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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78274 ;
ChEMBL	ChEMBL197308 ;
ChemSpider	390582 ;
PubChem CID	442027;
CompTox Dashboard (EPA)	DTXSID20331722 ;
	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

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; S. Gibbons. "P-168: The Resistance Modifying Activity of Ferruginol" (PDF). Archived from the original (PDF) on October 9, 2007. Cite journal requires |journal= (help)
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. hdl:10533/139107. PMID 18237473.

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[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; S. Gibbons. "P-168: The Resistance Modifying Activity of Ferruginol" (PDF). Archived from the original (PDF) on October 9, 2007. Cite journal requires |journal= (help)

[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. hdl:10533/139107. PMID 18237473.