Antinociceptive diterpene from Euphorbia decipiens

One myrsinol-type diterpene ester (1) isolated from Euphorbia decipiens was evaluated for analgesic activity in the acetic acid induced writhing test in mice. Different dose (5-20 mg/kg i.p.) of the compound showed significant antinociceptive activity, which was comparable to standard analgesic drugs, aspirin and ibuprofen (100 mg/kg i.p.).     

A new cytotoxic cembrane diterpene from the roots of Euphorbia pekinensis Rupr

A new cembrane diterpene, named (−)-(1S)-15-hydroxy-18-carboxycembrene, was isolated from petroleum ether extract of the roots of the Euphorbia pekinensis Rupr. To our knowledge, this compound is the first cembrane-type diterpenoid to be found in the family Euphorbiaceae. The structure was elucidated as (−)-(1S)-15-hydroxy-cembra -2E, 4Z, 7E, 11E-tetraen-18-oic acid by a combination of IR, HR-ESIMS, 1D- and 2D-NMR techniques. (−)-(1S)-15-hydroxy-18-carboxycembrene showed cytotoxic activity against all five human cancer cell lines tested.     

Two new diterpene derivatives from Euphorbia lunulata Bge and their anti-proliferative activities

A new ent-abietane-type diterpene lactone (1) and a new jatrophane-type diterpenoid (2), together with twelve known compounds including three diterpenes (3–5), five triterpenes (6–10) and four sterides (11–14) were isolated from the ethanol extract of the whole plant of Euphorbia lunulata Bge. The structure of compounds 1 and 2 was elucidated on the basis of 1D and 2D NMR spectra and the HR-ESI-MS data. The structure of compound 2 was further analyzed by an X-ray crystallographic study. The in vitro anti-proliferative activities against MCF-7 and NCI-H460 cell lines for compounds 1–5 (diterpene) were evaluated. The results showed marked activity for compound 1 against the two cell lines with the IC₅₀ values 19.5 (NCI-H460) and 18.6 (MCF-7) μM, while for cis-platinum (a positive cytotoxic control agent) 29.7 (NCI-H460) and 27.7 (MCF-7) μM. Compounds 2–5 exhibited moderate cytotoxic activities for the two cell lines with the IC₅₀ values ranging from 32.1 to 58.2 μM.     

Anti-inflammatory activity of the hydrosoluble fraction of Euphorbia royleana latex

The hydrosoluble fraction of Euphorbia royleana latex (AER), administered by gavage at doses of 50-200 mg/kg, showed dose-dependent anti-inflammatory and anti-arthritic effects in different acute and chronic test models in rats and mice. It reduced the exudate volume and the migration of leukocytes and showed a poor inhibitory effect on the granuloma formation induced by cotton pellets, while it had a low ulcerogenic score. The oral LD(50) was more than 1500 mg/kg in both rats and mice.     

New diterpene from Hedychium villosum.

The stems of Hedychium villosum yielded the new diterpenoid 1, named villosin, along with coronarin E and beta-sitosterol. Their structures were elucidated by spectroscopic methods including mono- and bi-dimensional NMR.     

Polycyclic diterpenoids from Euphorbia characias

In addition to widespread flavonoids, a collection of Euphorbia characias from Sardinia afforded 13 oxygenated diterpenoids of the atisane, abietane, pimarane, and kaurane type. Four of these compounds (1, 3a, 7a,b) are new. The accumulation of substantial amounts of biologically active diterpenoids of limited availability, like ent-atisanes endowed with anti-HIV activity and ent-abietanolides active on the central nervous system, makes E. characias an interesting source of lead compounds for biomedical research.     

A new diterpene dimer from the bark ofChamaecyparis obtusa

This paper describes characterization of diterpenes of the bark of Japanese cypress,Chamaecyparis obtusa (S. and Z.) Endl, without the resinous stem canker to learn the difference between the cypress bark affected with the canker. A diterpene dimer and two diterpenes, 6,12-dihydroxyabieta-8,11,13-trien-7-one and 6,12-dihydroxyabieta-5,8,11, 13-tetraen-7-one, were firstly isolated from Japanese cypress. The dimer, 6-(abieta-6,8,11, 13-tetraenyl-12-oxy)-7-methoxyabieta-8,11,13-trien-12-ol, was a new compound. It is a terpene indicative ofC. obtusa not infected with the resinous stem canker. Five known diterpenes were also isolated.     

Two new diterpenes from Euphorbia kansuensis

Two new lathyrane diterpenes, 3beta,5alpha-dihydroxy-15beta-cinnamoyloxy-14-oxolathyra-6Z,12E -diene (1) and 3beta,5alpha,20-trihydroxy-15beta-cinnamoyloxy-14-oxolathyra-6Z,12E-diene (2), were isolated from the roots of Euphorbia kansuensis. Their structures were determined by spectroscopic methods.     

Four new diterpenoids from the roots of Euphorbia fischeriana

Four new diterpenoids (1,4,5,9), together with 7 known diterpenoids (2,3,6–8,10,11), were isolated from the roots to Euphorbia fischeriana. On the basis of 1D and 2D NMR, HR-ESI-MS spectroscopic analysis, structures of the new compounds were elucidated as 11β-hydroxy-8,14-epoxy-ent-abieta-13(15)-en-16,12-olide (1), 3,20-dihydroxy-ent-1(10), 15-rosadiene (4), 3,7-dihydroxy-ent-1(10), 15-rosadiene (5), ingenol 6,7-epoxy-3- tetradecanoate (9). The compounds isolated were evaluated for their cytotoxicity against four cancer cell lines (A549, BEL7402, HCT116, and MDA-MB-231). Three ingenol diterpenoids (9–11) showed significant cytotoxicity against A549 with IC₅₀ value of 3.35, 2.85, 2.88 μg/mL, respectively.     

