Sesquiterpene Lactone Glycosides Research Articles

Rapid screening and identification of sesquiterpene lactones in Kudiezi injection based on high-performance liquid chromatography coupled with linear ion trap-orbitrap mass spectrometry

Sesquiterpene lactones are considered as the major active compounds in Kudiezi injection in virtue of their special structures and activities. Herein, an analytical method was developed for rapid screening and identification of sesquiterpene lactones in Kudiezi injection using high-performance liquid chromatography coupled with linear ion trap-orbitrap mass spectrometry (HPLC-LTQ-Orbitrap) in negative ion mode. First, two sesquiterpene lactone reference standards were analyzed to obtain their characteristic ESI-MS/MS fragmentation patterns. Second, based on extracted ion chromatography (EIC) data-mining method and characteristic fragmentation pathways analysis, sesquiterpene lactones in Kudiezi injection were rapidly screened and identified. Finally, an important parameter Clog P was adopted to discriminate the isomers of sesquiterpene lactones. As a result, 50 sesquiterpene lactones were characterized, including 9 sesquiterpene lactone aglycones, 39 sesquiterpene lactone glycosides, and 2 amino acid-sesquiterpene lactone conjugates. Among them, 13 compounds were tentatively identified as new compounds. The results demonstrated that the established method would be a rapid, effective analytical tool for screening and identification of sesquiterpene lactones in the complex system of natural medicines.

Two new sesquiterpene lactone glycosides from Cnicus benedictus

Two new sesquiterpene lactone glycosides, namely melitensin 15-O-β-D-glucoside (1) and 11β,13-dihydrosalonitenolide 15-O-β-D-glucoside (2), along with eight known compounds (3–10) were isolated from the aerial part of Cnicus benedictus L. Their structures were elucidated from analyses of extensive spectroscopic data. Compounds 1–6 all possessed an α-methyl-γ-lactone moiety. Moreover, compound 5 exhibited moderate activity against the growth of Aspergillus fumigatus, with IC50 values of 17.67 μg mL−1.

Picrotoxane Sesquiterpene Glycosides and a Coumarin Derivative from Coriaria nepalensis and Their Neurotrophic Activity

Two picrotoxane sesquiterpene lactone glycosides, nepalactones A (1) and B (2), and one new coumarin, nepalarin (3), were isolated from the root barks of the poisonous plant Coriaria nepalensis. Their structures were elucidated via HRESIMS and 1D and 2D NMR spectroscopic analyses, and further verified via transformation methods. In addition, compounds 1–3 and five semisynthetic congeners (1a–e) were assayed for the activity to induce neurite outgrowth in rat pheochromocytoma (PC12) cells. As a result, nepalactone A derivative 1c and nepalarin (3) significantly enhanced nerve growth factor (NGF)-mediated neurite outgrowth in PC12 cells.

ChemInform Abstract: Isolation of Two New Bioactive Sesquiterpene Lactone Glycosides from the Roots of Ixeris dentata

Abstractisolation and structure elucidation of two new sesquiterpene lactone glycosides (I) and (II)

Isolation of two new bioactive sesquiterpene lactone glycosides from the roots of Ixeris dentata.

Two new sesquiterpene lactone glycosides, 3-O-β-d-glucopyranosyl-8-hydroxy-(1,5,6,7,11)-guaia-3,10(14)-dien-12,6-olide (1) and 3-O-β-d-glucopyranosyl-8-(4-hydroxyphenylacetyloxy)-(1.5.6,7)-guaia-3,10(14),11(13)-trien-12,6-olide (2), and 12 known sesquiterpene lactone derivatives (3-14) were isolated from the roots of Ixeris dentata. Their structures were determined by extensive spectroscopic methods including 1D and 2D NMR and MS spectra data. All compounds were tested for their ability to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglial cell. 3-O-β-d-Glucopyranosyl-8-(4-hydroxyphenylacetyloxy)-(1.5.6,7)-guaia-3,10(14),11(13)-trien-12,6-olide (2) showed the most potent inhibitory activity at a concentration of 20μM.

ChemInform Abstract: Sesquiterpene Lactone Glycosides from the Roots of Ferula varia.

Abstractisolation and structure elucidation of seven new sesquiterpene lactone glycosides (I)‐(V)

Sesquiterpene Lactone Glycosides from the Roots of <i>Ferula varia</i>

Seven new sesquiterpene lactone glycosides (1-7) were isolated from the H2O-soluble fraction from the MeOH extract of the roots of Ferula varia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of compounds 1 and 2 were determined by modified Mosher's method.

Complete NMR spectral assignments of two lactucin‐type sesquiterpene lactone glycosides from Picris conyzoides

Complete (1)H and (13)C NMR signal assignments of two lactucin-type sesquiterpene lactone glycosides, derivatives of 11β,13-dihydrolactucin, isolated from roots of Picris conyzoides, were achieved by one- and two-dimensional NMR experiments, allowing the correction of previously published data for cichorioside B and the structure elucidation of its new ester with 3-hydroxy-2-methylpropanoic acid. In addition, seven known sesquiterpene lactones and three phenolic compounds were isolated from the plant material.

Two new sesquiterpene lactone glycosides from Artemisia frigida Willd.

