scholarly journals Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1959
Author(s):  
Hua Xiao ◽  
Guiyang Wang ◽  
Zhengdong Wang ◽  
Yi Kuang ◽  
Juan Song ◽  
...  
Keyword(s):  
Natural Products ◽  
Biological Activities ◽  
Structural Diversity ◽  
Related Factor ◽  
Nuclear Factor ◽  
Streptomyces Sp ◽  
Mild Conditions ◽  
Aromatic Polyketides ◽  
Marine Streptomyces ◽  
New Compounds

Angucyclinones are aromatic polyketides that possess impressive structural diversity and significant biological activities. The structural diversity of these natural products is attributed to various enzymatic or nonenzymatic modifications on their tetracyclic benz(a)anthracene skeleton. Previously, we discovered an unusual phenylamine-incorporated angucyclinone (1) from a marine Streptomyces sp. PKU-MA00218, and identified that it was produced from the nonenzymatic conversion of a C-ring-cleaved angucyclinone (2) with phenylamine. In this study, we tested the nonenzymatic conversion of 2 with more phenylamine analogues, to expand the utility of this feasible conversion in unusual angucyclinones generation. The (3-ethynyl)phenylamine and disubstituted analogues including (3,4-dimethyl)phenylamine, (3,4-methylenedioxy)phenylamine, and (4-bromo-3-methyl)phenylamine were used in the conversion of 2, which was isolated from the fermentation of Streptomyces sp. PKU-MA00218. All four phenylamine analogues were incorporated into 2 efficiently under mild conditions, generating new compounds 3–6. The activation of 3–6 on nuclear factor erythroid 2-related factor 2 (Nrf2) transcription were tested, which showed that 4 possessing a dimethyl-substitution gave most potent activity. These results evidenced that disubstitutions on phenylamine can be roughly tolerated in the nonenzymatic reactions with 2, suggesting extended applications of more disubstituted phenylamines incorporation to generate new bioactive angucyclinones in the future.

New Anthraquinones from a Marine Streptomyces sp. – Isolation, Structure Determination and Biological Activities

2006 ◽  
Vol 61 (11) ◽  
pp. 1450-1454 ◽  
Author(s):  
Hervé M. P. Poumale ◽  
Bonaventure T. Ngadjui ◽  
Elisabeth Helmke ◽  
Hartmut Laatscha
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Biological Activities ◽  
Acid Methyl Ester ◽  
Streptomyces Sp ◽  
Spectroscopic Analyses ◽  
Acid Methyl ◽  
Marine Streptomyces ◽  
New Compounds ◽  
Indole 3 Acetic Acid

Two new anthraquinones were isolated from the marine Streptomyces sp. B8000, in addition to the known metabolites 3,8-dihydroxy-1-propylanthraquinone-2-carboxylic acid (1a), indole-3- carboxylic acid, 2-desoxythymidin, indole-3-acetic acid methyl ester, N-acetyltyramine, and nicotinic acid. The structures of the new compounds were established as 8-hydroxy-3-methoxy-1- propylanthraquinone (2a) and 3,8-dihydroxy-1-propylanthraquinone (2c) on the basis of extensive spectroscopic analyses. Some derivatives were prepared and their biological activities were studied.

Marine Sponge-Associated Fungi as Potential Novel Bioactive Natural Product Sources for Drug Discovery: A Review

2020 ◽  
Vol 20 (19) ◽  
pp. 1966-2010
Author(s):  
Bin Zhang ◽  
Ting Zhang ◽  
Jianzhou Xu ◽  
Jian Lu ◽  
Panpan Qiu ◽  
...  
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Marine Sponge ◽  
Biological Activities ◽  
Structural Diversity ◽  
Bioactive Natural Products ◽  
Future Potential ◽  
New Compounds ◽  
Bioactive Natural Product ◽  
Structural Classes

Marine sponge-associated fungi are promising sources of structurally interesting and bioactive secondary metabolites. Great plenty of natural products have been discovered from spongeassociated fungi in recent years. Here reviewed are 571 new compounds isolated from marine fungi associated with sponges in 2010-2018. These molecules comprised eight different structural classes, including alkaloids, polyketides, terpenoids, meroterpenoids, etc. Moreover, most of these compounds demonstrated profoundly biological activities, such as antimicrobial, antiviral, cytotoxic, etc. This review systematically summarized the structural diversity, biological function, and future potential of these novel bioactive natural products for drug discovery.

