Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents

Bi, Jingjie; Wang, Wenqing; Du, Junxi; Chen, Kun; Cheng, Kui

doi:10.1016/j.ejmech.2019.06.059

Cited by 12 publications

(6 citation statements)

References 31 publications

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“…3). A closer look at the planar structure of compound 2 showed that it was constituted of a galloyl [21] and ethyl α -D-glucopyranoside [22]. Thus, compound 2 was identified as ethyl- O -(3′ -O -galloyl)- α - d -glucopyranoside.…”

Section: Results Discussion and Conclusionmentioning

confidence: 99%

Two New Phenolic Constituents from the Stems of Euphorbia griffithii

Kaunda

Zhang

2019

Nat. Prod. Bioprospect.

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Phytochemical studies on MeOH extract of stems of Euphorbia griffithii led to the isolation of one new hydrolyzable tannin dimer, corilagiffithiin (1) and one new galloyl-glucoside (2), alongside six known ones (3–8). Their structures and absolute configurations were determined by in depth spectroscopic analyses and comparison of their 1D NMR and MS data with literature reported values. Configurations of sugar moieties were determined by acidic hydrolysis and subsequent GC analysis of their corresponding trimethylsilylated l-cysteine adduct. At a concentration of 50 μM, compounds 1–3 showed no anti-inflammatory activities.Graphic Abstract Electronic supplementary materialThe online version of this article (10.1007/s13659-019-00223-2) contains supplementary material, which is available to authorized users.

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Section: Results Discussion and Conclusionmentioning

confidence: 99%

Two New Phenolic Constituents from the Stems of Euphorbia griffithii

Kaunda

Zhang

2019

Nat. Prod. Bioprospect.

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“…and our previous studies have shown that SAC-garlic acid conjugates have a good antiinflammatory effect [35]. In this study, we developed a new exogenous H 2 S donor drug MTC, and evaluated the biological activity and mechanism of MTC to further explore the protective mechanism of the drug against ischemia.…”

Section: Discussionmentioning

confidence: 99%

“…Low concentrations of exogenous H 2 S can protect neurons from ischemia-reperfusion injury [ 41 ]. Ischemia-reperfusion induces leukocyte activation that caused inflammation response [ 42 ], and our previous studies have shown that SAC-garlic acid conjugates have a good anti-inflammatory effect [ 35 ]. In this study, we developed a new exogenous H 2 S donor drug MTC, and evaluated the biological activity and mechanism of MTC to further explore the protective mechanism of the drug against ischemia.…”

Section: Discussionmentioning

confidence: 99%

“…Gallic acid and rivastigmine conjugate GA2 effectively prevented self-mediated Aβ aggregation as a new method against Alzheimer’s disease [ 34 ]. Previous studies in our laboratory have shown that SAC-garlic acid conjugates have good anti-inflammatory effect [ 35 ]. The above results suggest that the combination of the H 2 S donor derivative allylcysteine and gallic acid may have advantages over both neuroprotective and anti-inflammatory effects.…”

Section: Introductionmentioning

confidence: 99%

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The Protective Effects of Hydrogen Sulfide New Donor Methyl S-(4-Fluorobenzyl)-N-(3,4,5-Trimethoxybenzoyl)-l-Cysteinate on the Ischemic Stroke

Fan

Zhang

et al. 2022

Molecules

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In this paper, we report the design, synthesis and biological evaluation of a novel S-allyl-l-cysteine (SAC) and gallic acid conjugate S-(4-fluorobenzyl)-N-(3,4,5-trimethoxybenzoyl)-l-cysteinate (MTC). We evaluate the effects on ischemia-reperfusion-induced PC12 cells, primary neurons in neonatal rats, and cerebral ischemic neuronal damage in rats, and the results showed that MTC increased SOD, CAT, GPx activity and decreased LDH release. PI3K and p-AKT protein levels were significantly increased by activating PI3K/AKT pathway. Mitochondrial pro-apoptotic proteins Bax and Bim levels were reduced while anti-apoptotic protein Bcl-2 levels were increased. The levels of cleaved caspase-9 and cleaved caspase-3 were also reduced in the plasma. The endoplasmic reticulum stress (ERS) was decreased, which in turns the survival rate of nerve cells was increased, so that the ischemic injury of neurons was protected accordingly. MTC activated the MEK-ERK signaling pathway and promoted axonal regeneration in primary neurons of the neonatal rat. The pretreatment of MEK-ERK pathway inhibitor PD98059 and PI3K/AKT pathway inhibitor LY294002 partially attenuated the protective effect of MTC. Using a MCAO rat model indicated that MTC could reduce cerebral ischemia-reperfusion injury and decrease the expression of proinflammatory factors. The neuroprotective effect of MTC may be due to inhibition of the over-activation of the TREK-1 channel and reduction of the current density of the TREK1 channel. These results suggested that MTC has a protective effect on neuronal injury induced by ischemia reperfusion, so it may have the potential to become a new type of neuro-ischemic drug candidate.

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“…Aged garlic extract (Ohtani and Nishimura, 2020) Cancer, muscle atrophy Z-ajoene Crushed garlic (Lee et al, 2019a) Nephropathy Diallyl disulfide Garlic oil (Lin et al, 2019) Anti-inflammatory S-allyl-l-cysteine (SAC), SMU-8c Garlic acid conjugates (Bi et al, 2019) Liver Cancer…”

Section: Functional and Nutraceutical Propertiesmentioning

confidence: 99%

Garlic (Allium sativum L) and Its beneficial properties for health: A Review

Espinoza¹,

Valencia²,

Albarrán³

et al. 2020

Agroind. sci.

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Generally, chefs use garlic as an ingredient that enhances the sensory qualities of foods. However, recent studies have shown that garlic contains Sulphur compounds, which provide a health benefit. This review identifies and describes those constituents in garlic responsible for their anti-microbial, antioxidant, anti-inflammatory, and in some cases anti-cancer properties. Also, this review reports the chemical and nutritional contents of garlic (Allium sativum L.) and shows its health benefits for humans. A large variability and diversity in the nutritional content of garlic was found in the literature, including functional properties (antioxidant, antimicrobial, antifungal, and immunological), and many health benefit components, such as antihypertensive, hypolipidemic, antiatherogenic, anticarcinogenic, antitumor, antiaggregant, fibrinolytic, immunomodulatory, and antianemic. Allicin and ajoene were identified among some of the compounds in garlic which are beneficial for human health. Quantity varies depending on bulb maturity and harvest location, and values range between approximately 1mg/g and 9mg/g for allicin and 0.12 mg/g to 0.22 mg/g of garlic oil macerate for ajoene.

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Structure-activity relationship study and biological evaluation of SAC-Garlic acid conjugates as novel anti-inflammatory agents

Cited by 12 publications

References 31 publications

Two New Phenolic Constituents from the Stems of Euphorbia griffithii

Two New Phenolic Constituents from the Stems of Euphorbia griffithii

The Protective Effects of Hydrogen Sulfide New Donor Methyl S-(4-Fluorobenzyl)-N-(3,4,5-Trimethoxybenzoyl)-l-Cysteinate on the Ischemic Stroke

Garlic (Allium sativum L) and Its beneficial properties for health: A Review

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