Review Allenic and cumulenic lipids q Valery M. Dembitsky a, * , Takashi Maoka b a Department of Medicinal Chemistry and Natural Products, School of Pharmacy, P.O. Box 12065, Hebrew University, Jerusalem 91120, Israel b Research Institute for Production Development, 15 Shimogamo-Morimoto-Cho, Sakyo-Ku, Kyoto 606-0805, Kyoto Pharmaceutical University, Japan Received 14 May 2007; received in revised form 13 June 2007; accepted 2 July 2007 Abstract Nowadays, about 200 natural allenic metabolites, more than 2700 synthetic allenic compounds, and about 1300 cumu- lenic structures are known. The present review describes research on natural as well as some biological active allenic and cumulenic lipids and related compounds isolated from different sources. Intensive searches for new classes of pharmaco- logically potent agents produced by living organisms have resulted in the discovery of dozens of such compounds possess- ing high anticancer, cytotoxic, antibacterial, antiviral, and other activities. Known allenic and cumulenic compounds can be subdivided on several structural classes: fatty acids, hydrocarbons, terpenes, steroids, carotenoids, marine bromoal- lenes, peptides, aromatic, cumulenic, and miscellaneous compounds. This review emphasizes the role of natural and syn- thetic allenic and cumulenic lipids and other related compounds as an important source of leads for drug discovery. Ó 2007 Elsevier Ltd. All rights reserved. Keywords: Fatty acids; Lipids; Triacylglycerides; Hydrocarbons; Allenic; Cumulenic; Anticancer; Antiviral; Antibacterial; Terpenoids; Carotenoids; Steroids; Peptides; Aromatic; Synthetic Contents 1. Introduction ....................................................................... 329 2. Allenic fatty acids and derivatives ....................................................... 330 0163-7827/$ - see front matter Ó 2007 Elsevier Ltd. All rights reserved. doi:10.1016/j.plipres.2007.07.001 Abbreviations: AADC, aromatic acid decarboxylase; ABA, abscisic acid; a-Allenic-DOPA allenic analog of amino acid L-3,4-dihydr- oxyphenylalanine (L-DOPA); GABA, c-aminobutyric acid; HepG2, human hepatocellular liver carcinoma cell line; HUVEC, umbilical vein endothelial cells; LM, leucomycin; LOX, lipoxygenase; LPS, lipopolysaccharide; MGC, mammalian gene collection; MTT assay is a laboratory test and a standard colorimetric assay for measuring cellular proliferation; NF-kappa B, factor-kappa B; OAT, optically active triglycerides; Raji cells are a line of EBV-transformed lymphocytes with surface F c receptors; TNF-alpha, tumor necrosis factor; VDR, vitamin D nuclear receptor. q See Ref. [1] for a previous article giving additional information. * Corresponding author. Tel./fax: +972 2 590 2947. E-mail address: dvalery@cc.huji.ac.il (V.M. Dembitsky). Progress in Lipid Research 46 (2007) 328–375 www.elsevier.com/locate/plipres Progress in Lipid Research