Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H26O4 |
| Molecular Weight | 330.418 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@H]3OC(=O)[C@@]1(CCCC2(C)C)C4=C3C=C(C(C)C)C(O)=C4O
InChI
InChIKey=XUSYGBPHQBWGAD-PJSUUKDQSA-N
InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1
| Molecular Formula | C20H26O4 |
| Molecular Weight | 330.418 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Carnosol is an ortho-diphenolic diterpene with an abietane carbon skeleton with hydroxyl groups at positions C-11 and C-12 and a lactone moiety across the B ring. Carnosol is the product of oxidative degradation of carnosic acid. Carnosol is a naturally occurring phytopolyphenol found in rosemary that functions as an antioxidant, antimicrobial, and anticarcinogen. Carnosol has been shown to inhibit inductions of COX-2 by blocking PKC signaling. Carnosol is an inhibitor of AR and ER α. Several pre-clinical studies have suggested that carnosol selectively targets tumorigenic cell as opposed to non-tumorigenic cells and is safe and tolerable in animals. Carnosol has been
shown to elicit chemopreventive effects by (1) blocking the
bioactivation of carcinogens, (2) enhancing antioxidant and/or
detoxification enzyme activities, (3) suppressing tumor-promoting
inflammation, (4) inhibiting cell proliferation and inducing
apoptosis selectively in cancer cells, and (5) blocking tumor
angiogenesis and invasion.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095172 |
|||
Target ID: map04210 |
|||
Target ID: CHEMBL613758 |
8.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | 2003 Dec |
|
| Characterization of Cd-induced molecular events prior to cellular damage in primary rat hepatocytes in culture: activation of the stress activated signal protein JNK and transcription factor AP-1. | 2004 |
|
| Carnosol, a component of rosemary (Rosmarinus officinalis L.) protects nigral dopaminergic neuronal cells. | 2006 Nov 6 |
|
| Novel screening method for potential skin-whitening compounds by a luciferase reporter assay. | 2010 |
|
| Dual mechanisms of NF-kappaB inhibition in carnosol-treated endothelial cells. | 2010 May 15 |
|
| Carnosol, a constituent of Zyflamend, inhibits aryl hydrocarbon receptor-mediated activation of CYP1A1 and CYP1B1 transcription and mutagenesis. | 2012 Apr |
|
| Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | 2013 Oct |
Sample Use Guides
Oral administration
of carnosol (30 mg/kg body weight) for 5 days in a week
for 4 weeks suppressed the growth of human prostate cancer
(22Rv1) cells xenograft tumors in nude mice and decreased the
serum level of prostate-specific antigen in tumor-bearing mice.
When carnosol (200 mg/kg body weight) was administered
intraperitoneally for 5 days to rats challenged with DMBA, the
compound inhibited DMBA-DNA adduct formation and reduced
the multiplicity of mammary adenocarcinomas. Topical application of carnosol (3 or 10 μmol) prior to administration
of 12-O-tetradecanoyl phorbol-13-acetate (TPA) twice a
week for 20 weeks significantly inhibited the multiplicity of
papillomas in DMBA-initiated mouse skin.
Route of Administration:
Other
Osteoarthritic (OA) human chondrocytes were cultured in alginate beads for 4 days in presence or absence of carnosol (6 nM to 9 uM).
In chondrocytes, type II collagen expression was significantly enhanced in the presence of 3 uM carnosol (p = 0.008). MMP-3, IL-6, NO production and ADAMTS-4 expression were down-regulated in a concentration-dependent manner by carnosol (p<0.01). TIMP-1 production was slightly increased at 3 uM (p = 0.02) and ADAMTS-5 expression was decreased from 0.2 to 9 uM carnosol (p<0.05).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:37:23 UTC 2023
by
admin
on
Sat Dec 16 08:37:23 UTC 2023
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| Record UNII |
483O455CKD
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| Record Status |
Validated (UNII)
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| Record Version |
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m3122
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7680
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5957-80-2
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Carnosol
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DTXSID80904451
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39143
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483O455CKD
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