Carbon-13 NMR Spectra of Sesquiterpene Lactones

Budêšínský, Miloś; Šaman, David

doi:10.1016/s0066-4103(08)60027-7

Cited by 34 publications

(7 citation statements)

References 673 publications

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“…Relative to 66 , the carbonylic C-12 (δ C 179.70) undergoes a strong shielding (9 ppm) due to the non-conjugated carbonyl system. This chemical shift value was in agreement with those of dihydro guaianolide [ 62 ]. In addition, chemical shifts of the methyl group (δ C 15.74, δ H 1.31) indicated an α orientation as reported in compounds with similar configurations [ 29 ].…”

Section: Resultssupporting

confidence: 87%

Guaianolide Derivatives from the Invasive Xanthium spinosum L.: Evaluation of Their Allelopathic Potential

2022

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Ziniolide, xantholide B (11α-dihydroziniolide), and 11β-dihydroziniolide, three sesquiterpene lactones with 12,8-guaianolide skeletons, were identified as volatile metabolites from the roots of Xanthium spinosum L., an invasive plant harvested in Corsica. Essential oil, as well as hydrosol and hexane extracts, showed the presence of guaianolide analogues. The study highlights an analytical strategy involving column chromatography, GC-FID, GC-MS, NMR (1D and 2D), and the hemi-synthesis approach, to identify compounds with incomplete or even missing spectral data from the literature. Among them, we reported the 1H- and 13C-NMR data of 11β-dihydroziniolide, which was observed as a natural product for the first time. As secondary metabolites were frequently involved in the dynamic of the dispersion of weed species, the allelopathic effects of X. spinosum root’s volatile metabolites were assessed on seed germination and seedling growth (leek and radish). Essential oil, as well as hydrosol- and microwave-assisted extracts inhibited germination and seedling growth; root metabolite phytotoxicity was demonstrated. Nevertheless, the phytotoxicity of root metabolites was demonstrated with a more marked selectivity to the benefit of the monocotyledonous species compared to the dicotyledonous species. Ziniolide derivatives seem to be strongly involved in allelopathic interactions and could be the key to understanding the invasive mechanisms of weed.

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Section: Resultssupporting

confidence: 87%

Guaianolide Derivatives from the Invasive Xanthium spinosum L.: Evaluation of Their Allelopathic Potential

2022

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“…The 22 signals were assigned by to the resonances of seven quaternary, six CH, six CH 2 , and three CH 3 carbon atoms. Five signals could be readily assigned to an isovaleryl and two to an acetoxyl moiety (see Table 1) (Budesinsky and Saman, 1995). The remaining 15 carbons indicated the occurrence of a sesquiterpene skeleton.…”

Section: Resultsmentioning

confidence: 99%

Germacranolides from Mikania guaco

et al. 2001

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“…Altamisic acid (20 mg) was isolated pure from a 100 % MeOH wash of the silica gel column. Structures were elucidated using 1 H-and 13 C-NMR spectroscopy and mass spectrometry and by comparing spectroscopic data obtained for each compound with the published data [13], [14], [15], [16]. Psilostachyins A [17], B [18], and C [19] were originally isolated from A. psilostachya [17], [18], [20], paulitin and isopaulitin were previously isolated from A. cumanensis [15], while altamisic acid was previously isolated from A. tenuifolia [14].…”

Section: Methodsmentioning

confidence: 99%

Modulation of the G₂Cell Cycle Checkpoint by Sesquiterpene Lactones Psilostachyins A and C Isolated from the Common RagweedAmbrosia artemisiifolia

et al. 2005

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A phenotypic cell-based assay for inhibitors of the G (2) DNA damage checkpoint was used to screen plant extracts from the US National Cancer Institute Natural Products Repository. It revealed activity in a methanol extract from the common ragweed Ambrosia artemisiifolia. Assay-guided fractionation led to the identification of the sesquiterpene lactones psilostachyins A and C as novel checkpoint inhibitors. Elimination of their alpha,beta-unsaturated carbonyl group caused a loss of activity, suggesting that the compounds can bind covalently to target proteins through Michael addition. Psilostachyins A and C also blocked cells in mitosis and caused the formation of aberrant microtubule spindles. However, the compounds did not interfere with microtubule polymerization in vitro. The related sesquiterpene lactones psilostachyin B, paulitin and isopaulitin were also isolated from the same extract but showed no checkpoint inhibition. The identification of the target(s) of psilostachyins A and C may provide further insight into the signalling pathways involved in cell cycle arrest and mitotic progression.

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Carbon-13 NMR Spectra of Sesquiterpene Lactones

Cited by 34 publications

References 673 publications

Guaianolide Derivatives from the Invasive Xanthium spinosum L.: Evaluation of Their Allelopathic Potential

Guaianolide Derivatives from the Invasive Xanthium spinosum L.: Evaluation of Their Allelopathic Potential

Germacranolides from Mikania guaco

Modulation of the G₂Cell Cycle Checkpoint by Sesquiterpene Lactones Psilostachyins A and C Isolated from the Common RagweedAmbrosia artemisiifolia

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Carbon-13 NMR Spectra of Sesquiterpene Lactones

Cited by 34 publications

References 673 publications

Guaianolide Derivatives from the Invasive Xanthium spinosum L.: Evaluation of Their Allelopathic Potential

Guaianolide Derivatives from the Invasive Xanthium spinosum L.: Evaluation of Their Allelopathic Potential

Germacranolides from Mikania guaco

Modulation of the G2Cell Cycle Checkpoint by Sesquiterpene Lactones Psilostachyins A and C Isolated from the Common RagweedAmbrosia artemisiifolia

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Modulation of the G₂Cell Cycle Checkpoint by Sesquiterpene Lactones Psilostachyins A and C Isolated from the Common RagweedAmbrosia artemisiifolia