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

2021 ◽  
Author(s):  
Xingyu Lu ◽  
Amila A. Dissanayake ◽  
Chuqiao Xiao ◽  
Jie Gao ◽  
Mouming Zhao ◽  
...  

AbstractIn 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.

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3439
Author(s):  
Martha Mantzanidou ◽  
Eleni Pontiki ◽  
Dimitra Hadjipavlou-Litina

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.


2011 ◽  
Vol 2011 ◽  
pp. 1-6 ◽  
Author(s):  
Vanisree Mulabagal ◽  
Ruby L. Alexander-Lindo ◽  
David L. DeWitt ◽  
Muraleedharan G. Nair

Tea prepared from the aerial parts ofAntigonon leptopusis used as a remedy for cold and pain relief in many countries. In this study,A. leptopustea, prepared from the dried aerial parts, was evaluated for lipid peroxidation (LPO) and cyclooxygenase (COX-1 and COX-2) enzyme inhibitory activities. The tea as a dried extract inhibited LPO, COX-1 and COX-2 enzymes by 78%, 38% and 89%, respectively, at 100 g/mL. Bioassay-guided fractionation of the extract yielded a selective COX-2 enzyme inhibitory phenolic aldehyde, 2,3,4-trihydroxy benzaldehyde. Also, it showed LPO inhibitory activity by 68.3% at 6.25 g/mL. Therefore, we have studied other hydroxy benzaldehydes and their methoxy analogs for LPO, COX-1 and COX-2 enzymes inhibitory activities and found that compound1gave the highest COX-2 enzyme inhibitory activity as indicated by a 50% inhibitory concentration (IC50) at 9.7 g/mL. The analogs showed only marginal LPO activity at 6.25 g/mL. The hydroxy analogs6,7and9showed 55%, 61% and 43% of COX-2 inhibition at 100 g/mL. However, hydroxy benzaldehydes3and12showed selective COX-1 inhibition while compounds4and10gave little or no COX-2 enzyme inhibition at 100 g/mL. At the same concentration, compounds14,21and22inhibited COX-1 by 83, 85 and 70%, respectively. Similarly, compounds18,19and23inhibited COX-2 by 68%, 72% and 70%, at 100 g/mL. This is the first report on the isolation of compound1fromA. leptopustea with selective COX-2 enzyme and LPO inhibitory activities.


1997 ◽  
Vol 99 (3) ◽  
pp. 385-390 ◽  
Author(s):  
A. Borrell ◽  
L. Carbonell ◽  
R. Farras ◽  
P. Puig-Parellada ◽  
A. F. Tiburcio

Dyslipidemia and oxidative modifications of lipid are frequently associated in patients with chronic kidney diseases (CKD) and considered the most important risk factors for cardiovascular events. Melatonin is a well-known potent antioxidant and has beneficial effect on lipid metabolism. the study was designed to evaluate if Melatonin could improve lipid profile and ameliorates lipid peroxidation. This single blind placebo controlled clinical study carried out on 41 patients with CKD who were randomized into two groups, control groups (n=20) those who received placebo cap and melatonin group those who received 5mg melatonin (n=21). Lipid profile [total cholesterol (TC), triglyceride (TG), high-density lipoprotein (HDL-C), low-density lipoprotein (LDL-C)] and parameters of lipid peroxidation [oxidized LDL (oxLDL) and malondialdehyde (MDA) were measured before and after 12 weeks of the treatment. After 12 weeks of treatment, melatonin significantly increased HDL-C and decreased LDL-C compared to the initial value. The elevation in HDL-C and reduction in LDL-C were significantly different from that in placebo group. Also, both oxLDL and MDA levels significantly lowered by melatonin compared to the baseline and to the placebo group. Collectively, the results of our study showed that melatonin has advantageous effect on lipid profile and inhibit lipid peroxidation in patients with CKD.


