title: Avicequinone C isolated from Avicennia marina exhibits 5α-reductase-type 1 inhibitory activity using an androgenic alopecia relevant cell-based assay system.
abstract: Avicennia marina (AM) exhibits various biological activities and has been traditionally used in Egypt to cure skin diseases. In this study, the methanolic heartwood extract of AM was evaluated for inhibitory activity against 5α-reductase (5α-R) [E.C.1.3.99.5], the enzyme responsible for the over-production of 5α-dihydrotestosterone (5α-DHT) causing androgenic alopecia (AGA). An AGA-relevant cell-based assay was developed using human hair dermal papilla cells (HHDPCs), the main regulator of hair growth and the only cells within the hair follicle that are the direct site of 5α-DHT action, combined with a non-radioactive thin layer chromatography (TLC) detection technique. The results revealed that AM is a potent 5α-R type 1 (5α-R1) inhibitor, reducing the 5α-DHT production by 52% at the final concentration of 10 µg/mL. Activity-guided fractionation has led to the identification of avicequinone C, a furanonaphthaquinone, as a 5α-R1 inhibitor with an IC50 of 9.94 ± 0.33 µg/mL or 38.8 ± 1.29 µM. This paper is the first to report anti-androgenic activity through 5α-R1 inhibition of AM and avicequinone C.
authors.affiliation: Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand. ruchyj@gmail.com.
authors.forename: Ruchy
authors.initials: R
authors.lastname: Jain
authors.affiliation: Division of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, Thailand. oramon@kku.ac.th.
authors.forename: Orawan
authors.initials: O
authors.lastname: Monthakantirat
authors.affiliation: Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand. parkpoom.t@chula.ac.th.
authors.forename: Parkpoom
authors.initials: P
authors.lastname: Tengamnuay
authors.affiliation: Research Unit of Natural Product Biotechnology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand. dwanchai@chula.ac.th.
authors.forename: Wanchai
authors.initials: W
authors.lastname: De-Eknamkul
mesh_terms: D013741:3-Oxo-5-alpha-Steroid 4-Dehydrogenase / Q000378:metabolism; D058891:5-alpha Reductase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D000505:Alopecia / Q000201:enzymology*; D032407:Avicennia / Q000737:chemistry*; D002478:Cells, Cultured; D013196:Dihydrotestosterone / Q000378:metabolism; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006197:Hair / Q000166:cytology / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D010936:Plant Extracts / Q000494:pharmacology; D011809:Quinones / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D058891:5-alpha Reductase Inhibitors; D010936:Plant Extracts; D011809:Quinones; C000597823:avicequinone C; D013196:Dihydrotestosterone; D013741:3-Oxo-5-alpha-Steroid 4-Dehydrogenase