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

• Published in: Bioorganic chemistry 2020-08, Vol.101, p.104030-104030, Article 104030
• Main Authors: Liu, Yan-Ping, Yu, Xiao-Mei, Zhang, Wei, Wang, Ting, Jiang, Bo, Tang, Hao-Xuan, Su, Qin-Ting, Fu, Yan-Hui
• Format: Article
• Language: English
• Subjects: Anti-Inflammatory Agents - pharmacology; Anti-Inflammatory Agents - therapeutic use; Anti-inflammatory effects; Antiproliferative activities; Artocarpus heterophyllus; Cell Proliferation; Chromones - chemistry; Flavonoids - chemistry; Humans; Molecular Structure; Prenylated chromones; Prenylated flavonoids; Structure-Activity Relationship
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2020.104030

[Display omitted] •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 IC50 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 IC50 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.