IR and Vibrational Circular Dichroism Spectroscopy of Matrine- and Artemisinin-Type Herbal Products: Stereochemical Characterization and Solvent Effects

Zhang, Yuefei; Poopari, Mohammad Reza; Cai, Xiaoli; Savin, A. K.; Dezhahang, Zahra; Cheramy, Joseph; Xu, Yunjie

doi:10.1021/acs.jnatprod.5b01082

Cited by 35 publications

(30 citation statements)

References 45 publications

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“…The DF and CID spectral methods have been used to aid in the determination of the ACs of several compounds. 22,[32][33][34][35][36][37][38] In addition, the experimental EDF spectra of binaphthol showed differences due to solvent complexation that followed the trend in solvent polarity. 39 In CDSpecTech, the similarity index SI can be calculated for EA, VA, and Raman spectra, and ESI for ECD, VCD, VROA, EDF, VDF, and VROA spectra, using the parametric function equation 19.…”

Section: Technical Detailsmentioning

confidence: 96%

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CDSpecTech: A single software suite for multiple chiroptical spectroscopic analyses

Covington

Polavarapu

2017

Chirality

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The program CDSpecTech was developed to facilitate the analysis of chiroptical spectra, which include the following: vibrational circular dichroism (VCD) and corresponding vibrational absorption (VA) spectra; vibrational Raman optical activity (VROA) and corresponding vibrational Raman spectra; electronic circular dichroism (ECD) and corresponding electronic absorption (EA) spectra. In addition, the program allows for generating optical rotatory dispersion (ORD) as the Kramers-Kronig transform of ECD spectra. The simulation of theoretical spectra from transition strengths can be achieved using different bandshape profiles. The experimental and simulated theoretical spectra can be visually compared by displaying them together. A unique feature of CDSpecTech is performing spectral analysis using the ratio spectra; i.e., the dimensionless dissymmetry factor (DF) spectrum, which is the ratio of CD to absorption spectra, and the dimensionless circular intensity difference (CID) spectrum, which is the ratio of VROA to vibrational Raman spectra. The quantitative agreement between experimental and simulated theoretical spectra can also be assessed from the numerical similarity overlap between them. Two different similarity overlap methods are available. The program uses a graphical user interface which allows for ease of use and facilitates the analysis. All these features make CDSpecTech a valuable tool for the analysis of chiroptical spectra. The program is freely available on the World Wide Web.

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Section: Technical Detailsmentioning

confidence: 96%

“…The DF and CID spectral methods have been used to aid in the determination of the ACs of several compounds . In addition, the experimental EDF spectra of binaphthol showed differences due to solvent complexation that followed the trend in solvent polarity …”

Section: Program Descriptionmentioning

confidence: 99%

CDSpecTech: A single software suite for multiple chiroptical spectroscopic analyses

Covington

Polavarapu

2017

Chirality

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“…The studies showed that effectively accounting for solvent effects is critical to using IR and VCD spectroscopy which provide unique spectroscopic features to differentiate the potential stereoisomers. 134 (Figure 80). A VCD study for the AC determination of 280 provided evidence for the mutually dependent atropisomerism and absoluye configuration.…”

Section: Nitrogenated Compoundsmentioning

confidence: 99%

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

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“…The closeness of DF similarity scores with and without normalization indicates a corresponding closeness among the magnitudes of intensities in the calculated and experimental ratio spectra. This method was applied to a number of small molecules to aid in the determination of their ACs …”

Section: Computationalmentioning

confidence: 99%

Absolute configuration of an axially chiral sulfonate determined from its optical rotatory dispersion, electronic circular dichroism, and vibrational circular dichroism spectra

et al. 2017

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The absolute configuration (AC) of an axially chiral sulfonate (aCSO), 3,5-dimethyl-2-(naphthalen-1-yl)-6-(naphthalen-1-yl)benzenesulfonate (labeled as aCSO5), was investigated using optical rotatory dispersion (ORD), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) spectroscopies. All three methods led to the same conclusion and the AC of aCSO5 is reliably determined to be (-)-(aR, aR), or conversely (+)-(aS, aS).

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IR and Vibrational Circular Dichroism Spectroscopy of Matrine- and Artemisinin-Type Herbal Products: Stereochemical Characterization and Solvent Effects

Cited by 35 publications

References 45 publications

CDSpecTech: A single software suite for multiple chiroptical spectroscopic analyses

CDSpecTech: A single software suite for multiple chiroptical spectroscopic analyses

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Absolute configuration of an axially chiral sulfonate determined from its optical rotatory dispersion, electronic circular dichroism, and vibrational circular dichroism spectra

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