Chemistry and Pharmacology of Artocarpin: An Isoprenyl Flavone from Artocarpus Species

Abstract

Artocarpin is an isoprenyl flavone from Artocarpus species (Moraceae). Trees of the genus comprise about 50 species, and are native to tropical and subtropical Asia. First isolated from the root of A. heterophyllus (jackfruit), artocarpin has been reported in other Artocarpus species such as A. altilis, A. chempeden, A. kemando and A. maingayi. Recently, artocarpin has also been isolated from A. incisus, A. chama, A. lowii, A. anisophyllus, A. scortechinii, A. odoratissimus and A. hirsutus. It has a molecular formula of C26H28O6 and a 5,7,2’,4’-tetrahydroxylated structure with three benzene rings. Ring B has a 2’,4’-resorcinol moiety and there is a methoxy group at C-7 of ring A. At C-3 and C-6 of artocarpin are the isoprenyl substituents. Some data on the content of artocarpin in extracts and fractions of different solvents and species of Artocarpus have been presented. Other flavones prenylated at C-3 and C-6 include artelasticin, artelastofuran, cudraflavone C and norartocarpin. The inhibition of tyrosinase and melanogenesis are two skin-whitening activities of artocarpin. It protects UVB-induced skin damage. Besides its cosmeceutical activities of skin-whitening and photo protection, artocarpin possesses other pharmacological properties such as cytotoxic, anti-inflammatory, antioxidant, antimicrobial, antiandrogen, antitubercular, antiplasmodial, neuraminidase inhibitory, termiticidal and wound healing activities. In the conclusion, some research studies of interest for the future have been proposed.