Euphorbia Ebracteolata Research Articles

Phenolic glycosides and monoterpenoids from the roots of Euphorbia ebracteolata and their bioactivities

The bioactive substance investigation of Euphorbia ebracteolata obtained 17 compounds by various chromatographic techniques. Their structures were elucidated using widely spectroscopic data, including ESI-MS, HRESI-MS, CD, 1D- and 2D-NMR, which gave 5 new phenolic glucosides and 4 new monoterpenoids. The phenolic glucosides and monoterpenoids showed the inhibitory effect against the human carboxylesterase-2 (hCE-2) using a fluorescence bioassay in vitro, with the strongest inhibitor compound 4 (IC50 7.17μM). The antioxidant effects of these isolated compounds were evaluated using a DPPH scavenging assay. All of the phenolic acids displayed the DPPH scavenging effect, especially that eight compounds have better effect than vitamin C, with the IC50 values ranging from 4.52 to 7.52μM. Additionally, compounds 1–17 showed no cytotoxic effect against five human cancer cell lines by MTT assay.

Three new diterpenes with cytotoxic activity from the roots of Euphorbia ebracteolata Hayata

From the roots of Euphorbia ebracteolata Hayata, three new diterpenes, Ebracteolatas A–C, based on the rosane (1–2) and lathyrane (3) skeleton, were isolated together with four known ones (4–7). Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR techniques. Compounds 1, 6, and 7 exhibited moderate cytotoxic effects against five cancer cell lines.

ChemInform Abstract: ent‐Abietane‐Type Diterpenoids from the Roots of Euphorbia ebracteolata with Their Inhibitory Activities on LPS‐Induced NO Production in RAW 264.7 Macrophages.

AbstractFour new ent‐abietane diterpenoids, ebractenoids K—N, are isolated along with six known ones from the roots of Euphorbia ebracteolata.

Ent-Abietane-type diterpenoids from the roots of Euphorbia ebracteolata with their inhibitory activities on LPS-induced NO production in RAW 264.7 macrophages.

Ten ent-abietane diterpenoids (1-10), including four new (1-4) and six known ones (5-10) were isolated from the roots of Euphorbia ebracteolata. Their structures were determined by 1D, 2D NMR, and HRESIMS. Compounds 2, 4, and 7 exhibited significant inhibitory activities on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 macrophages with IC50 values of 0.69, 1.97, and 0.88μM, respectively. A primary structure-activity relationship was also discussed.

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

Purpose: To evaluate the effects of ebracteolatain A (EA) and ebracteolatain B (EB) from Euphorbia ebracteolata Hyata (Euphorbiaceae) on the proliferation of HepG2 cells and the possible mechanisms.Methods: EA and EB from E. ebracteolata were obtained by column chromatography. 3-(4,5- Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and flow cytometry assays were used to study the cytotoxic and pro-apoptotic activities of EA and EB against HepG2 cells. Western blot assay was used to investigate the possible mechanisms of action.Results: EA and EB were successfully isolated from E. ebracteolata by column chromatography. The results of MTT assay indicate that EA and EB have significant anti-proliferative activities against HepG2 cells in dose- and time-dependent manners with half maximal inhibitory concentration (IC50) of 28.48 and 31.72 μg/mL. respectively. The results of flow cytometry assay suggest that EA and EB significantly (p < 0.01) induced the apoptosis of HepG2 cells at the levels of 47.45 and 42.26 %, respectively. Western blot data indicate that EA and EB significantly (p < 0.05 or 0.01) down-regulated the expression levels of anti-apoptotic proteins (survivin and Bcl-2) and up-regulated the expression levels of proapoptotic proteins (Smac, Bax, c-caspase-3 and c-caspase-9) in mitochondria-mediated apoptotic pathway.Conclusion: EA and EB inhibit the proliferation of HepG2 cells, the probable mechanisms being associated with mitochondria-mediated apoptosis.Keywords: Euphorbia ebracteolata, Phloroglucinol derivatives, Mitochondria-mediated apoptosis, Flow cytometry, Western blot

Chemotaxonomic and chemical studies on two plants from genus of Euphorbia: Euphorbia fischeriana and Euphorbia ebracteolata

The phytochemical investigation of two plants from genus Euphorbia, Euphorbia fischeriana Steud and Euphorbia ebracteolata Hayata led to the isolation of 28 compounds. Among them, 1–3, 12–13, 20–21, 23–25, and 28 were obtained from E. fischeriana. 14–19, and 22 were acquired from E. ebracteolata. 4–11, and 26–27 were found in both of species, and 20 and 28 are isolated from E. fischeriana for the first time. In addition, acetophenone derivatives (7–9) and diterpenes (10–25) are the basis of E. fischeriana and E. ebracteolata. The abietane, atisane, and kaurane types of diterpenes and acetophenone derivatives could be regarded as good taxonomic markers for two medicinal plants, while lupane type triterpenoids，tigliane type diterpenoids and rosane diterpenes demonstrated differences of the two species.

ChemInform Abstract: Two New Rosane‐Type Diterpenoids from Euphorbia ebracteolata HAYATA.

