Biosynthesis of hyperforin and adhyperforin from amino acid precursors in shoot cultures of Hypericum perforatum.
Hyperforin and adhyperforin contribute to the antidepressant effects of Hypericum perforatum. The involvement of branched-chain amino acids in the biosynthesis of hyperforin and adhyperforin was demonstrated in H. perforatum shoot cultures. L-[U-(13)C(5)]Valine and L-[U-(13)C(6)]isoleucine, upon administration to the shoot cultures, were incorporated into acyl side chain of hyperforin and adhyperforin, respectively. Feeding the shoot cultures with unlabelled L-isoleucine at a concentration of 2mM induced a 3.7-fold increase in the production of adhyperforin. The addition of 3mM L-threonine, a precursor of isoleucine, stimulated a 2.0-fold increase in the accumulation of adhyperforin. The administration of L-valine at concentrations of 0-5mM had no stimulating effect on the hyperforin production in H. perforatum shoot cultures.
Karppinen
Katja
K
Department of Biology, University of Oulu, P.O. Box 3000, FIN-90014 Oulu, Finland. katja.karppinen@oulu.fi <katja.karppinen@oulu.fi>
Hokkanen
Juho
J
Tolonen
Ari
A
Mattila
Sampo
S
Hohtola
Anja
A
D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000378:metabolism; D002247:Carbon Isotopes; D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D020902:Hypericum / Q000378:metabolism*; D007532:Isoleucine / Q000737:chemistry / Q000378:metabolism; D007930:Leucine / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D018520:Plant Shoots / Q000166:cytology / Q000378:metabolism*; D053719:Tandem Mass Spectrometry; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*; D013912:Threonine / Q000737:chemistry / Q000378:metabolism; D014633:Valine / Q000737:chemistry / Q000378:metabolism
D000596:Amino Acids; D001643:Bridged Bicyclo Compounds; D002247:Carbon Isotopes; D013729:Terpenes; C423123:adhyperforin; D007532:Isoleucine; D013912:Threonine; D010696:Phloroglucinol; D007930:Leucine; D014633:Valine; C001654:hyperforin