Jatrophane Diterpenoids Research Articles

A New Jatrophane Diterpenoid from Euphorbia peplus

Aim To study the chemical constituents of Euphorbia peplus. Methods Compounds 1–3 were isolated and purified by silica gel column chromatography, MCI and Sephadex LH-20. Their structures were mainly elucidated by spectroscopic analysis and physicochemical characteristics. Results Three compounds were identified as euphopeplin A ( 1), 2 α, 5 α, 7 β, 8 α, 9 α, 14 β-hexaacetoxy-3β-benzoyloxy-15-hydroxyjatropha-6 (17), 11 E-diene ( 2) and 5α, 8α, 9β, 10β, 14α-pentaacetoxy-3β-benzoy-loxy-15-hydroxypepluane ( 3). Conclusion A new jatrophane diterpenoid, euphopeplin A ( 1) was isolated from Euphorbia peplus.

Chemical Constituents from the Whole Plant of Euphorbia altotibetic

AbstractFor Abstract see ChemInform Abstract in Full Text.

Chemical Constituents from the Whole Plant of Euphorbia altotibetic

AbstractFour new jatrophane diterpenoids, altotibetin A (1), altotibetin B (2), altotibetin C (3), altotibetin D (4), and nine known compounds, β‐sitosterol, cycloart‐23‐ene‐3β,25‐diol, cycloart‐25‐ene‐3β,24‐diol, lupeol acetate, scopoletin, kaempferol, uracil, uridine, astragalin, and daucosterol have been isolated from the whole plant of Euphorbia altotibetic Pauls. Their structures were established by spectral methods, and the configurations of 1 and 2 were confirmed by X‐ray analysis.

Jatrophane diterpenoids from Euphorbia mongolica as modulators of the multidrug resistance of L5128 mouse lymphoma cells.

The dried aerial parts of Euphorbia mongolica afforded three new acylated polyhydroxy diterpenoids based on the jatrophane framework. The structures were established by means of a combination of 1D and 2D NMR techniques and mass spectrometry as (2S,3S,4R,5R,7S,8R,13S,15R)-5alpha,7beta,8alpha-triacetoxy-3beta-benzoyloxy-15beta-hydroxyjatropha-6(17),11E-diene-9,14-dione (1), (2S,3S,4R,5R,7S,8S,9S13S,15R)-5alpha,7beta,8alpha,9alpha,15beta-pentaacetoxy-3beta-benzoyloxyjatropha-6(17),11E-dien-14-one (2), and (2S,3S,4R,5R,7S,8S,9S13S,15R)-3beta,7beta,8alpha,9alpha,15beta-pentaacetoxy-5alpha-benzoyloxyjatropha-6(17),11E-dien-14-one (3). When the isolates were assayed for multidrug resistance-reversing activity in a rhodamine 123 exclusion test using L5178 mouse lymphoma cells, all compounds demonstrated a concentration-dependent effect in inhibiting the efflux pump activity of these tumor cells in the range 11.2-112 microM.

Discovery and Biological Evaluation of a New Family of Potent Modulators of Multidrug Resistance: Reversal of Multidrug Resistance of Mouse Lymphoma Cells by New Natural Jatrophane Diterpenoids (I)‐(III) Isolated from Euphorbia Species.

Discovery and Biological Evaluation of a New Family of Potent Modulators of Multidrug Resistance: Reversal of Multidrug Resistance of Mouse Lymphoma Cells by New Natural Jatrophane Diterpenoids (I)‐(III) Isolated from Euphorbia Species.

Discovery and biological evaluation of a new family of potent modulators of multidrug resistance: reversal of multidrug resistance of mouse lymphoma cells by new natural jatrophane diterpenoids isolated from Euphorbia species.

The effects of 15 jatrophane diterpene polyesters (1-3 and 5-16) isolated from lipophilic extracts of Euphorbia serrulata, E. esula, E. salicifolia, and E. peplus (Euphorbiaceae) on the reversion of multidrug resistance of mouse lymphoma cells were examined. The structures of five new compounds (1-5) were elucidated by spectroscopic methods, including HRFABMS, ESIMS, (1)H-(1)H homonuclear and (1)H-(13)C heteronuclear correlations, long-range correlation spectra, and NOESY experiments. The stereochemistry and absolute configuration of one compound (3) were determined by X-ray crystallography. The structure-activity relationship is discussed.

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).

New jatrophane diterpenoid esters from Euphorbia turczaninowii.

Five new (1-5) and one known (6) jatrophane diterpenoid esters were isolated from the ethanol extract of the whole herb of Euphorbia turczaninowii. Their structures were established by extensive spectroscopic methods. The absolute stereochemistry of 3 beta,5 alpha,8 alpha,15 beta-tetraacetoxy-7 beta-benzoyloxyjatropha-6(17),11E-dien-9,14-dione (1) was confirmed by a single-crystal X-ray analysis coupled with the exciton chirality circular dichroism method. Compounds 1-6 were inactive when evaluated both in a mouse ear inflammation assay and for cytotoxicity against the B16 mouse melanoma cell line.

Jatrophane diterpenoids from Euphorbia esula

Two new jatrophane diterpenoids, esulatin D and E, have been isolated from the dichloromethane extract of the whole, undried plant of Euphorbia esula. The structures have been assigned on the basis of spectral analysis, including 2D NMR experiments.