Dataset Information

Diagnostically analyzing ¹H NMR spectra of sub-types in chaetoglobosins for dereplication.

ABSTRACT: ¹H-NMR spectra provide abundant diagnostic information including chemical shift values, splitting patterns, coupling constants, and integrals. Thus some key functional groups, and even planar structures could be elucidated on the basis of carefully analyzing the corresponding ¹H NMR spectrum. In this paper, the different sub-types of chaetoglobosins are classified according to the structural features, of which the ¹H NMR spectra are systematically summed up. Thus diagnostically analyzing the ¹H-NMR spectra could identify possible sub-types of chaetoglobosins, which could be used for dereplication. According to the analysis of this report, it implies that different new sub-types or new sub-type combinations in the key skeleton of chaetoglobosins might exist in nature. More importantly, dereplication based on ¹H NMR spectral analysis will not only provide a useful approach to determine the chaetoglobosins structures quickly, but also could set a good example for structural dereplication of other NPs.

SUBMITTER: Lin C

PROVIDER: S-EPMC9047530 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Diagnostically analyzing 1H NMR spectra of sub-types in chaetoglobosins for dereplication.

Lin Chen C Qin Jian-Chun JC Zhang Yong-Gang YG Ding Gang G

RSC advances 20200109 4

1H-NMR spectra provide abundant diagnostic information including chemical shift values, splitting patterns, coupling constants, and integrals. Thus some key functional groups, and even planar structures could be elucidated on the basis of carefully analyzing the corresponding 1H NMR spectrum. In this paper, the different sub-types of chaetoglobosins are classified according to the structural features, of which the 1H NMR spectra are systematically summed up. Thus ...[more]

PMID: 35494616

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Project description:Diffusion-ordered NMR spectroscopy (DOSY) can be used to analyze mixtures of compounds since resonances deriving from different compounds are distinguished by their diffusion coefficients (D). Previously, DOSY has mostly been used for organometallic and polymer analysis, we have now applied DOSY to investigate diffusion coefficients of structurally diverse organic compounds such as natural products (NP). The experimental Ds derived from 55 diverse NPs has allowed us to establish a power law relationship between D and molecular weight (MW) and therefore predict MW from experimental D. We have shown that D is also affected by factors such as hydrogen bonding, molar density and molecular shape of the compound and we have generated new models that incorporate experimentally derived variables for these factors so that more accurate predictions of MW can be calculated from experimental D. The recognition that multiple physicochemical properties affect D has allowed us to generate a polynomial equation based on multiple linear regression analysis of eight calculated physicochemical properties from 63 compounds to accurately correlate predicted D with experimental D for any known organic compound. This equation has been used to calculate predicted D for 217 043 compounds present in a publicly available natural product database (DEREP-NP) and to dereplicate known NPs in a mixture based on matching of experimental D and structural features derived from NMR analysis with predicted D and calculated structural features in the database. These models have been validated by the dereplication of a mixture of two known sesquiterpenes obtained from Tasmannia xerophila and the identification of new alkaloids from the bryozoan Amathia lamourouxi. These new methodologies allow the MW of compounds in mixtures to be predicted without the need for MS analysis, the dereplication of known compounds and identification of new compounds based solely on parameters derived by DOSY NMR.

Dataset Information

Diagnostically analyzing ¹H NMR spectra of sub-types in chaetoglobosins for dereplication.

Publications

Diagnostically analyzing <sup>1</sup>H NMR spectra of sub-types in chaetoglobosins for dereplication.

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