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Found 2 structures.
Displayed structures from 1 to 2
| b-D-Glcp-(1-1)-+ | R-2HOC18={t3}-(1-2)-S,R-9b1SphdC19 | Show graphically |
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Structure type: monomer
Trivial name: cerebroside B
Compound class: glycolipid, glycosphingolipid, glycoside, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.
glycoside, antimicrobial, fungi, food preservative, secondary metabolites
Publication DOI: 10.1016/j.tifs.2021.02.029A new oxysporidinone analogue (1) and a new 3-hydroxyl-2-piperidinone derivative (2), along with the known compounds (-)-4,6'-anhydrooxysporidinone (3), (+)-fusarinolic acid (4), gibepyrone D (5), beauvercin (6),cerevisterol (7), fusaruside (8), and (2S,2'R,3R,3'E,4E,8E)-1-O-D-glucopyranosyl-2-N-(2'-hydroxy-3'-octadecenoyl)-3-hydroxy-9-methyl-4,8-sphingadienine (9) were isolated from Fusarium oxysporum. Compounds 1-9 were evaluated for cytotoxicity using the MTT method against cancer cell lines, PC-3, PANC-1, and A549. Beauvericin showed cytotoxicity against PC-3, PANC-1, and A549 with IC(50) value of 49.5±3.8, 47.2±2.9, and 10.4±1.6μM, respectively. Beauvericin also exhibited anti-bacterial activity towards methicillin-resistant Staphylococcus aureus (MIC=3.125 μg/mL) and Bacillus subtilis (MIC=3.125 μg/mL).
cytotoxicity, antibacterial, Fusarium oxysporum, oxysporidinone analogues
NCBI PubMed ID: 21497643Sphingolipids (SPLs) are key components of the plasma membrane in yeast and filamentous fungi. These molecules are involved in a number of cellular processes, and particularly, SGLs are essential components of the highly polarized fungal growth where they are required for the formation of the polarisome organization at the hyphal apex. Aspergillus fumigatus, a human fungal pathogen, produce SGLs that are discriminated into neutral cerebrosides, glycosylinositolphosphoceramides (GIPCs) and glycosylphosphatidylinositol (GPI) anchors. In addition to complex hydrophilic head groups of GIPCs, A. fumigatus is, to date, the sole fungus that produces a GPI-anchored polysaccharide. These SPLs follow three different biosynthetic pathways. Genetics blockage leading to the inhibition of any SPL biosynthesis or to the alteration of the structure of SPL induces growth and virulence defects. The complete lipid moiety of SPLs is essential for the lipid microdomain organization and their biosynthetic pathways are potential antifungal targets but remains understudied.
Aspergillus fumigatus, GPI, glucosylceramide, GIPC
NCBI PubMed ID: 28652019A new natural mycotoxin was isolated from the fermentation broth of Trichoderma sp. Jing-8 and the structure was determined as alternariol 1'-hydroxy-9-methyl ether (1), together with twelve known compounds. The structures were elucidated on the basis of their 1D, 2D NMR spectra and mass spectrometric data. Compounds 1, 8 and 9 indicated inhibitions against germination of the seeds of cabbage with MICs < 3 μg/mL. The compound 1 showed the antibacterial activity against Bacillus subtilis and Staphylococcus aureus with MICs at 64 μg/mL. Compound 1 and 3 showed significant DPPH radical-scavenging activities with IC50 at 12 μg/mL, respectively. The OH at C-1' in compound 1 decreased the cytotoxicity of these mycotoxins. A primary structure-activity relationship about the alternariol derivatives was discussed. Compounds 2-7 and 8 were the first time to be isolated from the Trichoderma.
antibacterial activity, DPPH radical-scavenging activity, Trichoderma sp., metabolite; phytotoxicity
NCBI PubMed ID: 28278628Sphingolipids are biologically important and structurally distinct cell membrane components. Fusaruside (1) is a 10,11-unsaturated immunosuppressive fungal sphingolipid with medical potentials for treating liver injury and colitis, but its poor natural abundance bottlenecks its druggability. Here, fusaruside is clarified biosynthetically, and its efficacy-related 10,11-double bond can be generated under the regioselective catalysis of an unprecedented Δ10(E)-sphingolipid desaturase (Δ10(E)-SD). Δ10(E)-SD shares 17.7% amino acid sequence similarity with a C9-unmethylated Δ10-sphingolipid desaturase derived from a marine diatom, and 55.7% with Δ8(E)-SD from Fusarium graminearum. Heterologous expression of Δ10(E)-SD in Pichia pastoris has been established to facilitate a reliable generation of 1 through the Δ10(E)-SD catalyzed desaturation of cerebroside B (2), an abundant fungal sphingolipid. Site directed mutageneses show that the conserved histidines of Δ10(E)-SD are essential for the 10,11-desaturation catalysis, which is also preconditioned by the C9-methylation of the substrate. Moreover, Δ10(E)-SD confers improved survival and faster growth to fungal strains at low temperature and high salinity, in parallel with to higher contents of 1 in the mycelia. Collectively, the investigation describes a new Δ10(E)-sphingolipid desaturase with its heterologous expression fundamentalizing a biotechnological supply of 1, and eases the follow-up clarification of the immunosuppression and stress-tolerance mechanism
sphingolipids, biosurfactants, fusaruside, Fusarium graminearum, immunosuppression, stress-tolerance
NCBI PubMed ID: 25994332Six metabolites (1–6), including 1 new fusaric acid derivative, designated atransfusarin (1), and 5 known compounds, (3R,6R)-3-benzyl-6-isopropyl-4-methylmorpholine-2,5-dione (2), daucoterol (3), adenosine (4), cerebroside B (5), and 2,3-dihydroxypropyl (Z,Z)-9,12-octadecadienate (6), were isolated from the solid culture of an endophytic Alternaria atrans MP-7, associated with the medicinal plant Psidium guajava. The structure of the new compound was elucidated by spectral data. The antifungal test indicated that (3R,6R)-3-benzyl-6-isopropyl-4-methylmorpholine-2,5-dione (2) showed obvious inhibitory activity against Alternaria solani, Colletotrichum gloeosporioides, and Phyricularia grisea. Compared to fusaric acid (1a), even though the antifungal activity of atransfusarin (1) against A. solani, C. gloeosporioides, and P. grisea was greatly decreased, its inhibitory effect against Botrytis cinerea was still retained.