Two new diterpeniods, euphebracteolatins A and B (1 and 2, resp.) were isolated from Euphorbia ebracteolata Hayata, along with two known ones (3R)-ent-rosa-1(10),15-dien-3α-ol (3) and yuexiandajisu D (4). The structures were established by extensive spectroscopic analyses and comparison with literature data.

Anti-inflammatory Diterpenoids from the Roots of Euphorbia ebracteolata

Thirteen diterpenoids (1-13), including two new norditerpene lactones (1-2) and eight new rosane diterpenoids (3-10), were isolated from the roots of Euphorbia ebracteolata. The structures were determined by 1D and 2D NMR, HRESIMS, and electronic circular dichroism (ECD). The ECD-based empirical rule for α,β-unsaturated-γ-lactones was applied to determine the absolute configurations of 1 and 2. Compounds 7, 10, and 13 exhibited significant inhibition of nitric oxide production in RAW 264.7 lipopolysaccharide-induced macrophages, with IC50 values of 2.44, 2.76, and 1.02 μM, respectively.

Two New Rosane‐Type Diterpenoids from Euphorbia ebracteolataHayata

AbstractTwo new diterpeniods, euphebracteolatins A and B (1 and 2, resp.) were isolated from Euphorbia ebracteolata Hayata, along with two known ones (3R)‐ent‐rosa‐1(10),15‐dien‐3α‐ol (3) and yuexiandajisu D (4). The structures were established by extensive spectroscopic analyses and comparison with literature data.

Study on HPLC chromatograms of different processed Euphorbia ebracteolata products and content change of three chemical components

To prepare processed products with different methods, in order to study the impact of auxiliary materials and temperature on chemical components of Euphorbia ebracteolata, and establish specific chromatograms of different processed products. Wel-chorm-C18 column (4.6 mm x 250 mm, 5 microm) was used and eluted with a gradient program, with acetonitrile (A)-water(B). The column temperature was 25 degrees C, and the detection wave length was set at 226 nm. The aim was to determine the content of effective components in different processed products--ebracteolata cpd B, ebracteolata cpd C and jolkinolide B and establish respective characteristic fingerprints to compare with similarity. The results showed that the content of ebracteolata cpd B, ebracteolata cpd C first increased and then decreased with the rise in temperature. Different processed products showed significant difference in HPLC spectrograms, with a low similarity. This study showed great impacts of auxiliary materials and temperature on chemical components of E. ebracteolata. As the vinegar processing method had higher attenuation and and synergistic effects than other methods, the auxiliary material vinegar cannot be replaced by chemical reagent acetic acid.

Characterization of phloroglucinol derivatives and diterpenes in Euphorbia ebracteolata Hayata by utilizing ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry

Euphorbia ebracteolata Hayata (E. ebracteolata) is a Chinese herbal medicine used for the treatment of tumor diseases. An ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC–Q–TOF/MS) based chemical profiling approach was established for the rapid separation and characterization on phloroglucinol derivatives and diterpenes in E. ebracteolata. Three phloroglucinol derivatives and nine diterpenes were identified by exact mass measurement and were further confirmed by Ms2 data. In addition, the chemical profiles of six compounds were acquired by reference standards. Furthermore, the fragmentation rules of phloroglucinol derivatives and diterpenes of E. ebracteolata were analyzed, and each chromatographic peak was classified.

New diterpenoids from the roots of Euphorbia ebracteolata Hayata

Three new diterpenoids, ingenol-5β,20-O,O-isopropylidene-3β-palmitate (1), ingenol-5β,20-O,O-isopropylidene-3β-myristinate (2) and 3β,19-dihydroxy-1(10),15-rosadien-2-one (3), were isolated from the roots of Euphorbia ebracteolata Hayata. Their structures were deduced by spectroscopic means and analytic techniques.

Metabolism of Ebracteolata Compound B Studied In Vitro with Human Liver Microsomes, HepG2 Cells, and Recombinant Human Enzymes

Ebracteolata compound B (ECB) is one major active component of both Euphorbia ebracteolata and Euphorbia fischeriana, which have been extensively used as a tuberculocide in the Asian countries. The aim of our present study was to characterize ECB metabolism in human liver microsomes, HepG2 cells, and recombinant human enzymes. One monohydroxylation metabolite, determined by mass spectrometry to be 1-(2,4-dihydroxy-6-methoxy-3-methylphenyl)-2-hydroxyethanone, and one monoglucuronide, isolated and determined by hydrolysis with β-glucuronidase, mass spectrometry, and (1)H NMR to be 2-hydroxy-6-methoxy-3-methyl-acetophenone-4-O-β-glucuronide, were observed in human liver microsomal incubates in the presence of NADPH or UDP-glucuronic acid (UDPGA), respectively. However, the mixed incubation of ECB with human liver microsomes in the presence of both NADPH and UDPGA showed the monoglucuronide to be the most major metabolite, indicating that glucuronidation was probably the major clearance pathway of ECB in humans. No glucuronide and only trace monohydroxylation metabolite were observed in HepG2 cells. The cytochrome P450 and UDP-glucuronosyltransferase (UGT) isoenzymes were identified by using selective chemical inhibition and recombinant human enzymes. The results indicated that CYP3A4 was probably involved in ECB oxidative metabolism and UGT1A6 and UGT1A9 were important catalytic enzymes in ECB glucuronidation. The results from enzymatic kinetic analysis showed the oxidative metabolism in human liver microsomes; the glucuronidation in human liver microsomes and recombinant UGT1A6 exhibited a typical Michaelis-Menten pattern, but the glucuronidation in UGT1A9 exhibited a substrate inhibition pattern. UGT1A6 had the highest affinity compared with human liver microsomes and UGT1A9, indicating its important role in ECB glucuronidation.

