Prenylated chalcone

Chalcones Chalcones and dihydrochalcones can be considered as flavonoids with an open structure (see Fig. 5.1). Although dihydrochalcones such as phloretin glycosides and 3-hydroxyphloretin glycosides have been found in many fruits and vegetables (Tsao and others 2003 Arabbi and others 2004), the occurrence in general is rare (Tomas-Barberan and Clifford 2000). Prenylated chalcones such as xanthohumol are found in hops (Zhao and others 2005) (see Fig. 5.2). 

Abegaz, B.M. et al., Prenylated chalcones and flavanones from the leaves of Dorstenia kamer-uniana. Phytochemistry, 49, 1147, 1998. 

Several new flavanones were produced as biotransformation products of the prenyl-chalcone, xanthohumol, when this compound was incubated with the microorganism... 

Bhatt, P. and Dayal, R., Stipulin, a prenylated chalcone from Dalbergia stipulacea. Phytochemistry, 31, 719, 1992. 

They are flavonoids without the C-ring and are not frequently isolated from plants, possibly due to their instability. So, most of the chalcones presented in this review are synthetics [80, 79]. This kind of flavonoids, generally, are rather cytotoxic against human cancer cells. Thus, xantohumol, a prenylated chalcone from hops, inhibited the A-2780 cell line at a IC50 of 0.5 pM [56] and two synthetic chalcones inhibited the HeLa cell line at IC50 of 0.0038 pg/mL [80]. 

Vogel S, Ohmayer S, Brunner G, Heilmann J (2008) Natural and non-natural prenylated chalcones synthesis, cytotoxicity and anti-oxidative activity. Bioorg Med Chem 16 4286... 

Narender T, Shweta TK, Srinivasa Rao M, Srinivasa K, Puri SK (2005) Prenylated chalcones isolated from Crotalaria genus inhibit in vitro growth of the human malaria parasite Plasmodium falciparum. Bioorg Med Chem Lett 15 2453... 

Chalcones, dihydrochalcones and aurones are not particularly important components of plant food materials, but they occur as notable pigments of flowers of many ornamental plants, such as the common snapdragon Antirrhinum spp., Scrophulariaceae) (Asteraceae), cosmos Cosmos spp.) and dahlia Dahlia spp.) from the Asteraceae family. Chalcones are also pigments of legume seeds (9-99) and woods. Prenylated chalcones are found in hop cones (10-98). 

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