Diallyl Trisulfide,the Antifungal Component of Garlic Essential Oil and the Bioactivity of Its Nanoemulsions Formed by Spontaneous Emulsification

The aim of this study was to evaluate the chemical compounds of garlic essential oil (EO), and determine the antifungal efficacy of garlic EO and its major components, diallyl trisulfide and its nanoemulsions against wood-rotting fungi, Trametes hirsuta and Laetiporus sulphureus. GC-MS analysis revealed that the major constituents of garlic EO were diallyl trisulfide (39.79%), diallyl disulfide (32.91%), and diallyl sulfide (7.02%). In antifungal activity, the IC₅₀ value of garlic EO against T. hirsuta and L. sulphureus were 137.3 and 44.6 μg/mL, respectively. Results from the antifungal tests demonstrated that the three major constituents were shown to have good antifungal activity, in which, diallyl trisulfide was the most effective against T. hirsuta and L. sulphureus, with the IC₅₀ values of 56.1 and 31.6 μg/mL, respectively. The diallyl trisulfide nanoemulsions showed high antifungal efficacy against the examined wood-rotting fungi, and as the amount of diallyl trisulfide in the lipid phase increases, the antifungal efficacy of the nanoemulsions increases. These results showed that the nanoemulsions and normal emulsion of diallyl trisulfide have potential to develop into a natural wood preservative.     

Sesquiterpenoids from the Inflorescence of Ambrosia artemisiifolia

The successful invasion of Ambrosia artemisiifolia is largely due to allelopathy. As an invasive alien plant, A. artemisiifolia has spread rapidly in Asia and Europe. Studies have shown that sesquiterpenoids play an important role in plant allelopathy. However, it is unclear whether the inflorescence of A. artemisiifolia also contains allelopathic components. In this paper, our phytochemical research focuses on the inflorescence of A. artemisiifolia. Twenty sesquiterpenoids, including four new ones (1–4) were isolated through successive chromatographic columns and identified by spectroscopic methods. At a concentration of 200 μg/mL, all the compounds tested were evaluated for their allelopathic activities on seedling growth of wheat. Our results indicate that nine compounds inhibited both the root and shoot growth of seedlings. Compounds 14, 15, 17, and 20 significantly inhibited root length, which was more than 50% shorter than the control. This study identified the chemical profile of the sesquiterpenoids occurring in the inflorescence of A. artemisiifolia. The bioactivity screening results provide further understanding of the chemical basis of allelopathy in A. artemisiifolia.     

Research Advances of Bioactive Sesquiterpenoids Isolated from Marine-Derived Aspergillus sp.

Marine fungi Aspergillus sp. is an important source of natural active lead compounds with biological and chemical diversity, of which sesquiterpenoids are an extremely important class of bioactive secondary metabolites. In this paper, we review the sources, chemical structures, bioactivity, biosynthesis, and druggability evaluation of sesquiterpenoids discovered from marine fungi Aspergillus sp. since 2008. The Aspergillus species involved include mainly Aspergillus fumigatus, Aspergillus versicolor, Aspergillus flavus, Aspergillus ustus, Aspergillus sydowii, and so on, which originate from sponges, marine sediments, algae, mangroves, and corals. In recent years, 268 sesquiterpenoids were isolated from secondary metabolites of marine Aspergillus sp., 131 of which displayed bioactivities such as antitumor, antimicrobial, anti-inflammatory, and enzyme inhibitory activity. Furthermore, the main types of active sesquiterpenoids are bisabolanes, followed by drimanes, nitrobenzoyl, etc. Therefore, these novel sesquiterpenoids will provide a large number of potential lead compounds for the development of marine drugs.     

