Isolation of sterols from the marine fungus Corollospora lacera

2004 ◽  
Vol 50 (12) ◽  
pp. 1069-1072 ◽  
Author(s):  
Sabrena E MacKenzie ◽  
G Soundari Gurusamy ◽  
Adam Piórko ◽  
Douglas B Strongman ◽  
Tingmo Hu ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Chromatographic Separation ◽  
Prince Edward Island ◽  
Marine Fungi ◽  
Marine Fungus ◽  
Extraction Procedures ◽  
Ethylhexyl Phthalate ◽  
Weak Antibacterial Activity

Several marine fungi collected from the waters of Prince Edward Island, Canada, were screened for the presence of natural products exhibiting antibacterial activity. Both broths and mycelia of these fungi were studied using the bioassay-guided chromatographic separation. The 4 fractions from the extract of mycelia of Corollospora lacera exhibited weak antibacterial activity and were analyzed further. From these fractions, 2 sterols (5α,8α-epidioxyergosterol and 22E,24R-ergosta-7,22-diene-3β,5α,6β-triol) and a 3:1 mixture of linoleic and oleic acids were isolated. The presence of ergosterol was confirmed in dichloromethane extracts of mycelia of every fungus in this study and this sterol was isolated from the extract of mycelium of Corollospora lacera. Two other known compounds (5-hydroxymethylfuran-2-carbaldehyde and bis(2-ethylhexyl) phthalate), were isolated from the dichloromethane extract of mycelium of Monodictys pelagica. The phthalate was reported in the literature as a metabolite isolated from the fungi, but in our study it was proven to be an artifact of the culturing and (or) extraction procedures rather than a true fungal metabolite.Key words: marine fungus, sterols, metabolites.

Pyrone-derived Marine Natural Products: A Review on Isolation, Bio-activities and Synthesis

2020 ◽  
Vol 24 (4) ◽  
pp. 354-401 ◽  
Author(s):  
Keisham S. Singh
Keyword(s):  
Natural Products ◽  
Marine Natural Products ◽  
Marine Fungi ◽  
Kojic Acid ◽  
Biological Activities ◽  
Biological Significance ◽  
Pyrone Ring ◽  
Enol Ethers ◽  
Bioactive Natural Products ◽  
Marine Metabolites

Marine natural products (MNPs) containing pyrone rings have been isolated from numerous marine organisms, and also produced by marine fungi and bacteria, particularly, actinomycetes. They constitute a versatile structure unit of bioactive natural products that exhibit various biological activities such as antibiotic, antifungal, cytotoxic, neurotoxic, phytotoxic and anti-tyrosinase. The two structure isomers of pyrone ring are γ- pyrone and α-pyrone. In terms of chemical motif, γ-pyrone is the vinologous form of α- pyrone which possesses a lactone ring. Actinomycete bacteria are responsible for the production of several α-pyrone compounds such as elijopyrones A-D, salinipyrones and violapyrones etc. to name a few. A class of pyrone metabolites, polypropionates which have fascinating carbon skeleton, is primarily produced by marine molluscs. Interestingly, some of the pyrone polytketides which are found in cone snails are actually synthesized by actinomycete bacteria. Several pyrone derivatives have been obtained from marine fungi such as Aspergillums flavus, Altenaria sp., etc. The γ-pyrone derivative namely, kojic acid obtained from Aspergillus fungus has high commercial demand and finds various applications. Kojic acid and its derivative displayed inhibition of tyrosinase activity and, it is also extensively used as a ligand in coordination chemistry. Owing to their commercial and biological significance, the synthesis of pyrone containing compounds has been given attention over the past years. Few reviews on the total synthesis of pyrone containing natural products namely, polypropionate metabolites have been reported. However, these reviews skipped other marine pyrone metabolites and also omitted discussion on isolation and detailed biological activities. This review presents a brief account of the isolation of marine metabolites containing a pyrone ring and their reported bio-activities. Further, the review covers the synthesis of marine pyrone metabolites such as cyercene-A, placidenes, onchitriol-I, onchitriol-II, crispatene, photodeoxytrichidione, (-) membrenone-C, lihualide-B, macrocyclic enol ethers and auripyrones-A & B.

scholarly journals Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

2014 ◽  
Vol 10 ◽  
pp. 1228-1232 ◽  
Author(s):  
Jens Schmidt ◽  
Zeinab Khalil ◽  
Robert J Capon ◽  
Christian B W Stark
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Joint Effort ◽  
Natural Product Biosynthesis ◽  
New Members ◽  
Degree Of Oxidation ◽  
Rare Class

The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.

scholarly journals Synthesis and antibacterial activity of monocyclic 3-carboxamide tetramic acids

2013 ◽  
Vol 9 ◽  
pp. 1899-1906 ◽  
Author(s):  
Yong-Chul Jeong ◽  
Mark G Moloney
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Chemical Library ◽  
Rapid Construction ◽  
Tetramic Acids

A chemical library of carboxamide-substituted tetramates designed by analogy with antibacterial natural products, a method for their rapid construction, and the evaluation of their antibacterial activity is reported.

