Theoretical study on the structure and properties of crenulatin molecule in herb Rhodiola crenulata

Su, Xinxin; Zhang, Hong; Shao, Jian-Li; Wu, Huan

doi:10.1016/j.theochem.2007.08.034

Cited by 8 publications

(4 citation statements)

References 39 publications

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“…As has been shown by previous theoretical calculations, DFT method with Becke's three-parameter hybrid exchange functional and the LeeYang-Parr correlation functional (B3LYP) [26,27] is a cost-effective method for studying metal cation-ligand systems, and yielding binding energies in fairly good agreement with the experimental values [23,24,28,29]. So the structures of Crenulatin molecule (Crenulatin-a and Crenulatin-b) [10,11] and their complexes were full optimized first at the HF/3-21G level without any constraint. At this stationary point obtained, a refinement optimization was carried out at the B3LYP level of theory.…”

Section: Theory and Computational Detailssupporting

confidence: 55%

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Density functional theoretical study on attachment sites of Mg2+ and Ca2+ and metal ion affinity to Crenulatin molecule

Cheng

Zhao

et al. 2008

Struct Chem

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Crenulatin (C 25 H 20 O 10 ) is a flavonol derivative and has been isolated from the roots of Rhodiola crenulata (Hook. F. et Thoms.), a widely used medicinal herb. Magnesium and calcium cations play an important physiological role in biological systems. In this work, interactions of magnesium and calcium divalent cations with Crenulatin molecule were studied. Density functional theory (DFT) was used to determine coordination geometries and absolute metal ion affinities (MIA) for all possible stable complexes. The results show that calcium and magnesium cations are able to interact with the Crenulatin molecule through mono-, bi-, and tricoordination. B3LYP/ 6-31G(d) bond energies for all complexes reveal that magnesium cation has a greater affinity to Crenulatin molecule than calcium cation. The calculated value of Mg 2+ cation affinity, including the zero-point vibrational energy (ZPE) and basis set superposition error (BSSE), is 231.8 kcal mol -1 for the most stable complex. Entropy (DS) and free energy (DG) variations for the metalation processes considered here have also been reported.

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Section: Theory and Computational Detailssupporting

confidence: 55%

“…1) on the basis of 13 C NMR, 1 H-1 H COSY, and 1 H-13 C COSY spectrum [10]. The corresponding theoretical study on its geometry, electronic property, and antioxidant activity has also been reported [11].…”

Section: Introductionmentioning

confidence: 98%

Density functional theoretical study on attachment sites of Mg2+ and Ca2+ and metal ion affinity to Crenulatin molecule

Cheng

Zhao

et al. 2008

Struct Chem

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“…It could be concluded that ethyl gallate, gallic acid and herbacetin were three important components which could inhibit the growth of the five clinical pathogenic bacteria, and they might contribute to the antibacterial activity of EE. These results would provide more clues to reveal the material basis of R. crenulata in treating diarrhea and scald, which would also help to understand the traditional use in Chinese traditional medicine [ 35 ]. Furthermore, the antibacterial mechanism of the crude extracts and the identified compounds need to be elucidated more clearly, and an in vivo antibacterial activity experiment is required to be conducted in further study.…”

Section: Resultsmentioning

confidence: 99%

Phytochemical, Antibacterial and Antioxidant Activity Evaluation of Rhodiola crenulata

et al. 2020

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The chemical components, as well as the antibacterial and antioxidant activities of the essential oil (EO) and crude extracts prepared from Rhodiola crenulata were investigated. The essential oil was separated by hydrodistillation, and gas chromatography-mass spectrometry (GC-MS) was used to identify its constituents. A total of twenty-seven compounds was identified from the EO, and its major components were 1-octanol (42.217%), geraniol (19.914%), and 6-methyl-5-hepten-2-ol (13.151%). Solvent extraction and fractionation were applied for preparing the ethanol extract (crude extract, CE), petroleum ether extract (PE), ethyl acetate extract (EE), n-butanol extract (BE), and water extract (WE). The CE, EE and BE were abundant in phenols and flavonoids, and EE had the highest total phenol and total flavonoid contents. Gallic acid, ethyl gallate, rosavin and herbacetin were identified in the EE. The antibacterial activity results showed that the EO exhibited moderate inhibitory activity to the typical clinic bacteria, and EE exhibited the strongest antibacterial activity among the five extracts. For the compounds, ethyl gallate showed the strongest inhibitory activity to the test bacteria, and its minimum inhibitory concentration (MIC) value and minimum bactericidal concentration (MBC) value for all the tested bacteria was 0.24 mg/mL and 0.48 mg/mL, respectively. The results of antioxidant activity showed that both CE and EE exhibited strong antioxidant activities in the DPPH radical scavenging and Fe2+ reducing power tests, however, EO showed relatively weaker antioxidant ability. Ethyl gallate and rosavin exhibited excellent activity in the DPPH radical scavenging assay, and their IC50 value was 5.3 µg/mL and 5.9 µg/mL, respectively. Rosavin showed better reduction power activity than the other three compounds. These results could provide more evidence for the traditional use of R. crenulata, and would be helpful for improving its application further.