scholarly journals Recent Findings in Azaphilone Pigments

2021 ◽  
Vol 7 (7) ◽  
pp. 541
Author(s):  
Lúcia P. S. Pimenta ◽  
Dhionne C. Gomes ◽  
Patrícia G. Cardoso ◽  
Jacqueline A. Takahashi
Keyword(s):  
Water Solubility ◽  
Biological Activities ◽  
Low Cost ◽  
Scale Up ◽  
Structural Diversity ◽  
Downstream Processing ◽  
Global Market ◽  
Yield Improvement ◽  
Potential Applications ◽  
New Compounds

Filamentous fungi are known to biosynthesize an extraordinary range of azaphilones pigments with structural diversity and advantages over vegetal-derived colored natural products such agile and simple cultivation in the lab, acceptance of low-cost substrates, speed yield improvement, and ease of downstream processing. Modern genetic engineering allows industrial production, providing pigments with higher thermostability, water-solubility, and promising bioactivities combined with ecological functions. This review, covering the literature from 2020 onwards, focuses on the state-of-the-art of azaphilone dyes, the global market scenario, new compounds isolated in the period with respective biological activities, and biosynthetic pathways. Furthermore, we discussed the innovations of azaphilone cultivation and extraction techniques, as well as in yield improvement and scale-up. Potential applications in the food, cosmetic, pharmaceutical, and textile industries were also explored.

scholarly journals Chemical Diversity and Biological Activity of Secondary Metabolites Isolated from Indonesian Marine Invertebrates

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1898
Author(s):  
Fauzia Izzati ◽  
Mega Ferdina Warsito ◽  
Asep Bayu ◽  
Anggia Prasetyoputri ◽  
Akhirta Atikana ◽  
...  
Keyword(s):  
Natural Products ◽  
Bioactive Compounds ◽  
Marine Natural Products ◽  
Biological Function ◽  
Marine Invertebrates ◽  
Biological Activities ◽  
Structural Diversity ◽  
Chemical Diversity ◽  
Soft Corals ◽  
High Chemical

Marine invertebrates have been reported to be an excellent resource of many novel bioactive compounds. Studies reported that Indonesia has remarkable yet underexplored marine natural products, with a high chemical diversity and a broad spectrum of biological activities. This review discusses recent updates on the exploration of marine natural products from Indonesian marine invertebrates (i.e., sponges, tunicates, and soft corals) throughout 2007–2020. This paper summarizes the structural diversity and biological function of the bioactive compounds isolated from Indonesian marine invertebrates as antimicrobial, antifungal, anticancer, and antiviral, while also presenting the opportunity for further investigation of novel compounds derived from Indonesian marine invertebrates.

scholarly journals Bioactivity-Guided Purification of Novel Herbal Antioxidant and Anti-NO Compounds from Euonymus laxiflorus Champ.

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 120 ◽  
Author(s):  
Van Nguyen ◽  
San-Lang Wang ◽  
Anh Nguyen ◽  
Zhi-Hu Lin ◽  
Chien Doan ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Natural Products ◽  
Biological Activities ◽  
The Novel ◽  
Health Food ◽  
Ic50 Values ◽  
Comparable Activity ◽  
New Compounds ◽  
First Time ◽  
Antidiabetic Effects

Euonymus laxiflorus Champ., a medicinal herb collected in Vietnam, has been reported to show several potent bioactivities, including anti-NO, enzyme inhibition, hypoglycemic and antidiabetic effects. Recently, the antioxidant activity of Euonymus laxiflorus Champ. trunk bark (ELCTB) has also been reported. However, the active antioxidant and anti-NO constituents existing in ELCTB have not been reported in the literature. The objective of this study was to purify the active antioxidants from ELCTB and investigate the anti-NO effect of the major constituents. Twenty-two phenolics isolated from ELCTB, including 12 compounds newly isolated in this study (1–12) and 10 constituents obtained from our previous work, were evaluated for their antioxidant activity. Of these, 12 compounds (4–6, 9, 13–15, 18–22) showed a potent antioxidant capacity (FRS50 = 7.8–58.11 µg/mL), in comparison to α-tocopherol (FRS50 = 23 µg/mL). In the anti-NO activity tests, Walterolactone A (1a) and B (1b) β-d-glucopyranoside (13) demonstrated the most effective and comparable activity to that of quercetin with max inhibition and IC50 values of 100%, 1.3 µg/mL, and 100%, 1.21 µg/mL, respectively. The crude extract and its major compounds showed no cytotoxicity on normal cells. Notably, three constituents (9, 11, and 12) were identified as new compounds, another three constituents, including 1, 7, and 8, were found to be new natural products, constituents 9 and 13 were determined to be new antioxidants, and compound 13 was reported to have novel potent anti-NO activity for the first time. The results of this study contribute to the enrichment of new natural products and compounds, as well as the novel biological activity of constituents isolated from Euonymus laxiflorus Champ. The current study also indicates ELCTB as a rich natural source of active phenolics. It is suggested that ELCTB could be developed as a health food with promising antioxidant and anti-NO effects, as well as other beneficial biological activities.

