Bioactive prenylated coumarins as potential anti-inflammatory and anti-HIV agents from Clausena lenis

• Published in: Bioorganic chemistry Vol. 97; p. 103699
• Main Authors: Liu, Yan-Ping, Yan, Gui, Xie, Yu-Tong, Lin, Tian-Ci, Zhang, Wei, Li, Juan, Wu, Ying-Ju, Zhou, Jun-Yu, Fu, Yan-Hui
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.04.2020; Elsevier
• Subjects: Animals; Anti-HIV activities; Anti-HIV Agents - chemistry; Anti-HIV Agents - isolation & purification; Anti-HIV Agents - pharmacology; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; Anti-inflammatory effects; Biochemistry & Molecular Biology; Chemistry; Chemistry, Organic; Clauselenins A and B; Clausena - chemistry; Clausena lenis; Coumarins - chemistry; Coumarins - isolation & purification; Coumarins - pharmacology; HIV Infections - drug therapy; HIV Reverse Transcriptase - antagonists & inhibitors; HIV Reverse Transcriptase - metabolism; HIV-1 - drug effects; Humans; Life Sciences & Biomedicine; Mice; Models, Molecular; Physical Sciences; Prenylated coumarins; Prenylation; RAW 264.7 Cells; Science & Technology; Prenylated coumarins; Clauselenins A and B; Anti-inflammatory effects; Clausena lenis; Anti-HIV activities; GLYCOSIDES; CARBAZOLE ALKALOIDS; SEEDS; PEELS; LANSIUM; STEMS; DIMERIC COUMARIN; ROOTS; DERIVATIVES; CONSTITUENTS
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2020.103699

[Display omitted] •The chemical constituents from Clausena lenis were investigated.•Three new prenylated coumarins were isolated from the stems of C. lenis.•The anti-inflammatory effects and anti-HIV activities of all isolated compounds were evaluated in vitro.•Compounds 1–12 displayed significant anti-inflammatory effects with the IC50 values comparable to that of hydrocortisone.•Compounds 1–12 exhibited remarkable anti-HIV activities with the EC50 values in range of 0.17–9.08 µM. The phytochemical study on the stems of Clausena lenis resulted in the isolation of three new prenylated coumarins, clauselenins A–C (1–3), together with nine known prenylated coumarins (4–12). The chemical structures of new prenylated coumarins (1–3) were elucidated by means of comprehensive spectral analyses and the known compounds (4–12) were determined by means of comparing their experimental spectral data with those described data in the literatures. All isolated prenylated coumarins were assessed for their anti-inflammatory effects together with anti-HIV activities in vitro. Prenylated coumarins 1–12 displayed remarkable inhibitory effects against nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro with the IC50 values which are comparable to hydrocortisone. Meanwhile, prenylated coumarins 1–12 exhibited considerable anti-HIV-1 reverse transcriptase (RT) activities possessing EC50 values in the range of 0.17–9.08 µM. These findings indicate that the isolation and identification of these prenylated coumarins with pronounced anti-inflammatory effects as well as anti-HIV activities separated from the stems of C. lenis could be of great significance to the development of new anti-inflammatory and anti-HIV agents and their potential applications in the pharmaceutical industry.