The characterization of ficaprenol-10, -11 and 12 from the leaves of Ficus elastica (decorative rubber plant)

Abstract

Evidence from mass, nuclear-magnetic-resonance and infrared spectrometry and from gas-liquid and thin-layer chromatography is presented in favour of the presence of cis-trans-decaprenol, -undecaprenol and -dodecaprenol in the mixture of polyprenols (2.6mg./g.) isolated from leaf tissue of Ficus elastica. The trivial names ficaprenol-10, -11 and -12 are proposed. Nuclear-magnetic-resonance studies showed that each of these prenols contains three trans internal isoprene residues and a cis ;OH-terminal' isoprene residue. Ficaprenol-11 is the major component of the mixture. Chromatographic evidence suggests the presence also of small amounts of ficaprenol-9 and -13. The precise position of the three trans internal isoprene residues was not determined but it is suggested that these are adjacent to the omega-terminal isoprene residue and that the ficaprenols are formed from all-trans-geranylgeranyl pyrophosphate. It is also suggested that ficaprenol-10, -11, -12 and -13 are probably the same compounds as castaprenol-10, -11, -12 and -13.

Complete 1H and 13C signal assignment of prenol‐10 with 3D NMR spectroscopy

“…[42,43] Final purification of prenol-10 was performed on a silica gel column. [44] All NMR experiments for prenol-10 in 80 mM solution in benzene (C 6 D 6 ) were recorded at 298 K on a Varian NMR System 700 spectrometer equipped with a Performa XYZ PFG unit and using the 5-mm 1 H, 13 C, 15 N-triple resonance probehead with high power 1 H and 13 C π /2 pulses of 6.2 and 13.0 µs, respectively.…”

Membrane-bound UDP-Glucose

“…The allylic polyprenol ficaprenol was isolated from Ficus elastica leaves according to Stone et al (25) and phosphorylated by the method of Popjak et al (23). The purity of ficaprenol was checked by TLC and by IR and NMR spectrometry.…”

Effect of salt stress on prenol lipids in the leaves of Tilia 'Euchlora'

“…A characteristic feature of these compounds is their occurrence as a mixture ('family'), with a single predominant species and a Gaussian-like distribution of homologues (Stone et al 1967). It is postulated that the composition of the polyisoprenoid "family" in plant leaves is a characteristic feature of particular plant species and can be used as a chemotaxonomic marker (Chojnacki and Dallner 1988;Swiezewska and Danikiewicz 2005).…”