An isopimarane diterpene from Euphorbia ebracteolata Hayata

From the ethanolic extract of the roots of Euphorbia ebracteolata Hayata four compounds were isolated. They are 24-methylenecycloartanone, tirucallol, procesterol and a new isopimarane diterpene, namely yuexiandajisu C. The structure of yuexiandajisu C was elucidated by spectral analysis. The bioassay in vitro showed yuexiandajisu C exhibited immunomodulatory activity.     

Triterpenoids and a diterpene from Euphorbia iberica

From the aerial parts of Euphorbia iberica, an ingenane diterpene ester, ingenol 20-eicosanoate, and three ursanetype triterpenoids, 3beta-acetoxy-urs-12-ene-1beta,11alpha-diol, 3beta-( E)-coumaroyloxy-urs-12-ene, and 3beta-( Z)-coumaroyloxy-urs-12-ene have been isolated together with known cylcoartane-type triterpenes, a flavone, and coumarins. The first four compounds are new and their structures were determined by spectroscopic methods.     

A new diterpene from the processed roots of Euphorbia Kansui

A new diterpene has been isolated from the processed roots of Euphorbia Kansui. By means of physico-chemical evidences and spectral analysis, the structure was identified as 4-O-acetyl-5-O-benzoyl-3β-hydroxy-20-deoxyingenol (1).     

A new diterpene from the processed roots of Euphorbia Kansui

A new diterpene has been isolated from the processed roots of Euphorbia Kansui. By means of physico-chemical evidences and spectral analysis, the structure was identified as 4-O-acetyl-5-O-benzoyl-3β-hydroxy-20-deoxyingenol (1).     

A new diterpene from the processed roots of Euphorbia Kansui

A new diterpene has been isolated from the processed roots of Euphorbia Kansui. By means of physico-chemical evidences and spectral analysis, the structure was identified as 4-O-acetyl-5-O-benzoyl-3beta-hydroxy-20-deoxyingenol (1).     

Three new jatrophane polyesters and antiproliferative constituents from Euphorbia tuckeyana

Three new jatrophane diterpene polyesters named tuckeyanols A and B and euphotuckeyanol, as well as ten known compounds, helioscopinolides A, B, D and E, naringenin, aromadendrin, coniferaldehyde, 4,20-dideoxy-5-hydroxyphorbol 12,13-diisobutyrate, 4,20-dideoxy-5-hydroxyphorbol 12-benzoate-13-isobutyrate and dehydrodiconiferyl diacetate, were isolated from the methanolic extract of Euphorbia tuckeyana. Their structures were elucidated by physical and spectroscopic methods including 1 D and 2 D homo- and heteronuclear NMR techniques (COSY, HMQC, HMBC and NOESY), and HR-mass spectrometry. Four of the isolated compounds were investigated for their antiproliferative activity in three human gastrointestinal cancer cell lines: gastric (EPG85-257), pancreatic (EPP85-181) and colon (HT-29) carcinomas. Three of them have showed to be moderate inhibitors of the growth of gastric and pancreatic tumor cell lines.     

Cytotoxicities and anti-herpes simplex virus activities of diterpenes isolated from Euphorbia species

The cytotoxicities of nine diterpene polyesters obtained from Euphorbia species were assayed by measuring their effects on the growth of Vero cells. Their antiviral effects on the multiplication of Herpes simplex virus type 2 (HSV-2) were studied by using the virus yield reduction method in cell cultures. With the exception of the strongly cytotoxic 2alpha,5alpha,14beta-triacetoxy-3beta-benzoyloxy-8alpha,15beta-dihydroxy-7beta-isobutanoyloxy-9alpha-nicotinoyloxyjatropha-6(17),11E-diene (CC(50) 3.5 microg/ml), all the tested diterpenes exhibited a pronounced or moderate anti-herpes virus effect (IC(50) values between 2.5 and 8.3 microg/ml). The observed HSV-2 inhibitory activities were not associated with virucidal effects.     

