Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae).
The incorporation of [1-13C]-labeled glucose into the irregular monoterpene artemisia ketone, the regular monoterpenes camphor and beta-thujone, the sesquiterpene germacrene D, the diterpene trans-phytol and beta-sitosterol and isofucosterol has been studied in axenic cultures of Tanacetum vulgare L. (Asteraceae). Quantitative 13C NMR spectroscopic analysis of the resulting labeling patterns showed that the isoprene units of the monoterpenes and the diterpene are formed via the methylerythritol phosphate (MEP) pathway, whereas the isoprene building blocks of the sesquiterpene and the sterols originate from the mevalonic acid (MVA) pathway.
Umlauf
Dirk
D
FR 8.7, Pharmakognosie und Analytische Phytochemie der Universität des Saarlandes, 66041 Saarbrücken, Germany.
Zapp
Josef
J
Becker
Hans
H
Adam
Klaus Peter
KP
D000081008:Bicyclic Monoterpenes; D002164:Camphor / Q000378:metabolism; D004224:Diterpenes / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D039821:Monoterpenes / Q000378:metabolism*; D045788:Sesquiterpenes, Germacrane / Q000096:biosynthesis* / Q000737:chemistry; D012855:Sitosterols / Q000378:metabolism; D013265:Stigmasterol / Q000031:analogs & derivatives* / Q000378:metabolism; D031203:Tanacetum / Q000737:chemistry / Q000378:metabolism*; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*
D000081008:Bicyclic Monoterpenes; D004224:Diterpenes; D039821:Monoterpenes; D045788:Sesquiterpenes, Germacrane; D012855:Sitosterols; D013729:Terpenes; C494252:artemisia ketone; C015896:fucosterol; C025473:gamma-sitosterol; D002164:Camphor; C005790:beta-thujone; D013265:Stigmasterol; C494251:trans-phytol; C027259:germacrene D