scholarly journals Potentially Effective and Safe Anti-Helicobacter pylori Natural Products: Chemometric Study

2020 ◽  
Vol 71 (6) ◽  
pp. 267-273 ◽  
Author(s):  
Branislava D. Kocic ◽  
Dobrila M. Stankovic Dordevic ◽  
Marija V. Dimitrijevic ◽  
Marija S. Markovic ◽  
Dragoljub L. Miladinovic
Keyword(s):  
Helicobacter Pylori ◽  
Antibacterial Activity ◽  
Natural Products ◽  
Chemical Composition ◽  
Essential Oils ◽  
Principal Component ◽  
Synergistic Activity ◽  
Agglomerative Hierarchical Clustering ◽  
Naturally Occurring ◽  
H Pylori

The susceptibility of Helicobacter pylori to three essential oils (EOs), 12 naturally occurring monoterpene hydrocarbons, oxygenated and phenolic monoterpenes and three reference antibiotics were studied. Classification and comparison of essential oils and monoterpenes on the basis of their chemical composition and antibacterial activity were made by the utilization of principal component analyses (PCA) and agglomerative hierarchical clustering (AHC). The most abundant compound in the Thymus glabrescens Willd. and Thymus pulegioides L. EOs is geraniol (33.8% and 52.5%), while the main constituent in Satureja kitaibelii Wierzb. ex Heuff. EO is limonene (16,1%). The compound that was the most active against H. pylori was carvacrol. EOs of T. glabrescens and S. kitaibelii exhibit higher antibacterial ability in comparison with all monoterpenes, except carvacrol, probably based on the concept of synergistic activity of essential oil components. PCA separated essential oils based on chemical composition and explain 96.5% of the total variance in the first two principal components. Essential oils, phenolic monoterpenes and two antibiotics were classified in the same sub-cluster within AHC analyses. EOs of T. glabrescens and S. kitaibelii can be used to treat infections caused by H. pylori, as a potentially effective, cheap and safe natural products. Further research of antibacterial activity of selected monoterpenes, essential oils and standard antibiotic combinations, as well as clinical study are required.

scholarly journals A pharmacochemic investigation of Gomphrena celosioides (Amaranthaceae)

1986 ◽  
Vol 5 (1) ◽  
pp. 40-45 ◽  
Author(s):  
S. Botha ◽  
L. M. Van der Vijver
Keyword(s):  
Amino Acids ◽  
Nervous System ◽  
Antibacterial Activity ◽  
Autonomic Nervous System ◽  
Autonomic Nervous ◽  
Plant Parts ◽  
Gram Positive Bacteria ◽  
Phenolic Substances ◽  
Gomphrena Celosioides ◽  
Weak Antibacterial Activity

A chemical and biological screen was performed on Gomphrena celosioides (Amaranthaceae) known as prostrate globe amaranth. Chemical tests showed the presence of saponins, steroids, phenolic substances, flavonoids, amino acids, sugars and betacyanins in the plant. The roots exhibited a weak antibacterial activity against three Gram positive bacteria. An action on the autonomic nervous system of rats was shown by all the plant parts, when tested by the method of Malone and Robichaud. Sympathetic and parasympathetic symptoms were observed.

scholarly journals A Review of Anti-Inflammatory Compounds from Marine Fungi, 2000–2018

Marine Drugs ◽  
2019 ◽  
Vol 17 (11) ◽  
pp. 636 ◽  
Author(s):  
Jianzhou Xu ◽  
Mengqi Yi ◽  
Lijian Ding ◽  
Shan He
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Host Response ◽  
Marine Fungi ◽  
Tissue Injury ◽  
Fungal Metabolites ◽  
Bioactive Natural Products ◽  
Anti Inflammatory ◽  
Unique Mechanism ◽  
Inflammatory Action

Inflammation is a generalized, nonspecific, and beneficial host response of foreign challenge or tissue injury. However, prolonged inflammation is undesirable. It will cause loss function of involve organs, such as heat, pain redness, and swelling. Marine natural products have gained more and more attention due to their unique mechanism of anti-inflammatory action, and have considered a hotspot for anti-inflammatory drug development. Marine-derived fungi are promising sources of structurally unprecedented bioactive natural products. So far, a plethora of new secondary metabolites with anti-inflammatory activities from marine-derived fungi had been widely reported. This review covers 133 fungal metabolites described in the period of 2000 to 2018, including the structures and origins of these secondary metabolites.

