Terpenylated coumarins from the root bark of Ailanthus altissima (Mill.) Swingle

  • Phytochemistry. 2020 Jul:175:112361. doi: 10.1016/j.phytochem.2020.112361.
Zhi-Yang Yan  1 Tian-Ming Lv  1 Yu-Xi Wang  1 Shao-Chun Shi  1 Jing-Jie Chen  1 Bin-Lin  2 Qing-Bo Liu  1 Xiao-Xiao Huang  3 Shao-Jiang Song  1
Affiliations
  • 1. School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China.
  • 2. School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China; School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China.
  • 3. School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China. Electronic address: [email protected].
Abstract

Seven undescribed terpenylated Coumarins, named altissimacoumarin I-O, together with seven known compounds, altissimacoumarin C, altissimacoumarin E, altissimacoumarin G, altissimacoumarin H, puberulin, 7-(3-Methyl-2-butenyloxy)-6-methoxycoumarin and artelin were isolated from the root bark of Ailanthus altissima (Mill.) Swingle. Their structures were elucidated by comprehensive spectra data analysis, NMR calculation, DP4+ analysis and ACD/Structure Elucidator software simulation. The absolute configurations of altissimacoumarins K, L, M and N were determined by modified Mosher's method. All isolates were tested for their cytotoxic effect against two hepatoma carcinoma cell lines (HepG2, Hep3B). Altissimacoumarin C exhibited moderate cytotoxic effect against Hep3B cells, with IC50 of 45.21 μM.

Keywords
Ailanthus altissima (Mill.) Swingle; Modified Mosher's method; NMR calculation; Simaroubaceae; Terpenylated coumarins.
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