Polyacetylene alcohols

Matsunaga FI, Saita T, Nagumo F, Mori M, Katano M. (1995). A possible mechanism for the cytotoxicity of a polyacetylenic alcohol, panaxytriol inhibition of mitochondrial respiration. Cancer Chemother Pharmacol. 35(4) 291-96. 

Polyacetylene alcohols Mar. cosmop. Nepheliosp., Haplosclerida, and Lithistida, Porif Land Umbelliferae, Ang. Ohta 1999, Fu 1999 non-terminal C-branched class in PcHif Guerriero 1998. 

Active constituents found in most ginseng species include ginsenosides, polysaccharides, peptides, polyacetylenic alcohols, and fatty acids. There is a wide variation (2 to 20%) in the ginsenoside content of different species of ginseng. Moreover, pharmacological differences within a single species cultivated in two different locations have been reported. For example, the potency... 

S), 16(i )-Dihydroxy-octadeca-9Z, 17-diene-12,14-diyn-1 -yl acetate (polyacetylene alcohol acetic acid ester) Angelica pubescens (Apiaceae) [root = Du Huo] COX-1, 5-LOX... 

From the acetonic extract of the roots of B. rigidum two polyacetylene alcohols (12 and 13) were obtained. 

Nitz, S., M.H. Spraul, and F. Drawert. 1990. C polyacetylenic alcohols as the major constituents in roots of Petroselinum crispum Mill. ssp. tuberosum.. Agric. Food Cliem. 38 1445-1447. 

From the ether-soluble fraction, Takahashi etal. 134, 135) isolated sitosterol-P-D-glucoside, sitosterol, p-elemene (96), eremophilene (97) and a new polyacetylenic alcohol named panaxynol (98), the structure of which was elucidated as heptadeca-l,9(Z)-diene-4,6-diyn-3-ol by degradative and synthetic procedures. It is identical with carotatoxin from carrots 136) and falcarinol from Falcaria vulgaris 137). Recently two other polyacetylenic alcohols, 9,10-epoxy-3-hydroxyheptadeca-l-en-4,6-diyne [(99), panaxydol] 138) and heptadeca-l-en-4,6-diyn-3,9-diol (100) 139) were isolated from Ginseng roots by Wrobel et al. 

Bentley, R. K., D. Bhattacharjee, Sir R. H. Jones, and V. Thaller Natural Acetylenes. Part XXVIII. C-17-Polyacetylenic Alcohols from the Umbellifer Daucus carota L. (Carrot) Alkylation of Benzene by Acetylene (Vinyl) Carbinols in the Presence of Toluene-/ -sulphonic Acid. J. Chem. Soc. Section C (London) 1969, 685. 

Bentley, R.K., Bhattacharjee, D., Jones, E.R.H. et al (1969a) Natural acetylenes. Part XXVIII. Ci7-Polyacetylenic alcohols from the UmbeUifer Daucus carota L. (carrot) Alkylation of benzene by acetylenyl(vinyl)carbinols in the presence oftoluene-p-sulphonic acid. /. Chem. Soc. (C), 685-688. 

Fusetani, N., Y. Kato, S. Matsunaga, and K. Hashimoto Bioactive Marine Metabolites III. A Novel Polyacetylene Alcohol, Inhibitor of Cell Division in Fertilized Sea Urchin Eggs, from the Marine Sponge Tetrosia sp. Tetrahedron Lett. 24, 2771 (1983). 

Figure 19.68 Examples of polyacetylenic alcohols isolated from haplosclerid sponges.

Callyspongenols A-C, new cytotoxic C22-polyacetylenic alcohols from a Red Sea sponge, CaUyspon a species. J. Nat. Prod., 66, 679-681. 

There is also a series of polyacetylenic alcohols that are usually found in the Haploscleridae (Figures 19.68,19.69, and 19.70) but have also been identified in a polydinid asddian coUeded on the Atlantic coast of Spain (Vigo). All of these derivatives have a C21 carbon chain and two triple bonds. 

Gavagnin, M., Castelluccio, F., Antonelli, A., Templado, J., and Cimino, G. (2004) Unusual C21 linear polyacetylenic alcohols from an Atlantic ascidian. Lipids, 39, 681-685. 

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