Three new ent -abietane diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity in human tumor cell
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RESEARCH ARTICLE
Three new ent-abietane diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity in human tumor cell lines Minghui Li1 • Fang He1 • Yuan Zhou1 • Meigui Wang1 • Pingde Tao1 Qingmei Tu1 • Guanghui Lv1 • Xintao Chen1,2
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Received: 3 January 2019 / Accepted: 1 April 2019 The Author(s) 2019
Abstract Three new ent-abietane diterpenoids, termed fischerianoids A–C (1–3), were isolated and identified from the ethyl acetate extracts of roots of the medicinally valuable plant Euphorbia fischeriana. The planar and relative structures of 1–3 were established via high-resolution electrospray ionisation mass spectrometry and one- and two-dimensional nuclear magnetic resonance spectroscopic analyses, and the absolute configuration of 1 was further established via X-ray crystallography experiment. Compounds 1–3 showed selective inhibitory potency against certain human tumor cell lines with IC50 values ranging from 8.50 ± 0.13 to 35.52 ± 0.08 lM.
Graphical abstract
Keywords ent-Abietane diterpenoids Euphorbia fischeriana Structural elucidation Cytotoxicity Electronic supplementary material The online version of this article (https://doi.org/10.1007/s12272-019-01151-y) contains supplementary material, which is available to authorized users.
Introduction Minghui Li and Fang He have contributed equally to this work. & Guanghui Lv [email protected] & Xintao Chen [email protected] 1
Department of Pharmacy, Taihe Hospital, Hubei University of Medicine, Shiyan 442000, People’s Republic of China
2
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
Euphorbia fischeriana Steud, a perennial herbaceous plant of the Euphorbiaceae family, is widely distributed in northeastern mainland China (Wang et al. 2012). The roots of E. fischeriana, also named ‘‘Lang-du’’, are widely used in folk medicine for the treatment of edema, ascites, and cancer (Pan et al. 2011). More importantly, an extract of E. fischeriana is employed as the main ingredient of the drug ‘‘Jie-He-Ling’’, which is used in clinical practice to treat lymphoid and pulmonary tuberculosis (Li et al. 2016). Previous chemical investigations have suggested that the roots of this plant are a
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rich source of diterpenoids, triterpenoids, steroids, polysaccharides, and acetophenone derivatives, all of which have diverse biological properties, such as antibacterial, anti-inflammatory, anti-tuberculosis, and cytotoxic activities (Wang et al. 2017). Of these diterpenoids, jolkinolides A and B exhibit potential cytotoxic activities against Ehrlich ascites, sarcoma 180, and HeLa cells; meanwhile 17-hydroxyjolkinolide B is a promising anti-cancer drug candidate as it potently inhibits signal transducer and activator of transcription 3 signaling (Pan et al. 2011). Prostratin (12-deoxyphorbol-13-acetate) is a 12-deoxytiglia
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