Euphonoids A−G, cytotoxic diterpenoids from Euphorbia fischeriana. (October 2019)

• Record Type: Journal Article
• Authors: Yan, Xue-Long; Zhang, Jun-Sheng; Huang, Jia-Luo; Zhang, Yao; Chen, Jia-Qi; Tang, Gui-Hua; Yin, Sheng
• Is Part Of: Phytochemistry. Volume 166(2019)
• Publication Date: 2019-10
• Subjects: Euphorbia fischeriana (Euphorbiaceae) -- Diterpenoids -- Ent-abietanes -- Cytotoxicity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2019.112064
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Seven previously undescribed polycyclic diterpenoids, euphonoids A−G, including four ent -abietanes, two ent -atisanes, and one ent -kaurene, along with 26 known analogues were isolated from the roots of Euphorbia fischeriana . The structures of the undescribed compounds were elucidated by spectroscopic analysis, ECD calculations, and single crystal X-ray diffraction. Besides, the structure of a previously reported ent -abietane diterpenoid, fischeriabietane A, was revised. All the isolates were screened for the cytotoxicities against five cancer cell lines. Euphonoid A, fischeriabietane A, 11-oxo-ebracteolatanolide B, caudicifolin, jolkinolide B, and methyl-8, 11-3-dihydroxy-12-oxo- ent -abietadi-13, 15(17)-ene-16-oate showed significant inhibitory activities against human prostate cancer C4-2B and C4-2B/ENZR cell lines, with IC50 values being less than 10 μ M. The brief structure-activity relationships (SARs) of these diterpenoids were also discussed. Graphical abstract: Seven previously undescribed polycyclic diterpenoids along with 26 known analogues were isolated from the roots of Euphorbia fischeriana. Six compounds showed significant inhibitory activity against C4-2B and C4-2B/ENZR cell lines, with IC50 values being less than 10 μ M.Image 1 Highlights: Seven previously undescribed diterpenoids were isolated from Euphorbia fischeriana. Six compounds showed significant cytotoxicity against a panel of cancer cell lines. The brief structure-activity relationships of these diterpenoids were discussed.