Irritant and co-carcinogenic diterpene esters from the latex of Euphorbia cauducifolia L.

Ten (1–10) irritant and mild co-carcinogenic diterpene esters were isolated from the latex of Euphorbia cauducifolia L. using bioassay-guided countercurrent distribution and other chromatographic techniques. The isolated compounds were characterized on the basis of spectroscopic results and mass measurements. As an outcome, the ingenane-type esters were established with the following structures: 3-O-angeloyl-17-O-palmatoylingenol (1), 3-O-palmatoyl-5-O-angeloylingenol (2), 5-O-angeloyl-17-O-palmatoylingenol (3), 3-O-angeloyl-5-O-palmatoylingenol (4), 17-O-(2Z,4E,6Z)-2,4,6-tetradecatrienoyl-20-O-palmatoylingenol (5), 5-O-angeloyl-17-O-benzoylingenol (6), 5-O-angeloyl-17,20-diacetoxyingenol (7), 3-O-angeloyl-17-O-benzoyl-20-acetoxyingenol (8), 3-acetoxy-5-O-angeloyl-17-O-benzoylingenol (9), and 5-O-angeloyl-3,17,20-triacetoxyingenol (10). Their biological screening revealed that they are moderate irritants, and low to moderate tumor promoters compared to TPA, but hardly showed any solitary carcinogenic activity. The isolated esters represent new compounds and were not reported before from any source.     

New Diterpenoids from Euphorbia sieboldiana

From the acetone extract of roots of EUPHORBIA SIEBOLDIANA, three known diterpenes, ENT-atisane-3beta,16alpha,17-triol ( 1), ingenol ( 4), and helioscopinolide A ( 5) as well as two new diterpenes, 3beta- O-acetyl- ENT-atisane-16alpha,17-diol ( 2), and ingenol-20-palmitate ( 3) were isolated. Their structures were elucidated by spectroscopic methods and chemical transformations.     

Four new diterpenoids isolated from the Euphorbia rapulum

Four new diterpenoids named 1-epi-9-hydroxydepressin (1), 1-epi-8-hydroxydepressin (2), 2,13,9-trihydroxy-labda-8(17),12(E),14-triene (3) and tagalsin I (4) were isolated from Euphorbia rapulum. The structures of these compounds were elucidated by means of various spectroscopic methods. All the isolated compounds were evaluated for cytotoxic activities against HepG2, MCF-7, and C6 cell lines, and compound 4 showed moderate selective activity against MCF-7 cell line with an IC₅₀ value of 31.8 μM.     

New macrocyclic diterpenoids from Euphorbia esula

The structures of two new macrocyclic jatrophane diterpenoid esters from the whole herb of Euphorbia esula, were established as 11,14-epoxy-3beta,5alpha,7beta,8alpha,9alpha,15beta-hexaacetoxy-12-oxo-13alphaH-jatropha-6(17)-ene (1) and 1alpha,3beta-diacetoxy-5alpha,7beta-dibenzoyloxy-9,14-dioxo-11beta,12alpha-epoxy-2alpha,8alpha,15beta-trihydroxy-13betaH-jatropha-6(17)-ene (2) by a combination of 1D- and 2D-NMR techniques as well as UV, IR and mass spectral data. Bioassay evaluation of all isolates against the human tumor cell lines (B16, KB, SMMC and BGC) indicated that ester 2 was cytotoxic to B16 with the IC50 value being 1.81 microg/ml. In addition, the irritant activity assay indicated that both diterpenoids were inactive (ID(24)50 > 100 microg/ear).     

