Abstract
Luotonins are alkaloids from the aerial parts of Peganum nigellastrum Bunge. that display three major skeleton types. Luotonins A, B, and E are pyrroloquinazolino-quinoline alkaloids, luotonins C and D are canthin-6-one alkaloids, and luotonin F is a 4(3H)-quinazolinone alkaloid. All six luotonins have shown promising cytotoxicities towards selected human cancer cell lines, especially against leukemia P-388 cells. Luotonin A is the most active one, with its activity stemming from topoisomerase I-dependent DNA-cleavage. Such intriguing biological activities and unique structures have led not only to the development of synthetic methods for the efficient synthesis of these compounds, but also to interest in structural modifications for improving the biological properties. Recent progress in the study of luotonins is covered.
Highlights
The plant Peganum nigellastrum Bunge (Zygophyllaceae) has long been used in Chinese traditional medical practice for the treatment of rheumatism, abscesses, and diseases accompanying inflammation [1]
The six luotonins can be classified into three categories: luotonins A, B, and E are pyrroloquinazolinoquinoline alkaloids, luotonin F is a 4(3H)-quinazoline alkaloid, and luotonins C and D are canthin-6-one alkaloids
It should be noted that the inhibitory activities of luotonin A (IC50 = 28.5 μM) and F against topoisomerase II (Topo II) were somewhat related to their cytotoxicities [6,56]
Summary
The plant Peganum nigellastrum Bunge (Zygophyllaceae) has long been used in Chinese traditional medical practice for the treatment of rheumatism, abscesses, and diseases accompanying inflammation [1]. Additional luotonins such as luotonin C (2a) and D (2b) [4] and luotonin E (1c) and F (3) [5] were consecutively isolated from the same plant Most of these luotonins show promising cytotoxicity against leukemia P-388 cells [6,7,8] (see Table 1). More than 25 papers have been published, most of which cover the development of synthetic methods for the total synthesis and the structural modification of luotonin A. The present review covers roughly in chronological order the total synthesis of all six luotonins based on the synthetic strategies for the ring formation and the structure-biological activity relationship studies
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