Differential accumulation of hyperforin and secohyperforin in Hypericum perforatum tissue cultures.
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.
Charchoglyan
Armen
A
Yerevan State University, Faculty of Biology, Alex Manoogian Street 1, Yerevan, Armenia.
Abrahamyan
Arusyak
A
Fujii
Isao
I
Boubakir
Zakia
Z
Gulder
Tobias A M
TA
Kutchan
Toni M
TM
Vardapetyan
Hrachik
H
Bringmann
Gerhard
G
Ebizuka
Yutaka
Y
Beerhues
Ludger
L
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
D001643:Bridged Bicyclo Compounds; D010936:Plant Extracts; D013729:Terpenes; C525824:secohyperforin; D010696:Phloroglucinol; C001654:hyperforin