Euphopubescenol and euphopubescene, two new jatrophane polyesters, and lathyrane-type diterpenes from Euphorbia pubescens

The structures of euphopubescenol and euphopubescene, two new macrocyclic jatrophane diterpene polyesters, isolated from the whole dried plant of Euphorbia pubescens, were established as 5alpha,8alpha,15beta-triacetoxy-3alpha-benzoyloxy -4alpha-hydroxy -9,14-dioxo-13beta H-jatropha-6(17),11 E-diene ( 1) and 3beta,7beta,8beta,9alpha,14alpha,15beta-hexaacetoxy-2beta H-jatropha-5 E,11 E-diene ( 2) by 1D- and 2D-NMR (COSY, HMQC, HMBC and NOESY), IR, EI-MS and EI-FTICR-MS. Two known lathyrane derivatives, jolkinol A ( 3) and jolkinol A ( 4), whose (13)C-NMR spectra were assigned, were also isolated. Compounds 1 - 3 have been evaluated for their ability to inhibit the in vitro growth of three human tumour cell lines representing different tumour types, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer). They inhibited both MCF-7 and NCI-H460 cell lines, with GI50 values ranging between 40.9 microM and 95.3 microM, but were found to be ineffective as growth inhibitors of the SF-268 cell line.     

New 6(17)-epoxylathyrane diterpene: aellinane from Euphorbia aellenii induces apoptosis via mitochondrial pathway in ovarian cancer cell line

Euphorbia species have been used in traditional medicine in many countries for the treatment of cancer. This article aims to evaluate the capability of a new lathyrane diterpene isolated from Euphorbia aellenii to induce apoptosis in the Caov-4 cell line to determine the underlying mechanism of its anticancer effects. A new 6(17)-epoxylathyrane diterpenes: aellinane from Euphorbia aellenii was evaluated for viability of Caov-4 cells by MTT method. Apoptosis induction by lathyrane diterpene was confirmed by annexin V-FITC/PI staining, and caspase-6 activation. The Bcl2 and Bax protein content were detected by Western blot analysis. Finally, we employed the fluorescent ROS detection kit and fluorochrome JC-1 to determine ROS levels and loss of mitochondria membrane potential (ΔΨm) in Caov-4 cells, respectively. The results show that lathyrane diterpene has significant cytotoxic effect against Caov-4 cells. The IC50 value was 45?μM. Annexin V/propidium iodide (PI) staining and caspase-6 activity assay confirmed that lathyrane diterpene is able to induce apoptosis in Caov-4 cells. The results also demonstrate that lathyrane diterpene up-regulated Bax and down-regulated Bcl-2 proteins. Moreover, apoptotic effect of lathyrane diterpene was also related to ROS production and loss of mitochondrial membrane potential (ΔΨm). This study demonstrated that lathyrane diterpene has profound activity against Caov-4 cells. Analysis of apoptosis-related proteins revealed that lathyrane diterpene triggered the mitochondrion-mediated apoptosis pathway, which led to the loss of mitochondrial membrane potential (ΔΨm) and activation of caspase-6. Therefore, we believe that lathyrane diterpene might be a promising natural compound in ovarian cancer therapy.     

New alpha-pyrrolidinonoids and glycosides from Euphorbia humifusa

A phytochemical investigation on the constituents from Euphorbia humifusa Willd. has resulted in the isolation of three new alpha-pyrrolidinonoidal compounds, 5beta-methoxy-4beta-hydroxy-3-methylene-alpha-pyrrolidinone (1), 5beta-methoxy-4alpha-hydroxy-3-methylene-alpha-pyrrolidinone (2), and 5beta-butoxy-4alpha-hydroxy-3-methylene-alpha-pyrrolidinone (3), and three new glycosides including an indole glycoside, 3-(2-hydroxyethyl)-5-(1-O-beta-glucopyranosyloxy)-indole (4), an ionone glycoside, 3-oxo-7,8-dihydro-alpha-ionone-11-O-beta-glucoside (5), and a hemiterpene glycoside, 1-(4-hydroxy-2-methyl-2-buten-1-yl)-6- (3,4,5-trihydroxybenzoyl)-beta-d-glucose (6), along with 10 known compounds. Their structures were elucidated by analysis of 1D and 2D NMR spectral data. The structure of 1 was further confirmed by a single-crystal X-ray diffraction analysis.     