endophyte, antifungal activity, mycotoxin, Alternaria atrans, Psidium guajava, fusaric acid derivative
Publication DOI: 10.1177/1934578X19844116Tricholoma caligatum (Viv.) Ricken is an edible mushroom that belongs to matsutake group. The first chemical investigation of the three different extracts of Tricholoma caligatum resulted in two new compounds, 8-demethoxylascivol (1) and 8-epi-lascivol (2) and six known compounds, lascivol (3), trametenolic acid (4), ergosterol (5), ergosterol peroxide (6), 5a, 6a-epoxyergosterol (7), and cerebroside B (8). Their structures were elucidated by spectroscopic analyses including 1D and 2D NMR data. The biological activities of all the compounds were evaluated toward multiple targets related to inflammation and metabolic disorder such as NF-κΒ, iNOS and ROS. The findings of this study reveal that the edible mushroom Tricholoma caligatum could be a potential source for anti-inflammatory bioactive metabolites.
anti-inflammatory, Tricholoma caligatum, iNOS, NF-κΒ, lascivol
Publication DOI: 10.25135/rnp.139.19.04.1263| A | Show graphically |
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Structure type: monomer
Trivial name: adenosine, Adenosine
Compound class: glycoside, flavonoid glycoside, nucleoside
Contained glycoepitopes: IEDB_140947
Two new compounds named fischeacid and fischexanthone, together with eight known compounds, were obtained from the culture of a marine-derived fungus Neosartorya fischeri strain 1008F1. The structures of the new compounds were elucidated based on the spectroscopic data. Bioassays indicated that AGI-B4 and 3,4-dihydroxybenzoic acid showed potent inhibitory effect on the replication of tobacco mosaic virus, and AGI-B4 also possessed an inhibition of the cell proliferation of human gastric cancer cell line SGC-7901 and hepatic cancer cells BEL-7404.
cytotoxicity, Neosartorya fischeri, fischeacid, fischexanthone, antiphytoviral effect
NCBI PubMed ID: 21916772Fly agaric (Amanita muscaria) was investigated using a 1H NMR-based metabolomics approach. The caps and stems were studied separately, revealing different metabolic compositions. Additionally, multivariate data analyses of the fungal basidiomata and the type of soil were performed. Compared to the stems, A. muscaria caps exhibited higher concentrations of isoleucine, leucine, valine, alanine, aspartate, asparagine, threonine, lipids (mainly free fatty acids), choline, glycerophosphocholine (GPC), acetate, adenosine, uridine, 4-aminobutyrate, 6-hydroxynicotinate, quinolinate, UDP-carbohydrate and glycerol. Conversely, they exhibited lower concentrations of formate, fumarate, trehalose, α- and β-glucose. Six metabolites, malate, succinate, gluconate, N-acetylated compounds (NAC), tyrosine and phenylalanine, were detected in whole A. muscaria fruiting bodies but did not show significant differences in their levels between caps and stems (P value>0.05 and/or OPLS-DA loading correlation coefficient <0.4). This methodology allowed for the differentiation between the fruiting bodies of A. muscaria from mineral and mineral-organic topsoil. Moreover, the metabolomic approach and multivariate tools enabled to ascribe the basidiomata of fly agaric to the type of topsoil. Obtained results revealed that stems metabolome is more dependent on the topsoil type than caps. The correlation between metabolites and topsoil contents together with its properties exhibited mutual dependences.
