The edible seaweed Laminaria japonica contains cholesterol analogues that inhibit Lipid Peroxidation and Cyclooxygenase Enzymes

In this study, 5 sterols were isolated and purified from Laminaria japonica, commonly known as edible brown seaweed, and their structures were identified based on detailed chemical methods and spectroscopic analyses. Spectroscopic analyses characterized 5 sterols as 29-Hydroperoxy-stigmasta-5,24(28)-dien-3β-ol, saringosterol (24-vinyl-cholest-5-ene-3β,24-diol), 24-methylenecholesterol, fucosterol (stigmasta-5,24-diene-3β-ol), and 24-Hydroperoxy-24-vinyl-cholesterol. The bioactivities of these sterols were tested using lipid peroxidation (LPO) and cyclooxygenase (COX-1 and −2) enzyme inhibitory assays. Fucosterol exhibited the highest COX-1 and −2 enzyme inhibitory activities at 59 and 47%, respectively. Saringosterol, 24-methylenecholesterol and fucosterol showed higher LPO inhibitory activity at >50% than the other compounds. In addition, the results of molecular docking revealed that the 5 sterols were located in different pocket of COX-1 and −2 and fucosterol with tetracyclic skeletons and olefin methine achieved the highest binding energy (−7.85 and −9.02 kcal/mol) through hydrophobic interactions and hydrogen bond. Our results confirm the presence of 5 sterols in L. japonica and its significant anti-inflammatory and antioxidant activity.Graphical abstractHighlightsSterols 29-hydroperoxy-stigmasta-5,24(28)-dien-3β-ol and 24-hydroperoxy-24-vinyl-cholesterol are identified for the first time in L. japonica.Saringosterol, 24-methylenecholesterol and fucosterol showed strong LPO inhibitory activity.Fucosterol showed highest binding affinity for COX-1 and −2 enzymes through hydrophobic interactions.

Barley Melanoidins: Key Dietary Compounds With Potential Health Benefits

This paper is a review of the potential health benefits of barley melanoidins. Food melanoidins are still rather understudied, despite their potential antioxidant, antimicrobial, and prebiotic properties. Free radicals are villainous substances in humans produced as metabolic byproducts and causing cancers and cardiovascular diseases, and the melanoidins alleviate the effects of these free radicals. Malt is produced from cereal grains such as barley, wheat, and maize, and barley is predominantly used in beer production. Beer (alcoholic and non-alcoholic) is a widely consumed beverage worldwide and a good source of dietary melanoidins, which enhance the beers' flavor, texture, and sensorial properties. Melanoidins, the final products of the Maillard reaction, are produced at different stages during the brewing process. Beer melanoidins protect the cells from oxidative damage of DNA. The high reducing capacity of melanoidins can induce hydroxyl radicals from H2O2 in the presence of ferric ion (Fe3+). Melanoidins inhibit lipid peroxidation during digestion due to their chelating metal property. However, lower digestibility of melanoidins leads to less availability to the organisms but is considered to function as dietary fiber that can be metabolized by the lower gut microbiota and possibly incur prebiotic properties. Melanoidins promote the growth of Lactobacilli and Bifidobacteria in the gastrointestinal tract, preventing the colonization of potential pathogens. Barley is already popular through beer production and increasingly as a functional food. Considering this economic and industrial importance, more research to explore the chemical properties of barley melanoidins and corresponding health benefits as barley is warranted.

Pyrazoles and Pyrazolines as Anti-Inflammatory Agents

The five-membered heterocyclic group of pyrazoles/pyrazolines plays important role in drug discovery. Pyrazoles and pyrazolines present a wide range of biological activities. The synthesis of the pyrazolines and pyrazole derivatives was accomplished via the condensation of the appropriate substituted aldehydes and acetophenones, suitable chalcones and hydrazine hydrate in absolute ethanol in the presence of drops of glacial acetic acid. The compounds are obtained in good yields 68–99% and their structure was confirmed using IR, 1H-NMR, 13C-NMR and elemental analysis. The novel derivatives were studied in vitro for their antioxidant, anti-lipid peroxidation (AAPH) activities and inhibitory activity of lipoxygenase. Both classes strongly inhibit lipid peroxidation. Compound 2g was the most potent lipoxygenase inhibitor (IC50 = 80 µM.) The inhibition of the carrageenin-induced paw edema (CPE) and nociception was also determined, with compounds 2d and 2e being the most potent. Compound 2e inhibited nociception higher than 2d. Pyrazoline 2d was found to be active in a preliminary test, for the investigation of anti-adjuvant-induced disease (AID) activity. Pyrazoline derivatives were found to be more potent than pyrazoles. Docking studies of the most potent LOX inhibitor 2g highlight hydrophobic interactions with VAL126, PHE143, VAL520 and LYS526 and a halogen bond between the chlorine atom and ARG182.

