Metabolites of Lachnellulafuscosanguinea (Rehm). Part 1. The isolation, structure determination, and synthesis of lachnelluloic acid

1985 ◽  
Vol 63 (6) ◽  
pp. 1161-1165 ◽  
Author(s):  
William A. Ayer ◽  
J. Daniel Figueroa Villar
Keyword(s):  
Antifungal Activity ◽  
Total Synthesis ◽  
Causative Agent ◽  
Structure Determination ◽  
Liquid Culture ◽  
Antifungal Agents ◽  
Dutch Elm Disease ◽  
Spectroscopic Methods

The metabolites produced in liquid culture by the fungus Lachnellulafuscosanguinea (Rehm) Dennis have been examined and two antifungal agents, lachnelluloic acid and lachnellulone, have been isolated. The structure of lachnelluloic acid has been established as (−)-4-hydroxy-3-octanoyl-6-pentyl-5,6-dihydro-2-pyrone (1) by chemical and spectroscopic methods. The total synthesis of racemic lachnelluloic acid, starting from 6,8-tridecanedione (6) is reported. Lachnelluloic acid (1) shows strong antifungal activity against Ceratocystisulmi, the causative agent of Dutch elm disease.

Total synthesis of the potent antifungal agents bengazole C and E

2009 ◽  
Vol 74 (6) ◽  
pp. 887-900 ◽  
Author(s):  
Álvaro Enríquez-García ◽  
Steven V. Ley
Keyword(s):  
Natural Products ◽  
Antifungal Activity ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Antifungal Agents ◽  
Nitrile Oxide ◽  
Total Syntheses ◽  
Unique Structure

The bengazoles are marine natural products with unique structure, containing two oxazole rings flanking a single carbon. They show very potent antifungal activity. The total syntheses of bengazole C and E are described following a convergent route which involves diastereoselective cycloaddition of an appropriately substituted nitrile oxide with a butane-1,2-diacetal-protected alkenediol as the key step.

Antifungal Activity of a Polyacetylene against the Fungal Pathogen of Japanese Oak from the Liquid Culture of the Edible Mushroom, Hypsizygus marmoreus

2013 ◽  
Vol 68 (3) ◽  
pp. 293-295 ◽  
Author(s):  
Yoshihito Shiono ◽  
Masatomo Haga ◽  
Hiromasa Koyama ◽  
Testuya Murayama ◽  
Takuya Koseki
Keyword(s):  
Antifungal Activity ◽  
Fungal Pathogen ◽  
Liquid Culture ◽  
Pathogenic Fungus ◽  
Edible Mushroom ◽  
Spectroscopic Methods ◽  
Oak Wilt ◽  
Organic Extract ◽  
Hypsizygus Marmoreus ◽  
Raffaelea Quercivora

Three polyacetylene compounds, 1, 2 and 3, have been isolated from the organic extract of a liquid culture of Hypsizygus marmoreus (Peck.) Bigelow (Japanese name: Bunashimeji). The structures of 1, 2 and 3 were determined by using spectroscopic methods. Compound 3 is new, and was identified as 8(E)-decene-4,6-diyn-1,2,10-triol. Compound 1 exhibits antifungal activity against the pathogenic fungus Raffaelea quercivora responsible for Japanese oak wilt

Synthesis and Antifungal Activity of Coumarins Derivatives Against Sporothrix spp.

2018 ◽  
Vol 18 (2) ◽  
pp. 164-171 ◽  
Author(s):  
Luana da S.M. Forezi ◽  
Luana Pereira Borba-Santos ◽  
Mariana F.C. Cardoso ◽  
Vitor F. Ferreira ◽  
Sonia Rozental ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Antifungal Agents ◽  
Sporothrix Schenckii ◽  
Public Health Problem ◽  
Domestic Animals ◽  
Coumarin Derivatives ◽  
Sporothrix Brasiliensis ◽  
Synthetic Routes ◽  
Effective Drugs

Sporotrichosis is a serious public health problem in Brazil that affects human patients and domestic animals, mainly cats. Thus, the search for new antifungal agents is required also due to the emergence and to the lack of effective drugs available in the therapeutic arsenal. The aim of this study was to evaluate the in vitro antifungal profile of two synthetic series of coumarin derivatives against Sporothrix schenckii and Sporothrix brasiliensis. The three-components synthetic routes used for the preparation of coumarin derivatives have proved to be quite efficient and compounds 16 and 17 have been prepared in good yields. The inhibitory activity of nineteen synthetic coumarins derivatives 16a-i and 17a-j were evaluated against Sporothrix spp. yeasts and the most potent compounds were 16b and 17i. However, according to concentrations able to inhibit (minimum inhibitory concentrations) and kill (minimum fungicidal concentrations) the cells, 17i was more effective than 16b against Sporothrix spp. Thus, 17i exhibited good antifungal activity against S. brasiliensis and S. schenckii, suggesting that it is an important scaffold for the development of novel antifungal agents.