The investigation of EtOAc-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new sesquiterpene lactone glycosides, named as artemofriginoside A and artemofriginoside B. Their structures were characterized as 3β-(β-d-glucopyranosyloxy)-8β-(p-hydroxyphenylacetyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (1) and β-(β-d-glucopyranosyloxy)-8β-(2-hydroxy-3-methylbutanoyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (2), on the basis of 1D and 2D NMR spectral analysis.

Sesquiterpene lactones in a hairy root culture of Cichorium intybus.

A transformed root culture of Cichorium intybus L. (Asteraceae) was found to produce sesquiterpene lactones of guaiane and germacrane type. Lactucopicrin, 8-desoxylactucin and three sesquiterpene lactone glycosides: crepidiaside B, sonchuside A and ixerisoside D were isolated from the roots. The yield of 8-desoxylactucin reached 0.03 g l(-1) at the early stationary phase of the culture.

Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum.

Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2alpha- O-beta- D-glucopyranosyl-5alpha, 11alpha H-eudesma-4(15)-en-12,8beta-olide ( 1), 2alpha- O-beta- D-glucopyranosyl-5alpha H-eudesma-4(15),11(13)-dien-12,8beta-olide ( 2), 2alpha-acetoxy-5alpha-hydroxy-11alpha H-eudesma-4(15)-en-12,8beta-olide ( 3) and 2alpha,5alpha-dihydroxy-11alphaH-eudesma-4(15)-en-12,8beta-olide ( 4) by spectroscopic methods including 2D NMR techniques ( (1)H- (1)H COSY, (1)H- (1)H NOESY, HMQC, HMBC) and chemical transformations. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibacterial activity, while compound 4 showed appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell).

Sesquiterpene Lactone Glycosides from Arnica longifolia

Flowers of ARNICA LONGIFOLIA were investigated for the occurrence of sesquiterpene lactone glycosides. A mixture containing the two isomeric 11alpha,13-dihydro- and 11beta,13-dihydro-4 H-tomentosin glucosides, previously isolated from A. AMPLEXICAULIS and A. MOLLIS, together with the two isomeric 11alpha,13-dihydro- and 11beta,13-dihydro-4 H-carabrone glucosides were found in A. LONGIFOLIA. All carbon and proton shifts of the glycosides could be assigned by their 2D-COSY and 2D-HETCOR spectra and spectroscopy of their respective aglycones, obtained via enzymatic hydrolysis.

Sesquiterpene and diterpene glycosides from Xanthium spinosum

Two new sesquiterpene lactone glycosides and three new kaurene glycosides closely related to carboxyatractyloside and atractyloside, together with the 3′, 4′-didesulphated-carboxyatractyloside and 3′, 4′-didesulphated-atractyloside, were isolated from the aerial parts of Xanthium spinosum. Their structures were established by spectroscopic methods ( 1H, 13C, DEPT 13C NMR and FAB mass spectr).

Chemistry of glandular trichomes in Hymenoxys and related genera

All currently recognized taxa from the genera Amblyolepis (one species), Dugaldia (three species), Hymenoxys (22 taxa in 21 species), Macdougalia (one species), Plateilema (one species), Plummera (two species) and Tetraneuris (15 taxa in eight species) were examined for chemical constituents accumulated in capitate glandular trichomes. Fifty-nine high pressure liquid chromatography (HPLC) peaks were detected, over 70% of which could be tenatatively assigned to known compounds of the sesquiterpene lactone, monoterpene and inositol types. This is the first report of sesquiterpene lactone glycosides, monoterpene glycosides and a myoinositol derivative in capitate glandular trichomes. Apart from Amblyolepis and Plateilema, which did not afford anlyzable glandular trichomes, sesquiterpene lactones of the pseudoguaianolide type were present in all species, and guaianolides were found in all but two, Hymenoxys anthemoides and H. chrysanthemoides. Compound patterns of the Hymenoxys, Plummera, Dugaldia and Macdougalia species were very similar to one another, but they differed from those of Hymenoxys texana and all taxa of Tetraneuris, which lacked modified pseudoguaianolides (secohelenanolides), but contained monoterpene glycosides. Taxonomic implications of compound patterns in the species examined includes: (1) incorporation of Dugaldia, Plummera and Macdougalia into a broader concept of Hymenoxys; and (2) recognition of Tetraneuris as a distinct genus. Hymenoxys texana requires further investigation since its morphology is typical of Hymenoxys, but its chemistry is typical of Tetraneuris.

Sesquiterpene lactone glycosides and ionone derivative glycosides from Sonchus asper

Five new sesquiterpene glycosides, sonchusides E-I, and three new ionone derivative glycosides, sonchuionosides A-C, together with a known sesquiterpene glycoside, sonchuside D, and a known ionone derivative glycoside, icariside B 1 have been isolated from Sonchus asper. The structures of the new compounds were established on the basis of chemical and spectral data.

Sesquiterpene lactones and lactone glycosides from Hymenoxys species

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSesquiterpene lactones and lactone glycosides from Hymenoxys speciesWerner Herz, K. Aota, Miroslav Holub, and Zdenek SamekCite this: J. Org. Chem. 1970, 35, 8, 2611–2624Publication Date (Print):August 1, 1970Publication History Published online1 May 2002Published inissue 1 August 1970https://doi.org/10.1021/jo00833a029RIGHTS & PERMISSIONSArticle Views156Altmetric-Citations45LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (2 MB) Get e-Alerts Get e-Alerts