Emulsifying Properties of Rhamnolipids and Their In Vitro Antifungal Activity against Plant Pathogenic Fungi

Simple SummaryThe components of the rhamnolipid products of various sources are usually significantly different. This may hinder the application of rhamnolipid products. The rhamnolipid products with known structural components were used to test their emulsifying properties toward solvents in pesticide and their antifungal performance against plant pathogenic fungi. The results showed that the different components of rhamnolipids had no significant effect on the emulsifying performance, however, increased amounts of di-rhamnolipids in products exhibited stronger antifungal activity. We hope this work will be helpful to promote the application of rhamnolipids as pesticide adjuvants.AbstractRhamnolipids have significant emulsifying activity and the potential to become a component of pesticide emulsifier. Rhamnolipids are usually composed of two main components: mono-rhamnolipids (Rha-C₁₀-C₁₀) and di-rhamnolipids (Rha₂-C₁₀-C₁₀). The proportion of di-rhamnolipids in the products ranged between 15% and 90%, affected by the production strains and fermentation process. In this paper, three kinds of rhamnolipid products containing di-rhamnolipids proportions, of 25.45, 46.46 and 89.52%, were used to test their emulsifying ability toward three conventional solvents used in pesticide (S-200, xylene, cyclohexanone) and antifungal activities against five strains of plant pathogenic fungi (Phytophthora capsici, Phytophthora parasitica var.nicotianae, Colletotrichum destructivum, Colletotrichum sublineolum, Fusarium oxysporum). The results indicated that although the CMC of the three rhamnolipids were significantly different, their emulsification properties had no remarkable differences, at a concentration of 10 g/L. However, their antifungal activities were significantly different: the more di-rhamnolipids, the stronger the antifungal activity. This work helps to promote the application of rhamnolipids as pesticides adjuvants.     

Supercritical CO2 Plant Extracts Show Antifungal Activities against Crop-Borne Fungi

Fungal infections of cultivated food crops result in extensive losses of crops at the global level, while resistance to antifungal agents continues to grow. Supercritical fluid extraction using CO₂ (SFE-CO₂) has gained attention as an environmentally well-accepted extraction method, as CO₂ is a non-toxic, inert and available solvent, and the extracts obtained are, chemically, of greater or different complexities compared to those of conventional extracts. The SFE-CO₂ extracts of Achillea millefolium, Calendula officinalis, Chamomilla recutita, Helichrysum arenarium, Humulus lupulus, Taraxacum officinale, Juniperus communis, Hypericum perforatum, Nepeta cataria, Crataegus sp. and Sambucus nigra were studied in terms of their compositions and antifungal activities against the wheat- and buckwheat-borne fungi Alternaria alternata, Epicoccum nigrum, Botrytis cinerea, Fusarium oxysporum and Fusarium poae. The C. recutita and H. arenarium extracts were the most efficacious, and these inhibited the growth of most of the fungi by 80% to 100%. Among the fungal species, B. cinerea was the most susceptible to the treatments with the SFE-CO₂ extracts, while Fusarium spp. were the least. This study shows that some of these SFE-CO₂ extracts have promising potential for use as antifungal agents for selected crop-borne fungi.     

Nano-Size Characterization and Antifungal Evaluation of Essential Oil Molecules-Loaded Nanoliposomes

Nanoliposomes, bilayer vesicles at the nanoscale, are becoming popular because of their safety, patient compliance, high entrapment efficiency, and prompt action. Several notable biological activities of natural essential oils (EOs), including fungal inhibition, are of supreme interest. As developed, multi-compositional nanoliposomes loaded with various concentrations of clove essential oil (CEO) and tea tree oil (TTO) were thoroughly characterized to gain insight into their nano-size distribution. The present work also aimed to reconnoiter the sustainable synthesis conditions to estimate the efficacy of EOs in bulk and EO-loaded nanoliposomes with multi-functional entities. Following a detailed nano-size characterization of in-house fabricated EO-loaded nanoliposomes, the antifungal efficacy was tested by executing the mycelial growth inhibition (MGI) test using Trichophyton rubrum fungi as a test model. The dynamic light scattering (DLS) profile of as-fabricated EO-loaded nanoliposomes revealed the mean size, polydispersity index (PdI), and zeta potential values as 37.12 ± 1.23 nm, 0.377 ± 0.007, and −36.94 ± 0.36 mV, respectively. The sphere-shaped morphology of CEO and TTO-loaded nanoliposomes was confirmed by a scanning electron microscope (SEM). The existence of characteristic functional bands in all tested counterparts was demonstrated by attenuated total reflection-Fourier transform infrared (ATR-FTIR) spectroscopy. Compared to TTO-loaded nanoliposomes, the CEO-loaded nanoliposomes exhibited a maximum entrapment efficacy of 91.57 ± 2.5%. The CEO-loaded nanoliposome fraction, prepared using 1.5 µL/mL concentration, showed the highest MGI of 98.4 ± 0.87% tested against T. rubrum strains compared to the rest of the formulations.     

