Targeted isolation of diterpenoids and sesquiterpenoids from Daphne gemmata E. Pritz. ex Diels using molecular networking together with network annotation propagation and MS2LDA

Zhou, Wenbai; Hou, Jiao-Yang; Li, Qian; Wang, Yujue; Wang, Jiayi; Jiang, Ming-Hao; Yao, Guo-Dong; Huang, Xiao‐Xiao; Song, Shao‐Jiang

doi:10.1016/j.phytochem.2022.113468

Cited by 7 publications

(8 citation statements)

References 69 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The molecular networking was manipulated by the method described previously. 18 Fractions B1 and B2 were analyzed using the Bruker COMPACT spectrometer. The gradient elution was conducted with CH 3 CN (A)/H 2 O (B) (20:80 to 95:5) for 50 min.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Fractions B1 and B2 were analyzed by molecular networking. The molecular networking was manipulated by the method described previously . Fractions B1 and B2 were analyzed using the Bruker COMPACT spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…ECD calculations for 9 – 11 were conducted by Gaussian 09 as described before. , The conformational analysis of 9 – 11 was manipulated by Spartan software employing MMFF94. , At the B3LYP/6-31G(d) level, these conformers of 9 – 11 were optimized. Using the TDDFT method, optimized conformers were computed at the B3LYP/6-311+G(d,p) level.…”

Section: Methodsmentioning

confidence: 99%

“…The NMR calculation for 11 was conducted by Gaussian 09 as described before. , The NMR calculation of 11 was conducted at the mPW1PW91/6-311+G(d,p) level in DMSO. The calculated NMR data were averaged in view of Boltzmann distribution theory and its relative Gibbs free energy.…”

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Utilization of the By-Product of Corn: Guided Identification of Bioactive Terpenoids from Stigma Maydis (Corn Silk)

Zhou

Niu

et al. 2023

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

Stigma maydis (corn silk) (S. maydis) is a food-based by-product of maize and possesses great nutritional and pharmaceutical value. This study aimed to explore bioactive components from S. maydis. By the guidance of bioactivity-guided approach and Global Natural Products Social (GNPS) molecular networking, 12 terpenoids were discovered from S. maydis. The structures of 11 undescribed compounds (1–11) were determined by detailed spectroscopic analyses, single-crystal X-ray diffraction analysis, specific rotation calculations, electronic circular dichroism (ECD) calculations, and NMR calculations. The neuroprotective and acetylcholinesterase (AChE) inhibitory effects of 1–12 were examined, and most of them showed significant or moderate activities. The underlying neuroprotective mechanism of 4 and 5 was revealed by Hoechst 33258, AO-EB, and JC-1 staining assays. This work illustrated the potential of S. maydis as a prospective natural source of bioactive compounds in food and pharmaceutical industries.

show abstract

Section: ■ Materials and Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Utilization of the By-Product of Corn: Guided Identification of Bioactive Terpenoids from Stigma Maydis (Corn Silk)

Zhou

Niu

et al. 2023

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Therefore, employing several tools in conjunction increases the accuracy in the identification and characterisation of natural products. As such, computational tools such as molecular networking 13–15 and MS2LDA 16,17 have been developed, and they allow the visualisation of compounds that share unique fragmentation patterns and substructures as molecular families. The introduction of molecular networking and its complementary tools has enabled mass spectral mining from multiple data sets 18,19 .…”

Section: Introductionmentioning

confidence: 99%

Rationalising the retro‐Diels‐Alder fragmentation pattern of viscutins using electrospray interface‐tandem mass spectrometry coupled to theoretical modelling