NCBI PubMed ID: 25437454A novel nucleoside, 9-β-D-ribopyranosylpurine (2), along with three known nucleosides, adenosine (1), uridine (3) and nebularine (4), were isolated from the edible mushroom, Tricholoma japonicum. The structure of 2 was determined as 9-β-D-ribopyranosylpurine by comparing the reported spectral data of 2 with that of a synthetic compound. Isolation of the glycoside, which contains the sugar ribopyranose, from natural resources is very unusual. There are reports on the synthesis of 9-β-D-ribopyranosylpurine (2), but this is the first report on the isolation from natural resources. The antiproliferative activity of compounds 1-4 was evaluated using human umbilical vein endothelial cells. Compound 4 showed the highest inhibitory activity
Antiproliferative activity, Tricholoma japonicum, nucleoside
NCBI PubMed ID: 25976547Cordyceps militaris is a type of entomogenous fungi and has been widely used as a medicinal fungus in Asia. Cordycepin produced by C. militaris has also been found to protect the liver. Moreover, deep ocean water (DOW) was proven to increase the functional compounds of functional fungi-fermented products. However, the regulation of the metals in DOW is still unclear. Therefore, this study investigated the effect of DOW and certain major ions on the production of cordycepin and adenosine of C. militaris. The results indicated that, compared with using ultra-pure water (UPW), using DOW to cultivate C. militaris in a submerged culture increases the production of biomass and adenosine (p < 0.05). In the results of solid culture, the concentration of DOW exhibits a dose effect on cordycepin production. DOW contains ions that can improve the effectiveness of cordycepin, such as Mg2+, Na+, Ca2+, Fe2+, and NO3-, whereas the ion Cl- features an inhibitory effect. Moreover, Mg2+, Na+, K+, Ca2+, Fe2+, and SO42- can increase the production of adenosine, whereas Cl- cannot. However, the synthetic water made from various types of sodium salts (MgCl2, NaCl, KCl, CaCl2, FeCl2) had nearly the same effect on cordycepin production as that of DOW
Ions, Cordyceps militaris, cordycepin, deep ocean water, adenosine
NCBI PubMed ID: 26272480Determination of nucleosides is important for the quality control of Cordyceps species due to their physiological and pharmacological actions. Herein, a simple and rapid reversed-phase high performance liquid chromatography-photodiode array detection (RP-HPLC-DAD) method was developed for simultaneous determination of eleven nucleosides, i.e. uracil, cytidine, uridine, inosine, guanosine, adenine, thymine, adenosine, 2’-deoxyuridine, 2’-deoxyadenosine, and 3’-deoxyadenosine. The separation was performed on a Shimadzu VP-ODS column (4.6 × 250 mm i.d. 5 μm) using a gradient elution with a methanol/water mobile phase in 14 min. The calibration curves of 11 analytes showed good linearity with high correlation coefficients (R2 > 0.9997) within the test ranges. The limits of detection (LOD) and quantification (LOQ) of 11 analytes were less than 0.01 μg/mL. The overall relative standard deviations for intra- and inter-day were lower than 2.7 and 5.0%, respectively. Under the developed method, it was found adenosine was the most abundant nucleoside, and two unique nucleosides, i.e. 2’-deoxyuridine, and 2’-deoxyadenosine were detected in cultured medicinal macrofungus C. taii. This work demonstrated that the developed method has been successfully applied for the rapid analysis of nucleosides in cultured Cordyceps, and is expected to be used for the quality control of related pharmaceutical products.
Cordyceps, RP-HPLC-DAD, nucleosides, quantitative detection
WWW link: https://www.researchgate.net/publication/280520171_Simple_and_Rapid_Method_for_Simultaneous_Determination_of_Eleven_Nucleosides_and_Nucleobases_in_Medicinal_Macrofungus_Cordyceps_taiiNatural products play an important role in promoting health with relation to the prevention of chronic inflammation. N(6)-(2-Hydroxyethyl)adenosine (HEA), a physiologically active compound in the medicinal mushroom Cordyceps cicadae, has been identified as a Ca2+ antagonist and shown to control circulation and possess sedative activity in pharmacological tests. The fruiting body of C. cicadae has been widely applied in Chinese medicine. However, neither the anti-inflammatory activities of HEA nor the fruiting bodies of C. cicadae have been carefully examined. In this study, we first cultured the fruiting bodies of C. cicadae and then investigated the anti-inflammatory activities of water and methanol extracts of wild and artificially cultured C. cicadae fruiting bodies. Next, we determined the amount of three bioactive compounds, adenosine, cordycepin, and HEA, in the extracts and evaluated their synergistic anti-inflammatory effects. Moreover, the possible mechanism involved in anti-inflammatory action of HEA isolated from C. cicadae was investigated. The results indicate that cordycepin is more potent than adenosine and HEA in suppressing the lipopolysaccharide (LPS)-stimulated release of pro-inflammatory cytokines by RAW 264.7 macrophages; however, no synergistic effect was observed with these three compounds. HEA attenuated the LPS-induced pro-inflammatory responses by suppressing the toll-like receptor (TLR)4-mediated nuclear factor-κB (NF-κB) signaling pathway. This result will support the use of HEA as an anti-inflammatory agent and C. cicadae fruiting bodies as an anti-inflammatory mushroom
anti-inflammatory activity, nucleoside, Cordyceps cicadae, TLR4 suppression