Guaiane Sesquiterpenoids Isolated from the Fruits of Torilis japonica and Their Cytotoxic Activity

Two new guaiane sesquiterpenoids, 11‐(acetyloxy)‐1,8‐dihydroxyguai‐4‐en‐3‐one ( 5 ) and (1α,6β)‐1,6‐dihydroxytorilin ( 6 ), were isolated from the fruits of Torilis japonica (Umbelliferae), along with four known sesquiterpenes, torilin ( 1 ), torilolone ( 2 ), (1β)‐1‐hydroxytorilin ( 3 ), and (1α)‐1‐hydroxytorilin ( 4 ). During the phytochemical investigation, daucosterol, friedelin, and epifriedelanol were also isolated from the plant for the first time. The structures of the new sesquiterpenoids 5 and 6 were determined by comprehensive analyses of MS and NMR spectroscopic data. These isolates were evaluated against human breast cancer cells (MCF‐7) and Lewis lung carcinoma (LLC) cells. Compounds 1, 3 , and 4 exhibited cytotoxic activity against the LLC cells with IC₅₀ values of 31.3, 32.5, and 34.0 μg/ml, respectively. However, no significant cytotoxicity was found against the MCF‐7 cells for any of the compounds tested.     

Synthesis and Nano-Sized Characterization of Bioactive Oregano Essential Oil Molecule-Loaded Small Unilamellar Nanoliposomes with Antifungal Potentialities

The development of greener nano-constructs with noteworthy biological activity is of supreme interest, as a robust choice to minimize the extensive use of synthetic drugs. Essential oils (EOs) and their constituents offer medicinal potentialities because of their extensive biological activity, including the inhibition of fungi species. However, their application as natural antifungal agents are limited due to their volatility, low stability, and restricted administration routes. Nanotechnology is receiving particular attention to overcome the drawbacks of EOs such as volatility, degradation, and high sensitivity to environmental/external factors. For the aforementioned reasons, nanoencapsulation of bioactive compounds, for instance, EOs, facilitates protection and controlled-release attributes. Nanoliposomes are bilayer vesicles, at nanoscale, composed of phospholipids, and can encapsulate hydrophilic and hydrophobic compounds. Considering the above critiques, herein, we report the in-house fabrication and nano-size characterization of bioactive oregano essential oil (Origanum vulgare L.) (OEO) molecules loaded with small unilamellar vesicles (SUV) nanoliposomes. The study was focused on three main points: (1) multi-compositional fabrication nanoliposomes using a thin film hydration–sonication method; (2) nano-size characterization using various analytical and imaging techniques; and (3) antifungal efficacy of as-developed OEO nanoliposomes against Trichophyton rubrum (T. rubrum) by performing the mycelial growth inhibition test (MGI). The mean size of the nanoliposomes was around 77.46 ± 0.66 nm and 110.4 ± 0.98 nm, polydispersity index (PdI) of 0.413 ± 0.015, zeta potential values up to −36.94 ± 0.36 mV were obtained by dynamic light scattering (DLS). and spherical morphology was confirmed by scanning electron microscopy (SEM). The presence of OEO into nanoliposomes was displayed by attenuated total reflection Fourier-transform infrared (ATR-FTIR) spectroscopy. Entrapment efficiency values of 79.55 ± 6.9% were achieved for OEO nanoliposomes. In vitro antifungal activity of nanoliposomes tested against T. rubrum strains revealed that OEO nanoliposomes exhibited the highest MGI, 81.66 ± 0.86%, at a concentration of 1.5 µL/mL compared to the rest of the formulations. In summary, this work showed that bioactive OEO molecules with loaded nanoliposomes could be used as natural antifungal agents for therapeutical purposes against T. rubrum.     

