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Antibacterial and antioxidant activity of naphthofuranquinones from the twigs of tropical mangrove Avicennia officinalis

Assaw S, Mohd Amir MIH, Khaw TT, Bakar K, Mohd Radzi SA, Mazlan NW

Nat Prod Res, 2020 Aug;34(16):2403-2406.
PMID: 30600710 DOI: 10.1080/14786419.2018.1538220

Mangrove plants are endowed with various biologically active compounds which have potent antibacterial and antioxidant properties. In present study, a bioactivity-guided fractionation for antibacterial and antioxidant active metabolites from the twigs of Avicennia officinalis collected from Kuala Selangor Nature Park, Selangor, Malaysia gave 13 major fractions. The antibacterial activity of A. officinalis fractions using well-diffusion showed strong selectivity on the Gram-positive bacteria (Staphylococcus epidermidis, S. aureus and Bacillus subtilis) with minimum inhibition concentration (MIC) values of 0.156-5.00 mg/mL. However, no antibacterial activities were observed on the Gram-negative bacteria (Vibrio cholera, Enterobacter cloacae and Escherichia coli). The active antibacterial fractions were further isolated using several chromatographic techniques to give two naphthofuranquinones, namely, avicenol C (1) and stenocarpoquinone B (2). Meanwhile, the antioxidant activity of A. officinalis fractions were evaluated using DPPH radical scavenging assay exhibited low antioxidant activities. Molecular structure of the naphthofuranquinones was elucidated using 1 D and 2 D NMR spectroscopy.

Matched MeSH terms: Quinones/isolation & purification*; Quinones/pharmacology
Fulltext Browning metabolism and quality of fresh-cut drumstick (Moringa oleifera) as influenced by acidulant treatments

Siddiqui MW, Homa F, Nayyer MA, Ghatak A, Yousuf B, Aftab MA, et al.

J Food Sci Technol, 2020 Jun;57(6):2010-2016.
PMID: 32431327 DOI: 10.1007/s13197-019-04233-3

Though fresh-cut products save our time, but they are very much prone to enzymatic browning that drastically affects product's quality and marketability. Drumstick pods are considered as super food due to high nutritional contents. However, the fresh-cut pods are prone to brown discoloration. The enzyme activities promote the softening and cut-surface browning of pods, thus deteriorates their texture, decreases consumer appeal and shortens the shelf life. So, we aimed to assess the effect of citric (1%) and ascorbic (1%) acid treatments on quality attributes of fresh-cut drumsticks at 3-d interval during storage (5 ± 1 °C). In general there was an increase in lignin and quinone contents, while phenolic content was decreased during storage. However, samples subjected to ascorbic acid dip had higher phenolic content, lower rate of lignin formation, and reduced membrane permeability. Enzyme activities (polyphenol oxidase and peroxidase) were found to increase during storage, however, samples treated with ascorbic acid showed lower activities than that of the control and citric acid treated samples. The reduced enzyme activities resulted in the reduced browning incidence and maintained the quality. Therefore, postharvest dip of fresh-cut drumstick in to ascorbic acid (1%) could be suggested to increase the shelf life with reduced browning during low temperature storage.

Matched MeSH terms: Quinones
Performance of sequencing batch biofilm and sequencing batch reactors in simultaneous p-nitrophenol and nitrogen removal

Goh CP, Seng CE, Sujari AN, Lim PE

Environ Technol, 2009 Jun;30(7):725-36.
PMID: 19705610 DOI: 10.1080/09593330902911689

The objective of this study is to evaluate the performance of sequencing batch biofilm reactors (SBBRs) and sequencing batch reactor (SBR) in the simultaneous removal of p-nitrophenol (PNP) and ammoniacal nitrogen. SBBRs involved the use of polyurethane sponge cubes and polyethylene rings, respectively, as carrier materials. The results demonstrate that complete removal of PNP was achievable for the SBR and SBBRs up to the PNP concentration of 350 mg/l (loading rate of 0.368 kg/m3 d). At this loading rate, the average ammoniacal nitrogen removal efficiency for the SBR and SBBR (with polyethylene rings) was reduced to 86% and 96%, respectively. However, the SBBR (with polyurethane sponge cubes) still managed to achieve an almost 100% ammoniacal nitrogen removal. Based on the results, the performance of the SBBRs was better than that of SBR in PNP and ammoniacal nitrogen removal. The results of the gas chromatography mass spectroscopy, high-performance liquid chromatography and ultraviolet-visible analyses indicate that complete mineralization of PNP was achieved in all of the reactors.