喙荚云实种子中的新二萜

目的研究喙荚云实的化学成分。方法采用多种色谱方法分离纯化,依据理化性质、波谱数据分析进行结构鉴定。结果从喙荚云实的体积分数为95%的乙醇回流提取物中分离鉴定了1个二萜类化合物。结论此二萜类化合物为新化合物。     

New phenylpropane and anti-inflammatory diterpene derivatives from Amentotaxus formosana

One new diterpene, 8(14),15-sandaracopimaradiene-2alpha,3beta,18-triol (1), two new phenylpropane derivatives, i.e., (E)-methyl 2-(3,4-methylene-dioxyphenyl)-3-methoxypropenoate (2) and (E)-2-(3,4-methylene-dioxyphenyl)-3-methoxypropenoic acid (3), and two known diterpenes, ent-8(14),15-sandaracopimaradiene-2alpha,18-diol (4) and 8(14),15-sandaracopimaradiene-2alpha,18,19-triol (5), were isolated from the heartwoods and barks of Amentotaxus formosana, respectively. The anti-inflammatory activity of the diterpenes 1, 4, and 5 was assessed in vitro by determining their inhibitory effects on the chemical mediators released from mast cells, neutrophils, macrophages, and microglial cells. Compounds 1, 4, and 5 showed significant concentration-dependent inhibitory effects on the release of beta-glucuronidase from rat neutrophils in response to formyl-Met-Leu-Phe/cytochalasin B (fMLP/CB) with IC50 values of 5.5 +/- 1.8, 8.4 +/- 2.9 and 19.2 +/- 3.3 microM, respectively. Compounds 1 and 5 also showed significant concentration-dependent inhibitory effects on superoxide anion generation in rat neutrophils stimulated with fMLP/CB and phorbol 12-myristate 13-acetate (PMA) with IC50 values of 12.6 +/- 1.2 and 9.4 +/- 1.7, and 10.7 +/- 3.3 and 12.9 +/- 0.9 microM, respectively.     

Anti-inflammatory activity of sugiol, a diterpene isolated from Calocedrus formosana bark

Sugiol is a diterpene which was isolated and purified from alcohol extracts of the bark of Calocedrus formosana Florin (Cupressaceae). Although sugiol has low inhibitory activity against the DPPH radical, it could effectively reduce intracellular reactive oxygen species (ROS) production in lipopolysaccharide (LPS)-stimulated macrophages. The present study investigated the potential anti-inflammatory activity of sugiol, and the relationship between signal transduction and inflammatory cytokines in vitro. A dose of 30 microM of sugiol was effectively inhibitory for proIL-1beta, IL-1beta and TNF-alpha production, suggesting that sugiol is bioactive against inflammation. Moreover, sugiol reveals a capacity for suppressing the activation of mitogen-activated protein kinases (MAPKs), including extracellular signal-regulated kinase (ERK), c-Jun NH2-terminal kinase (JNK), and p38 mitogen-activated protein kinase (p38) activated by LPS-stimulation in J774A.1 murine macrophages. A low dosage of 10 microM of sugiol completely inhibited ERK1/2 phosphorylation, while 30 microM effectively inhibited JNK1/2 and p38 phosphorylation in LPS-stimulated macrophages. In addition, sugiol significantly inhibited LPS-induced ROS production. Our studies suggest that sugiol's efficacy in inhibiting the inflammatory cytokines of IL-1beta and TNF-alpha could be attributed to a reduction of the ROS that leads to a decrease in the phosphorylation of MAPKs.     

New abietane-type diterpene glycosides from the roots of Tripterygium wilfordii

Two new abietane diterpene glycosides, wilfordosides A (1) and B (2), were isolated from the roots of Tripterygium wilfordii. The structures of compounds 1 and 2 were established using spectroscopic methods including extensive 1D and 2D NMR analysis, in combination with chemical reactions.