Chisosiamens A–E, five new ring-intact limonoids with isomerized furan ring from the fruit of Chisocheton siamensis

Wang, Zefan; Zhang, Panpan; Cui, Letian; Li, Qiurong; Kong, Ling–Yi; Luo, Jun

doi:10.1016/j.fitote.2021.104873

Cited by 8 publications

(10 citation statements)

References 14 publications

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“…Adapted from ref. 117 It is apparent that for the most classic example of 1,2-diol bis-benzoates, a positive torsional angle θ (or positive chirality) always corresponds to a positive value of the geometrical factor and hence a positive exciton couplet: The exciton chirality rule is fully fulfilled for these systems. The same occurs for any other bischromophoric derivative of 1,2-diols, such as psubstituted benzoates, 2-naphthoates, 2-anthroates, and so on.…”

Section: Geometrical Factor Plotsmentioning

confidence: 99%

“…The drawing used to establish the sign of exciton chirality is shown in Figure 13A ; the supposedly positive chirality was apparently in keeping with the experimental positive ECD couplet. 117 The adopted viewpoint is, however, equivocal, because it diverges a lot from the ideal viewpoint along the line connecting the TDMs. In Figure 13B , we use a truncated model of 23 that preserves the limonoid skeleton (with the γ‐lactone ring replaced by a methyl group at C17, 23a ).…”

Section: Quantitative Predictions Of Exciton‐coupled Ecd Spectramentioning

confidence: 99%

“…Adapted from ref. 117 , copyright 2021, with permission from Elsevier. (B) Lowest energy DFT conformer of 23a , displaying faint negative exciton chirality; the angles relevant for applying the ECM are measured as: α = 30°, β = 42°, γ = −4.4°…”

Section: Quantitative Predictions Of Exciton‐coupled Ecd Spectramentioning

confidence: 99%

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ECD exciton chirality method today: a modern tool for determining absolute configurations

Pescitelli

2021

Chirality

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The application of the exciton chirality method (ECM) to interpret electronic circular dichroism (ECD) spectra is a well-established and still popular approach to assign the absolute configuration (AC) of natural products, chiral organic compounds, and organometallic species. The method applies to compounds containing at least two chromophores with electric dipole allowed transitions (e.g., π-π* transitions). The exciton chirality rule correlates the sign of an exciton couplet (two ECD bands with opposite sign and similar intensity) with the overall molecular stereochemistry, including the AC. A correct application of the ECM requires three main prerequisites: (a) the knowledge of the molecular conformation, (b) the knowledge of the directions of the electric transition moments (TDMs), and (c) the assumption that the exciton coupling mechanism must be the major source of the observed ECD signals. All these prerequisites can be easily verified by means of quantum-mechanical (QM) calculations. In the present review, we shortly introduce the general principles that underpin the use of the ECM for configurational assignments and survey its applications, both classic ones and some reported in the recent literature. Based on these examples, we will stress the advantages of the ECM but also the key requisites for its correct application. Additionally, we will discuss the dependence of the couplet sign on geometrical parameters (angles α,β,γ between TDMs), which can be helpful for discerning the sign of exciton chirality in ambiguous situations. Finally, we will present a molecular orbital (MO) description of the exciton coupling phenomenon.

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Section: Geometrical Factor Plotsmentioning

confidence: 99%

Section: Quantitative Predictions Of Exciton‐coupled Ecd Spectramentioning

confidence: 99%

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ECD exciton chirality method today: a modern tool for determining absolute configurations

Pescitelli

2021

Chirality

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“…About 223 new ring-intact limonoids were discovered in the last decade, accounting for 14.0% of the total, second only to rearranged limonoids (Tables S1.1–S1.3†). According to previous studies, these limonoids can be divided into the azadirone-class ( A1–A58 ), 79–109 cedrelone-class ( A59–A99 ), 97,99,102,105,110–115 havanensin-class ( A100–A121 ), 97,98,108,116–130 trichilin-class ( A122–A168 ), 119,120,122,125,131–140 vilasinin-calss ( A169–A206 ) 82,87,122,128,132,141–153 (Fig. 5), and others ( A207–A223 ).…”

Section: Latest Limonoids Discovered From the Meliaceae Familymentioning

confidence: 98%

Research progress of meliaceous limonoids from 2011 to 2021

Luo

Sun

et al. 2022

Nat. Prod. Rep.

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“…Limonoids mainly exist in Meliaceae and Rutaceae plants and have attracted the extensive attention of researchers due to their abundant structural types and significant pharmacological activities, such as inhibiting tumor growth, regulating body metabolism, and inhibiting inflammatory disorders. − Due to the increasing demand for anti-inflammatory agents, the potential of natural products as safe and effective therapeutic drugs has received increasing attention. It has been reported that munronoid I, toonaolide K, etc., can inhibit NLRP3 inflammasome activation, , suggesting that meliaceous limonoids may play an anti-inflammatory role by inhibiting the activation of the NLRP3 inflammasome.…”

mentioning

confidence: 99%

Inhibition of the P2X7/NLRP3 Inflammasome Signaling Pathway by Deacetylgedunin from Toona sinensis

Tang

Zhang

et al. 2022

J. Nat. Prod.

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Limonoids are considered the effective part in Meliaceae plants that exert anti-inflammatory effects. Gedunin-type limonoids specifically have antiinflammatory effects. However, the role of gedunin-type limonoids in the inflammatory diseases mediated by NLRP3 inflammasome remains to be explored. We found that deacetylgudunin (DAG), a gedunin-type limonoid from Toona sinensis, had similar anti-inflammatory effects and lower toxicity than gedunin. Further studies showed that DAG down-regulated the NF-κB pathway, inhibited K + efflux and ROS release, inhibited ASC oligomerization, and significantly weakened the interaction of NLRP3 with ASC and NEK7. Furthermore, DAG could not further inhibit IL-1β secretion and K + efflux when combined with the P2X7 inhibitor A438079. In conclusion, our research revealed that DAG exerted an antiinflammatory effect by inhibiting the P2X7/NLRP3 signaling pathway and enriched the application of gedunin-type limonoids in inflammatory diseases driven by the NLRP3 inflammasome.

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Chisosiamens A–E, five new ring-intact limonoids with isomerized furan ring from the fruit of Chisocheton siamensis

Cited by 8 publications

References 14 publications

ECD exciton chirality method today: a modern tool for determining absolute configurations

ECD exciton chirality method today: a modern tool for determining absolute configurations

Research progress of meliaceous limonoids from 2011 to 2021

Inhibition of the P2X7/NLRP3 Inflammasome Signaling Pathway by Deacetylgedunin from Toona sinensis

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