Matched MeSH terms: Quinones/chemistry
Quantitation of Protein Cysteine-Phenol Adducts in Minced Beef Containing 4-Methyl Catechol

Arsad SS, Zainudin MAM, De Gobba C, Jongberg S, Larsen FH, Lametsch R, et al.

J Agric Food Chem, 2020 Feb 26;68(8):2506-2515.
PMID: 32013414 DOI: 10.1021/acs.jafc.9b07752

Thiol groups of cysteine (Cys) residues in proteins react with quinones, oxidation products of polyphenols, to form protein-polyphenol adducts. The aim of the present work was to quantify the amount of adduct formed between Cys residues and 4-methylcatechol (4MC) in minced beef. A Cys-4MC adduct standard was electrochemically synthesized and characterized by liquid chromatography-mass spectrometry (LC-MS) as well as NMR spectroscopy. Cys-4MC adducts were quantified after acidic hydrolysis of myofibrillar protein isolates (MPIs) and LC-MS/MS analysis of meat containing either 500 or 1500 ppm 4MC and stored at 4 °C for 7 days under a nitrogen or oxygen atmosphere. The concentrations of Cys-4MC were found to be 2.2 ± 0.3 nmol/mg MPI and 8.1 ± 0.9 nmol/mg MPI in meat containing 500 and 1500 ppm 4MC, respectively, and stored for 7 days under oxygen. The formation of the Cys-4MC adduct resulted in protein thiol loss, and ca. 62% of the thiol loss was estimated to account for the formation of the Cys-4MC adduct for meat containing 1500 ppm 4MC. Furthermore, protein polymerization increased in samples containing 4MC as evaluated by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), and the polymerization was found to originate from protein-polyphenol interactions as evaluated by a blotting assay with staining by nitroblue tetrazolium.

Matched MeSH terms: Quinones/chemistry
Fulltext Demethylbelamcandaquinone B (Dmcq B) Is the Active Compound of Marantodes pumilum var. alata (Blume) Kuntze with Osteoanabolic Activities

Ahmad Hairi H, Jamal JA, Aladdin NA, Husain K, Mohd Sofi NS, Mohamed N, et al.

Molecules, 2018 Jul 11;23(7).
PMID: 29997309 DOI: 10.3390/molecules23071686

Phytoestrogens have attracted considerable attention for their potential in the prevention of postmenopausal osteoporosis. Recently, a phytoestrogen-rich herbal plant, Marantodes pumilum var. alata (Blume) Kuntze was reported to protect against bone loss in ovariectomized rat. However, the bioactive compound responsible for these effects and the underlying mechanism were not known. Through bioassay-guided isolation, demethylbelamcandaquinone B (Dmcq B) was isolated and identified from Marantodes pumilum var. alata leaf extract. In terms of its bone anabolic effects, Dmcq B was at par with 17β-estradiol (E2), in promoting the proliferation, differentiation and mineralization of osteoblast cells. Dmcq-B increased early differentiation markers, collagen content and enzymatic ALP activity. It was demonstrated to regulate BMP2 signaling pathway which further activated the transcription factor, osterix. Subsequently, Dmcq B was able to increase the osteocalcin expression which promoted matrix mineralization as evidenced by the increase in calcium deposition. Dmcq B also reduced the protein level of receptor activator of NF-κβ ligand (RANKL) and promoted osteoprotegerin (OPG) protein expression by osteoblast cells, therefore hastening bone formation rate by decreasing RANKL/OPG ratio. Moreover, Dmcq B was able to increase ER expression, postulating its phytoestrogen property. As the conclusion, Dmcq B is the active compound isolated from Marantodes pumilum var. alata leaves, regulating osteoanabolic activities potentially through the BMP2 and ER signaling pathways.

