Panaxydiol

J Agric Food Chem. 2005 Apr 6;53(7):2518-23.

Polyacetylenes from the Apiaceae vegetables carrot, celery, fennel, parsley, and parsnip and their cytotoxic activities.[Pubmed: 15796588]

A dichloromethane extract of root celery yielded falcarinol, falcarindiol, Panaxydiol, and the new polyacetylene 8-O-methylfalcarindiol.
METHODS AND RESULTS:
The structure of the new compound was established by one- and two-dimensional (1D and 2D) NMR, mass spectrometry, and optical rotation data. Nonpolar extracts of roots and bulbs of carrots, celery, fennel, parsley, and parsnip were investigated for their content of polyacetylenes by high-performance liquid chromatography with diode array detection (HPLC-DAD). All five species contained polyacetylenes, although carrots and fennel only in minor amounts. Additionally, the cytotoxicity of the four polyacetylenes against five different cell lines was evaluated by the annexin V-PI assay.
CONCLUSIONS:
Falcarinol proved to be the most active compound with a pronounced toxicity against acute lymphoblastic leukemia cell line CEM-C7H2, with an IC(50) of 3.5 micromol/L. The possible chemopreventive impact of the presented findings is discussed briefly.

Chem Pharm Bull (Tokyo). 2004 Apr;52(4):418-21.

Synthesis of panax acetylenes: chiral syntheses of acetylpanaxydol, PQ-3 and panaxydiol.[Pubmed: 15056955]

METHODS AND RESULTS:
Acetylpanaxydol (1-Ac), PQ-3 (2) and Panaxydiol (3) and their optical isomers were synthesized from L-(+)-diethyl tartrate. The absolute configurations of 1-Ac, 2 and 3 were determined to be 1-Ac (3R,9R,10S), 2 (9R,10S) and 3 (3R,10S), respectively, by comparisons of their optical rotations and the NMR data of their MTPA esters with those of natural products.