HPLC-qTOF-MS/MS-Based Profiling of Flavan-3-ols and Dimeric Proanthocyanidins in Berries of Two Muscadine Grape Hybrids FLH 13-11 and FLH 17-66

Yuzuak, Seyit; Ballington, James R.; Xie, De‐Yu

doi:10.3390/metabo8040057

Cited by 64 publications

(42 citation statements)

References 24 publications

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“…From the group flavan-3-ols, all identified compound (monomers, dimers, trimers) were found in grape seed samples and their identification was largely based on the evaluated MS fragments and previously reported data about phytochemicals found in wine and grapes [27]. Presence of compounds 47 (gallocatechin), 54 (catechin), 56 (epigallocatechin), 60 (epicatechin), and 62 (catechin 3-O-gallate) were confirmed using available standards.…”

Section: Flavan-3-olsmentioning

confidence: 64%

Phenolic Profiles of Leaves, Grapes and Wine of Grapevine Variety Vranac (Vitis vinifera L.) from Montenegro

Šuković

Knežević

Gašić

et al. 2020

Foods

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Vranac, an old autochthonous red grapevine variety of Montenegro, was first mentioned in a historical document published in the 15th century. As currently the study of indigenous varieties is of particular importance, the subject of this work was detailed characterization of phenolic compounds in the autochthonous grapevine variety Vranac, from the Montenegrin Podgorica subregion. Phenolic profiles of leaves, berries (skin, seeds, and pulp were examined separately) and young monovarietal wine were determined using ultra-high performance liquid chromatography (UHPLC) with linear trap quadrupole (LTQ)—Orbitrap XL mass spectrometry (MS). Total phenolic content (TPC) and radical scavenging activity (RSA) were higher for the grape seeds extracts, followed by extracts of grape skins and pulps. As expected, the total anthocyanin content (TAC) was higher in grape skin than in wine. A total of one hundred twenty nine compounds (forty two phenolic acids and their derivatives, twenty three flavan-3-ols, twenty one flavanols, five stilbenes and thirty eight anthocyanins) were identified in the investigated extracts. To our best knowledge, this is the first report of tentative identification of (epi)catechin 3-O-coumarate in grape seed and chalcan-flavan 3-ol dimers in wine and grape seed.

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Section: Flavan-3-olsmentioning

confidence: 64%

Phenolic Profiles of Leaves, Grapes and Wine of Grapevine Variety Vranac (Vitis vinifera L.) from Montenegro

Šuković

Knežević

Gašić

et al. 2020

Foods

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“…Green tea (Zhao et al, 2017 ; Wang P. et al, 2020 ), two muscadine grape cultivar berries (including seeds and skin) (Yuzuak et al, 2018 ), and dark chocolate and cacao (Takahashi et al, 1999 ; Schewe et al, 2001 ) are rich in flavan-3-ol gallates and dimeric PAs. To understand whether these plant products could inhibit the M pro activity of SARS-Cov-2, we extracted flavan-3-ol gallates and dimeric PAs from the five types of materials and then completed in vitro assays.…”

Section: Resultsmentioning

confidence: 99%

“…This product is composed of newly leaves (0.8–1.2 cm in length) of early spring sprouts (harvested around April 5 every year), which were harvested in 2019. Ripen muscadine grape berries of FLH 13-11 and FLH 17-66 were collected in 2011 and 2012, ground into powder in liquid nitrogen, freeze dried, and stored in −80°C freezer (Yuzuak et al, 2018 ). Cacao ( Theobroma cacao ) seed powder and dark chocolate used were obtained from Ecuador in 2019.…”

Section: Methodsmentioning

confidence: 99%

“…Flavan-3-ols and proanthocyanidins (PAs) are two groups of plant flavonoids ( Figure 2 ; Xie and Dixon, 2005 ). They commonly exist in fruits, food products, and beverages, such as grape (Iacopini et al, 2008 ; Zhu et al, 2014 ; Yuzuak et al, 2018 ; Rousserie et al, 2019 ), strawberry (Lopez-Serrano and Barcelo, 1997 ; Fossen et al, 2004 ; Fischer et al, 2014 ), persimmon (Akagi et al, 2009 ), cranberry (Foo et al, 2000a , b ), blueberry (Gu et al, 2002 ), cacao nuts (Murphy et al, 2003 ; Miller et al, 2009 ), chocolate (Schewe et al, 2002 ; Serafini et al, 2003 ), green tea (Liu et al, 2012 ; Zhao et al, 2017 ; Wang P. et al, 2020 ), and wines (Monagas et al, 2003 ). Common flavan-3-ol aglycones in these plant products include (–)-epicatechin (EC), (+)-catechin (CA), (–)-epigallocatechin (EGC), (+)-gallocatechin (GC), (–)-epiafzelechin (EAF), and (+)-afzelechin (AF) ( Figure 2 ; Xie and Dixon, 2005 ).…”

Section: Introductionmentioning

confidence: 99%

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Docking Characterization and in vitro Inhibitory Activity of Flavan-3-ols and Dimeric Proanthocyanidins Against the Main Protease Activity of SARS-Cov-2

Zhu

Xie

2020

Front. Plant Sci.