Antifungal Activity and In Silico Studies on 2-Acylated Benzo- and Naphthohydroquinones

The high rates of morbidity and mortality due to fungal infections are associated with a limited antifungal arsenal and the high toxicity of drugs. Therefore, the identification of novel drug targets is challenging due to the several resemblances between fungal and human cells. Here, we report the in vitro antifungal evaluation of two acylphenols series, namely 2-acyl-1,4-benzo- and 2-acyl-1,4-naphthohydroquinones. The antifungal properties were assessed on diverse Candida and filamentous fungi strains through the halo of inhibition (HOI) and minimal inhibitory concentration (MIC). The antifungal activities of 2-acyl-1,4-benzohydroquinone derivatives were higher than those of the 2-acyl-1,4-naphthohydroquinone analogues. The evaluation indicates that 2-octanoylbenzohydroquinone 4 is the most active member of the 2-acylbenzohydroquinone series, with MIC values ranging from 2 to 16 μg/mL. In some fungal strains (i.e., Candida krusei and Rhizopus oryzae), such MIC values of compound 4 (2 and 4 μg/mL) were comparable to that obtained by amphotericin B (1 μg/mL). The compound 4 was evaluated for its antioxidant activity by means of FRAP, ABTS and DPPH assays, showing moderate activity as compared to standard antioxidants. Molecular docking studies of compound 4 and ADMET predictions make this compound a potential candidate for topical pharmacological use. The results obtained using the most active acylbenzohydroquinones are promising because some evaluated Candida strains are known to have decreased sensitivity to standard antifungal treatments.     

阿舒假囊酵母合成的精油及其抗真菌活性与机理

利用发酵法对阿舒假囊酵母进行发酵, 用萃取法和水蒸气蒸馏法从发酵液中提取精油; 通过气相色谱-质谱(GC-MS)法确定其成分; 分别利用抑菌圈和二倍稀释法实验法测定了精油的抗真菌能力、 最小抑菌浓度和最小杀菌浓度; 利用荧光标记法、 精油处理酵母后细胞内容物检测法及透射电子显微镜研究了精油的抗菌机理. 结果表明, 阿舒假囊酵母发酵法得到的精油产率为0.54 g/L. 用GC-MS法鉴定了22种化学成分, 占精油总量的98.82%. 精油主要由单萜、 倍半萜、 芳香醇和倍半萜烃类物质组成. 精油对白色念珠菌、 光滑念珠菌、 热带念珠菌、 季也蒙念珠菌、 新型隐球菌和酿酒酵母具有良好的抗菌活性, 其最小抑菌浓度分别为31.25, 31.25, 62.5, 31.25, 15.625和15.625 μg/mL; 最小杀菌浓度分别为62.5, 62.5, 125.0, 62.5, 31.25和31.25 μg/mL. 结果表明, 精油的抗菌机理可能是破坏真菌的细胞壁、 细胞膜, 使胞内物质外泄, 最终导致真菌死亡. 该研究结果为发酵法合成精油及其应用提供了新思路.     

基于真菌14α-去甲基化酶的非氮唑类抗真菌先导化合物的设计、合成及其体外抗真菌活性研究

基于真菌羊毛甾醇14α-去甲基化酶(CYP51)活性位点的三维结构设计并合成了新型四氢异喹啉类抗真菌先导化合物. 体外抗真菌活性研究显示: 设计的先导化合物具有较好的抗真菌活性. 其中化合物5f和5g对于5种测试菌的抗真菌活性强于或相当于对照药物氟康唑. 先导分子通过与靶酶活性腔氨基酸残基的非共价键结合产生抗真菌作用, 避免与血红素辅基Fe原子发生配位结合, 为一类具有新作用机理的非氮唑类抗真菌先导化合物. 本研究为抗真菌药物研究提供了新的结合方式及结构类型.     

