1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose (PGG) analogs: design, synthesis, anti-tumor and anti-oxidant activities

Shaikh, Qurat-ul-ain; Yang, Meng; Memon, Khadim Hussain; Lateef, Mehreen; Du, Na; Wan, Shengbiao; Deslandes, Éric; Zhang, Lijuan; Tao, Jiang

doi:10.1016/j.carres.2016.04.021

Cited by 26 publications

(17 citation statements)

References 34 publications

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“…In the HPLC/ESI/MS analysis four gallotannins were identified. published a review article about penta-galloyl glucose, 36 showing that this molecule has important functional properties as an antimicrobial, 37 anti-inflammatory, 38 anticarcinogenic, 39 and antidiabetic agent. 40 The main polyphenol xanthone identified in the in mango by-products.…”

Section: Identification Of Polyphenolic Compounds By Hplc/esi/ms Analysismentioning

confidence: 99%

Ultrasound‐microwave‐assisted extraction of polyphenolic compounds from Mexican “Ataulfo” mango peels: Antioxidant potential and identification by HPLC/ESI/MS

Ordoñez-Torres

Torres-León

Hernández‐Almanza

et al. 2020

Phytochemical Analysis

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Introduction: Mango is used in traditional medicine in many countries. However, the processing by-products are not currently used and generate large pollution problems and high handling costs.Objective: To study the effect of different parameters in the extraction of polyphenolic compounds from mango peels using modern and ecological ultrasound-microwave-assisted extraction technology.Methodology: Various parameters of these processes were studied: the extract was recovered by liquid chromatography using Ambetlite XAD-16. The total polyphenol content was determined by Folin-Ciocalteu's and HCl-butanol methods. Antioxidant activity was determined by 2,2 0 -azino-bis (3-ethylbenzothiazoline-6-sulphonic acid (ABTS+), 1,10-diphenyl-2-20-picrylhydrazyl (DPPH), and lipid oxidation inhibition methods. The recovered compounds were identified by high-performance liquid chromatography-mass spectrometry (HPLC-MS).Results: The best extraction conditions were solid/liquid ratio of 1/5 g/mL, ethanol percentage of 50%, and an extraction time of 10 min. Under these conditions, the total polyphenol content was 54.15 mg/g, and the antioxidant activities were greater than 90% inhibition in the three assays evaluated. According to the high-performance liquid chromatography/electrospray ionization/mass spectrometry (HPLC/ESI/MS) analysis, nine polyphenolic compounds were identified; most of them were gallotannins, such as pentagalloyl glucose. Conclusion:Ultrasound-microwave-assisted extraction was shown to be effective and allowed the recovery of antioxidant polyphenolic compounds. The results indicated that mango peel extracts can be used as natural antioxidant components in the pharmaceutical and functional food industries.Anahi Ordoñez-Torres and Cristian Torres-León contributed equally to this work.

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Section: Identification Of Polyphenolic Compounds By Hplc/esi/ms Analysismentioning

confidence: 99%

Ultrasound‐microwave‐assisted extraction of polyphenolic compounds from Mexican “Ataulfo” mango peels: Antioxidant potential and identification by HPLC/ESI/MS

Ordoñez-Torres

Torres-León

Hernández‐Almanza

et al. 2020

Phytochemical Analysis

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“…However, debenzylation failed even after 48 h; (2) TiCl 4 in dry DCM at −20 °C under Ar for 1 h, previously used for synthesis of 1,2,3,4,6-penta-caffeoyl- d -glucopyranose with intact olefinic bonds [30], gave only the saturated product 10 in our hands; (3) Different polyhydroxycinnamic acids were reported to be debenzylated using AlCl 3 /DMAP in dry DCM (0 °C, 48 h) [31], debenzylation of our compound 39 using this approach was unsuccessful as no reaction occurred. Therefore, we were unable to obtain respective cinnamic acid derivatives.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues

Heřmánková-Vavříková

Křenková

Petrásková

et al. 2017

IJMS

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Isoquercitrin, (IQ, quercetin-3-O-β-d-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6″. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin). The enzymatic procedure gave no products with “hydroxyaromatic” acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case of p-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. Reducing capacity of the cinnamate, gallate and 4-hydroxyphenylpropanoate towards Folin-Ciocalteau reagent was significantly lower than that of IQ, while other derivatives displayed slightly better or comparable capacity. Compared to isoquercitrin, most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, but they showed significantly better 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS) scavenging activity and were substantially more active in the inhibition of tert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes. The most active compounds were the hydroxyphenylpropanoates.