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We report to use the main protease (Mpro) of SARS-Cov-2 to screen plant flavan-3-ols and proanthocyanidins. Twelve compounds, (–)-afzelechin (AF), (–)-epiafzelechin (EAF), (+)-catechin (CA), (–)-epicatechin (EC), (+)-gallocatechin (GC), (–)-epigallocatechin (EGC), (+)-catechin-3-O-gallate (CAG), (–)-epicatechin-3-O-gallate (ECG), (–)-gallocatechin-3-O-gallate (GCG), (–)-epigallocatechin-3-O-gallate (EGCG), procyanidin A2 (PA2), and procyanidin B2 (PB2), were selected for docking simulation. The resulting data predicted that all 12 metabolites could bind to Mpro. The affinity scores of PA2 and PB2 were predicted to be −9.2, followed by ECG, GCG, EGCG, and CAG, −8.3 to −8.7, and then six flavan-3-ol aglycones, −7.0 to −7.7. Docking characterization predicted that these compounds bound to three or four subsites (S1, S1′, S2, and S4) in the binding pocket of Mpro via different spatial ways and various formation of one to four hydrogen bonds. In vitro analysis with 10 available compounds showed that CAG, ECG, GCG, EGCG, and PB2 inhibited the Mpro activity with an IC50 value, 2.98 ± 0.21, 5.21 ± 0.5, 6.38 ± 0.5, 7.51 ± 0.21, and 75.3 ± 1.29 μM, respectively, while CA, EC, EGC, GC, and PA2 did not have inhibitory activities. To further substantiate the inhibitory activities, extracts prepared from green tea (GT), two muscadine grapes (MG), cacao, and dark chocolate (DC), which are rich in CAG, ECG, GAG, EGCG, or/and PB2, were used for inhibitory assay. The resulting data showed that GT, two MG, cacao, and DC extracts inhibited the Mpro activity with an IC50 value, 2.84 ± 0.25, 29.54 ± 0.41, 29.93 ± 0.83, 153.3 ± 47.3, and 256.39 ± 66.3 μg/ml, respectively. These findings indicate that on the one hand, the structural features of flavan-3-ols are closely associated with the affinity scores; on the other hand, the galloylation and oligomeric types of flavan-3-ols are critical in creating the inhibitory activity against the Mpro activity.

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“…Compounds eluted at 9.76 and 10.64 min, were assigned respectively to gallocatechin 3-O-glucoside and epigallocatechin 3-O-glucoside ( Figure 8) based on previous reported data concerning the flavan-3-ols fragmentation [41,42]. The losses of 162 and 178 Da, indicating the presence of an O-glucose unit, and the fragment ions m/z 345 and 275, common in flavan-3-ols (Figure 8), are the main characteristic of these compounds.…”

Section: Flavan-3-ol Derivativesmentioning

confidence: 99%

Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes

et al. 2020

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Ethnopharmacological surveys on Portuguese flora reveal that Genista tridentata L. is a shrub used in traditional medicine for the treatment of various inflammation-related health problems, although scientific support of its benefits is still necessary. In order to establish the anti-inflammatory potential of G. tridentata and support its traditional use, ethanolic extracts of three sections of the plant (root, stem, and leaves) were subjected to in vitro evaluation of anti-inflammatory activity using lipopolysaccharide (LPS)-stimulates macrophages as an inflammation model. Simultaneously, we also aimed to establish the extracts’ flavonoids profile. The ethanolic extracts, obtained by Soxhlet extraction, profile of the three sections confirmed their richness in flavonoids, being three prenylated flavonoids isolated and characterized in the root, including a new natural compound, the 3-methoxymundulin. The extracts from the three plant sections showed strong antioxidant activity at the cellular level and significantly inhibit the LPS-triggered NO production by downregulating Nos2 gene transcription and consequently iNOS expression. Additionally, root and stem extracts also decreased the LPS-induced transcription of the pro-inflammatory genes Il1b, Il6, and Ptgs2. Thus, the results support the anti-inflammatory properties attributed to G. tridentate preparations. Relevantly, the roots of the shrub, plant part not used, is an unexplored source of compounds with pharmacological and nutraceutical value.

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HPLC-qTOF-MS/MS-Based Profiling of Flavan-3-ols and Dimeric Proanthocyanidins in Berries of Two Muscadine Grape Hybrids FLH 13-11 and FLH 17-66

Cited by 64 publications

References 24 publications

Phenolic Profiles of Leaves, Grapes and Wine of Grapevine Variety Vranac (Vitis vinifera L.) from Montenegro

Phenolic Profiles of Leaves, Grapes and Wine of Grapevine Variety Vranac (Vitis vinifera L.) from Montenegro

Docking Characterization and in vitro Inhibitory Activity of Flavan-3-ols and Dimeric Proanthocyanidins Against the Main Protease Activity of SARS-Cov-2

Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes

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