Cytotoxic Diterpenoids from the Roots ofEuphorbia ebracteolata

Abstract

Three new diterpenoids, yuexiandajisu D (1), E (2) and F were isolated from the roots of Euphorbia ebracteolata, along with eight known diterpenoids, jolkinolide B (4), jolkinolide A, ent-11alpha-hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide (6), ent-(13S)-hydroxyatis-16-ene-3,14-dione, ent-3beta,(13S)-dihydroxyatis-16-en-14-one, ent-3-oxokaurane-16alpha,17-diol, ent-16alpha,17-dihydroxyatisan-3-one and ent-atisane-3beta,16alpha,17-triol. The structures of all compounds were deduced using spectroscopic methods and confirmed for 1 and 2 by single-crystal X-ray diffraction. A biogenetic pathway for the formation of 1 and 2 is proposed briefly. Cytotoxic activities were evaluated against ANA-1, B 16 and Jurkat tumor cells. Jolkinolide B (4) displayed modest activity on ANA-1, B 16 and Jurkat tumor cells with IC50 values 4.46 x 10(-2), 4.48 x 10(-2), 6.47 x 10(-2) microM, and ent-11alpha-hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide (6) showed significant activity against ANA-1 and Jurkat cells with IC50 values 7.12 x 10(-3) and 1.79 x 10(-2) microM. Compound 1 was found to be slightly active against ANA-1 cells with an IC50 value 2.88 x 10(-1)microM. Structure-activity relationships of isolated compounds are also discussed.

Isolation and antibacterial activity of triterpenes from <i>Euphorbia kamerunica</i> Pax

“…The Euphorbia is known to contain skin irritants and co-carcinogenic principles in the form of esters of the structurally related diterpenes ingenane and daphanane (Hecker, 1978;Evans and Taylor, 1983;Hecker et al, 1984). Earlier studies undertaken on this genus have revealed the presence of triterpenes (Lima et al, 2003), diterpenes (Shi et al, 2005), macrocyclic diterpenes (Redei, et al, 2003) and aromatic compounds (Oksuz et al, 2002).…”

17-Hydroxy-jolkinolide B Inhibits Signal Transducers and Activators of Transcription 3 Signaling by Covalently Cross-Linking Janus Kinases and Induces Apoptosis of Human Cancer Cells

“…The dried plant roots of Euphorbia fischeriana Steud (Euphorbiaceae), known as ''lang-du'' in traditional Chinese medicine, have long been used for the treatment of cancer, edema, and ascites (36)(37)(38)(39). Diterpenoids are major chemical constituents of the roots constituting f0.1% of the plant's total mass.…”

Ebracteolatain A and Ebracteolatain B Induce Apoptosis of Human Hepatoma Cell Line (HepG2)

“…Many study reports [3][4][5][6] have confirmed that E. ebracteolata can be used to treat cancer. In the present study, we studied the effects of EA and EB from E. ebracteolata on the proliferation of HepG2 cells and the possible mechanisms in vitro by MTT, flow cytometry and Western blot assays.…”

“…Yuexiandajisu D from E. ebracteolata inhibits the proliferation of HCT-8, KB, A549, Bel-7402 and BGC-823 cells [5]. Jolkinolide B and ent-11α-hydroxyabieta-8 (14),13(15)-dien-16,12α-olide from E. ebracteolata show cytotoxicity activities against ANA-1, B16 and Jurkat cells [6]. In addition, the terpenoids from Euphorbia L. show cytotoxic activities against SMMC-7221, L342, MCc80-3, U937 and HeLa cells, and their anti-cancer mechanisms may be related to apoptosis [7,8].…”

“…Currently, a few researches have reported the anti-cancer activities of E. ebracteolata [3][4][5][6]. It is reported that the water extract of E. ebracteolata induces the apoptosis of P388 lymphocytic leukemia cells by regulating the expression levels of Bax and Bcl-2 [3].…”