NCBI PubMed ID: 26394068A reliable ultra-high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UHPLC-ESI-MS/MS) method for the fast simultaneous determination of 13 nucleosides and nucleobases in Cordyceps sinensis (C. sinensis) with 2-chloroadenosine as internal standard was developed and validated. Samples were ultrasonically extracted in an ice bath thrice, and the optimum analyte separation was performed on an ACQUITY UPLC(TM) HSS C18 column (100 mm × 2.1 mm, 1.8 μm) with gradient elution. All targeted analytes were separated in 5.5 min. Furthermore, all calibration curves showed good linear regression (r > 0.9970) within the test ranges, and the limits of quantitation and detection of the 13 analytes were less than 150 and 75 ng/mL, respectively. The relative standard deviations (RSDs) of intra- and inter-day precisions were <6.23%. Recoveries of the quantified analytes ranged within 85.3%-117.3%, with RSD < 6.18%. The developed UHPLC-ESI-MS/MS method was successfully applied to determine nucleosides and nucleobases in 11 batches of C. sinensis samples from different regions in China. The range for the total content in the analyzed samples was 1329-2057 µg/g
Cordyceps sinensis, nucleosides, UHPLC-ESI-MS/MS, nucleobases
NCBI PubMed ID: 26690105Cordyceps sinensis, also called DongChongXiaCao (winter worm, summer grass) in Chinese, is becoming increasingly popular and important in the public and scientific communities. This study summarizes the chemical constituents and their corresponding pharmacological actions of Cordyceps sinensis. Many bioactive components of Cordyceps sinensis have been extracted including nucleoside, polysaccharide, sterol, protein, amino acid, and polypeptide. In addition, these constituents’ corresponding pharmacological actions were also shown in the study such as anti-inflammatory, antioxidant, antitumour, antiapoptosis, and immunomodulatory actions. Therefore can use different effects of C. sinensis against different diseases and provide reference for the study of Cordyceps sinensis in the future
polysaccharides, Cordyceps sinensis, nucleosides, sterol compounds
NCBI PubMed ID: 25960753Cicada flowers, which are edible and medicinal mushrooms, are the fruiting bodies of Isaria cicadae, a fungus that is parasitic on the larvae of cicada pupae. We hypothesize that host factors might possess stimulatory activity on metabolite synthesis in Isaria cicadae. Here, we first compared the microbial community structures of different wild cicada flowers across geographical regions, compartments, and growth stages via high-throughput sequencing. Isaria cicadae TZC-3, an isolate of the most abundant operational taxonomic unit (OTU6782) in all the fungal communities, was isolated from wild cicada flowers. Furthermore, the effects of cicada pupae on metabolite synthesis in Isaria cicadae TZC-3 were studied in submerged culture. The contents of intercellular polysaccharides, adenosine, N6-(2-hydroxyethyl)-adenosine, free amino acids, and hydrolyzed monosaccharides in the mycelia cultured with cicada pupa powder (4%) were significantly increased as compared with the contents in the control group. This indicates that a cicada pupa can act as an elicitor for metabolite synthesis in Isaria cicadae.
high-throughput sequencing, microbial community
NCBI PubMed ID: 31298527The aim of this study was to use high hydrostatic pressure treatment to enhance the extraction efficiency of the active components from the fruiting bodies of Antrodia cinnamomea, and compare with those obtained by shake and ultrasonic extraction methods. The conditions of high pressure extraction (HPE) at 600 MPa, a liquid/solid ratio of 40:1, and 3 min of treatment yielded triterpenoids and adenosine concentrations of 410.41 mg/100 mL and 0.47 mg/100 mL, respectively, which did not differ significantly from those with the two other treatments-shake extraction at 180 rpm for 8 h and ultrasonic extraction at 50 Hz for 60 min. The HPE extracts significantly attenuated reactive oxygen species, nitric oxide and prostaglandin E2 production in lipopolysaccharide-stimulated RAW 264.7 cells than shake extracts did. SEM micrographs revealed that high-pressure caused physical morphological damage to the mycelium of fruiting bodies, such as distortion and disruption of mycelial cells, and increased the mass-transfer effectiveness of the solvent and solute. HPE can be employed as an efficient extraction technique for production of bioactive ingredients that might have a potential application in food and related industries.
SEM, Antrodia cinnamomea, ultrasonic, high-pressure extraction
NCBI PubMed ID: 31477970The study of metabolomics in natural products using the diverse analytical instruments including GC-MS, LC-MS, and NMR is useful for the exploration of physiological and biological effects and the investigation of drug discovery and health functional foods. Cordyceps militaris has been very attractive to natural medicine as a traditional Chinese medicine, due to its various bioactive properties including anti-cancer and anti-oxidant effects. In this study, we analyzed the metabolite profile in 50% ethanol extracts of C. militaris fruit bodies from three development periods (growth period, matured period, and aging period) using 1H-NMR, and identified 44 metabolites, which are classified as 16 amino acids, 10 organic acids, 5 carbohydrates, 3 nucleotide derivatives, and 10 other compounds. Among the three development periods of the C. militaris fruit body, the aging period showed significantly higher levels of metabolites including cordycepin, mannitol (cordycepic acid), and β-glucan. Interestingly, these bioactive metabolites are positively correlated with antitumor growth effect; the extract of the aging period showed significant inhibition of HepG2 hepatic cancer cell proliferation. These results showed that the aging period during the development of C. militaris fruit bodies was more highly enriched with bioactive metabolites that are associated with cancer cell growth inhibition.