Oxidative Stability, Microbial Safety, and Sensory Properties of Flaxseed (Linum usitatissimum L.) Oil Infused with Spices and Herbs

In our study, we assessed whether the addition of basil, fennel, oregano, rosemary, and chili can improve oxidative stability and sensory properties of flaxseed oil (FO) during 180 days of storage or induce oil contamination by microorganisms. Results showed that addition of spices and herbs in FO affected the hydrolytic changes, but far less than 2% of free fatty acids after storage, which was in line with regulations. Further, the addition of spices and herbs in FO decreased peroxide value (even up to 68.7% in FO with oregano) vs. FO whose value increased during storage, indicating increased oxidative stability and prolongation of shelf life of infused oils. The antioxidant activity of the infused oils ranged from 56.40% to 97.66%. In addition, the phenol content was higher in all infused oils (6.81–22.92 mg/kg) vs. FO (5.44 mg/kg), indicating that herbs and spices could scavenge free radicals and inhibit lipid peroxidation, while sensory analysts showed that FO infused with chili had the lowest bitterness intensity. According to the presence of certain microorganisms, results highlighted the need to develop new methods for inactivating microorganisms that would not only provide a microbial safety, but also preserve the beneficial properties of the oils/products.

Combined Lycium babarum polysaccharides and C-phycocyanin increase gastric Bifidobacterium relative abundance and protect against gastric ulcer caused by aspirin in rats

Background Non-steroidal anti-inflammatory drugs such as aspirin are used for the treatment of cardiovascular disease. Chronic use of low-dose aspirin is associated with the occurrence of gastric ulcer. The aim of this study was to investigate the healing potential of Lycium barbarum polysaccharides (LBP) from Chinese Goji berry and C-phycocyanin (CPC) from Spirulina platensis on gastric ulcer in rats. Methods Male Sprague–Dawley rats were divided into five groups: normal, aspirin (700 mg/kg bw), LBP (aspirin + 100 mg/kg bw/d LBP), CPC (aspirin + 50 mg/kg bw/d CPC), and MIX (aspirin + 50 mg/kg bw/d LBP + 25 mg/kg bw/d CPC) groups. Gastric ulcer was developed by daily oral feeding of aspirin for 8 weeks. Treatments were given orally a week before ulcer induction for 9 weeks. Results The MIX group elevated gastric cyclooxygenase-1, prostaglandin E2, and total nitrite and nitrate levels by 139%, 86%, and 66%, respectively, compared with the aspirin group (p < 0.05). Moreover, the MIX group reduced lipid peroxides malondialdehyde levels by 78% (p < 0.05). The treatment of LBP and/or CPC increased gastric Bifidobacterium relative abundance by 2.5–4.0 times compared with the aspirin group (p < 0.05). Conclusions We conclude that combined LBP and CPC enhance gastroprotective factors, inhibit lipid peroxidation, and increase gastric Bifidobacterium relative abundance. Combined LBP and CPC have protective potential against gastric ulcer caused by aspirin in rats.