Moyo,

Novokoza,

Tavengwa

et al. 2023

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale: Although mass spectrometry (MS) is a powerful tool in structural elucidation of unknown flavonoids based on their unique fragmentation patterns, proposing the correct fragmentation mechanism is still a challenge from tandem mass spectrometry data only. In recent years, computational tools such as molecular networking and MS2LDA have played a major role in the identification of structurally related compounds through an in-depth survey of their fragmentation patterns.Methods: Therefore, in this study, three viscutin molecules in Viscum combreticola Engl. crude extracts were characterised using ultra-high-performance liquid chromatography-quadrupole-time-of-flight tandem mass spectrometry and MS2LDA, a computational tool. Ion-trap mass spectrometry and density functional theoretical modelling were used as confirmatory tools to rationalise the unique fragmentation patterns observed for these molecules.Results: Here, MS2LDA revealed the presence of a unique Mass2Motif in all the three viscutin molecules at m/z 137, which was confirmed to be a 1,3 A À RDA (retro-Diels-Alder) fragmentation product using liquid chromatography-ion-trap mass spectrometry and density functional theoretical modelling. Moreover, MS2LDA proved to be useful in differentiating this spectral feature that was specific to viscutin molecules in the presence of other isobaric ions at m/z 137 occurring in compounds in other molecular families. Conclusion:Therefore, the results of the current study showed that computational tools such as MS2LDA are essential in uncovering some gas-phase fragmentation reactions of molecules in MS and that theoretical modelling is a powerful tool in rationalising these reactions in metabolite identification. | INTRODUCTIONViscum combreticola Engl. (Santalacaeae), a perennial and evergreen leafless semi-parasitic plant, is native to southern and tropical Africa. 1,2 Combretum erythrophyllum, Acacia karroo, Pseudolachnostylis maprouneifolia Pax and Sclerocarya birrea 1,3 are some of the common host plants of V. combreticola Engl. The phytochemistry of different species of Viscum is complex, consisting of various classes of secondary metabolites such as viscotoxins, lectins, flavonoids, hydroxycinnamic acid derivatives, terpenoids, coumarins, lignans,

show abstract

Feature‐based molecular networking with MS2LDA to profile compounds in Lanbuzheng based on ultra‐high‐performance liquid chromatography‐quadrupole Exactive Orbitrap high‐resolution mass spectrometry

Kong,

Tian,

et al. 2024

J of Separation Science

View full text Add to dashboard Cite

Lanbuzheng (Geum japonicum Thunb. var. chinense Bolle), a plant found in Southwest China, is a traditional Chinese medicine that promotes hematopoiesis and antioxidant functions. Many of its chemical constituents remain unknown, posing challenges both to understanding its pharmacological mechanisms and to conducting quality control research. In this work, ultra‐high performance liquid chromatography coupled with quadrupole Exactive Orbitrap high‐resolution mass spectroscopy was used for profiling the composition of Lanbuzheng. Using positive ion mass spectrometry data enriched from Lanbuzheng extract, feature‐based molecular networking (FBMN) was constructed and associated with Mass2Motifs substructures using MS2LDA. Prediction and validation of unknown constituents of Lanbuzheng using a custom‐built compound library, SIRIUS, and network annotation propagation, achieved a semi‐automated annotation of the molecular network. Based on the custom‐built library comprising 206 compounds and the FBMN clustering results, the constituents in Lanbuzheng primarily include tannins, triterpenes, flavonoids, and phenolics. Using only 65 pre‐identified compounds as references, 210 unknown compounds were annotated in various polarity regions of Lanbuzheng. Results of the current work indicate that molecular networks enable the efficient annotation of compounds in complex systems, laying the groundwork for the preliminary identification of pharmacologically active constituents of Lanbuzheng.

show abstract

Targeted isolation of diterpenoids and sesquiterpenoids from Daphne gemmata E. Pritz. ex Diels using molecular networking together with network annotation propagation and MS2LDA

Cited by 7 publications

References 69 publications

Utilization of the By-Product of Corn: Guided Identification of Bioactive Terpenoids from Stigma Maydis (Corn Silk)

Utilization of the By-Product of Corn: Guided Identification of Bioactive Terpenoids from Stigma Maydis (Corn Silk)

Rationalising the retro‐Diels‐Alder fragmentation pattern of viscutins using electrospray interface‐tandem mass spectrometry coupled to theoretical modelling

Feature‐based molecular networking with MS2LDA to profile compounds in Lanbuzheng based on ultra‐high‐performance liquid chromatography‐quadrupole Exactive Orbitrap high‐resolution mass spectrometry

Contact Info

Product

Resources

About