Prenylated coumarins from the fruits of Artocarpus heterophyllus with their potential anti-inflammatory and anti-HIV activities

Abstract

A phytochemical investigation on the fruits of Artocarpus heterophyllus led to the isolation and characterisation of a new prenylated coumarin, artoheteronin (1), together with six known analogues (2−7). The chemical structure of 1 was elucidated using extensive spectral methods and the known compounds (2−7) were identified by comparing their spectral data with those reported in the literature. All known compounds (2–7) were isolated from the genus Artocarpus for the first time. The anti-inflammatory and anti-HIV activities of all isolated prenylated coumarins (1–7) were assessed in vitro. As a result, compounds 1–7 displayed notable inhibitory effects against nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro with the IC₅₀ values in range of 0.58 ± 0.06 to 6.29 ± 0.12 μM. Meanwhile, compounds 1–7 exhibited notable anti-HIV-1 reverse transcriptase (RT) activities possessing EC₅₀ values in the range of 0.18 to 9.12 µM.

Graphical Abstract

Keywords:

• Carpus heterophyllus
• prenylated coumarins
• artoheteronin
• anti-inflammatory activities
• anti-HIV-1 activities

Supplementary material

Supplementary material relating to this article is available online, alongside Table S1, Table S2 and Figures S1 − S7.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by the Key Research and Development Project of Hainan Province (No. ZDYF2019049), the Natural Science Foundation of Hainan Province (No. 2019RC198 and 220RC596), the Key Research and Development Project of Haikou (No. 2020054), the Key Science and Technology Project of Nanjing Administration for Market Regulation (No. KJ2019046), and the Undergraduate Innovation and Entrepreneurship Training Project (No. 202011658003, 202011658012, S202011658009S and S202011658029).