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“… 9 Finally, PGG treatment was determined to be safe locally and systemically, which has been supported by others. 11 , 19 …”

Section: Discussionmentioning

confidence: 99%

Chemical stabilization of the extracellular matrix attenuates growth of experimentally induced abdominal aorta aneurysms in a large animal model

Simionescu

Casco

Turner³

et al. 2020

JVS-Vascular Science

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Objective The goal of the present study was to test the safety and efficacy of chemical stabilization of the arterial extracellular matrix as a novel nonoperative treatment of abdominal aortic aneurysms (AAAs) in a clinically relevant large animal model. Methods To achieve matrix stabilization, we used 1,2,3,4,6-pentagalloylglucose (PGG), a noncytotoxic polyphenolic agent capable of binding to and stabilizing elastin and collagen against the action of degrading enzymes. We first optimized the therapeutic PGG formulation and time of exposure by in vitro testing on porcine aortas using phenol histologic staining with iron chloride, elastic recoil assays, and PGG quantification as a function of tissue thickness. We then induced AAAs in 16 swine using sequential balloon angioplasty and elastase/collagenase and calcium chloride treatment of the infrarenal segment. We monitored AAA induction and development using digital subtraction angiography. At 2 weeks after induction, after the AAAs had reached ∼66% arterial expansion, the swine were randomly assigned to 2 groups. In the treatment group, we delivered PGG to the aneurysmal aorta endoluminally using a weeping balloon and evaluated the AAA diameters using digital subtraction angiography for another 10 weeks. The control swine did not receive any treatment. For the safety evaluation, we collected blood and performed comprehensive metabolic panels and complete blood counts every 2 to 3 weeks for all the animals. The swine were routinely monitored for neurologic and physical attributes such as behavior, inactivity, alertness, appetite, discomfort, and weight gain. After euthanasia and full necropsy, we analyzed the AAA tissue samples for PGG content, elastic recoil, and histologic features. Results In vitro, a single 2.5-minute intraluminal delivery of 0.3% PGG to the swine aorta was sufficient for PGG to diffuse through the entire thickness of the porcine arterial tissues and to bind with high affinity to the elastic lamellae, as seen by positive iron chloride staining, a reduction of elastic recoil, and an increase in PGG content. In vivo, the control swine AAA tissues were thickened and showed the typical aspects of AAA, including chronic inflammation, adventitial reactivity, smooth muscle cell proliferation, elastic lamellae degradation, and medial and adventitial calcification. Similar aspects were noted in the PGG-treated arteries, except for the lack of calcification and an apparent diminished hyperplasia. PGG treatment was effective in reducing AAA expansion and reversing the process of AAA dilation by reducing the aortic diameters to ≤30% by week 12 ( P < .05). PGG was specifically localized to the aneurysmal segments as seen by histologic examination, the reduction of elastic recoil, and an increase in PGG content. PGG treatment did not affect the swine's neurologic or physical attributes, weight, blood chemistry, blood cells, or functionality of remote orga...

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1,2,3,4,6-Pentakis[-O-(3,4,5-trihydroxybenzoyl)]-α,β-D-glucopyranose (PGG) analogs: design, synthesis, anti-tumor and anti-oxidant activities

Cited by 26 publications

References 34 publications

Ultrasound‐microwave‐assisted extraction of polyphenolic compounds from Mexican “Ataulfo” mango peels: Antioxidant potential and identification by HPLC/ESI/MS

Ultrasound‐microwave‐assisted extraction of polyphenolic compounds from Mexican “Ataulfo” mango peels: Antioxidant potential and identification by HPLC/ESI/MS

Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues

Chemical stabilization of the extracellular matrix attenuates growth of experimentally induced abdominal aorta aneurysms in a large animal model

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