In Vitro Evaluation of Antibacterial and Antifungal Activity of Biogenic Silver and Copper Nanoparticles: The First Report of Applying Biogenic Nanoparticles against Pilidium concavum and Pestalotia sp. Fungi

There is increased attention paid to metallic nanoparticles due to their intensive use in various branches of agriculture and biotechnology, such as pest management, nanosensors, gene delivery, seed treatment, etc. There has been growing interest in applying environmentally friendly strategies for synthesizing nanoparticles without using substances which are hazardous to the environment. Biological practices for the synthesis of nanoparticles have been considered as possible ecofriendly alternatives to chemical synthesis. In the present study, we used biogenic silver and copper nanoparticles which were prepared by a previously reported green method. Moreover, the problem of chemical residues, which usually remain along with chemically synthesized nanoparticles and limit their application, was solved by developing such a green synthesis approach. To study the antibacterial activity of silver and copper nanoparticles, Pseudomonas aeruginosa was used; for the evaluation of antifungal activity, the pathogenic fungi Botrytis cinerea, Pilidium concavum and Pestalotia sp. were applied. To the best of our knowledge, this study represents the first time that the antifungal impact of a nanoparticle has been tested on Pilidium concavum and Pestalotia sp. Silver nanoparticles were found to be the more effective antimicrobial agent against all examined pathogens in comparison to copper nanoparticles. Data from such investigations provide valuable preliminary data on silver nanoparticle-based compounds or composites for use in the management of different pathogens.     

Antifungal Activity of Alpha-Mangostin against Colletotrichum gloeosporioides In Vitro and In Vivo

We investigated alpha-mangostin (α-mangostin, α-MG), a xanthone natural product extracted from the pericarp of mangosteen (Garcinia mangostana), for its antifungal activities and possible mechanism against Colletotrichum gloeosporioides, which causes mango anthracnose. The results demonstrated that α-MG had a relatively high in vitro inhibitory activity against C. gloeosporioides among 20 plant pathogenic fungi. The median effective concentration (EC₅₀) values of α-MG against mycelial growth were nearly 10 times higher than those of spore germination inhibition for both strains of C. gloeosporioides, the carbendazim-sensitive (CBD-s) and carbendazim-resistant (CBD-r). The results suggested that α-MG exhibited a better inhibitory effect on spore germination than on the mycelial growth of C. gloeosporioides. Further investigation indicated that the protective effect could be superior to the therapeutic effect for mango leaves for scab development. The morphological observations of mycelium showed that α-MG caused the accumulation of dense bodies. Ultrastructural observation further revealed that α-MG caused a decrease in the quantity and shape of the swelling of mitochondria in the mycelium cells of C. gloeosporioides. In addition, bioassays disclosed that the inhibitory activity of α-MG on spore germination was reduced by adding exogenous adenosine triphosphate (ATP). These results suggested that the mode of action of α-MG could be involved in the destruction of mitochondrial energy metabolism. The current study supports α-MG as a natural antifungal agent in crop protection.     

Antimicrobial Compounds Isolated from Endolichenic Fungi: A Review

A lichen is a symbiotic relationship between a fungus and a photosynthetic organism, which is algae or cyanobacteria. Endolichenic fungi are a group of microfungi that resides asymptomatically within the thalli of lichens. Endolichenic fungi can be recognized as luxuriant metabolic artists that produce propitious bioactive secondary metabolites. More than any other time, there is a worldwide search for new antibiotics due to the alarming increase in microbial resistance against the currently available therapeutics. Even though a few antimicrobial compounds have been isolated from endolichenic fungi, most of them have moderate activities, implying the need for further structural optimizations. Recognizing this timely need and the significance of endolichenic fungi as a promising source of antimicrobial compounds, the activity, sources and the structures of 31 antibacterial compounds, 58 antifungal compounds, two antiviral compounds and one antiplasmodial (antimalarial) compound are summarized in this review. In addition, an overview of the common scaffolds and structural features leading to the corresponding antimicrobial properties is provided as an aid for future studies. The current challenges and major drawbacks of research related to endolichenic fungi and the remedies for them have been suggested.     

Antifungal,anti-inflamatory and neuritogenic activity of newly-isolated compounds from Disporopsis aspersa

Abstract

A new ester (1) and a terpenoid (2) were isolated from the dried whole plant of Disporopsis aspersa (H_UA) E_NGL. ex D_IELS for the first time and their structures were elucidated, as well as their biological activities are described. The two compounds all showed good antifungal activities, especially furanone (2) exhibited better antifungal activity against Pseudoperonospora cubensis and Phytophthora infestans with EC₅₀ value of 22.82, 18.90?μg/mL, respectively. Compound 1 exhibited a significant promotion on the neurite outgrowth in NGF-induced PC-12 cells, and moderate inhibition on the NO production induced by lipopolysaccharide (LPS) in BV-2 microglial cells.     