Neuroprotective Effects of Medicinal Plants in Cerebral Hypoxia and Anoxia: A Systematic Review

Background: Hypoxia and anoxia are dangerous and sometimes irreversible complications in the central nervous system (CNS), which in some cases lead to death. Objective: The aim of this review was to investigate the neuroprotective effects of medicinal plants in cerebral hypoxia and anoxia. Methods: The word hypox*, in combination with some herbal terms such as medicinal plant, phyto* and herb*, was used to search for relevant publications indexed in the Institute for Scientific Information (ISI) and PubMed from 2000-2019. Results: Certain medicinal plants and herbal derivatives can exert their protective effects in several ways. The most important mechanisms are the inhibition of inducible nitric oxide synthase (iNOS), production of NO, inhibition of both hypoxia-inducible factor 1α and tumor necrosis factor-alpha activation, and reduction of extracellular glutamate, N-Methyl-D-aspartic and intracellular Ca (2+). In addition, they have an antioxidant activity and can adjust the expression of genes related to oxidant generation or antioxidant capacity. These plants can also inhibit lipid peroxidation, up-regulate superoxide dismutase activity and inhibit the content of malondialdehyde and lactate dehydrogenase. Moreover, they also have protective effects against cytotoxicity through down-regulation of the proteins that causes apoptosis, anti-excitatory activity, inhibition of apoptosis signaling pathway, reduction of pro-apoptotic proteins, and endoplasmic reticulum stress that causes apoptosis during hypoxia, increasing anti-apoptotic protein, inhibition of protein tyrosine kinase activation, decreasing proteases activity and DNA fragmentation, and upregulation of mitochondrial cytochrome oxidase. Conclusion: The results indicated that medicinal plants and their compounds mainly exert their neuroprotective effects in hypoxia via regulating proteins that are related to antioxidant, anti-apoptosis and anti-inflammatory activities.

5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

The five membered heterocyclic oxazole group plays an important role in drug discovery. Oxazolones present a wide range of biological activities. In this article the synthesis of 4-substituted-2-phenyloxazol-5(4H)-ones from the appropriate substituted aldehydes via an Erlenmeyer–Plochl reaction is reported. Subsequently, the corresponding benzamides were produced via a nucleophilic attack of a secondary amine on the oxazolone ring applying microwave irradiation. The compounds are obtained in good yields up to 94% and their structures were confirmed using IR, 1H-NMR, 13C-NMR and LC/MS data. The in vitro anti-lipid peroxidation activity and inhibitory activity against lipoxygenase and trypsin induced proteolysis of the novel derivatives were studied. Inhibition of carrageenin-induced paw edema (CPE) and nociception was also determined for compounds 4a and 4c. Oxazolones 2a and 2c strongly inhibit lipid peroxidation, followed by oxazolones 2b and 2d with an average inhibition of 86.5%. The most potent lipoxygenase inhibitor was the bisbenzamide derivative 4c, with IC50 41 μM. The benzamides 3c, 4a–4e and 5c were strong inhibitors of proteolysis. The replacement of the thienyl moiety by a phenyl group does not favor the protection. Compound 4c inhibited nociception higher than 4a. The replacement of thienyl groups by phenyl ring led to reduced biological activity. Docking studies of the most potent LOX inhibitor highlight interactions through allosteric mechanism. All the potent derivatives present good oral bioavailability.

The Possible Protective Effect of Resveratrol on DiazinonInduced Oxidative Stress and Hepatic Injury

Diazinon, one of the most known organophosphate pesticides (OPs), has harmful effects on human organs. Acetylcholinesterase inhibition, oxidative stress, and inflammation are the major mechanisms of diazinon toxicity. Diazinon has several toxic effects on the liver. Resveratrol (RES) is a natural polyphenol compound with antitumor, anti-diabetic, anti-obesity, anti-oxidant, anti-aging, and anti-inflammatory effects. This compound can inhibit lipid peroxidation, protein oxidation, and DNA damage. Moreover, it can induce sirt-1, PI3K/AKT, and HO-1 pathways (negative regulators of inflammatory pathways). A large body of evidence indicated that resveratrol can attenuate liver damage by organophosphates. In this short review, we discuss the significant role of this phytoestrogen and antioxidant against the hepatotoxic effect of diazinon as an OP. With elucidation of the role of this supplement in reducing harmful effects of diazinon, it can be used as a protective agent in people at risk of adverse effects of diazinon.