Two new cytotoxic acetophenone derivatives from Euphorbia ebracteolata Hayata

Two new acetophenone derivatives were isolated from the roots of Euphorbia ebracteolata Hayata, their structures were elucidated as 2,4-dihydroxy-6-methoxyl-methylene-3-methyl-acetophenone (1) and 2-dihydroxy-6-methoxyl-methylene-3-methyl-acetophenone-4-O-β- d-glucopyranoside (2) on the basis of chemical and spectroscopic methods including 1D- and 2D-NMR techniques, and their cytotoxic activities were investigated by using the MTT method.

Two novel phloroglucinol derivatives from Euphorbia ebracteolata hayata

Two new phloroglucinol derivatives, named ebracteolatain A and ebracteolatain B, along with three known phloroglucinol derivatives were isolated from Euphorbia ebracteolata Hayata., and their structures were elucidated as 3,3′-diacetyl-2,4′-dimethoxy-2′,4,6,6′-tetrahydroxy-5′-methyl diphenylmethane (1) and 1-[3,5-bis-(3-acetyl-2,6-dihydroxy-4-methoxy-benzyl)-2,4,6-trihydroxy-phenyl]-ethanone (2) on the basis of spectroscopic techniques and chemical methods.

Yuexiandajisu D, a novel 18-nor-rosane-type dimeric diterpenoid from Euphorbia ebracteolata Hayata

Yuexiandajisu D, a novel 18-nor-rosane-type dimeric diterpenoid, was isolated from the roots of Euphorbia ebracteolata Hayata. Its structure was elucidated as 6,3′:7,2′-diepoxy-di-2,3-dihydroxy-18-nor-ros-1(10),2,4,15-tetraene by spectroscopic techniques (HSQC, HMBC, DQF-COSY, TOCSY, NOESY) and chemical methods. Yuexiandajisu D showed moderate cytotoxic activity against cancer cell lines on HCT-8 and Bel-7402, with IC50 values of 2.66 and 3.76 μM, respectively.

Acetophenone Derivatives and Sesquiterpene fromEuphorbia ebracteolata

Two new acetophenone derivatives and a new sesquiterpene, along with four known acetophenone compounds, were isolated from the roots of Euphorbia ebracteolata. The structures of the new compounds were identified as 2,2',4,4'-tetrahydroxy-6,6'-dimethoxy-3,3'-dimethyl-7,5'-bisacetophenone, 2,4-dihydroxy-6-methoxy-3-methylacetophenone 4-O-alpha-L-arabinofuranosyl-(1-->6)-beta- D-glucopyranoside and decahydro-1a,4a,7,7-tetramethyl-1H-cycloprop[e]azulene-2,5-diol (1a R,2 R,4a S,5 S,7a R,7b R) using 1D and 2D NMR spectroscopy and X-ray crystallography.

Cytotoxic Diterpenoids from the Roots ofEuphorbia ebracteolata

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.

Two new flavonol glycosides from Gymnema sylvestre and Euphorbia ebracteolata

Two new flavonol glycosides, namely kaempferol 3- O-β- d-glucopyranosyl-(1 → 4)-α- l-rhamnopyranosyl-(1 → 6)-β- d-galactopyranoside ( 1 ) and quercetin 3- O-6″-(3-hydroxyl-3-methylglutaryl)-β- d-glucopyranoside ( 2 ), have been isolated from the aerial parts of Gymnema sylvestre and Euphorbia ebracteolata, respectively. Their structures were determined on the basis of chemical and spectroscopic methods.

Identification and characterisation of the chinese herb Langdu by LC-MS/MS analysis.

An LC-MS/MS method has been developed for the identification of three species of herb used as the traditional Chinese medicine Langdu, namely Stellera chamaejasme L., Euphorbia ebracteolata Hayata and E. fischeriana Steud. As these herbs contain different mixtures of marker compounds, they could be unambiguously differentiated from each other by comparing their respective characteristic segmental multiple reaction monitoring profiles. The profiles indicated that S. chamaejasme contained daphnetin, skimmetine, stellerin, chamaechromone and neochamaejasmin, E. fischeriana contained ebracteolata compound B, ingenol, jolkinolide B and fischeriana A, whilst E. ebracteolata contained ebracteolata compounds B and C along with ingenol. These results were confirmed from the respective MS/MS spectra. The method has been successfully applied to differentiate these herbs from the related species Alocasia macrorrhiza (L.) Schott and E. kansui Liou.