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“…Both autopeak were surrounded by two correlation squares with positive cross-peaks in a[CO2] and e[CO2] spectrum, indicating that the centralized peak was important and correlated with many compounds crossing with it. Peaks around 920 -705 cm -1 are attributed to additional vibrations associated with C-H out-of-plane vibrations from anthocyanin bands based on the tetra-substituted pyrylium nucleus [40], while range between 1200 -900 cm -1 contains functional groups for carbohydrates (sucrose, glucose and fructose) [30,41]. For easy comparison, the information on the positions and correlations of the auto-peaks in Figure 3 are summarized in Table 2.…”

Section: Two-dimentional Correlation Ir (2d-ir) Spectrum Analysis Of mentioning

confidence: 99%

RAPID INVESTIGATION OF THE METABOLITE CONTENT IN HIBISCUS SABDARIFFA var. UKMR-2 CULTIVATED UNDER THE INFLUENCE OF ELEVATED CO2 USING TRI-STEP FT-IR SPECTROSCOPY

Ali

Latip

2020

Jurnal Teknologi

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Rapid methods based on untargeted analysis technique such as Fourier Transform Infrared (FT-IR) spectroscopy can provide much faster and easier solution for food authentication. However, studies on the metabolite content in UKMR-2 calyces using FT-IR spectroscopy has not been reported yet in any previous studies. Thus, the present study was performed to analyze the differences in metabolite content in UKMR-2 calyces under the influences of different [CO2] treatment by applying tri-step infrared based fingerprinting. The UKMR-2 plant cultivation was exposed to ambient [CO2] (400 µmol/mol) and elevated [CO2] (800 µmol/mol) treatment. The UKMR-2 calyx extracts were analysed by conventional infrared (1D-IR), second derivative infrared (SD-IR) and two-dimensional correlation infrared (2D-IR) spectroscopy. The 1D-IR spectrum results revealed a similar absorption spectrum in the range of 1900 - 650 cm-1, which suggest similar major metabolites content present in both extracts. For SD-IR spectrum, both treatments clearly showed have more peaks with different shape, position and intensity in the range of 1650 - 1450 cm-1 and 1200 - 950 cm-1, which is likely to have different flavonoid and carbohydrate content in UKMR-2 calyces. The 2D-IR synchronous correlation spectrum in the range of 1000 – 650 cm-1 clearly distinguished the metabolite content in the UKMR-2 calyx extract from different [CO2] treatment. Therefore, this tri-step infrared based fingerprinting has the potential as one of the effective methods to discriminate extract samples with similar infrared fingerprint features and indicate that the metabolite content in UKMR-2 calyces were influenced by different [CO2] treatments.

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Theoretical study on the structure and properties of crenulatin molecule in herb Rhodiola crenulata

Cited by 8 publications

References 39 publications

Density functional theoretical study on attachment sites of Mg2+ and Ca2+ and metal ion affinity to Crenulatin molecule

Density functional theoretical study on attachment sites of Mg2+ and Ca2+ and metal ion affinity to Crenulatin molecule

Phytochemical, Antibacterial and Antioxidant Activity Evaluation of Rhodiola crenulata

RAPID INVESTIGATION OF THE METABOLITE CONTENT IN HIBISCUS SABDARIFFA var. UKMR-2 CULTIVATED UNDER THE INFLUENCE OF ELEVATED CO2 USING TRI-STEP FT-IR SPECTROSCOPY

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