2021 ◽  
Vol 3 (8) ◽  
Author(s):  
Muhammad Yasir ◽  
Basit Zeshan ◽  
Nur Hardy A. Daud ◽  
Izzah Shahid ◽  
Hafza Khalid

Abstract There is a need for more efficient and eco-friendly approaches to overcome increasing microbial infections. Bacteriocins and chitinases from Bacillus spp. can be powerful alternatives to conventional antibiotics and antifungal drugs, respectively. The purpose of this study was to assess the inhibitory potential of bacteriocins and chitinase enzymes against multiple resistant bacterial and fungal pathogens. Bacterial isolates were selected by growth on minimal salts medium and after that were morphologically and biochemically characterized. The physiochemical characterization of bacteriocins was carried out. The inhibitory potential of bacteriocins towards six pathogenic bacteria was determined by the well diffusion assay while chitinase activity towards three fungal strains was determined by the dual plate culture assay. Two bacterial strains (WW2P1 and WRE4P2), out of nine showed inhibition of K. pneumonia, P. aeruginosa, E. coli and MRSA while WW4P2 was positive against S. typhimurium and E. coli and WRE10P2 against P. aeruginosa, S. pneumoniae. Two bacterial isolates (WW3P1 and WRE10P2) were chosen for further study on the basis of their antifungal activities. Of these, WW3P1 isolate was more effective against A. fumigatus as well as A. niger. The proteinaceous nature of the bacteriocins was confirmed by treatment of the crude extract with proteinase K. It was found that the inhibitory activity of strain WW3P1 against E. coli was highest at 20 °C, and against S. pneumoniae it was at 20 °C and pH 10 after treatment with EDTA. Inhibition by strain the WRE10P2 against P. aeruginosa was highest at 20 °C and pH 14. It was found that EDTA increased the inhibitory activity of strain WW2P1 against P. aeruginosa, K. pneumoniae and E. coli by 2 ± 0.235, 3.5 ± 0.288, 2.5 ± 1.040 times, respectively, of strain WRE4P2 against P. aeruginosa and E. coli by 2.5 ± 0.763, 2.7 ± 0.5 times, respectively, and of strain WRE10P2 against S. pneumoniae by 3 ± 0.6236 times. The isolates have promising inhibitory activity, which should be further analyzed for the commercial production of antimicrobials. Article highlights The current study aimed to isolate the microbiome from wheat plant (Triticum aestivum L.), to screen for bacteriocin production and to assess its antimicrobial activity against human pathogens. Forty-one phenotypically different bacterial colonies were subjected to bacteriocin purification from which 25 colonies showed positive reactions. These 25 bacterial isolates were screened against six different human bacterial pathogens using the well diffusion method to check the antimicrobial activity. Out of nine bacterial isolates, WW3P1 and WRE10P2 were able to degrade the chitin and utilize it as their sole energy source. Strain WRE4P2 exhibited partial inactivation in its activity against MRSA after treatment with proteinase K.


2018 ◽  
Vol 2 ◽  
Author(s):  
K.K. Asanka Sanjeewa ◽  
You-Jin Jeon

Seaweeds play a vital role as a source of food and ingredients in traditional Korean medicine. Koreans consume seaweed as fresh vegetables, salad, soups, or snacks. There are several edible brown seaweed species are abundant along the shores of the Korean peninsula, such as Ecklonia cava, Hizikia fusiforme, Laminaria japonica, Pelvetia siliquosa, Sargassum fulvellum, and Undaria pinnatifida. With the growing body of scientific evidence, it is clear that these brown seaweeds are not only good substitutes for land vegetables but also a good source of bioactive secondary metabolites. The secondary metabolites identified from edible Korean brown seaweeds (phlorotannins, sulfated polysaccharides, pigments, and sterols) have the potential to be developed as functional food ingredients. However, seaweeds consumption and their industrial level applications as functional materials are limited compared to the land vegetables. Insufficient awareness about health benefits of seaweeds might be the reason for this issue. Thus, in this review health promotion properties associated with edible Korean brown seaweeds are summarized. The present study might therefore increase consumption and industrial use of brown seaweeds.


2016 ◽  
Vol 51 (12) ◽  
pp. 1945-1953 ◽  
Author(s):  
Hong-Ting Victor Lin ◽  
Wen-Jung Lu ◽  
Guo-Jane Tsai ◽  
Chien-Te Chou ◽  
Hsin-I Hsiao ◽  
...  

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