| 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
CC(C)C1=CC2=C(C(O)=C1O)[C@@]34CCCC(C)(C)[C@@H]3C[C@@H]2OC4=O
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
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.
CNS Activity
Originator
Approval Year
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 RECORD
