7-O-Methylrosmanol | CAS:113085-62-4 | Manufacturer ChemFaces

7-O-Methylrosmanol

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Description:

7-O-methylrosmanol can effectively suppress FSK-induced luciferase expression under the control of the CRE, PEPCK-C and G6Pase gene promoters, it may contribute to its antihyperglycemic activity.

Targets:

cAMP | CRE | PEPCK-C | G6Pase

In vitro:

J Nat Prod. 1993 Aug;56(8):1426-30.

Inhibitory effect of carnosic acid on HIV-1 protease in cell-free assays.[Pubmed: 8229021]

METHODS AND RESULTS:
In order to find new effective HIV protease inhibitors, two diterpenes (carnosic acid [1] and carnosol [5]) were isolated from rosemary (Rosmarinus officinalis L.), and rosmanol [2] and semisynthetic derivatives (7-O-Methylrosmanol [3], 7-O-ethylrosmanol [4], and 11,12-O,O-dimethylcarnosol [6]) were prepared. The inhibitory activity of all six compounds against HIV-1 protease was tested. The carnosic acid [1] showed the strongest inhibitory effect (IC90 = 0.08 micrograms/ml). The same compound was also assayed against HIV-1 virus replication (IC90 = 0.32 micrograms/ml).
CONCLUSIONS:
The cytotoxic TC90 on H9 lymphocytes was 0.36 micrograms/ml, which is very close to the effective antiviral dose. Additionally, the tested compounds did not inhibit cellular aspartic proteases cathepsin D and pepsin at the concentration range up to 10 micrograms/ml.

7-O-Methylrosmanol Description

Source:	The herbs of Rosmarinus officinalis
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Phytother Res. 2013 Jun;27(6):906-10.

Phenolic diterpenes from rosemary suppress cAMP responsiveness of gluconeogenic gene promoters.[Pubmed: 22927089]

The cAMP/protein kinase A/cAMP response element (CRE)-binding protein pathway is important for various physiological aspects including regulation of gluconeogenic gene expression. Rosemary, a well-known herb, has been reported to decrease blood glucose levels.
METHODS AND RESULTS:
We found that methanol extracts of rosemary suppressed forskolin (FSK)-stimulated luciferase expression under the control of CRE, as well as the promoters for cytosolic phosphoenolpyruvate carboxykinase (PEPCK-C) and glucose-6-phosphatase (G6Pase) catalytic subunit genes in human hepatoma HepG2 cells. Three abietane-type diterpenes and two flavonoids were isolated from the rosemary extracts. Among these, 7-O-Methylrosmanol (1) and royleanonic acid (3) effectively suppressed FSK-induced luciferase expression under the control of the CRE, PEPCK-C and G6Pase gene promoters. PEPCK-C and G6Pase, which play a key role in the homeostatic regulation of blood glucose levels, are important for managing type II diabetes mellitus.
CONCLUSIONS:
Therefore, the ability of rosemary and its components to suppress cAMP responsiveness of the PEPCK-C or G6Pase gene may contribute to its antihyperglycemic activity.

Structure Identification:

J Nat Prod. 2009 Aug;72(8):1385-9.

Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone.[Pubmed: 19711987 ]

METHODS AND RESULTS:
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).
CONCLUSIONS:
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.

Product Name	7-O-Methylrosmanol
Price:	$318 / 10 mg
CAS No.:	113085-62-4
Catalog No.:	CFN96974
Molecular Formula:	C₂₁H₂₈O₅
Molecular Weight:	360.45 g/mol
Purity:	>=98%
Type of Compound:	Diterpenoids
Physical Desc.:	Powder
Source:	The herbs of Rosmarinus officinalis
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Antihyperglycemic Compound Library Diterpenoids Compound Library cAMP Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.7743 mL	13.8715 mL	27.7431 mL	55.4862 mL	69.3577 mL
5 mM	0.5549 mL	2.7743 mL	5.5486 mL	11.0972 mL	13.8715 mL
10 mM	0.2774 mL	1.3872 mL	2.7743 mL	5.5486 mL	6.9358 mL
50 mM	0.0555 mL	0.2774 mL	0.5549 mL	1.1097 mL	1.3872 mL
100 mM	0.0277 mL	0.1387 mL	0.2774 mL	0.5549 mL	0.6936 mL

CFN91824	Rosmaquinone	121927-71-7	344.4	C₂₀H₂₄O₅
CFN96974	7-O-Methylrosmanol	113085-62-4	360.45	C₂₁H₂₈O₅
CFN92990	7beta-Methoxyrosmanol	24703-38-6	360.44	C₂₁H₂₈O₅
CFN91119	7-Ethoxyrosmanol	111200-01-2	374.5	C₂₂H₃₀O₅
CFN99102	Carnosic acid	3650-09-7	332.43	C₂₀H₂₈O₄
CFN89377	12-O-Methylcarnosic acid	62201-71-2	346.46	C₂₁H₃₀O₄
CFN92286	11-Hydroxy-12-methoxyabietatriene	16755-54-7	316.5	C₂₁H₃₂O₂
CFN90366	11-Hydroxy-sugiol	88664-08-8	316.43	C₂₀H₂₈O₃
CFN92243	Salvinolone	120278-22-0	314.4	C₂₀H₂₆O₃
CFN97924	14-Deoxycoleon U	88664-09-9	330.4	C₂₀H₂₆O₄