nuclear magnetic resonance, β-glucan, metabolomics, Cordyceps militaris, cordycepin, anti-cancer effect
NCBI PubMed ID: 31336431The purpose of this study was to investigate the bacterial community of wild Cordyceps cicadae and explore its effect on the production of N6-(2-hydroxyethyl)-adenosine (HEA) and three nucleosides in C. cicadae. Illumina high-throughput sequencing technology was used to analyse the bacterial community in wild C. cicadae. After C. cicadae was isolated and bacteria were isolated from wild C. cicadae, we identified four bacterial strains that independently altered HEA and nucleoside production in a coculture with C. cicadae and four bacteria separately. After cocultivation, the HEA yield from C. cicadae increased markedly. The bacteria in wild C. cicadae did not produce HEA, and the levels of three nucleosides decreased significantly. Both 16S rRNA and community analyses showed close evolutionary relationships and high abundance ratios for the four selected bacterial strains. Some bacteria exist in wild C. cicadae and have a high abundance ratio. Moreover, the isolated bacteria inhibited the growth of C. cicadae and prevented the production of HEA in axenic cultures. We discuss the bacterial community in wild C. cicadae and provide a new way to increase HEA production in C. cicadae by coculture with bacterial strains isolated from wild C. cicadae.
coculture, nucleosides, Cordyceps cicadae, illumina high-throughput sequencing, N6-(2-hydroxyethyl)-adenosine
NCBI PubMed ID: 31463998Cordyceps cicadae is an entomogenous fungus that has been used as a valuable traditional Chinese herbal tonic, however, it can be difficult to discern the false from the genuine. In this study, the macroscopic IR fingerprint methods containing Fourier transform infrared spectroscopy (FT-IR) and second derivative infrared spectroscopy (SD-IR) were used to elucidate wild C. cicadae. The TOPSIS (Technique for Order Preference by Similarity to Ideal Solution) method was used to comprehensively evaluate C. cicadae from different geographical origins based on the macroscopic infrared spectroscopy (IR) fingerprint. The FT-IR spectra of C. cicadae exhibited the major characteristics of the absorptive peaks of carbohydrates, lipids and nucleosides at the position of 3291, 2925, 2845, 1651, 1547, 1455, 1080 and 950 1/cm. The high resolution of SD-IR further amplified the difference and revealed the potentially characteristic IR absorption spectrum. TOPSIS evaluation showed that C. cicadae from Anhui possess the strongest intensity of absorption bands among all the samples. Notably, FT-IR combined with SD-IR can effectively reveal the overall chemical components without damaging medicinal materials, and TOPSIS methods can provide a novel scientific evidence for comprehensively assessing different origins of wild C. cicadae.
Cordyceps cicadae, Fourier transform infrared spectroscopy (FT-IR), geographical origins, second derivative infrared spectroscopy (SD-IR), TOPSIS (Technique for Order Preference by Similarity to Ideal Solution) method
NCBI PubMed ID: 30785045Cultured Cordyceps militaris is very popular. To gain dynamic insight into activity markers in fruiting body of Cordyceps militaris (C. militaris) in Bombyx mori (B. mori), also named silkworm. The development stages of samples at 3, 9, 12, 19, 27, and 33 days after inoculation (DAI) were collected. HPLC coupled with diode array detection and evaporative light-scattering detection method (HPLC-DAD-ELSD) was used to determine eight makers, including six nucleosides and two carbohydrates from the samples. C. militaris cultured 33 DAI with fifth star silkworm larva could accumulate higher levels of cordycepin (13.43 mg/g) than the highest reported cordycepin (8.57 g/L). The contents of cordycepin, adenosine, and trehalose were gradually increased with the formation of C. militaris fruiting bodies on silkworm larva, while mannitol was decreased. The change of guanosine was similar to uracil. Results suggested that mannitol could be accumulated in a short period during mycelium growth and could metabolize and transform into energy store and trehalose during fruit body formation. The inosine in the insect was completely utilized and transformed. The synergistic formation of cordycepin and adenosine or differences in metabolized pathways are a great possibility according to the same trend. Highlights: This research offered some reference to further find a certain regularity or metabolic mechanism.