Antifungal activity of Annona coriacea Mart. ethanol extracts against the aetiological agents of cryptococcosis

Cryptococcosis is an opportunistic disease with a worldwide distribution. This disease is caused by fungi of the genus Cryptococcus, and its treatment is limited to several antifungals. In this study, the antifungal, cytotoxic and mutagenic properties of ethanol extracts from the bark and leaves of Annona coriacea were evaluated against the standard Cryptococcus species and clinical yeast specimens. Both extracts of A. coriacea showed inhibitory activity of 1.5 mg/mL for all of the yeasts tested. The number of viable cells at the lowest tested concentration was 0.187 mg/mL. The extracts that were tested showed inhibitory activity and reduced the fungal growth of the Cryptococcus gattii species and Cryptococcus neoformans species complexes, suggesting that this plant may be an effective alternative treatment for cryptococcosis.     

In Vitro Antifungal Activity and Mechanism of Ag3PW12O40 Composites against Candida Species

Fungal infections pose a serious threat to human health. Polyoxometalates (POMs) are metal–oxygen clusters with potential application in the control of microbial infections. Herein, the Ag₃PW₁₂O₄₀ composites have been synthesized and verified by Fourier transform infrared (FT-IR) spectrum, transmission electron microscopy (TEM), scanning electron microscope (SEM), elemental analysis, and X-ray diffraction (XRD). The antifungal activities of Ag₃PW₁₂O₄₀ were screened in 19 Candida species strains through the determination of minimum inhibitory concentration (MIC) by the microdilution checkerboard technique. The minimum inhibitory concentration (MIC₅₀) values of Ag₃PW₁₂O₄₀ are 2~32 μg/mL to the Candida species. The MIC₈₀ value of Ag₃PW₁₂O₄₀ to resistant clinical isolates C. albicans HL963 is 8 μg/mL, which is lower than the positive control, fluconazole (FLC). The mechanism against C. albicans HL963 results show that Ag₃PW₁₂O₄₀ can decrease the ergosterol content. The expressions of ERG1, ERG7, and ERG11, which impact on the synthesis of ergosterol, are all prominently upregulated by Ag₃PW₁₂O₄₀. It indicates that Ag₃PW₁₂O₄₀ is a candidate in the development of new antifungal agents.     

Exploring Peptaibol’s Profile,Antifungal, and Antitumor Activity of Emericellipsin A of Emericellopsis Species from Soda and Saline Soils

Features of the biochemical adaptations of alkaliphilic fungi to exist in extreme environments could promote the production of active antibiotic compounds with the potential to control microorganisms, causing infections associated with health care. Thirty-eight alkaliphilic and alkalitolerant Emericellopsis strains (E. alkalina, E. cf. maritima, E. cf. terricola, Emericellopsis sp.) isolated from different saline soda soils and belonging to marine, terrestrial, and soda soil ecological clades were investigated for emericellipsin A (EmiA) biosynthesis, an antifungal peptaibol previously described for Emericellopsis alkalina. The analysis of the Emericellopsis sp. strains belonging to marine and terrestrial clades from chloride soils revealed another novel form with a mass of 1032.7 Da, defined by MALDI-TOF Ms/Ms spectrometers, as the EmiA lacked a hydroxyl (dEmiA). EmiA displayed strong inhibitory effects on cell proliferation and viability of HCT 116 cells in a dose- and time-dependent manners and induced apoptosis.     

索式法提取芫荽茎叶精油的化学组成及其抗菌活性

以乙醚为溶剂,采用索式萃取法萃取新鲜香菜,以0.252%的产率获得了芳香精油.利用GC-MS分析仪对精油进行了分析,检测出60个成分,解析了占精油94.200%的41个成分,其中,酯类化合物占57.755%,烷烃类化合物11.300%,醛类化合物16.168%,芳香族化合物8.077%.与水蒸汽蒸馏法获得的精油以及香菜原汁的抗菌作用进行了比较,结果显示水蒸汽蒸馏法和索式法提取的精油对大肠杆菌,白葡萄球菌具有很强的抑制作用,但是,香菜精油和原汁对米曲霉、黑曲霉完全没有抑菌作用.