Ferruginol
 | |
| Names | |
|---|---|
| IUPAC name
(4bS,8aS)-4b,8,8-Trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol | |
| Identifiers | |
514-62-5  | |
| ChEBI | CHEBI:78274  |
| ChEMBL | ChEMBL197308 |
| ChemSpider | 390582 |
| |
| Jmol-3D images | Image |
| PubChem | 442027 |
| |
| Properties | |
| C20H30O | |
| Molar mass | 286.45 g/mol |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
Ferruginol is a natural phenol and a meroterpene (a chemical compound containing a terpenoid substructure) that has been isolated from the needles of the redwood Sequoia sempervirens. The terpenoid part is a diterpene of the abietane chemical class.
Research published in 2005 found that this and other compound of the class from Sequoia have anti-tumor properties, and showed in vitro human colon, breast, and lung tumor reduction and reduction in oncogene transformed cells as well. Specific activity of tumor growth inhibition (GI) is 2-5 micrograms/milliliter.[1]
Ferruginol has also been found to have antibacterial activity.[2][3] Gastroprotective effects of ferruginol have also been noted.[4]
References
- ↑ Son, Kh; Oh, Hm; Choi, Sk; Han, Dc; Kwon, Bm (Apr 2005). "Anti-tumor abietane diterpenes from the cones of Sequoia sempervirens". Bioorganic & Medicinal Chemistry Letters 15 (8): 2019–21. doi:10.1016/j.bmcl.2005.02.057. PMID 15808460.
- ↑ E.C.J. Smith, G.W. Kaatz, E.M. Williamson and S. Gibbons. "P-168: The Resistance Modifying Activity of Ferruginol" ([DEAD LINK]).
- ↑ C. Flores, J. Alarcón, J. Becerra, M. Bittner, M. Hoeneisen, M. Silva (2001). "EXTRACTABLE COMPOUNDS OF NATIVE TREES: CHEMICAL AND BIOLOGICAL STUDY I: Bark of Prumnopytis andina (Podocarpaceae) and Austrocedrus chilensis (Cupressaceae)". Bol. Soc. Chil. Quím. 46 (1). doi:10.4067/S0366-16442001000100010.
- ↑ Areche, Carlos; Theoduloz, Cristina; Yáñez, Tania; Souza-Brito, Alba R. M.; Barbastefano, VíCtor; De Paula, DéBora; Ferreira, Anderson L.; Schmeda-Hirschmann, Guillermo; Rodríguez, Jaime A. (2008). "Gastroprotective activity of ferruginol in mice and rats: effects on gastric secretion, endogenous prostaglandins and non-protein sulfhydryls". Journal of Pharmacy and Pharmacology 60 (2): 245–51. doi:10.1211/jpp.60.2.0014. PMID 18237473.