Cordyceps militaris, cordycepin, adenosine, HPLC-DAD-ELSD, Bombyx mori
NCBI PubMed ID: 30442223Six metabolites (1–6), including 1 new fusaric acid derivative, designated atransfusarin (1), and 5 known compounds, (3R,6R)-3-benzyl-6-isopropyl-4-methylmorpholine-2,5-dione (2), daucoterol (3), adenosine (4), cerebroside B (5), and 2,3-dihydroxypropyl (Z,Z)-9,12-octadecadienate (6), were isolated from the solid culture of an endophytic Alternaria atrans MP-7, associated with the medicinal plant Psidium guajava. The structure of the new compound was elucidated by spectral data. The antifungal test indicated that (3R,6R)-3-benzyl-6-isopropyl-4-methylmorpholine-2,5-dione (2) showed obvious inhibitory activity against Alternaria solani, Colletotrichum gloeosporioides, and Phyricularia grisea. Compared to fusaric acid (1a), even though the antifungal activity of atransfusarin (1) against A. solani, C. gloeosporioides, and P. grisea was greatly decreased, its inhibitory effect against Botrytis cinerea was still retained.
endophyte, antifungal activity, mycotoxin, Alternaria atrans, Psidium guajava, fusaric acid derivative
Publication DOI: 10.1177/1934578X19844116According to the World Health Organization, neurological and neurodegenerative diseases are highly debilitating and pose the greatest threats to public health. Diseases of the nervous system are caused by a particular pathological process that negatively affects the central and peripheral nervous systems. These diseases also lead to the loss of neuronal cell function, which causes alterations in the nervous system structure, resulting in the degeneration or death of nerve cells throughout the body. This causes problems with movement (ataxia) and mental dysfunction (dementia), both of which are commonly observed symptoms in Alzheimer's disease, Parkinson's disease, Huntington's disease, and multiple sclerosis. Medicinal mushrooms are higher fungi with nutraceutical properties and are low in calories and fat. They are also a rich source of nutrients and bioactive compounds such as carbohydrates, proteins, fibers, and vitamins that have been used in the treatment of many ailments. Medicinal mushrooms such as Pleurotus giganteus, Ganoderma lucidium, and Hericium erinaceus are commonly produced worldwide for use as health supplements and medicine. Medicinal mushrooms and their extracts have a large number of bioactive compounds, such as polysaccharide β-glucan, or polysaccharide-protein complexes, like lectins, lactones, terpenoids, alkaloids, antibiotics, and metal-chelating agents. This review will focus on the role of the medicinal properties of different medicinal mushrooms that contain bioactive compounds with a protective effect against neuronal dysfunction. This information will facilitate the development of drugs against neurodegenerative diseases.
medicinal mushrooms, Ganoderma, bioactive compounds, Pleurotus, neurodegenerative diseases, Cyathus, Sarcodon, Hericium, Antrodia, neurological disorder
NCBI PubMed ID: 32663897A rapid, sensitive and reliable indicator displacement assay (IDA) for specific detection of 2'- and 3'-deoxyadenosine (2'-dAde and 3'-dAde), the latter is also known as cordycepin, was established. The formation of inclusion complex between protonated acridine orange (AOH+) and cucurbit[7]uril (CB7) resulted in the hypochromic shift of fluorescent emission from 530 nm to 512 nm. Addition of cordycepin to the highly fluorescent AOH+/CB7 complex resulted in a unique tripartite AOH+/CB7/dAde complex with diminished fluorescence, and such reduction in emission intensity serves as the basis for our novel sensing system. The detection limits were 11 and 82 μM for 2'- and 3'-deoxyadenosine, respectively. The proposed method also demonstrated high selectivity toward 2'- and 3'-deoxyadenosine, owing to the inability of other deoxynucleosides, nucleosides and nucleotides commonly found in Cordyceps spp. to displace the AOH+ from the AOH+/CB7 complex, which was confirmed by isothermal titration calorimetry (ITC), UV-Visible and proton nuclear magnetic resonance (1H-NMR) spectroscopy. Our method was successfully implemented in the analysis of cordycepin in commercially available Ophiocordyceps and Cordyceps supplements, providing a novel and effective tool for quality assessment of these precious fungi with several health benefits.
fluorescence, detection, fungi, cordycepin, acridine orange, cucurbit uril, indicator displacement assay
NCBI PubMed ID: 32353945Nucleosides and related compounds have vital physiological and pharmacological activities. In this study, on-line preconcentration using electrokinetic supercharging (EKS)-sweeping method was proposed to enhance the efficiency of the capillary electrophoresis separation of the nucleosides and related compounds. The separation conditions, including the pH of the borate buffer (terminating electrolyte), the concentration and pH of the phosphate buffer (leading electrolyte), the concentration of sodium dodecyl sulfate (SDS) and the electrokinetic injection (EKI) time, were investigated in detail. The optimum EKS-sweeping conditions were as follows: 40 mM sodium phosphate buffer at pH 2.0 containing 50 mM SDS as the BGE, 120 mM sodium phosphate buffer at pH 2.0 as the leading electrolyte, 30 mM borate buffer at pH 12.0 as the terminating electrolyte, and EKI of the sample at −10 kV for 30 s. The separation was performed by micellar electrokinetic chromatography at −5 kV. Under these conditions, the sensitivity values of five analytes were enhanced from 26 to 109-fold compared to a standard capillary zone electrophoresis (CZE) procedure. The intra- and inter-day repeatability values (as the relative standard deviation) were less than 1.1% and 5.2% for the migration time and lower than 4.4% and 4.8% for the peak areas. Finally, the developed method was successfully applied for the determination of nucleosides and related compounds in Chinese cordyceps samples.