Evaluating the In Vitro Potential of Natural Extracts to Protect Lipids from Oxidative Damage

Lipid peroxidation is a chemical reaction known to have negative impacts on living organisms’ health and on consumer products’ quality and safety. Therefore, it has been the subject of extensive scientific research concerning the possibilities to reduce it, both in vivo and in nonliving organic matrices. It can be started by a variety of oxidants, by both ROS-dependent and -independent pathways, all of them reviewed in this document. Another feature of this reaction is the capacity of lipid peroxyl radicals to react with the non-oxidized lipids, propagating the reaction even in the absence of an external trigger. Due to these specificities of lipid peroxidation, regular antioxidant strategies—although being helpful in controlling oxidative triggers—are not tailored to tackle this challenge. Thus, more suited antioxidant compounds or technologies are required and sought after by researchers, either in the fields of medicine and physiology, or in product development and biotechnology. Despite the existence of several laboratory procedures associated with the study of lipid peroxidation, a methodology to perform bioprospecting of natural products to prevent lipid peroxidation (a Lipid Peroxidation Inhibitory Potential assay, LPIP) is not yet well established. In this review, a critical look into the possibility of testing the capacity of natural products to inhibit lipid peroxidation is presented. In vitro systems used to peroxidize a lipid sample are also reviewed on the basis of lipid substrate origin, and, for each of them, procedural insights, oxidation initiation strategies, and lipid peroxidation extent monitoring are discussed.

KOMBINASI ASAP CAIR TONGKOL JAGUNG (Zea mays L.) DAN SARI LEMON CUI (Citrus microcarpa) DALAM MENGHAMBAT PEMBENTUKAN PEROKSIDASI LIPID

ABSTRAKPenelitian ini bertujuan untuk mempelajari kombinasi asap cair tongkol jagung dan sari lemon cui dalam menghambat pembentukkan peroksidasi lipid. Penelitian ini menggunakan metode untuk menganalisis kandungan total fenolik, penangkal radikal bebas (DPPH), uji vitamin C dan peroksidasi lipid dengan menggunakan spektrofotometer UV-Vis. Hasil penelitian menunjukkan kandungan total fenolik dari kombinasi asap cair tongkol jagung dan sari lemon F1 (57,94 µg/mL), F2 (82,21 µg/mL), F3 (77,85 µg/mL) F4 (59,94 µg/ mL) dan F5 (93,94 µg/mL). Penangkal radikal bebas (DPPH) kombinasi asap cair tongkol jagung dan sari lemon cui F1 (78,20%), F2 (68,76%), F3 (73,93%) F4 (75,10%) dan F5 (65,75%). Kandungan vitamin C dari kombinasi asap cair tongkol jagung dan sari lemon cui F2 (73,04 µg/mL), F3 (25,25 µg/mL), F4 (183,04 µg/mL) dan F5 (292,16 µg/mL). Kombinasi dari asap cair tongkol jagung dan sari lemon cui dalam penghambat pembentukkan peroksidasi lipid pada ikan cakalang dengan konsentrasi 10% tanpa kombinasi asap cair tongkol jagung dan sari lemon cui menunjukkan peroksidasi lipid yang tinggi yaitu 1,217 dalam empat hari. Kombinasi asap cair tongkol jagung dan sari lemon cui mengandung fenolik yang bertindak sebagai antioksidan dan dapat menghambat peroksidsi lipid pada ikan cakalang. ABSTRACTSersermudy et al., 2019. This research aims to study a combination of corncob liquid smoke and cui lemon juice in inhibiting the formation of lipid peroxidation. This research used a method to analyze the content of total phenolic, free radicidal (DPPH), vitamin C and lipid peroxidation using a UV-Vis spectrophotometer. The results showed a combination of total phenolic from a combination of corncobs and lemon juice F1 57.94 F2 82.21 F3 77.85 F4 59.94 and F5 93.94 μg / mL. Free radical scavenging (DPPH) a combination of liquid corncob and lemon juice cui F1 (78.20%), F2 (68.76%) F3 (73.93%), F4 (75.10%) and F5 (65.75%). Vitamin C content from a combination of liquid corncob smoke and lemon juice cui F2 (73.04 µg/mL), F3 (125.25 µg/mL) F4 (183.04 µg/mL) and F5 (292.16 μg/mL). The combination of corncob liquid smoke and cui lemon juice in the formation of lipid peroxidation in 10% of skipjack tuna without the combination of corn cob liquid smoke and cui lemon juice showed high lipid peroxidation of 1.217 in four days. The combination of corncob liquid smoke and lemon cui juice contains phenolic which acts as an antioxidant and can inhibit lipid peroxidation in skipjack.