Nepenthes insignis uses a C2-portion of the carbon skeleton of L-alanine acquired via its carnivorous organs, to build up the allelochemical plumbagin.
Tropical pitcher plants (Nepenthes) catch animals in their specialized cup-shaped leaves, digest the prey by secreting enzymes, and actively take up the resulting compounds. The benefit of this behaviour is the ability to grow and compete in nutrient-poor habitats. Our present in vitro study shows that not only the nitrogen of alanine fed to the carnivorous organs is used by the plant but that in addition intact C2-units derived from C-2 and C-3 of stable isotope labelled L-alanine serve as building blocks, here exemplarily for the synthesis of the secondary metabolite plumbagin, a potent allelochemical. This result adds a new facet to the benefit of carnivory for plants. The availability of plumbagin by a de novo synthesis probably enhances the plants' fitness in their defence against phytophagous and pathogenic organisms. A missing specific uptake or CoA activation mechanism might be the reason that acetate fed to the pitchers was not incorporated into the naphthoquinone plumbagin. The dihydronaphthoquinone glucosides rossoliside and plumbaside A, here isolated for the first time from Nepenthes, by contrast, showed no incorporation after feeding of any of the two precursors, suggesting these compounds to be storage forms with probably very low turnover rates.
Rischer
Heiko
H
Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Hamm
Andreas
A
Bringmann
Gerhard
G
D000409:Alanine / Q000378:metabolism*; D002244:Carbon / Q000378:metabolism*; D004463:Ecology; D020387:Food Chain; D005960:Glucosides / Q000378:metabolism; D019684:Magnoliopsida / Q000737:chemistry / Q000378:metabolism*; D009285:Naphthoquinones / Q000737:chemistry / Q000378:metabolism*; D019346:Sodium Acetate / Q000378:metabolism
D005960:Glucosides; D009285:Naphthoquinones; D019346:Sodium Acetate; D002244:Carbon; D000409:Alanine; C014758:plumbagin