Antifúngicos poliénicos. Mecanismo de acción y aplicaciones

2020 ◽  
Vol 63 (2) ◽  
pp. 7-17
Author(s):  
Evelyn Rivera-Toledo ◽  
Alan Uriel Jiménez-Delgadillo ◽  
Patricia Manzano-Gayosso
Keyword(s):  
Antifungal Activity ◽  
Key Words ◽  
Secondary Metabolism ◽  
Amphotericin B ◽  
Antifungal Agents ◽  
Fungal Infections ◽  
Variable Number ◽  
Therapeutic Failure ◽  
Morbidity And Mortality ◽  
Clinical Use

The first compounds with specific antifungal activity were identified in the middle of the last century as a product of the secondary metabolism of bacteria of the order Actinomycetales, and their clinical use significantly diminished the morbidity and mortality associated with severe fungal infections. Many of such biosynthetic compounds are characterized by a chemical polygenic structure, with a variable number of carbon-carbon double bonds. Currently, besides polygenic antimycotics, there are other antifungal agents, such as the azole compounds, that have less toxicity in patients; however, cases of therapeutic failure with such compounds have been documented, therefore, the use of polygenics is still the best alternative in such cases. This review presents data about the properties and applications of antifungal-polygenic compounds using amphotericin B as a model. Key words: Amphotericin B; antifungal polyenes; ergosterol

The protonation of the ethylenediphosphinetetraacetate anion and the crystal structure of the bis (hydrogen bromide) of ethylenediphosphinetetraacetic acid

1981 ◽  
Vol 46 (12) ◽  
pp. 3063-3073 ◽  
Author(s):  
Jana Podlahová ◽  
Bohumil Kratochvíl ◽  
Vratislav Langer ◽  
Josef Šilha ◽  
Jaroslav Podlaha
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Structure Determination ◽  
Free Acid ◽  
Hydrogen Bromide ◽  
Carboxyl Groups ◽  
Spectroscopic Methods ◽  
X Ray ◽  
Partial Formation

The equilibria and mechanism of addition of protons to the ethylenediphosphinetetraacetate anion (L4-) were studied in solution by the UV, IR, 1H and 31P NMR spectroscopic methods. A total of six protons can be bonded to the anion. They are added stepwise, first with partial formation of zwitterions containing P-H bonds, which then dissociate with formation of the free acid, H4L, where all four protons are bonded in carboxyl groups. The formation of zwitterions is strongly dependent on the concentration. In the final stage, the acid bonds two additional protons to form the bis-phosphonium cation, H6L2+. A number of isostructural salts containing this cation, H4L.2 HX (X = Cl, Br, I), have been prepared. The X-ray crystal structure determination of the bromide confirmed the expected arrangement. The bromide crystals are monoclinic, a = 578.2, b = 1 425.0, c = 1 046.7 pm, β = 103.07° with a space group of P21/c, Z = 2. The final R factor was 0.059 based on 1 109 observed reflections. The structure consists of H6L2+ cations containing protons bonded to phosphorus atoms (P-H distance 134 pm) and of bromide anions, located in gaps which are also sufficiently large for I- anions in the isostructural iodide. The interbonding of phosphonium cations proceeds through hydrogen bonds, C-OH...O=C, in which the O...O distance is 275.3 pm.

scholarly journals Bacillus megaterium-Mediated Synthesis of Selenium Nanoparticles and Their Antifungal Activity against Rhizoctonia solani in Faba Bean Plants

2021 ◽  
Vol 7 (3) ◽  
pp. 195
Author(s):  
Amr H. Hashem ◽  
Amer M. Abdelaziz ◽  
Ahmed A. Askar ◽  
Hossam M. Fouda ◽  
Ahmed M. A. Khalil ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Vicia Faba ◽  
Root Rot ◽  
Antifungal Agents ◽  
Damping Off ◽  
Growth Promoters ◽  
Root Rot Disease ◽  
Rot Disease

