Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase.
The methanolic extract of the fruits of Torilis japonica showed a potent inhibition against 5 alpha-reductase activity in vitro. Bioassay-guided fractionation of the methanol extract of the fruits followed by repeated silica gel chromatography led to the isolation of an active principle and its structure was identified as torilin on the basis of spectroscopic data. Torilin (IC50 = 31.7 +/- 4.23 microM) showed a stronger inhibition of 5 alpha-reductase than alpha-linolenic acid (IC50 = 160.3 +/- 24.62 microM) but was weaker than finasteride. (IC50 = 0.38 +/- 0.06 microM). Simple guaiane-type compounds, such as (-)-guaiol and guaiazulene showed weak inhibitory effects on the 5 alpha-reductase activity with IC50 values of f 81.6 microM and 100.8 microM, respectively, while azulene was not active. These results suggest that both degrees of unsaturation and the side-chain in the guaiane skeleton are important for the manifestation of 5 alpha-reductase inhibition.
Park
Won Seok
WS
Son
Eui Dong
ED
Nam
Gae Won
GW
Kim
Soo Hyun
SH
Noh
Min Soo
MS
Lee
Byeong Gon
BG
Jang
Ih Seop
IS
Kim
Se Eun
SE
Lee
Jung Joon
JJ
Lee
Chang Hoon
CH
D013741:3-Oxo-5-alpha-Steroid 4-Dehydrogenase / Q000187:drug effects*; D058891:5-alpha Reductase Inhibitors; D019661:Apiaceae; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D018120:Finasteride / Q000494:pharmacology; D005638:Fruit; D006801:Humans; D020128:Inhibitory Concentration 50; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology; D012717:Sesquiterpenes / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D045789:Sesquiterpenes, Guaiane; D017962:alpha-Linolenic Acid / Q000494:pharmacology
D058891:5-alpha Reductase Inhibitors; D004791:Enzyme Inhibitors; D010936:Plant Extracts; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; D017962:alpha-Linolenic Acid; D018120:Finasteride; D013741:3-Oxo-5-alpha-Steroid 4-Dehydrogenase; C112694:torilin