In this study, we present a proposal for the physical and chemical quality control of the powder of the species T. parthenium (feverfew) and its hydroalcoholic extract obtained by percolation. The sesquiterpene lactone parthenolide, the main active compound of this plant, was quantifi ed by HPLC and its content was found to be 0.49% in the powder and 1.06% in the extract. The total content of f...

A concise, efficient and scalable synthesis of thapsigargin and nortrilobolide from commercially available (R)-(-)-carvone was developed. Our synthetic strategy is inspired by nature's carbon-carbon bond formation sequence, which facilitates the construction of a highly functionalized sesquiterpene lactone skeleton in five steps via an enantioselective ketone alkylation and a diastereoselective...

This short review article covers some useful applications of alkynyltungsten compounds to the syntheses of complex lactones. Two types of cyclizations will be emphasized: (1) cycloalkenylation of tungsten-alkynol compounds with aldehydes to give α-alkylidene oxacarbeniums, further leading to α-alkylidene lactones and (2) intramolecular [3+2]-cycloaddition of epoxides to give bicyclic lactones. ...

Artemisinin 1, dihydro-epideoxyarteannuin B 2 and deoxyartemisinin 3 were isolated from the sequiterpene lactone-enriched fraction obtained from the crude ethanolic extract of Artemisia annua L. These compounds were tested on ethanol and indomethacin-induced ulcer models. Compound 1 did not afford cytoprotection under the experimental models tested. Only compounds 2 and 3 decreased the ulcerati...

An unusual dimeric guaianolide, artemilinin A (1) and a sesquiterpene-monoterpene lactone, isoartemisolide (2), were isolated from the leaves of Artemisia argyi. Their structures were elucidated on the basis of extensive spectroscopic analysis (IR, HR-ESIMS, 1D- and 2D-NMR), and the absolute configurations were determined by CD spectra and quantum chemical ECD calculation. Furthermore, in in vi...

The reactivity of parthenolide (PRT), a natural sesquiterpene lactone from Tanacetum parthenium (Asteraceae), with human serum albumin (HSA) was studied by UHPLC/+ESI-QqTOF MS analysis after tryptic digestion of albumin samples after incubation with this compound. It was found that the single free cysteine residue, C34, of HSA (0.6 mM) reacted readily with PRT when incubated at approximately 13...

Chicory is a perennial plant grown in different parts of the world, used as forage for livestock, as folklore remedies, or as a vegetable addition in human diets. There are several varieties of the chicory plant, known differently globally due to its numerous medicinal, culinary, and nutritional qualities. Most parts of the plant contain a potpourri of nutrients ranging within carbohydrates, pr...

Dehydro-leucodin [systematic name: (1S,6S,2R)-9,13-dimeth-yl-5-methyl-ene-3-oxatricyclo-[8.3.0.0(2,6)]trideca-9,12-diene-4,11-dione], C(15)H(16)O(3), is a guanolide isolated from Artemisia douglasiana. The fused-ring system contains a seven-membered ring that adopts a chair conformation, a fused planar cyclo-pentenone ring and a five-membered lactone ring fused in envelope conformation. The abs...

Feverfew (Tanacetum parthenium) is a medicinal herb that has long enjoyed traditional use as a remedy for migraine headache pain. The aerial parts of Feverfew (flowers, leaves and stems) contain parthenolide (a sesquiterpene lactone) which is believed to be responsible for the plant's biological activity. Dried feverfew aerial parts should contain approximately 0.2-0.5 wt.% parthenolide and adu...

Lactones of methyl 3-O-[(R)and (S)-1-carboxyethyl]-a-D-gluco-, galactoand manno-pyranoside were prepared by treatment of the sugar derivatives in acetic acid. The lactones were formed between the 1-carboxyethyl substituent and 2-OH or 4-OH in different proportions depending on the stereochemistry of the parent compounds. Relative formation rates in acetic acid-d4 and hydrolysis rates in buffere...