scholarly journals Activation of the Nuclear Factor E2-Related Factor 2 Pathway by Novel Natural Products Halomadurones A–D and a Synthetic Analogue

Marine Drugs ◽  
2013 ◽  
Vol 11 (12) ◽  
pp. 5089-5099 ◽  
Author(s):  
Thomas Wyche ◽  
Miranda Standiford ◽  
Yanpeng Hou ◽  
Doug Braun ◽  
Delinda Johnson ◽  
...  
Keyword(s):  
Natural Products ◽  
Related Factor ◽  
Synthetic Analogue ◽  
Nuclear Factor

scholarly journals Roles of Dietary Bioactive Peptides in Redox Balance and Metabolic Disorders

2021 ◽  
Vol 2021 ◽  
pp. 1-27
Author(s):  
Qinqin Qiao ◽  
Liang Chen ◽  
Xiang Li ◽  
Xiangyang Lu ◽  
Qingbiao Xu
Keyword(s):  
Protein Kinase ◽  
Metabolic Disorders ◽  
Molecular Mechanisms ◽  
Bioactive Peptides ◽  
Binding Protein ◽  
Biological Activities ◽  
Redox Balance ◽  
Angiotensin Converting Enzyme Inhibition ◽  
Related Factor ◽  
Nuclear Factor

Bioactive peptides (BPs) are fragments of 2–15 amino acid residues with biological properties. Dietary BPs derived from milk, egg, fish, soybean, corn, rice, quinoa, wheat, oat, potato, common bean, spirulina, and mussel are reported to possess beneficial effects on redox balance and metabolic disorders (obesity, diabetes, hypertension, and inflammatory bowel diseases (IBD)). Peptide length, sequence, and composition significantly affected the bioactive properties of dietary BPs. Numerous studies have demonstrated that various dietary protein-derived BPs exhibited biological activities through the modulation of various molecular mechanisms and signaling pathways, including Kelch-like ECH-associated protein 1/nuclear factor erythroid 2-related factor 2/antioxidant response element in oxidative stress; peroxisome proliferator-activated-γ, CCAAT/enhancer-binding protein-α, and sterol regulatory element binding protein 1 in obesity; insulin receptor substrate-1/phosphatidylinositol 3-kinase/protein kinase B and AMP-activated protein kinase in diabetes; angiotensin-converting enzyme inhibition in hypertension; and mitogen-activated protein kinase and nuclear factor-kappa B in IBD. This review focuses on the action of molecular mechanisms of dietary BPs and provides novel insights in the maintenance of redox balance and metabolic diseases of human.

Secondary metabolites, their structural diversity, bioactivity, and ecological functions: An overview

2019 ◽  
Vol 4 (6) ◽  
Author(s):  
Berhanu M. Abegaz ◽  
Henok H. Kinfe
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Structural Diversity ◽  
Building Blocks ◽  
Narrative Texts ◽  
Ecological Functions ◽  
Acetyl Coenzyme A ◽  
Primary Metabolites ◽  
Geranyl Diphosphate ◽  
Aromatic Polyketides

