Ferruginol

Ferruginol

Names
IUPAC name (4bS,8aS)-4b,8,8-Trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol
Identifiers
CAS Number	514-62-5
ChEBI	CHEBI:78274
ChEMBL	ChEMBL197308
ChemSpider	390582
Jmol interactive 3D	Image
PubChem	442027
InChI InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1 Key: QXNWVJOHUAQHLM-AZUAARDMSA-N InChI=1/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1 Key: QXNWVJOHUAQHLM-AZUAARDMBU
SMILES Oc1c(cc2c(c1)[C@]3(CCCC([C@@H]3CC2)(C)C)C)C(C)C
Properties
Chemical formula	C20H30O
Molar mass	286.45 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

1. 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.
2. E.C.J. Smith, G.W. Kaatz, E.M. Williamson and S. Gibbons. "P-168: The Resistance Modifying Activity of Ferruginol" (PDF). Archived from the original (PDF) on October 9, 2007.
3. 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.
4. 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.