Cardenolide and Neutral Lipid Biosynthesis from Malonate in Digitalis lanata

Abstract

Digitalis lanata plants were grown on water culture in a controlled environment and in the young, growing leaves free sterols (0.335 µmol/g FW), triacylglycerols (0.97 µmol/g FW) and cardenolides (1.82 µmol/g FW) were the major apolar and polar lipids. The cardenolide-containing fraction from these tissues was separated into 26 cardenolides by HPLC. The 5 major components (accounting for 60 % of the occurring glycosides) lanatosides A and C, acetyldigoxin, acetyldigitoxin, and glucoevatromonoside were identified by FABMS. Incorporation experiments with [2-¹⁴ C]-acetate, [2-¹⁴ C]-malonate, [2-¹⁴ C]-mevalonate, and [U-¹⁴ C]-sucrose (absorbed by excised, young, growing leaves) showed the labelling of all the occurring cardenolides after a 3 day incorporation period (as judged by HPLC). Comparing the simultaneous synthesis of labelled sterols and triacylglycerols, malonate could be considered as the most effective precursor in cardenolide synthesis, reaching an incorporation value of 4.1 % in a 4 day incorporation period. A time-course experiment revealed a temporary accumulation of ¹⁴C in glucoevatromonoside, which may play a role as an intermediate in cardenolide production of Digitalis lanata.

Key words

Biosynthesis - cardenolide - Digitalis lanata - malonate