Diketopiperazines and 2H-pyran-2-ones with antioxidant activity from the rice fermented with Aspergillus luchuensis

Sun, Shanshan; Ma, Ke; Tao, Qiaoqiao; Han, Junjie; Li, Bao; Liu, Li; Liu, Hongwei

doi:10.1016/j.fitote.2018.01.016

Cited by 12 publications

(8 citation statements)

References 14 publications

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“…Among the components that have been identified from CB08035-SYP and CB08035-SCA extracts are included phenyl-acetic acid, 4hydroxyphenyl-acetic acid, 3-chloro-4-hydoxyphenyl-acetic acid and a mixture of unidentified diketopiperazines (Davis et al, 2005;Evidente, et al, 2005;Seya et al, 1989). Important substrates for the gut microbiota include natural antioxidants including phenylacetic acid derivatives (Nahar et al, 2005) and diketopiperazines (Prakash et al, 2002;Borthwick, 2012;Sun et al, 2018). Hence these extracts reveal to be a promising source of compounds with potential against oxidative stress.…”

Section: Introductionmentioning

confidence: 99%

Protective effects of culture extracts (CB08035-SCA and CB08035-SYP) from Marinobacter hydrocarbonoclasticus (strain CB08035) against oxidant-induced stress in human colon carcinoma Caco-2 cells

Martínez

Arés

Martínez

et al. 2020

Food and Chemical Toxicology

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Section: Introductionmentioning

confidence: 99%

Protective effects of culture extracts (CB08035-SCA and CB08035-SYP) from Marinobacter hydrocarbonoclasticus (strain CB08035) against oxidant-induced stress in human colon carcinoma Caco-2 cells

Martínez

Arés

Martínez

et al. 2020

Food and Chemical Toxicology

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“…Investigation on the biological activities of prenylated DKP alkaloids disclosed antioxidant activity in the literature [ 27 , 28 ]. It is reported that excessive accumulation of free radical and synchronous reduced the antioxidant defense mechanisms and can induce complications of diabetes mellitus [ 15 ].…”

Section: Resultsmentioning

confidence: 99%

Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c

Huang

et al. 2021

Marine Drugs

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Six new DIKETOPIPERAZINE alkaloids aspergiamides A–F (1–6), together with ten known alkaloids (7–16), were isolated from the mangrove endophytic fungus Aspergillus sp. 16-5c. The structures of the new compounds were elucidated based on 1D/2D NMR spectroscopic and HR-ESIMS data analyses. The absolute configurations of aspergiamides A-F were established based on the experimental and calculated ECD data. All the compounds were evaluated for the antidiabetic activity against α-glucosidase and PTP1B enzyme. The bioassay results disclosed compounds 1 and 9 exhibited significant α-glucosidase inhibitory with IC50 values of 18.2 and 7.6 μM, respectively; compounds 3, 10, 11, and 15 exhibited moderate α-glucosidase inhibition with IC50 values ranging from 40.7 to 83.9 μM; while no compounds showed obvious PTP1B enzyme inhibition activity.

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“…The theoretical approach is important, especially for DKPs that are not readily obtained by synthesis. In fact, theoretical ECD has recently become an important approach for stereochemical analysis of structurally complex DKPs from natural sources [ 21 , 22 ]. Another possible alternative approach is the use of vibrational CD (VCD), which has become a powerful method for determining absolute configuration of natural products [ 23 ].…”

Section: Discussionmentioning

confidence: 99%

Unambiguous Stereochemical Assignment of Cyclo(Phe-Pro), Cyclo(Leu-Pro), and Cyclo(Val-Pro) by Electronic Circular Dichroic Spectroscopy

et al. 2021

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2,5-diketopiperazines (DKPs) are cyclic dipeptides ubiquitously found in nature. In particular, cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) are frequently detected in many microbial cultures. Each of these DKPs has four possible stereoisomers due to the presence of two chirality centers. However, absolute configurations of natural DKPs are often ambiguous due to the lack of a simple, sensitive, and reproducible method for stereochemical assignment. This is an important problem because stereochemistry is a key determinant of biological activity. Here, we report a synthetic DKP library containing all stereoisomers of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro). The library was subjected to spectroscopic characterization using mass spectrometry, NMR, and electronic circular dichroism (ECD). It turned out that ECD can clearly differentiate DKP stereoisomers. Thus, our ECD dataset can serve as a reference for unambiguous stereochemical assignment of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) samples from natural sources. The DKP library was also subjected to a biological screening using assays for E. coli growth and biofilm formation, which revealed distinct biological effects of cyclo(D-Phe-L-Pro).

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Diketopiperazines and 2H-pyran-2-ones with antioxidant activity from the rice fermented with Aspergillus luchuensis

Cited by 12 publications

References 14 publications

Protective effects of culture extracts (CB08035-SCA and CB08035-SYP) from Marinobacter hydrocarbonoclasticus (strain CB08035) against oxidant-induced stress in human colon carcinoma Caco-2 cells

Protective effects of culture extracts (CB08035-SCA and CB08035-SYP) from Marinobacter hydrocarbonoclasticus (strain CB08035) against oxidant-induced stress in human colon carcinoma Caco-2 cells

Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c

Unambiguous Stereochemical Assignment of Cyclo(Phe-Pro), Cyclo(Leu-Pro), and Cyclo(Val-Pro) by Electronic Circular Dichroic Spectroscopy

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