Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups

Shen, Hong; Wu, Shanshan; Cai, He; Wang, Yimin; Liu, Songbai

doi:10.1016/j.jff.2017.07.036

Cited by 6 publications

(7 citation statements)

References 24 publications

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“…The aromatic ring hydrogens of A-, B-, and C-rings were found at 5.94 and 5.84, 6.83 and 6.42, 4.97, 3.46, 2.50, and 2.65 ppm, respectively. The proton signals were in line with previous report [ 38 ]. The COS-CAT conjugate showed characteristic proton signals of COS and partial signals of CAT.…”

Section: Resultssupporting

confidence: 91%

Chitooligosaccharide Conjugates Prepared Using Several Phenolic Compounds via Ascorbic Acid/H2O2 Free Radical Grafting: Characteristics, Antioxidant, Antidiabetic, and Antimicrobial Activities

Mittal

Singh

Zhang

et al. 2022

Foods

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Chitooligosaccharide (COS)-polyphenol (PPN) conjugates prepared using different PPNs, including gallic, caffeic, and ferulic acids, epigallocatechin gallate, and catechin, at various concentrations were characterized via UV-visible, FTIR, and 1H-NMR spectra and tested for antioxidant, antidiabetic, and antimicrobial activities. Grafting of PPNs with COS was achieved. The highest conjugation efficiency was noticed for COS-catechin (COS-CAT), which was identified to have the highest total phenolic content (TPC) out of all the conjugates (p < 0.05). For antioxidant activities, DPPH and ABTS radical scavenging activities (DPPH-RSA and ABTS-RSA, respectively), oxygen radical absorbance capacity (ORAC), ferric reducing antioxidant power (FRAP), and metal chelating activity (MCA) of all the samples were positively correlated with the TPC incorporated. COS-CAT had higher DPPH-RSA, ABTS-RSA, ORAC, and FRAP than COS and all other COS-PPN conjugates (p < 0.05). In addition, COS-CAT also showed the highest antidiabetic activity of the conjugates, as determined by inhibitory activity toward α-amylase, α-glucosidase, and pancreatic lipase (p < 0.05). COS-CAT also had the highest antimicrobial activity against all tested Gram-negative and Gram-positive bacteria (p < 0.05). Overall, grafting of PPNs, especially CAT on COS, significantly enhanced bioactivities, including antioxidant and antimicrobial, which could be used to retard spoilage and enhance shelf-life of various food systems. Moreover, the ability of COS-CAT to inhibit digestive enzymes reflects its preventive effect on diabetes mellitus and its complications.

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Section: Resultssupporting

confidence: 91%

Chitooligosaccharide Conjugates Prepared Using Several Phenolic Compounds via Ascorbic Acid/H2O2 Free Radical Grafting: Characteristics, Antioxidant, Antidiabetic, and Antimicrobial Activities

Mittal

Singh

Zhang

et al. 2022

Foods

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“…13 C NMR, δ 192.51, 164.49, 161.07, 160.53, 142.55, 135.37, 130.90, 129.56, 128.93, 127.77, 105.51, 102.98, 93.26, 92.45, 56.62, 27.22, 14.90. The 1 H NMR spectrum of CAR–ACR-1 showed that the active hydrogen on the C 7 –OH group ( δ H 10.72) disappeared, while the active hydrogen on the C 9 –OH group ( δ H 14.49) still existed, 31,32 which proved that ACR was connected with the C-8 position and formed a new six-membered ring with the hydroxyl group at C-7. Additionally, the molecular formula of CAR–ACR-1 was postulated to be C 19 H 18 O 5 using HRMS data at m / z 327.1225 [M + H] + (calculated 327.1209 [M + H] + ) (Fig.…”

Section: Resultsmentioning

confidence: 98%

“…S1 †) but different retention times (RTs of 5.51 and 12.68 min). Their MS 2 spectra displayed fragment ions at m/z 283 [M − 44 + H] + (loss of one [-CHOH-CH 2 -] group), 30,31 suggesting that the two products were isomers and mono-ACR adducts conjugated with CAR/ALP. Based on the NMR data given below, one peak (RT = 5.51 min) was ALP-ACR, and the other peak (RT = 12.68 min) was CAR-ACR-1.…”

Section: Lc-ms/ms Analysis Of the Adducts Of Car And Alp With Acr In ...mentioning

confidence: 99%

Dual effects of cardamonin/alpinetin and their acrolein adducts on scavenging acrolein and the anti-bacterial activity from Alpinia katsumadai Hayata as a spice in roasted meat

et al. 2022

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“…determine the structure profile of these compounds by Hong et al (2017). The recorded NOESY spectrum of the modified (+)-catechin hydrate is presented in Figure 2-a.…”

Section: Structure Elucidationmentioning

confidence: 99%

“…The full (a) and enlarged (highlighted area by red rectangle in the full spectrum, b) NOESY spectrum of catechin.The NOESY correlation of the hydroxyl protons is also shown in the chemical structure (b). Reprinted fromHong et al (2017) with permission from Elsevier.…”

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confidence: 99%

A review on nuclear overhauser enhancement (NOE) and rotating-frame overhauser effect (ROE) NMR techniques in food science: Basic principles and applications

Doost

Akbari

Stevens

et al. 2019

Trends in Food Science & Technology

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The characterization of the original chemical structure and induced changes of micro-and macro-molecules using analytical techniques with concise and detailed outcomes is potentially one of the major challenges for food scientists. To this end, the non-invasive nuclear magnetic resonance (NMR) technique can play a significant role through employment of different NMR methods. The Nuclear Overhauser effect (NOE) and rotating-frame Overhauser effect (ROE) techniques are powerful NMR methods that have attracted great interest because they provide precise information about the three dimensional spatial structure of the molecules, as well as about possible chemical reactions and interactions. Scope and approach In this article, we reviewed the basic principles as well as applications of two NMR techniques: Nuclear Overhauser effect spectroscopy (NOESY) and rotating-frame Overhauser effect spectroscopy (ROESY). Hereby, we focused mainly on the applications and importance of these techniques in food science research. Both the structural (configuration and conformation) changes and the complexes formed by interacting compounds could be better studied using these techniques. Key findings and conclusions The inter-and intra-molecular interactions within food-based ingredient mixtures, as well as configurational and conformational analyses can be more efficiently studied with the aid of NOESY and ROESY. These methods as complementary analysis tools can be exploited for the straightforward elucidation of the spatial proximity of either novel, native or modified compounds. In the future, these techniques may be helpful to better understand the interaction between polymers, such as protein-polysaccharide interactions.

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Instant structure profiling of substituted catechins by chemical shift fingerprint of hydrogens of phenolic hydroxyl groups

Cited by 6 publications

References 24 publications

Chitooligosaccharide Conjugates Prepared Using Several Phenolic Compounds via Ascorbic Acid/H2O2 Free Radical Grafting: Characteristics, Antioxidant, Antidiabetic, and Antimicrobial Activities

Chitooligosaccharide Conjugates Prepared Using Several Phenolic Compounds via Ascorbic Acid/H2O2 Free Radical Grafting: Characteristics, Antioxidant, Antidiabetic, and Antimicrobial Activities

Dual effects of cardamonin/alpinetin and their acrolein adducts on scavenging acrolein and the anti-bacterial activity from Alpinia katsumadai Hayata as a spice in roasted meat

A review on nuclear overhauser enhancement (NOE) and rotating-frame overhauser effect (ROE) NMR techniques in food science: Basic principles and applications

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