Antitumor Acetylenic Lipids

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This article describes antitumor acetylenic lipids and related compounds obtained from living organisms. Acetylenic lipids belong to a class of molecules containing triple bond(s). They are found in algae, plants, fungi, microorganisms, and marine invertebrates. Although polyacetylenes are common as components of terrestrial plants, fungi, and bacteria, it is only within the last 50 years that biologically active polyacetylenes having unusual structural features have been reported from plants, cyanobacteria, algae, 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, anti-fungal, HIV inhibitory and immunosuppressive properties. There is no doubt that they are of great interest, especially for the medical, pharmacological, medicinal chemistry, and/or pharmaceutical industries. This review presents structures and describes cytotoxic activities of more than 90 acetylenic lipids, including fatty acids, glycerides, sterols and carotenoids isolated from living organisms.

Natural acetylenic and/or polyacetylenic metabolites have been isolated from a wide variety of plants, fungal species, and marine algae and invertebrates. Many of them display important biological activities, namely antitumor, antibacterial, antimicrobial, antifungal, and other chemical and medicinal properties. More than 1000 acetylenic metabolites have been isolated and identified from plants, fungi, micro-organisms, and other organisms. Naturally occurring acetylenic lipids possessing an acetylenic unit, as well as polyacetylenes, are of particular interest as many of them display important biological activities, namely antitumor, antibacterial, antimicrobial, antifungal, and others. This paper describes acetylenic antitumor lipids that are deemed as naturally occurring.

The antitumor acetylenic compounds 2-cis-dehydro-matricaria acid, 2-trans-dehydromatricaria acid, cis-dehydromatricaria Me ester, and trans-dehydromatricaria Me ester were obtained from roots of Solidago virga-aurea (Compositae), and also from other species. Polyacetylene -hydroxy-octadeca-tetraynoic acid, referred to as minquartynoic acid, from M. guianensis stem bark showed cytotoxic activity against P-388 murine lymphocytic leukemia in vitro. The P-388 ED50 of the pure compound was 0.2 µg/mL, and it was also active in the brine shrimp larvicidal bioassay with an LC50 of 5 µg/mL. These biological activities could account for the alleged efficacy of the plant in folk usage. More recently, minquartynoic acid was isolated from the air-dried bark of Coula edulis, the twigs of Ochanostachys amentacea (both plants belonging to the Olacaceae), and from Minquartia guianensis bark. In addition, acetylenic acids were isolated from the twigs of Ochanostachys amentacea, and their cytotoxic activities determined.

Minquartynoic acid also showed moderate in vitro activity against Plasmodium falciparum and Leishmania major, and strongly inhibited phytohaemagglutinin A - induced proliferation of human lymphocytes. Three acetylenic acids: octadeca-8,10-diynoic, (Z)-octadec-12-ene-8,10-diynoic, and octadeca--triynoic acids were isolated from aqueous acetone extracts of stems and leaves. All compounds showed inhibitory activity against cancer cell invasion (MM1) in vitro (Table 2). Five C16-acetylenic fatty acids, hexadec-8-ynoic acid, hexadec-10-ynoic acid, hexadeca-8,10- diynoic, hexadeca-6,8,10-trienoic, and hexadeca-triynoic acids were prepared and their inhibitory activity against cancer cell invasion examined.