Ferulic acid esters from Euphorbia hylonoma

Octacosyl cis-ferulate (1), along with the trans isomer (2), cholest-5-en-3beta-ylhexadecanoate, chrysophanol and octadecanoic acid was isolated from the roots of Euphorbia hylonoma.     

Macrocyclic diterpenoids from the Iranian plant Euphorbia bungei Boiss

An acetone extract from the aerial parts of Euphorbia bungei afforded three new (2, 3 and 5) and one known (4) macrocyclic diterpenoids. Several cycloartane triterpenoids were also obtained, two of which (6a and 6b) were assayed for antiviral effects. The structures of all new compounds were elucidated using modern spectroscopic methods including 2D NMR and HRMS.     

A new kaurane diterpene dimer from Parinari campestris

A new kaurane diterpene dimer, 15-oxozoapatlin-13alpha-yl-10'alpha,16'alpha-dihydroxy-9'alpha-methyl-20'-nor-kauran-19'-oic acid gamma-lactone-17'-oate (1), together with the known 13-hydroxy-15-oxozoapatlin (2), 10alpha,13alpha,16alpha,17-tetrahydroxy-9alpha-methyl-15-oxo-20-nor-kauran-19-oic acid gamma-lactone (3), 2alpha,10alpha,13alpha,16alpha,17-pentahydroxy-9alpha-methyl-15-oxo-20-nor-kauran-19-oic acid (19,10)-lactone (4), 3alpha,10alpha,13alpha,16alpha,17-pentahydroxy-9alpha-methyl-15-oxo-20-nor-kauran-19-oic acid gamma-lactone (5), and 1beta,16alpha,17-trihydroxy-ent-kaurane (6) were isolated from the leaves of Parinari campestris and identified on the basis of detailed spectral analysis, including 2D NMR spectrometry and ESI-MS.     

Diterpenes inhibiting NO production from Euphorbia helioscopia

Three new jatrophane diterpenes (1–3), an unreported spectroscopic data jatrophane diterpenene (4), and nine known analogues (5–13) have been isolated from the whole plants of Euphorbia helioscopia. Their structures were established by detailed spectroscopic data analyses (IR, ESIMS, HR-ESIMS, and 1D and 2D NMR), and the structure of 1 was confirmed by X-ray crystallography. The diterpenes showed inhibitory activities on LPS-induced NO production in murine microglial BV-2 cells.     

A new diterpene from the leaves of Andrographis paniculata Nees

Phytochemical investigation of the ethanol extract of the leaves of Andrographis paniculata yielded one novel diterpene (13R, 14R) 3, 13, 14, 19-tetrahydroxy-ent-labda-8 (17), 11-dien-16, 15-olide 1 which has an uncommon cis-diol groups in the lactone moiety, and 3, 19-isopropylidene-14-deoxy-ent-labda-8 (17), 13-dien-16, 15-olide 2, probably an artifact diterpene, together with eight known diterpenoids 3–10. The structures of these compounds were determined on the basis of spectral methods. The structure and stereochemistry of 1 was confirmed by X-ray crystallographic analyses.     

A new labdane diterpene from Vitex cauliflora Moldenke from the Madagascar rainforest

Fractionation of an antiplasmodial ethanolic extract from the aerial parts of Vitex cauliflora led to the isolation of the new labdane diterpene 1 together with the known triterpene uvaol. The structure of the new compound 1 was established as 3-oxo,15,17,18-triacetoxy-labda-7,13E-diene on the basis of spectroscopic data (1D and 2D NMR, MS).     

A new abietane diterpene from Glyptostrobus pensilis

A new abietane diterpene, glypensin A (1) and four known compounds, 12-acetoxy-ent-labda-8(17), 13E-dien-15-oic acid (2), quercetin 3-O-α-L-arabinofuranoside (3), quercetin 3-O-β-D-galactopyranoside (4), β-sitosterol (5) were isolated from the branches and leaves of Glyptostrobus pensilis (Staut.) Koch. Their structures were determined by MS, 1D- and 2D-NMR means. Compound 1 showed cytotoxicity on human chronic myeloid leukemia cell line K562 (IC₅₀ = 21.2 μM).     

New anti-HBV caryophyllane-type sesquiterpenoids from Euphorbia humifusa Willd

Activity-guided fractionation of Euphorbia humifusa for anti-HBV activity led to the isolation of two novel sesquiterpenoids, named humifusane A (1) and humifusane B (2). Their structures were elucidated by spectral data to show that they have a caryophyllane-type precursor structure. The two new sesquiterpenoids showed anti-HBV activities through specifically inhibiting the secretion of HBsAg in HepG2.2.15.     

A new cytotoxic casbane diterpene from Euphorbia pekinensis

A new cytotoxic casbane diterpene, named pekinenal, was isolated from the roots of Euphorbia pekinensis. Its structure was elucidated as 5α-hydroxy-1βH,2αH-casba-3Z,7E,11E-triene-18-al by a combination of 1D- and 2D-NMR techniques and confirmed by X-ray crystallography. Pekinenal showed cytotoxic activity against all four human cancer cell lines tested.     

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.     

Screening of antioxidant activity of three Euphorbia species from Turkey

Euphorbia acanthothamnos, E. macroclada and E. rigida were investigated for their antioxidant activity. The antioxidant potential of extracts of E. acanthothamnos, E. macroclada and E. rigida was evaluated using different complementary antioxidant tests.