nucleosides, nucleobases, Chinese cordyceps, electrokinetic supercharging, micellar electrokinetic chromatography, sweeping
Publication DOI: 10.1080/00032719.2020.1725033Cordyceps cicadae (Mig.) Massee is one of the oldest and well-known traditional Chinese medicine (TCM), with its uses recorded as far back as the 5th century A.D. For centuries, C. cicadae has been used as food, tonic and folk medicine to treat malaria, palpitations, cancer, fever, diabetes, eye diseases, dizziness, and chronic kidney diseases. Although C. cicadae has been used as TCM for over 1600 years, it is not the most popular amongst the Cordyceps family. Cordyceps Sinensis (C. sinensis) and Cordyceps militaris (C. militaris) are the most studied and widely used, with a number of commercially available products derived from these two Cordyceps species. This review seeks to look at the research that has been conducted on C. cicadae over the past 30 years, reporting on the biological activities, development and utilization. This information was compared to that focused on C. sinensis and C. militaris. A literature search was conducted on different scientific search engines including, but not limited to "Web of Science", "ScienceDirect" and "Google Scholar" to identify published data on C. cicadae, I. cicadae, P. cicadae, C. sinensis and C. militaris. Research conducted on C. cicadae over the past two decades have shown that it poses similar biological properties and chemical composition as C. sinensis and C. militaris. C. cicadae has been reported to grow in many geographic locations, as compared to C. sinensis, and can be artificially cultivated via different methods. There exists sufficient evidence that C. cicadae has medicinal benefits and contain bioactive compounds similar to those found on C. sinensis and C. militaris. However, more research and standardization methods are still needed to directly compare C. cicadae with C. sinensis and C. militaris, in order to ascertain the suitability of C. cicadae as an alternative source of Cordyceps products.
Cordyceps militaris, Cordyceps sinensis, Cordyceps cicadae (Isaria cicadae), entomogenous fungi, utilization
NCBI PubMed ID: 32305637Product quality control is a prerequisite for ensuring safety, effectiveness, and stability. However, because of the different strain species and fermentation processes, there was a significant difference in quality. As a result, they should be clearly distinguished in clinical use. Among them, the fermentation process is critical to achieving consistent product quality. This study aims to introduce near-infrared spectroscopy analysis technology into the production process of fermented Cordyceps powder, including strain culture, strain passage, strain fermentation, strain filtration, strain drying, strain pulverizing, and strain mixing. First, high performance liquid chromatography (HPLC) was used to measure the total nucleosides content in the production process of 30 batches of fermented Cordyceps powder, including uracil, uridine, adenine, guanosine, adenosine, and the process stability and interbatch consistency were analyzed with traditional Chinese medicine (TCM) fingerprinting, followed by the near-infrared spectroscopy (NIRS) combined with partial least squares regression (PLSR) to establish a quantitative analysis model of total nucleosides for online process monitoring of fermented Cordyceps powder preparation products. The model parameters indicate that the established model with good robustness and high measurement precision. It further clarifies that the model can be used for online process monitoring of fermented Cordyceps powder preparation products.
fermentation, Cordyceps, nucleosides, near-infrared spectroscopy
NCBI PubMed ID: 33354379Tolypocladium guangdongense has a similar metabolite profile to Ophiocordyceps sinensis, a highly regarded fungus used for traditional Chinese medicine with high nutritional and medicinal value. Although the genome sequence of T. guangdongense has been reported, relatively little is known about the regulatory networks for fruiting body development and about the metabolite biosynthesis pathways. In order to address this, an analysis of transcriptome and proteome at differential developmental stages of T. guangdongense was performed. In total, 9076 genes were found to be expressed and 2040 proteins were identified. There were a large number of genes that were significantly differentially expressed between the mycelial stage and the stages. Interestingly, the correlation between the transcriptomic and proteomic data was low, suggesting the importance of the post-transcriptional processes in the growth and development of T. guangdongense. Among the genes/proteins that were both differentially expressed during the developmental process, there were numerous heat shock proteins and transcription factors. In addition, there were numerous proteins involved in terpenoid, ergosterol, adenosine and polysaccharide biosynthesis that also showed significant downregulation in their expression levels during the developmental process. Furthermore, both tryptophan and tryptamine were present at higher levels in the primordium stage. However, indole-3-acetic acid (IAA) levels continuously decreased as development proceeded, and the enzymes involved in IAA biosynthesis were also clearly differentially downregulated. These data could be meaningful in studying the molecular mechanisms of fungal development, and for the industrial and medicinal application of macro-fungi.
