Acetylenic Aquatic Anticancer Agents and Related Compounds

Abstract

Although acetylenes are common as components of terrestrial plants, it is only within the last 30 years that biologically active polyacetylenes having unusual structural features have been reported from aquatic organisms: cyanobacteria, algae, fungi, invertebrates, and other sources. Naturally occurring aquatic acetylenes are of particular interest since many of them display important biological activities and possess antitumor, antibacterial, antimicrobial, antifouling, antifungal, pesticidal, phototoxic, HIV inhibitory, and immuno-suppressive properties. There is no doubt that they are of great interest, especially for the medicinal and/or pharmaceutical industries. This review presents structures and describes cytotoxic and anticancer activities of more than 230 acetylenic metabolites isolated from aquatic organisms. With the computer program PASS some additional biological activities are also predicted, which point toward possible new applications of these compounds. This review emphasizes the role of aquatic acetylenic compounds as an important source of leads for drug discovery.

Anticancer activity of natural and synthetic acetylenic lipids

“…ATPase activities of cells from Sarcoma 180 and rat liver were slightly inhibited by panaxydol (5). Activities of 5′-nucleotidase and succinate cytochrome C reductase in Sarcoma 180 cells and in rat liver, respectively, were significantly inhibited in a dose-dependent manner by panaxynol (6) (33).…”

“…Thus, panaxydol (5), panaxynol (falcarinol) (6), and panaxytriol (7) are present in red ginseng powder at concentrations of 297, 250, and 320 µg/g, respectively. The antitumor alcohols panaxydol and panaxynol, isolated from a powder of the root of P. ginseng, inhibited the growth of various kinds of cultured tumor cell lines (28)(29)(30)(31)(32).…”

“…Other isolated polyacetylenic alcohols-panaxynol (6) and heptadeca-1,8-diene-4,6-diyne-3,10-diol (20) (Saposhnikoviae radix: Fang Feng in Chinese Medicine) and falcarindiol (21) (from Peucedani radix, Qian Hu), 9,10-epoxy-16-hydroxy-octadeca-17-ene-12,14-diyne-1-al (22) (from Foeniculi fructus, bitter fennel) as well as panaxydol 5, panaxynol (6), and panaxytriol (7) (from Panax ginseng)-inhibited the growth of cells from a human gastric adenocarcinoma cell line, MK-1, in a dose-dependent manner (48)(49)(50)(51).…”

“…Extensive pharmacological screening performed on aquatic species resulted in discovery of novel antitumor agents (1,5,6). The purpose of this review is to summarize antitumor and cytotoxic properties of 318 terrestrial and aquatic acetylenic natural products, belonging to diverse structural classes, including aliphatic and cyclic polyketides, terpenes, steroids, lipids, carotenoids, and peptides.…”

“…Natural acetylenic lipids and their derivatives have been isolated from a wide variety of plant species, cultures of higher fungi, and marine invertebrates (1)(2)(3)(4)(5)(6)(7)(8). Many of them display important biological activities, including antitumor, antibacterial, antimicrobial, antifungal, phototoxic, and other chemical and medicinal properties (9,10).…”