Matched MeSH terms: Quinones/pharmacology*; Quinones/chemistry
Fulltext What influences the use of local crude herbs among patients with chronic diseases? preliminary screening of phytochemicals

Deepa, R., Yin Yee, S., Afiqah Zulaikha R., Yun Li, C., Zhee Shah, C., Mei Ling, L., et al.

Malaysian Journal of Medicine and Health Sciences, 2019;15(102):51-51.
MyJurnal

Introduction: The use of crude herbs for well-being as well as curation and prevention of ailments is evident globally, including Malaysia. To understand the effectiveness and reliability, the presence of phytochemical compounds as the factor influencing the use of crude herbs shall be determined. This study was conducted to screen the presence of phytochemical compounds in the local crude herbs consumed by patients with chronic diseases. This is part of
a larger study, where a cross-sectional study was conducted and reported elsewhere. Methods: In total, 15 types of crude herbs were reported by the patients with chronic diseases attending government health clinic at Kampar, Perak. The herbs were extracted using hot and standard cold methods respectively. Results: All the 15 crude herbs’ hot and cold extracts revealed the presence of eight phytochemical compounds, namely, phenols, quinones, tannins, terpenoids, saponins, flavonoids, glycosides, and alkaloids at varying intensity. Saponins, alkaloids, and glycosides were present in all the crude herbs extracts. However, terpenoids, tannins, and phenols were absent in Orthosiphon stamineus, Clinacanthus nutans, and Pandanus amaryllifolius extracts respectively. However, the cold extracts exhibited a higher intensity of phytochemicals compared to hot extracts. The present study confirms the presence of
phytochemicals in the local crude herbs consumed by patients with chronic diseases. The screened phytochemicals are bioactive compounds that possess medicinal properties that may trigger the patients to treat their diseases’ underlying conditions. However, the use of prescribed medicine, particularly among aging patients must be taken into account while consuming crude herbs. Conclusion: The findings of this study indicate that structured-evidence based crude herbs use interventions for patients with chronic diseases is warranted.

Matched MeSH terms: Quinones
Fulltext Partial purification and characterization of polyphenol oxidase from round brinjal (S. melongena var. depressum)

Ng, A.W.R., Wong, C.W.

International Food Research Journal, 2015;22(2):826-831.
MyJurnal

Polyphenol oxidase (PPO) catalyzes the conversion of phenolic compounds into o-quinones which will lead to food browning. This phenomenon causes huge implications on food industries, as it degrades food quality over time. By combining both ammonium sulphate precipitation and gel filtration chromatography, PPO was partially purified up to 5.26-fold with 11.23% yield. The enzyme activity was 5120 EU/mL using 4-methylcatechol as substrate. Maximal PPO activity was found at 30oC, pH 5.0 for 4-methylcatechol and 40°C, pH 6.0 for catechol. The PPO showed a higher affinity towards 4-methylcatechol but higher thermal stability when reacting with catechol. The Km and Vmax values were 5.00 mM, 2000 EU/ml for 4-methylcatechol and 10.79 mM, 526.32 EU/ml for catechol. Energy for inactivation (Ea) obtained using 4-methylcatechol and catechol were 12.57 kJ/mol and 14.23 kJ/mol from respective substrates. Sodium disulfite was a better inhibitor where 79.17% of PPO inhibition was achieved. The isolation and characterization of round brinjal PPO serves as a guideline to predict the behavior of enzyme, leading to effective prevention of its browning during processing and storage.

Matched MeSH terms: Quinones
Chemical profile of compounds from lichens of Bukit Larut, Peninsular Malaysia

Laily B. Din, Zuriati Zakaria, Mohd Wahid Samsudin, Elix JA

Sains Malaysiana, 2010;39.