Abstract Natural products are also called secondary metabolites to distinguish them from the primary metabolites, i.e. those natural compounds like glucose, amino acids, etc. that are present in every living cell and are used and required in the essential life processes of cells. Natural products are classified according to their metabolic building blocks into alkaloids, fatty acids, polyketides, phenyl propanoids and aromatic polyketides, and terpenoids. The structural diversity of natural products is explored using the scaffold approach focusing on the characteristic carbon frameworks.  Aside from discussing specific alkaloids that are either pharmacologically (e.g. boldine, berberine, galantamine, etc.) or historically (caffeine, atropine, lobeline, etc.) important alkaloids, a single chart is presented which shows the typical scaffolds of the most important subclasses of alkaloids.  How certain classes of natural products are formed in nature from simple biochemical ‘building blocks’ are shown using graphical schemes. This has been done for a typical tetra-ketide (6-methylsalicylic acid) from acetyl coenzyme A, or in general to all the major subclasses of terpenes.   An important aspect of understanding the structural diversity of natural products is to recognize how some compounds can be visualized as key intermediates for enzyme mediated transformation to several other related structures.  This is seen in the case of how arachidonic acid can transform into prostaglandins, or geranyl diphosphate to various monoterpenes, or squalene epoxide to various pentacyclic triterpenes, or cholesterol transforming to sex hormones, bile acids and the cardioactive cardenolides and bufadienolides. These are presented in carefully designed schemes and charts that are appropriately placed in the relevant sections of the narrative texts.  The ecological functions and pharmacological properties of natural products are also presented showing wherever possible how the chemical scaffolds have led to developing drugs as well as commercial products like sweeteners.

scholarly journals Bioactive compounds from marine Streptomyces sp.: Structure identification and biological activities

2019 ◽  
Vol 57 (5) ◽  
pp. 628-635
Author(s):  
Aya E. S. Abd-Ellatif ◽  
Ahmed S. Abdel-Razek ◽  
Abdelaaty Hamed ◽  
Maha M Soltan ◽  
Hesham S. M. Soliman ◽  
...  
Keyword(s):  
Bioactive Compounds ◽  
Biological Activities ◽  
Structure Identification ◽  
Streptomyces Sp ◽  
Marine Streptomyces

scholarly journals Galangin Activates Nrf2 Signaling and Attenuates Oxidative Damage, Inflammation, and Apoptosis in a Rat Model of Cyclophosphamide-Induced Hepatotoxicity

Biomolecules ◽  
2019 ◽  
Vol 9 (8) ◽  
pp. 346 ◽  
Author(s):  
Aladaileh ◽  
Abukhalil ◽  
Saghir ◽  
Hanieh ◽  
Alfwuaires ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Dna Damage ◽  
Liver Injury ◽  
Oxidative Damage ◽  
Biological Activities ◽  
B Cell Lymphoma ◽  
Heme Oxygenase 1 ◽  
Related Factor ◽  
Nuclear Factor ◽  
Quinone Acceptor

Cyclophosphamide (CP) is a widely used chemotherapeutic agent; however, its clinical application is limited because of its multi-organ toxicity. Galangin (Gal) is a bioactive flavonoid with promising biological activities. This study investigated the hepatoprotective effect of Gal in CP-induced rats. Rats received Gal (15, 30 and 60 mg/kg/day) for 15 days followed by a single dose of CP at day 16. Cyclophosphamide triggered liver injury characterized by elevated serum transaminases, alkaline phosphatase (ALP) and lactate dehydrogenase (LDH), and histopathological manifestations. Increased hepatic reactive oxygen species, malondialdehyde, nitric oxide, and oxidative DNA damage along with declined glutathione and antioxidant enzymes were demonstrated in CP-administered rats. CP provoked hepatic nuclear factor-kappaB (NF-κB) phosphorylation and increased mRNA abundance of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), and tumor necrosis factor-alpha (TNF-α) and interleukin-1 beta (IL-1β) both expression and serum levels. Gal prevented CP-induced liver injury, boosted antioxidants and suppressed oxidative stress, DNA damage, NF-κB phosphorylation and pro-inflammatory mediators. Gal diminished Bax and caspase-3, and increased B-cell lymphoma-2 (Bcl-2) in liver of CP-administered rats. In addition, Gal increased peroxisome proliferator-activated receptor gamma (PPARγ) expression and activated hepatic nuclear factor erythroid 2-related factor 2 (Nrf2) signaling showed by the increase in Nrf2, NAD(P)H: quinone acceptor oxidoreductase-1 (NQO-1) and heme oxygenase 1 (HO-1) in CP-administered rats. These findings suggest that Gal prevents CP hepatotoxicity through activation of Nrf2/HO-1 signaling and attenuation of oxidative damage, inflammation and cell death. Therefore, Gal might represent a promising adjuvant therapy to prevent hepatotoxicity in patients on CP treatment.

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