Cordyceps, bioactive ingredient biosynthesis-related enzymes, growth and development, correlation analysis, omics analysis
NCBI PubMed ID: 32802280Cisplatin (CISP) is an efficacious anticancer agent used in chemotherapy, however, the constraint to its clinical utility is the stray organ toxicity including testicular damage linked to oxidative and inflammatory cascades. This study aimed to explore the protective effect of nucleosides-rich extract from Cordyceps cicadae (NRCE) against CISP-induced testicular damage in rats. Rats were subjected to prophylactic oral administration of NRCE (50, 100 and 400 mg/kg body weight/day) for 7 days prior to testicular toxicity induced by CISP (10 mg/kg, ip) and were sacrificed after 72 h post-CISP injection. Cisplatin caused significant deficits in sperm count, viability and motility, testosterone and follicle stimulating hormone (FSH) compared to normal control. It depressed testicular activities of glutathione peroxidase (GSH-Px), superoxide dismutase (SOD), catalase (CAT), total antioxidant content (TAC), whereas malondialdehyde (MDA) increased remarkably. CISP considerably increased tumor necrosis factor alpha (TNF-α) and interleukin-1 beta (IL-1β) with alterations in testis histology compared to normal control. Interestingly, NRCE pretreatment inhibited the CISP-induced alterations in reproductive indices, restored the antioxidant activities in testes as well as inflammatory mediators and histology comparable to control. Our findings demonstrate that NRCE could prevent CISP testicular damage via inhibition of oxidative stress and pro-inflammation in rats.
inflammation, oxidative stress, nucleosides, Cordyceps cicadae, cisplatin
NCBI PubMed ID: 33007148A new nucleoside, a new natural product nucleoside, and two new pyrrole alkaloids derivatives with eight known compounds were isolated from the fruiting body of Cordyceps militaris. The structures of the new compounds were elucidated through extensive analysis of spectroscopic data including 1D and 2D NMR, HRESIMS, IR and UV. All the isolated compounds were detected for their bioactivities against LPS-induced NO production in RAW 264.7 cells. Unfortunately, all the isolates have shown no obvious activity.
Cordyceps militaris, anti-inflammatory activity, nucleoside, pyrrole alkaloid
NCBI PubMed ID: 30580621Cordyceps militaris (bei-chong-chaw, northern worm grass) is a precious and edible entomopathogenic fungus, which is widely used in traditional Chinese medicine (TCM) as a general booster for the nervous system, metabolism, and immunity. Saccharides, nucleosides, mannitol, and sterols were isolated from this fungus. The biological activity of C. militaris was attributed to the saccharide and nucleoside contents. In this study, the aqueous methanolic fraction of C. militaris fruiting bodies exhibited a significant anti-inflammatory activity. Bioactivity-guided fractionation of the active fraction led to the isolation of eight compounds, including one new and two known cerebrosides (ceramide derivatives), two nucleosides, and three sterols. Cordycerebroside A (1), the new cerebroside, along with soyacerebroside I (2) and glucocerebroside (3) inhibited the accumulation of pro-inflammatory iNOS protein and reduced the expression of COX-2 protein in LPS-stimulated RAW264.7 macrophages. This is the first study on the isolation of cerebrosides with anti-inflammatory activity from this TCM.
anti-inflammatory, cerebrosides, Cordyceps militaris, LPS-stimulated RAW264.7 macrophages, fungal fruiting bodies
NCBI PubMed ID: 26853111Uptake and metabolism of 6-benzyladenine (BA) werestudied in Actinidia deliciosa explants grown onventilated liquid Murashige and Skoog medium, usingcellulose plugs as explant support, after 0.5, 1, 2,8, 16, and 24h, 15 and 35 days of exposure to 14.8 kBqof 8-[14C] BA. Absorption of the BA is a rapidprocess and in the first half hour of culture 65% ofthe initial amount had disappeared from the medium.Exogenous BA was transformed into 7-β-D-glucopyranosyl-BA, 9-β-D-glucopyranosyl-BA, [9G]BA, 3-β-D-glucopyranosyl-BA, 9-β-D-ribofuranosyl-BA, [9R]BA, adenine, adenosine,and 5′-monophosphate of [9R]BA, [9R-5′P]BA. During thefirst 8h BA levels in the culture medium decreased,being converted into the active forms [9R]BA and[9R-5′P]BA. The excess of BA absorbed was inactivatedby glucosidation yielding [9G]BA. Ventilated culturesfavoured metabolization of active forms into inactivecompounds and this could be related to the lack ofhyperhydric shoots.
metabolism, cytokinins, Actinidia deliciosa, benzyladenine, kiwifruit
Publication DOI: 10.1023/A:1006328819324Sixteen compounds were isolated from the aerial parts of Solanum incanum L. These compounds included ten flavonoids (1-10), chlorogenic acid (11), adenosine (12), benzyl-O-β-D-xylopyranosyl(1→2)-β-D-glucopyranoside (13), and three phenylalkanoic acids (14-16). The structures were determined from their physical and spectral data. Among these compounds, kaempferol 3-O-(6″′-O-2,5-dihydroxycinnamoyl)-β-D-glucopyranosyl (1→2) β-D-glucopyranoside (10) was identified as a new compound.
flavonoids, aerial parts, Solanum incanum L., ch1orogenic acid, miscellaneous compounds
Publication DOI: 10.1002/jccs.200000029| New query | Export IDs | Home | Help |
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