The lichen collection from Bukit Larut, Taiping, Malaysia in 1999 included Bulbothrix isidiza, Chrysothrix xanthina, Cladonia adspersa, C. verticillata, Coccocarpia palmicola, Heterodermia flabellata, H. japonica, H. obscurata, Hypotrachyna imbricatula, Leptogium azureum, Parmelinella wallichiana, Parmotrema tinctorum, P. clavuliferum, P. reticulatum, Pertusaria sp., Physma byrsaeum, Usnea baileyi and Usnea rubrotincta. Secondary metabolites could not be detected in three lichens, Coccocarpia palmicola, Leptogium azureum and Physma byrsaeum by HPLC and TLC analysis. The other 15 lichen species showed the presence of ten classes of compounds, depsides (10 compounds), depsidones (16), quinones (5), xanthones (2), naphthopyrones (1), pulvinic acid derivatives (1), diphenylethers (1), dibenzofurans (1), aliphatic acids (4) and terpenoids (3).

Matched MeSH terms: Quinones
Paracoccus rhizosphaerae sp. nov., isolated from the rhizosphere of the plant Crossostephium chinense (L.) Makino (Seremban)

Kämpfer P, Lai WA, Arun AB, Young CC, Rekha PD, Martin K, et al.

Int J Syst Evol Microbiol, 2012 Nov;62(Pt 11):2750-2756.
PMID: 22286908 DOI: 10.1099/ijs.0.039057-0

A Gram-negative, coccoid-shaped bacterium, strain CC-CCM15-8(T), was isolated from a rhizosphere soil sample of the plant Crossostephium chinense (L.) Makino (Seremban) from Budai Township, Chiayi County, Taiwan. 16S rRNA gene sequence analysis clearly allocated strain CC-CCM15-8(T) to the Paracoccus cluster, showing highest similarities to the type strains of 'Paracoccus beibuensis' (98.8%), Paracoccus homiensis (97.6%), Paracoccus aestuarii (97.7%) and Paracoccus zeaxanthinifaciens (97.7%). The fatty acid profile, comprising C(18:1)ω7c as the major component and C(10:0) 3-OH as the characteristic hydroxylated fatty acid, supported the placement of strain CC-CCM15-8(T) within the genus Paracoccus. The polyamine pattern consisted of putrescine and spermidine as major components. Ubiqinone Q-10 was the major quinone type (95%); ubiquinone Q-9 was also detected (5%). The complex polar lipid profile consisted of diphosphatidylglycerol, phosphatidylethanolamine, phosphatidylglycerol, phosphatidylcholine, and unidentified phospholipids, lipids and glycolipids. Levels of DNA-DNA relatedness between strain CC-CCM15-8(T) and 'P. beibuensis' LMG 25871(T), P. aestuarii DSM 19484(T), P. zeaxanthinifaciens LMG 21993(T) and P. homiensis KACC 11518(T) were 24.9% (34.8%, reciprocal analysis), 15.7% (17.5%), 17.7% (23.4%) and 16.0% (25.4%), respectively. Physiological and biochemical test results allowed the phenotypic differentiation of strain CC-CCM15-8(T) from its closest relatives in the genus Paracoccus. Based on the data presented, it is concluded that strain CC-CCM15-8(T) represents a novel species of the genus Paracoccus, for which the name Paracoccus rhizosphaerae sp. nov. is proposed. The type strain is CC-CCM15-8(T) (=LMG 26205(T)=CCM 7904(T)).

