title: Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase.
abstract: 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.
authors.forename: Won Seok
authors.initials: WS
authors.lastname: Park
authors.forename: Eui Dong
authors.initials: ED
authors.lastname: Son
authors.forename: Gae Won
authors.initials: GW
authors.lastname: Nam
authors.forename: Soo Hyun
authors.initials: SH
authors.lastname: Kim
authors.forename: Min Soo
authors.initials: MS
authors.lastname: Noh
authors.forename: Byeong Gon
authors.initials: BG
authors.lastname: Lee
authors.forename: Ih Seop
authors.initials: IS
authors.lastname: Jang
authors.forename: Se Eun
authors.initials: SE
authors.lastname: Kim
authors.forename: Jung Joon
authors.initials: JJ
authors.lastname: Lee
authors.forename: Chang Hoon
authors.initials: CH
authors.lastname: Lee
mesh_terms: 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
chemical_list: 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