Highly oxygenated and structurally diverse diterpenoids from Euphorbia helioscopia.

A phytochemical investigation on the aerial part of Euphorbia helioscopia (Euphorbiaceae) led to the isolation of 22 highly oxygenated diterpenoids with structural types of ent-abietane, ent-kaurane, lathyrane, ent-atisane and ingenane. 17 of them, named euphelionolides A - N, 16-epi-18-hydroxy-abbeokutone, as well as eupheliotriols A and B, were identified to be previously undescribed compounds by extensive analysis of spectroscopic data. The stereostructures of euphelionolides A - K were determined by single crystal X-ray diffraction combined with analysis of substituent effects and comparison of optical characteristics. Eupheliotriol B is the first example of natural occurring lathyrol with 12Z-ene, while ent-atisanes are the first reported from the title plant. Furthermore, euphelionolides F and L exhibited significant cytotoxicity against MCF-7 and PANC-1 cell lines.

Wang WP ，Jiang K ，Zhang P ，Shen KK ，Qu SJ ，Yu XP ，Tan CH ... -  《-》

Diterpenoids from Euphorbia helioscopia and their enhancement of NK cell-mediated killing of NSCLC cells.

Fourteen previously undescribed diterpenoids, including an unusual diterpenoid (1) with a 9,10-seco-jatrophane skeleton, ten jatrophane-type diterpenoids (2-11), two lathyrane-type diterpenoids (12, 13), and an abietane-type diterpenoid (14), together with thirty-six known ones (15-50), were isolated from the whole plants of Euphorbia helioscopia L. The structures of the new isolates were characterized by spectroscopic methods, single-crystal X-ray diffraction analysis, and computational prediction of ECD and chemical shifts. Thirty-nine abundant diterpenoids were evaluated for their enhancement of NK cell-mediated killing of NSCLC cells. As a result, compounds 24, 33, and 41 were found to significantly enhance the killing activity of NK cells towards H1299-luci cells and A549-luci cells at the concentration of 2.5 μM.

Mu HY ，Gong CY ，Zhang RJ ，Chen ZH ，Zhu SG ，Zhao WM ... -  《-》

Cytotoxic ent-Abietane-type diterpenoids from the roots of Euphorbia ebracteolata.

Euphoroids A-C (1-3), three new ent-abietane-type diterpenoids, together with ten known analogues (4-13) were obtained from the roots of Euphorbia ebracteolata. The structures of these compounds were determined by extensive spectroscopic data analysis, including UV, HRESIMS, 1D-, and 2D-NMR data. The inhibitory effects of compounds 1-13 on human cancer cells were determined using the MTT assay. The results revealed that new compounds 2 and 3 showed moderate cytotoxic activities against human cancer cell lines. Especially, compound 3 displayed selective cytotoxic effect agains cancer cell lines.

Han C ，Peng Y ，Wang Y ，Huo X ，Zhang B ，Li D ，Leng A ，Zhang H ，Ma X ，Wang C ... -  《-》

Euphonoids A-G, cytotoxic diterpenoids from Euphorbia fischeriana.

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 μM. The brief structure-activity relationships (SARs) of these diterpenoids were also discussed.

Yan XL ，Zhang JS ，Huang JL ，Zhang Y ，Chen JQ ，Tang GH ，Yin S ... -  《-》

Five New Diterpenoids from the Seeds of Euphorbia lathyris.

A new premyrsinane-type diterpenoid, premylanin (1), and four new lathyrane-type diterpenoids named Euphorbia Factors L30 -L33 (2-5) were isolated from the seeds of Euphorbia lathyris, together with thirteen known ones (6-18). Their structures were elucidated through spectroscopic analyses, including IR, UV, HR-ESI-MS, 1D- and 2D-NMR. The cytotoxicities of compounds 1-4 and 6-18 against HCT116, MCF-7, 786-0, HepG2 cell lines were evaluated, and compound 13 exhibited considerable cytotoxic activities with an IC50 values of 6.44, 8.43, 15.3, 9.32 μm, respectively.

Wang Q ，Zhen YQ ，Gao F ，Huang S ，Zhou XL ... -  《-》