Chemical Properties and Biological Activities of Cyclopentenediones: A Review
Zuzana Sevcikova, Milan Pour, David Novak, Jitka Ulrichova and Jan Vacek
Affiliation: Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacky University, Hnevotinska 3, 775 15 Olomouc, Czech Republic.
Cyclopentenediones (CPDs) are secondary metabolites of higher plants, fungi, algae, cyanobacteria and
bacteria. A common denominator of CPDs is the cyclopent-4-ene-1,3-dione skeleton (1), which is modified by several
functional groups. The heterogeneity of these substitutions is reflected in around one hundred CPDs reported to date. Most
of the derivatives were isolated primarily from plant sources. Synthetic analogues were then prepared with new biological
activities and more interesting pharmacological potential. Antifungal substances called coruscanones (2, 3) are the most
studied of the CPDs. Other intensely investigated CPDs include lucidone (4), linderone (5), asterredione (6), involutone
(7), nostotrebin 6 (8), TX-1123 (9), G2201-C (10), madindolines (11, 12) and many others. In addition to antibacterial and
antifungal effects, a broad spectrum of biological activities for CPDs has been reported in the past two decades, especially
anti-inflammatory, cytostatic and specific enzyme inhibitory activities. The CPD skeleton has been identified in a number
of substances isolated from the plant kingdom; hence, CPDs can be referred to as a new group of natural bioactive
substances. The main goal of this review is to define CPDs with respect to basic chemistry, isolation, synthetic approaches
and description of their biological effects. Special attention is given to a detailed view into biological activities of CPDs
in vitro and their phamacological potential.
Keywords: Biological activity, cyclopentenediones, chemical properties, coruscanones, pharmacological potential, synthesis.
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