title: Differential accumulation of hyperforin and secohyperforin in Hypericum perforatum tissue cultures.
abstract: Hyperforin is a pharmacologically active constituent of Hypericum perforatum (St. John's wort). In vitro cultures of this medicinal plant were found to contain hyperforin and three related polyprenylated acylphloroglucinol derivatives. The accumulation of these compounds was coupled to shoot regeneration, with secohyperforin being the major constituent in morphogenic cultures. The structure of secohyperforin was elucidated online by LC-DAD, -MS, and -NMR. In multiple shoot cultures, the ratio of hyperforin to secohyperforin was strongly influenced by the phytohormones N6-benzylaminopurine (BAP) and naphthalene-1-acetic acid (NAA). While increasing concentrations of BAP stimulated the formation of hyperforin, increasing concentrations of NAA elevated the level of secohyperforin. No differential stimulation was observed after elicitor treatment. Hyperforin and secohyperforin are proposed to arise from a branch point in the biosynthetic pathway.
authors.affiliation: Yerevan State University, Faculty of Biology, Alex Manoogian Street 1, Yerevan, Armenia.
authors.forename: Armen
authors.initials: A
authors.lastname: Charchoglyan
authors.forename: Arusyak
authors.initials: A
authors.lastname: Abrahamyan
authors.forename: Isao
authors.initials: I
authors.lastname: Fujii
authors.forename: Zakia
authors.initials: Z
authors.lastname: Boubakir
authors.forename: Tobias A M
authors.initials: TA
authors.lastname: Gulder
authors.forename: Toni M
authors.initials: TM
authors.lastname: Kutchan
authors.forename: Hrachik
authors.initials: H
authors.lastname: Vardapetyan
authors.forename: Gerhard
authors.initials: G
authors.lastname: Bringmann
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Ebizuka
authors.forename: Ludger
authors.initials: L
authors.lastname: Beerhues
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002478:Cells, Cultured; D008401:Gas Chromatography-Mass Spectrometry; D020902:Hypericum / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D035261:Plant Components, Aerial; D010936:Plant Extracts / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry* / Q000378:metabolism; D046509:Tissue Culture Techniques
chemical_list: D001643:Bridged Bicyclo Compounds; D010936:Plant Extracts; D013729:Terpenes; C525824:secohyperforin; D010696:Phloroglucinol; C001654:hyperforin