Matched MeSH terms: Quinones/analysis
Synergistic action of compounds isolated from the hexane extract of Ardisia crispa root against tumour-promoting effect, in vitro

Yeong LT, Abdul Hamid R, Saiful Yazan L, Khaza'ai H, Awang Hamsin DE

Nat Prod Res, 2014;28(22):2026-30.
PMID: 24836304 DOI: 10.1080/14786419.2014.917415

An isomeric mixture of α,β-amyrin (triterpene) and 2-methoxy-6-undecyl-1,4-benzoquinone (quinone) isolated from the Ardisia crispa root hexane (ACRH) extract was reported to possess anti-inflammatory properties in vivo. Considering the close association between inflammation and cancer, on top of the lack of antitumour study on those compounds, this study aimed to determine the potential of both compounds against tumour promotion in vitro, either as single agent or in combination. Triterpene and quinone compounds, as well as triterpene-quinone fraction (TQF) and ACRH were subjected to inhibition of Epstein-Barr virus-early antigen (EBV-EA) activation assay for that purpose. Compared with curcumin (positive control), inhibition against EBV-EA activation occurred in the order: ACRH>TQF ≥ curcumin>α,β-amyrin ≥ 2-methoxy-6-undecyl-1,4-benzoquinone. These findings reported, for the first time, the antitumor-promoting effect of α,β-amyrin and 2-methoxy-6-undecyl-1,4-benzoquinone from the roots of A. crispa, which was enhanced when both compounds act in synergy.

Matched MeSH terms: Quinones/pharmacology*; Benzoquinones/isolation & purification; Benzoquinones/pharmacology; Benzoquinones/chemistry
Amycolatopsis saalfeldensis sp. nov., a novel actinomycete isolated from a medieval alum slate mine

Carlsohn MR, Groth I, Tan GYA, Schütze B, Saluz HP, Munder T, et al.

Int J Syst Evol Microbiol, 2007 Jul;57(Pt 7):1640-1646.
PMID: 17625209 DOI: 10.1099/ijs.0.64903-0

Three actinomycetes isolated from the surfaces of rocks in a medieval slate mine were examined in a polyphasic taxonomic study. Chemotaxonomic and morphological characteristics of the isolates were typical of strains of the genus Amycolatopsis. The isolates had identical 16S rRNA gene sequences and formed a distinct phyletic line towards the periphery of the Amycolatopsis mediterranei clade, being most closely related to Amycolatopsis rifamycinica. The organisms shared a wide range of genotypic and phenotypic markers that distinguished them from their closest phylogenetic neighbours. On the basis of these results, a novel species, Amycolatopsis saalfeldensis sp. nov., is proposed. The type strain is HKI 0457(T) (=DSM 44993(T)=NRRL B-24474(T)).

Matched MeSH terms: Quinones/analysis
Comprehensive studies of the anti-inflammatory effect of tetraprenyltoluquinone, a quinone from Garcinia cowa Roxb

Dewi IP, Dachriyanus, Aldi Y, Ismail NH, Hefni D, Susanti M, et al.

J Ethnopharmacol, 2024 Feb 10;320:117381.
PMID: 37967776 DOI: 10.1016/j.jep.2023.117381

ETHNOPHARMACOLOGICAL RELEVANCE: Garcinia cowa Roxb. is called asam kandis in West Sumatra. This plant contains several quinone compounds, including tetraprenyltoluquinone (TPTQ). The bioactivity of this compound has been tested as an anticancer agent. However, reports regarding its anti-inflammatory effects are still limited, especially against coronavirus disease (Covid-19).
AIM OF THE STUDY: This study explores the anti-inflammatory effect of TPTQ in silico, in vitro, and in vivo.
MATERIALS AND METHODS: In silico testing used the Gnina application, opened via Google Colab. The TPTQ structure was docked with the nuclear factor kappa B (NF-ĸB) protein (PDB: 2RAM). In vitro testing began with testing the cytotoxicity of TPTQ against Raw 264.7 cells, using the 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) method. A phagocytic activity test was carried out using the neutral red uptake method, and interleukin-6 (IL-6) and tumor necrosis factor alpha (TNF-α) secretion tests were carried out using the enzyme-linked immunosorbent assay (ELISA) method. In vivo, tests were carried out on mice by determining cluster of differentiation 8+ (CD8+), natural killer cell (NK cell), and IL-6 parameters, using the ELISA method.
RESULTS: TPTQ has a lower binding energy than the native ligand and occupies the same active site as the native ligand. TPTQ decreased the phagocytosis index and secretion of IL-6 and TNF-α experimentally in vitro. TPTQ showed significant downregulation of CD8+ and slightly decreased NK cells and IL-6 secretion in vivo.
CONCLUSION: The potent inhibitory effect of TPTQ on the immune response suggests that TPTQ can be developed as an anti-inflammatory agent, especially in the treatment of Covid-19.

