7-O-Methylrosmanol - CAS 113085-62-4
Catalog number: 113085-62-4
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C21H28O5
Molecular Weight:
360.444
COA:
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Chemical Family:
Diterpenoids
Description:
7-O-Methylrosmanol is a natural diterpenoid compound found in several plants.
Purity:
>97%
Appearance:
Powder
Synonyms:
7alpha-Methoxyrosmanol;7-Methylrosmanol
MSDS:
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Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
Density:
1.3±0.1 g/cm3
1.Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities.
Marrero JG;Andrés LS;Luis JG J Nat Prod. 2002 Jul;65(7):986-9.
The known diterpenes rosmanol (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 Salviain 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.
2.Constituents of sage (Salvia officinalis) with in vitro affinity to human brain benzodiazepine receptor.
Kavvadias D;Monschein V;Sand P;Riederer P;Schreier P Planta Med. 2003 Feb;69(2):113-7.
Benzodiazepine receptor binding assay-guided fractionation of the methanol extract from sage leaves ( Salvia officinalis L.) revealed three flavones and two abietane diterpenes functioning as benzodiazepine receptor-active components. Structural elucidation of the isolated pure compounds was performed by UV, EI-MS, ESI(pos)-MS/MS, as well as 1H- and 13C-NMR techniques. The flavones apigenin, hispidulin and cirsimaritin competitively inhibited 3H-flumazenil binding to the benzodiazepine receptor with IC50 values of 30, 1.3 and 350 microM, respectively. In addition, the affinities of the newly discovered diterpene receptor ligands, i. e., 7-methoxyrosmanol and galdosol, were characterized. 7-Methoxyrosmanol exhibited an IC50 value of 7.2 microM and galdosol showed the strongest binding activity to the benzodiazepine receptor with an IC50 value of 0.8 microM.
3.Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone.
Marrero JG;Moujir L;Andrés LS;Montaño NP;Araujo L;Luis JG J Nat Prod. 2009 Aug;72(8):1385-9. doi: 10.1021/np900047p.
The new aromatic diterpenes 7beta-O-benzylrosmanol (3), 7beta-O-benzyl-11,12-di-O-methylrosmanol (4), and 7alpha-thiophenylcarnosic acid (5) have been obtained by partial synthesis from carnosol (1), an abundant natural diterpene present in Salvia species. The structures of these compounds were established from their physical and spectroscopic data. The known diterpenes sagequinone methide A (6), 7beta-O-methylrosmanol (7), 7-O-methylrosmanol (8), and rosmaquinone B (9) were obtained from rosmanol (2). The spectroscopic data of these semisynthetic diterpenes were identical to data reported in the literature. In addition, the new semisynthetic isorosmaquinone (10) was obtained from isorosmanol (12). The proton resonances of rosmaquinone (11) are reassigned based on 2D NMR spectroscopy. These compounds, as well as eight known analogues, were evaluated for cytotoxic and antimicrobial activities.
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