(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one Chemical Properties

Melting point:

290-292 °C (decomp)

Boiling point:

185-205 °C(Press: 0.1 Torr)

Density 

1.049±0.06 g/cm3(Predicted)

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

8.71±0.60(Predicted)

color 

White to off-white

LogP

6.770 (est)

(4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one Usage And Synthesis

Uses

Sugiol is an abietane diterpenoid, can be isolated from Calocedrus formosana bark. Sugiol has anti-inflammatory activity, could effectively reduce intracellular reactive oxygen species (ROS) production in lipopolysaccharide (LPS)-stimulated macrophages[1].

Definition

ChEBI: Sugiol is an abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group. It has a role as a plant metabolite, an antiviral agent, an antineoplastic agent, an antioxidant and a radical scavenger. It is an abietane diterpenoid, a carbotricyclic compound, a meroterpenoid, a member of phenols and a cyclic terpene ketone. It is functionally related to a ferruginol.

Cytotoxicity

IC50 (μg/mL): <50 (SW620, HCT116,MDA-MB-231, NCI-H23, and A549)(Son et al. 2005)
IC50 (μg/mL): >30.04 (MRC-5, PC-3),23.98 (A549), 20.62 (Hl-60), 26.4(PANC-1), 10.82 (BxPC-3) (Li et al.2013).

target

ROS | IL Receptor | TNF-α | MAPK | ERK | JNK | p38MAPK

IC 50

ERK1; ERK2; p38 MAPK; JNK1; JNK2; IL-1β

References

[1] Chao KP, et al. Anti-inflammatory activity of sugiol, a diterpene isolated from Calocedrus formosana bark. Planta Med. 2005 Apr;71(4):300-5. DOI:10.1055/s-2005-864094