Juglomycins G-J: Isolation from Streptomycetes and Structure Elucidation

2005 ◽  
Vol 60 (2) ◽  
pp. 183-188 ◽  
Author(s):  
R. P. Maskey ◽  
H. Lessmann ◽  
S. Fotso ◽  
I. Grün-Wollny ◽  
H. Lackner ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Absolute Configuration ◽  
Structure Elucidation ◽  
Mass Spectra ◽  
2D Nmr ◽  
Cd Spectra ◽  
Streptomyces Spp ◽  
Nmr Data ◽  
Related Compounds ◽  
Weak Antibacterial Activity

From the Streptomyces spp. 815 and GW4184, four new 4-juglon-2-ylbutyric acid derivatives, the juglomycins G - J (3a, 4a, 4c, 5c), have been isolated and characterised. The structures were derived from the 1D and 2D NMR data and mass spectra and confirmed by comparison with structurally related compounds. The absolute configuration was deduced from the CD spectra. The new natural products exhibited weak antibacterial activity similar to juglomycin A (5a).

scholarly journals Safety Assessment of Castoreum Extract as a Food Ingredient

2007 ◽  
Vol 26 (1) ◽  
pp. 51-55 ◽  
Author(s):  
G. A. Burdock
Keyword(s):  
Antibacterial Activity ◽  
Human Subject ◽  
Safety Assessment ◽  
Adverse Reactions ◽  
Skin Sensitization ◽  
Scent Glands ◽  
Food Ingredient ◽  
Routes Of Administration ◽  
Weak Antibacterial Activity

Castoreum extract (CAS NO. 8023–83–4; FEMA NO. 2261) is a natural product prepared by direct hot-alcohol extraction of castoreum, the dried and macerated castor sac scent glands (and their secretions) from the male or female beaver. It has been used extensively in perfumery and has been added to food as a flavor ingredient for at least 80 years. Both the Flavor and Extract Manufacturers Association (FEMA) and the Food and Drug Administration (FDA) regard castoreum extract as generally recognized as safe (GRAS). Acute toxicity studies in animals indicate that castoreum extract is nontoxic by both oral and dermal routes of administration and is not irritating or phototoxic to skin. Skin sensitization has not been observed in human subject tests. Castoreum extract possesses weak antibacterial activity. A long historical use of castoreum extract as a flavoring and fragrance ingredient has resulted in no reports of human adverse reactions. On the basis of this information, low-level, long-term exposure to castoreum extract does not pose a health risk. The objective of this review is to evaluate the safety-in-use of castoreum extract as a food ingredient.

scholarly journals Antibacterial and Antifungal Activity of Three Monosaccharide Monomyristate Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3692 ◽  
Author(s):  
Jumina ◽  
Mutmainah ◽  
Purwono ◽  
Kurniawan ◽  
Syah
Keyword(s):  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Myristic Acid ◽  
Antimicrobial Agents ◽  
Mass Spectral ◽  
Food Industries ◽  
Gram Positive Bacteria ◽  
Microbial Infections ◽  
Antibacterial And Antifungal ◽  
Weak Antibacterial Activity

Microbial infections remains a serious challenge in food industries due to their resistance to some of the well-known antibacterial and antifungal agents. In this work, a novel monomyristoyl ester (fructosyl monomyristate) and two other derivatives (i.e., glucosyl and galactosyl monomyristates) were successfully synthesized from myristic acid and monosaccharides in two-step reactions. First, the myristic acid was converted to myristoyl chloride, and then the myristoyl chloride was reacted with fructose, glucose and galactose separately to produce the corresponding monosaccharide monomyristate derivatives. The structures of the synthesized products were confirmed by Fourier transform infrared (FTIR), proton and carbon nuclear magnetic resonance (1H- and 13C-NMR), and mass spectral (MS) data. The monomyristates esters were obtained in reaction yields of 45.80%–79.49%. The esters were then evaluated for their antimicrobial activity using the disc diffusion test. It was found that the esters exhibited a medium antibacterial activity against gram-positive bacteria; however, they showed a weak antibacterial activity against gram-negative bacteria. Amongst the esters, galactosyl myristate yielded the highest antibacterial activity against Salmonella typhimurium, Staphylococcus aureus and Bacillus subtilis, while glucosyl monomyristate exhibited the highest antibacterial activity only against Escherichia coli. Additionally, all products showed remarkable antifungal activity against Candida albicans. These findings demonstrate that monosaccharide monomyristate derivatives are promising for use as biocompatible antimicrobial agents in the future.

scholarly journals Eugenia uniflora L.: potential uses as a bioactive plant

2018 ◽  
Vol 85 (0) ◽  
Author(s):  
Gabriela Silva Moura ◽  
Ivan Júnior de Oliveira ◽  
Lisandro Tomas da Silva Bonome ◽  
Gilmar Franzener
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Pseudomonas Aeruginosa ◽  
Antibacterial Activity ◽  
Natural Products ◽  
Total Phenolics ◽  
Antioxidant Compounds ◽  
Review Of The Literature ◽  
Bioactive Substances ◽  
Eugenia Uniflora

ABSTRACT: Natural products extracted from plants have always played an important role in the discovery of bioactive substances. This work carried out a review of the literature on the bioactive activities of Eugenia uniflora L. (Surinam cherries), as a potential plant in the various uses, be it medicinal, antimicrobial, antioxidant, insecticide and protective. In the literature, studies were found to confirm the antibacterial activity of E. uniflora leaves extract on Streptococcus, Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli. The presence of antioxidant compounds as total phenolics, such as anthocyanins and flavonoids, induction in the protection of plants by phytoalexins, as well as insecticidal and anthelmintic effects by the use of the extract of the E. uniflora tree. Although these different potential biotics of E. uniflora have already been reported, further studies are still needed on the use of natural products extracted from E. uniflora for employment for different purposes.

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