an efficient alternative method to obtain these compounds. Additionally, the known diterpene 16-hydroxyrosmanol (10) and a new aromatic diterpene 11 were obtained from 16-hydroxycarnosol (9) by reaction with Ph3P/NBS in CH2Cl2. The structure of the new compound 11 was established from its spectroscopic data as 12,16-epoxycarnosol.
Marrero, Joaquin G.,Andres, Lucia S.,Luis, Javier G.
p. 986 - 989
(2007/10/03)