Prenylated chromones and flavonoids from Artocarpus heterophyllus with their potential antiproliferative and anti-inflammatory activities.

• The chemical constituents from Artocarpus heterophyllus were investigated. • Two new prenylated chromones were isolated from A. heterophyllus. • The antiproliferative and anti-inflammatory effects of 1 – 12 were evaluated in vitro. • 1 – 12 showed significant antiproliferative activities equivalent to cisplatin. • 1 – 12 exhibited remarkable anti-inflammatory effects comparable to hydrocortisone. Two new prenylated chromones, artoheterophines A (1) and B (2), five known prenylated chromones (3 – 7), as well as five known biogenetically related prenylated flavonoids (8 – 12) were isolated and characterized from the stems and leaves of A. heterophyllus. Their chemical structures were unambiguously determined through comprehensive spectral data analyses. The antiproliferative and anti-inflammatory effects of all these isolated prenylated chromones and flavonoids were evaluated in vitro. As a result, compounds 1 – 12 showed notable inhibitory effects against various human cancer cell lines with IC 50 values ranging from 0.36 ± 0.02 to 22.09 ± 0.16 μM. Meanwhile, compounds 1 – 12 exhibited significant inhibitory activities on nitric oxide (NO) production holding IC 50 values in the range of 0.48 ± 0.05–19.87 ± 0.21 µM. These research results suggest that the isolation and characterization of these prenylated chromones (1 – 7) and flavonoids (8 – 12) holding significant antiproliferative and anti-inflammatory activities could be significant to the discovery and development of new natural anti-tumor and anti-inflammatory drugs. The findings also provides a phytochemical evidence for further development and utilization of the stems and leaves of A. heterophyllus in health and pharmaceutical products. [ABSTRACT FROM AUTHOR]