Carnosol
Carnosol is a naturally occurring phenolic diterpene found in rosemary (Rosemarinus officinalis, Labiatae). It has been known that an extract of rosemary leaves contains high antioxidative activity. Ninety percent of this antioxidative activity can be attributed to carnosol and carnosic acid. Carnosic acid is easily converted to carnosol by oxidation. Carnosol has mlitiple beneficial medicinal effects including anti-inflammatory, anti-microbial and anti-cancer activities in various disease models. Carnosol may possess important neuroprotective effects against rotenone-induced DA neuronal damage. Naturally occurring antioxidants reduce the risk of neurodegenerative diseases. In addition, carnosol and carnosic acid promoted the synthesis of nerve growth factor in glial cells. Carnosol-mediated neuroprotection in DA neurons is involved in the attenuation of caspase-3 activity, which was induced by rotenone. Furthermore, carnosol-mediated tyrosine hydroxylase (TH) increase, which is dependent on the Raf-mitogen-activated protein kinase (MEK)-extracellliar signal-regliated kinase (ERK)1/2 signaling pathway, is responsible for the neuroprotection in SN4741 DA cells. (PMID: 17047462 ). Carnosol, a phenolic diterpene compound of the labiate herbs rosemary and sage, is an activator of the human peroxisome proliferator-activated receptor gamma (PPARgamma), a ligand activated transcription factor, belonging to the metazoan family of nuclear hormone receptors. Activation of PPARgamma increases the transcription of enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose. Hence, PPARgamma represents the major target for the glitazone type of drugs currently being used clinically for the treatment of type 2 diabetes. (PMID: 16858665 ).
Structure for HMDB02121 (Carnosol)
C20H26O4
330.424
330.183109317
(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one
(1R,8S,10S)-3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one
5957-80-2
XUSYGBPHQBWGAD-PJSUUKDQSA-N
This compound belongs to the class of chemical entities known as diterpene lactones. These are diterpenoids containing a lactone moiety.
Chemical entities
Organic compounds
Lipids and lipid-like moleclies
Prenol lipids
Diterpene lactones
Aromatic heteropolycyclic compounds
Expected but not Quantified
Solid
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
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None
None
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668
FDB014814
C00003410
390568
C09069
Not Available
Not Available
Not Available
HMDB02121
HMDB02121
Not Available
442009
Not Available
468005
- Kim SJ, Kim JS, Cho HS, Lee HJ, Kim SY, Kim S, Lee SY, Chun HS: Carnosol, a component of rosemary (Rosmarinus officinalis L.) protects nigral dopaminergic neuronal cells. Neuroreport. 2006 Nov 6;17(16):1729-33. [PubMed:17047462 ]
- Rau O, Wurglics M, Paulke A, Zitzkowski J, Meindl N, Bock A, Dingermann T, Abdel-Tawab M, Schubert-Zsilavecz M: Carnosic acid and carnosol, phenolic diterpene compounds of the labiate herbs rosemary and sage, are activators of the human peroxisome proliferator-activated receptor gamma. Planta Med. 2006 Aug;72(10):881-7. Epub 2006 Jul 20. [PubMed:16858665 ]