Seco-iridoid glycosides from the Gentiana olivieri Griseb and their bioactivities.

The ethanol extract of the Gentiana olivieri Griseb plant was subjected to an investigation to ascertain the presence of its iridoid constituents. By means of HPLC and TLC monitoring, a total of thirteen previously unreported seco-iridoid glucosides olivierisecoside A-M, as well as seven known seco-iridoid glycosides and one known iridoid glycoside were isolated. Their structures were elucidated by a comprehensive spectroscopic data analysis and ECD calculations. The absolute configuration of olivierisecoside D was further confirmed through single-crystal X-ray diffraction analysis. All the identified compounds were characterized as aromatic conjugated seco-iridoid glucosides, with olivierisecoside F-I representing a particularly rare subtype known as the morroniside type seco-iridoids. In vitro testing of the isolated compounds revealed their potential anti-inflammatory and hepatoprotective effects. The results showed olivieroside B and 6'-gentisoyl-8-epi-kingiside have good anti-inflammatory activities in LPS induced RAW264.7 cells. Additionally, olivierisecoside M exhibited some improvements in PA-induced L02 and HepG2 cells damage, known compound loganin showed slight hepatoprotective effect in PA-induced HepG2 cells damage.

Jatrophane diterpenoids from Euphorbia microcarpa (prokh.) krylov with multidrug resistance modulating activity.

Eight undescribed jatrophane diterpenoids, namely euphomicrophane A-H, together with thirteen known diterpenes were isolated from the whole plant extracts of Euphorbia microcarpa (Prokh.) Krylov. Among them, euphomicrophane C and F were possessed the endo-type core structure that naturally rarely appeared. The structures of the purified undescribed compounds were established by extensive spectroscopic and spectrometric analysis, and the single-crystal X-ray diffraction analysis was used to determine the absolute configuration of euphomicrophane E, elusone A and euphorbesulin G. All the isolates were screened for their reversal abilities on P-glycoprotein-mediated multidrug resistant cancer cell line MCF-7/ADR. Compounds euphomicrophane G-H and 3ß,7ß,8α,9α,15ß-pentaacetoxy-5ß-benzoyloxyjatropha-6(17)-11E-dien-14-one were showed potential chemoreversal effect with reversal fold values 18.67, 17.15, and 16.76 at a concentration of 10.0 µM, being equal to or stronger than the positive drug verapamil (16.68).

Coumarinolignans with Reactive Oxygen Species (ROS) and NF-κB Inhibitory Activities from the Roots of Waltheria indica.

Seven new coumarinolignans, walthindicins A-F (1a, 1b, 2-5, 7), along with five known analogs (6, 8-11), were isolated from the roots of Waltheria indica. The structures of the new compounds are determined by detailed nuclear magnetic resonance (NMR), circular dichroism (CD) with extensive computational support, and mass spectroscopic data interpretation. Compounds were tested for their antioxidant activity in Human Cervical Cancer cells (HeLa cells). Compounds 1a and 6 showed higher reactive oxygen species (ROS) inhibitory activity at 20 µg/mL when compared with other natural compound-based antioxidants such as ascorbic acid. Considering the role of ROS in nuclear-factor kappa B (NF-κB) activation, compounds 1a and 6 were evaluated for NF-κB inhibitory activity and showed a concentration-dependent inhibition in Human Embryonic Kidney 293 cells (Luc-HEK-293).

Pyrrolizidine alkaloids and unusual millingtojanine A-B from Jacobaea vulgaris (syn. Senecio jacobaea L.).

Four undescribed pyrrolizidine alkaloids (seneciojanine A-D), two enantiomeric pairs of unusual alkaloids (millingtojanine A-B) with a unique tricyclic core, and nine known pyrrolizidine alkaloids were isolated from whole plant extracts of Jacobaea vulgaris Gaertn. The structures of the undescribed compounds were established by extensive spectroscopic and spectrometric analyses and comparison of theoretical and experimental ECD data. Several of the structures were also confirmed by X-ray diffraction analysis. Seneciojanine A-D possess a rare natural necine moiety with an α,ß-unsaturated carbonyl group located at C-3 and a hydroxyl substituent at C-8.