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(+)-Germacrene A Biosynthesis
The Committed Step in the Biosynthesis of Bitter Sesquiterpene Lactones in Chicory

Jan-Willem de Kraker, Maurice C.R. Franssen1, *, Aede de Groot, Wilfried A. König, and Harro J. Bouwmeester1

Department of Organic Chemistry, Wageningen Agricultural University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands (J.-W.d.K., M.C.R.F., A.d.G.); Research Institute for Agrobiology and Soil Fertility, P.O. Box 14, 6700 AA Wageningen, The Netherlands (J.-W.d.K., H.J.B.); and Institute of Organic Chemistry, Hamburg University, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany (W.A.K.)

The leaves and especially the roots of chicory (Cichorium intybus L.) contain high concentrations of bitter sesquiterpene lactones such as the guianolides lactupicrin, lactucin, and 8-deoxylactucin. Eudesmanolides and germacranolides are present in smaller amounts. Their postulated biosynthesis through the mevalonate-farnesyl diphosphate-germacradiene pathway has now been confirmed by the isolation of a (+)-germacrene A synthase from chicory roots. This sesquiterpene cyclase was purified 200-fold using a combination of anion-exchange and dye-ligand chromatography. It has a Km value of 6.6 µM, an estimated molecular mass of 54 kD, and a (broad) pH optimum around 6.7. Germacrene A, the enzymatic product, proved to be much more stable than reported in literature. Its heat-induced Cope rearrangement into (-)-beta -elemene was utilized to determine its absolute configuration on an enantioselective gas chromatography column. To our knowledge, until now in sesquiterpene biosynthesis, germacrene A has only been reported as an (postulated) enzyme-bound intermediate, which, instead of being released, is subjected to additional cyclization(s) by the same enzyme that generated it from farnesyl diphosphate. However, in chicory germacrene A is released from the sesquiterpene cyclase. Apparently, subsequent oxidations and/or glucosylation of the germacrane skeleton, together with a germacrene cyclase, determine whether guaiane- or eudesmane-type sesquiterpene lactones are produced.

1   Both of these authors contributed equally to this manuscript; e-mail M.C.R.F.: maurice.franssen{at}bio.oc.wau.nl; fax 31-317-48-4914; e-mail H.J.B.: H.J.Bouwmeester{at}ab.dlo.nl; fax 31-317-42-3110.
*   Corresponding author.

Plant Physiol. (1998) 117: 1381-1392
Copyright Clearance Center:   0032-0889/98/117//12
© 1998 American Society of Plant Physiologists




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