Rhizoctonia root-rot disease causes severe economic losses in a wide range of crops, including Vicia faba worldwide. Currently, biosynthesized nanoparticles have become super-growth promoters as well as antifungal agents. In this study, biosynthesized selenium nanoparticles (Se-NPs) have been examined as growth promoters as well as antifungal agents against Rhizoctonia solani RCMB 031001 in vitro and in vivo. Se-NPs were synthesized biologically by Bacillus megaterium ATCC 55000 and characterized by using UV-Vis spectroscopy, XRD, dynamic light scattering (DLS), and transmission electron microscopy (TEM) imaging. TEM and DLS images showed that Se-NPs are mono-dispersed spheres with a mean diameter of 41.2 nm. Se-NPs improved healthy Vicia faba cv. Giza 716 seed germination, morphological, metabolic indicators, and yield. Furthermore, Se-NPs exhibited influential antifungal activity against R. solani in vitro as well as in vivo. Results revealed that minimum inhibition and minimum fungicidal concentrations of Se-NPs were 0.0625 and 1 mM, respectively. Moreover, Se-NPs were able to decrease the pre-and post-emergence of R. solani damping-off and minimize the severity of root rot disease. The most effective treatment method is found when soaking and spraying were used with each other followed by spraying and then soaking individually. Likewise, Se-NPs improve morphological and metabolic indicators and yield significantly compared with infected control. In conclusion, biosynthesized Se-NPs by B. megaterium ATCC 55000 are a promising and effective agent against R. solani damping-off and root rot diseases in Vicia faba as well as plant growth inducer.

N-(5-Amino-9H-benzo[a]phenoxazin-9-ylidene)propan-1-aminium chlorides as antifungal agents and NIR fluorescence probes

2021 ◽  
Author(s):  
Rui P. C. L. Sousa ◽  
João C. C. Ferreira ◽  
Maria João Sousa ◽  
M Sameiro Sameiro T T Gonçalves
Keyword(s):  
Antifungal Activity ◽  
Antifungal Agents ◽  
Nile Blue ◽  
Fluorescence Probes ◽  
Cell Labelling ◽  
Nir Fluorescence ◽  
High Antifungal Activity

The search for benzo[a]phenoxazines, Nile Blue derivatives, with high antifungal activity and cell labelling capacity based on our previously published works in this type of compounds, led us to the...

scholarly journals Synthetic Histidine-Rich Peptides Inhibit Candida Species and Other Fungi In Vitro: Role of Endocytosis and Treatment Implications

2006 ◽  
Vol 50 (8) ◽  
pp. 2797-2805 ◽  
Author(s):  
Jingsong Zhu ◽  
Paul W. Luther ◽  
Qixin Leng ◽  
A. James Mixson
Keyword(s):  
Nucleic Acid ◽  
Antifungal Activity ◽  
Antifungal Agents ◽  
Fungal Growth ◽  
Nucleic Acid Delivery ◽  
Histatin 5 ◽  
Ph Buffering ◽  
Endosomal Acidification

ABSTRACT A family of histidine-rich peptides, histatins, is secreted by the parotid gland in mammals and exhibits marked inhibitory activity against a number of Candida species. We were particularly interested in the mechanism by which histidine-rich peptides inhibit fungal growth, because our laboratory has synthesized a variety of such peptides for drug and nucleic acid delivery. In contrast to naturally occurring peptides that are linear, peptides made on synthesizers can be varied with respect to their degrees of branching. Using this technology, we explored whether histidine-lysine (HK) polymers of different complexities and degrees of branching affect the growth of several species of Candida. Polymers with higher degrees of branching were progressively more effective against Candida albicans, with the four-branched polymer, H2K4b, most effective. Furthermore, H2K4b accumulated efficiently in C. albicans, which may indicate its ability to transport other antifungal agents intracellularly. Although H2K4b had greater antifungal activity than histatin 5, their mechanisms were similar. Toxicity in C. albicans induced by histatin 5 or branched HK peptides was markedly reduced by 4,4′-diisothiocyanato-stilbene-2,2′-disulfonate, an inhibitor of anion channels. We also determined that bafilomycin A1, an inhibitor of endosomal acidification, significantly decreased the antifungal activity of H2K4b. This suggests that the pH-buffering and subsequent endosomal-disrupting properties of histidine-rich peptides have a role in their antifungal activity. Moreover, the ability of the histidine component of these peptides to disrupt endosomes, which allows their escape from the lysosomal pathway, may explain why these peptides are both effective antifungal agents and nucleic acid delivery carriers.

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