Matched MeSH terms: Quinones
Fulltext Low dose triterpene-quinone fraction from Ardisia crispa root precludes chemical-induced mouse skin tumor promotion

Yeong LT, Abdul Hamid R, Saiful Yazan L, Khaza'ai H, Mohtarrudin N

BMC Complement Altern Med, 2015;15(1):431.
PMID: 26638207 DOI: 10.1186/s12906-015-0954-3

Drastic increment of skin cancer incidence has driven natural product-based chemoprevention as a promising approach in anticancer drug development. Apart from its traditional usages against various ailments, Ardisia crispa (Family: Myrsinaceae) specifically its triterpene-quinone fraction (TQF) which was isolated from the root hexane extract (ACRH) was recently reported to exert antitumor promoting activity in vitro. This study aimed at determining chemopreventive effect of TQF against chemically-induced mouse skin tumorigenesis as well as elucidating its possible pathway(s).

Matched MeSH terms: Quinones/administration & dosage*
Fulltext Antidiabetic, Antihyperlipidemic, Antioxidant, Anti-inflammatory Activities of Ethanolic Seed Extract of Annona reticulata L. in Streptozotocin Induced Diabetic Rats

Wen W, Lin Y, Ti Z

Front Endocrinol (Lausanne), 2019;10:716.
PMID: 31708869 DOI: 10.3389/fendo.2019.00716

Annona reticulata L. (Bullock's heart) is a pantropic tree commonly known as custard apple, which is used therapeutically for a variety of maladies. The present research was carried out to evaluate the possible protective effects of Annona reticulata L. (A. reticulata) ethanolic seed extract on an experimentally induced type 2 diabetes rat model. Male Albino Wistar rats were randomly divided into five groups with six animals in each group viz., control rats in group I, diabetic rats in group II, diabetic rats with 50 and 100 mg/kg/bw of ethanolic seed extract of A. reticulata in groups III and IV, respectively, and diabetic rats with metformin in group V. Treatment was given for 42 consecutive days through oral route by oro-gastric gavage. Administration of A. reticulata seed extract to diabetes rats significantly restored the alterations in the levels of body weight, food and water intake, fasting blood glucose (FBG), insulin levels, insulin sensitivity, HbA1c, HOMA-IR, islet area and insulin positive cells. Furthermore, A. reticulata significantly decreased the levels of triglycerides, cholesterol, LDL, and significantly increased the HDL in diabetic rats. A. reticulata effectively ameliorated the enzymatic (ALT, AST, ALP, GGT) and modification of histopathological changes in diabetic rats. The serum levels of the BUN, creatinine levels, uric acid, urine volume, and urinary protein were significantly declined with a significant elevation in CCr in diabetic rats treated with A. reticulata. MDA and NO levels were significantly reduced with an enhancement in SOD, CAT, and GPx antioxidant enzyme activities in the kidney, liver, and pancreas of diabetic rats treated with A. reticulata. Diabetic rats treated with A. reticulata have shown up-regulation in mRNA expression levels of nuclear factor erythroid 2-related factor 2 (Nrf2), NAD(P)H:quinone oxidoreductase 1 (NQO1), Heme oxygenase-1 (HO-1) and protein expression level of Nrf2 with diminution in Keap1 mRNA expression level in pancreas, kidney, and liver. From the outcome of the current results, it can be inferred that seed extract of A. reticulata exhibits a protective effect in diabetic rats through its anti-diabetic, anti-hyperlipidemic, antioxidant and anti-inflammatory effects and could be considered as a promising treatment therapy in the treatment of diabetes mellitus.

Matched MeSH terms: Quinones

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