Recent trends in the structural revision of natural products

Chhetri, Bhuwan Khatri; Lavoie, Serge; Sweeney-Jones, Anne Marie; Kubanek, Julia

doi:10.1039/c8np00011e

Cited by 145 publications

(148 citation statements)

References 134 publications

(158 reference statements)

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“…[1] However,m isinterpretations of spectroscopic and/or physical data have often been known to result in structural misassignments.S uch occurrences are particularly prevalent in the natural product (NP) arena, where complex atom connectivities and stereochemical complexity abound. [3] There are now numerous in silico methods to help with structure elucidation by predicting spectra (e.g., NMR, [4] ECD [5] )from chemical structure input or conversely by predicting chemical structure from spectroscopic data (e.g.,A CDLabs [6] ). [3] There are now numerous in silico methods to help with structure elucidation by predicting spectra (e.g., NMR, [4] ECD [5] )from chemical structure input or conversely by predicting chemical structure from spectroscopic data (e.g.,A CDLabs [6] ).…”

Section: In Memory Of Paul Von Raguø Schleyer and Julius Bredtmentioning

confidence: 99%

“…[2] Considering the extensive time and spectroscopic demands (e.g., NMR, IR, UV-vis,MS, CD) involved in correctly elucidating an ovel natural product, the prevalence of misassignments in the literature is perhaps understandable. [3] There are now numerous in silico methods to help with structure elucidation by predicting spectra (e.g., NMR, [4] ECD [5] )from chemical structure input or conversely by predicting chemical structure from spectroscopic data (e.g.,A CDLabs [6] ). Yeti ns pite of these new technologies, misassignments continue to appear.X -ray crystallographic analysis in principle enables definitive structural elucidation, but in the NP arena the requisite quantities of material and suitable crystals are not always available,a nd furthermore misinterpretations are not unprecedented.…”

Section: In Memory Of Paul Von Raguø Schleyer and Julius Bredtmentioning

confidence: 99%

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Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

2019

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Structural misassignments of natural products are prevalent in the literature.Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance,s uch that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is astrategy for predicting the isolabilities of oxygen-substituted bridgehead natural products based on calculations of olefin strain energies,N MR chemical shifts and coupling constants (DU8 +). This approachp rovides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.

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Section: In Memory Of Paul Von Raguø Schleyer and Julius Bredtmentioning

confidence: 99%

Section: In Memory Of Paul Von Raguø Schleyer and Julius Bredtmentioning

confidence: 99%

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

2019

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“…Such occurrences are particularly prevalent in the natural product (NP) arena, where complex atom connectivities and stereochemical complexity abound . Considering the extensive time and spectroscopic demands (e.g., NMR, IR, UV‐vis, MS, CD) involved in correctly elucidating a novel natural product, the prevalence of misassignments in the literature is perhaps understandable . There are now numerous in silico methods to help with structure elucidation by predicting spectra (e.g., NMR, ECD) from chemical structure input or conversely by predicting chemical structure from spectroscopic data (e.g., ACDLabs).…”

Section: Figurementioning

confidence: 99%

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

2019

View full text Add to dashboard Cite

Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.

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“…Chinese herbal medicine are important sources of anticancer drug development [10,11]. Parthenolide, an abundant sesquiterpene, which was first found in the medicinal plant feverfew (Tanacetum parthenium) [12].…”

Section: Introductionmentioning

confidence: 99%

Parthenolide inhibits the growth of non-small cell lung cancer by targeting epidermal growth factor receptor

Huang

et al. 2020

Preprint

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Background: EGFR tyrosine kinase inhibitors (TKIs) have been developed for the treatment of EGFR mutated NSCLC. Parthenolide, a natural product of parthenolide, which belongs to the sesquiterpene lactone family and has a variety of biological and therapeutic activities, including anti-cancer effects. However, its effect on non-small cell lung cancer is little known. Methods: The CCK-8 assay and colony formation assays were used to assess cell viability. Flow cytometry was used to measure the cell apoptosis. In silico molecular docking was used to evaluate the binding of parthenolide to EGFR. Network pharmacology analysis was was used to evaluate the key gene of parthenolide target NSCLC. Western blotting was used to evaluate the key proteins involved apoptosis and EGFR signalling. The effect of parthenolide treatment in vivo was determined by using a xenograft mouse model. Results: In this study, parthenolide could induce apoptosis and growth inhibition in the EGFR mutated lung cancer cells. Parthenolide also reduces the phosphorylation of EGFR as well as its downstream signaling pathways MAPK/ERK and PI3K/Akt. Molecular docking analysis of EGFR binding site with parthenolide show that the anti-cancer effect of parthenolide against NSCLC is mediated by a strong binding to EGFR. Network pharmacology analysis show parthenolide suppresses NSCLC via inhibition of EGFR expression. In addition, parthenolide inhibits the growth of H1975 xenografts in nude mice, which is associated with the inhibition of the EGFR signaling pathway. Conclusions: Taken together, these results demonstrate effective inhibition of parthenolide in NSCLC cell growth by targeting EGFR through downregulation of ERK and AKT expression, which could be promisingly used for patients carrying the EGFR mutation.

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Recent trends in the structural revision of natural products

Cited by 145 publications

References 134 publications

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Parthenolide inhibits the growth of non-small cell lung cancer by targeting epidermal growth factor receptor

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