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Quitosana comercial de media massa molar (400.000 gmol -1 )e seu derivado quaternizado hidrossoluvel N,N,N -trimetilquitosana foram avaliados em condicoes laboratoriais, em analises in vitro, como agentes inibidores do crescimento de Penicillium expansum . Formulacoes nas concentracoes de 0,1; 1,0; 5,0 e 10,0 gL -1 de cada polimero foram preparadas...
Maize is the main food in Mexico since it constitutes the food base of millions of Mexicans. However, production is affected by the presence of mycotoxin-producing fungi, such as Aspergillus, Penicillium, and Fusarium. In order to prevent the growth of these pathogens, the efficacy of high molecular weight commercial chitosan was evaluated to prolo...
Quantification of microorganisms is critical for studies of microbiology. The aim of this study was to explore the efficiency of the drop plate method for quantify a fungi isolated from soils. For this, some fungi isolated from Papalotla-Tlaxcala, México soils were characterized as Penicillum sp. and one of them was chosen to be quantified by the d...
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... This metabolite showed the protective effect on ER stress-induced cell death in HT22 cells, as well as the inhibitory effect on the interleukin 10 (IL-10)-induced CD163 expression in HMDMs, at a concentration of 20 μg/mL, with no cytotoxicity at the same concentration, which look promising (Ishiuchi et al., 2020). From the alga-derived fungus Penicillium thomii KMM 4645A, another meroterpenoid, namely, austalide H acid ethyl ester (441), was obtained (Sobolevskaya et al., 2016). Studies on the Penicillium chrysogenum XNM-12, a marine algal-derived endophytic fungus, contained a meroterpenoid, oxalicine C (442), which is the first instance of an oxalicine alkaloid having a cleaved α-pyrone ring. ...
Plant endophytes have been considered as novel sources of naturally occurring compounds with
various biological activities, including cytotoxic, antimicrobial, anti-inflammatory, anticancer,
herbicides, antileishmanial and antioxidant. A variety of specialised products, comprising
terpenoids, alkaloids, polyketides, phenolic compounds, coumarins, and quinone derivatives
have been reported from various strains. An increasing number of products, especially
terpenoids, are being isolated from endophytes. Herein, the isolated new terpenoids from plant
endophytic fungi, their hosts, as well as biological activities, from January 2011 until the end of
2020 are reviewed. In this period, 516 terpenoids are classified into monoterpenes (5),
sesquiterpenes (299), diterpenes (76), sesterterpens (22), meroterpenes (83), triterpenes (29), and
other terpenoids (2), were isolated from different plant endophytic fungi species.
... ing austalide H acid (610), austalide P acid butyl ester (611), austalide P acid (612), austalide Q acid (613), 13-deoxy-austalide Q acid (614), 17-O-demethylaustalide B (615), 13-O-deacetylaustalide I (616), 13-deacetoxyaustalide I (617), 17S-dihydroaustalide K (618) from strains P. lividum Westling KMM 4663; 253 austalide H acid ethyl ester (619)254 and austalide H acid butyl ester (620)253 from P. thomii Maire KMM 4645. In bioactivity analysis, compounds 610-613, 616-617, and 619-620 showed potent inhibition of the enzyme endo-1,3-β-D-glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis with IC 50 values ranging from 0.01-2 μM (ref. ...
Fungal meroterpenoids are secondary metabolites from mixed terpene-biosynthetic origins. Their intriguing chemical structural diversification and complexity, potential bioactivities, and pharmacological significance make them attractive targets in natural product chemistry, organic synthesis, and biosynthesis. This review provides a systematic overview of the isolation, chemical structural features, biological activities, and fungal biodiversity of 1585 novel meroterpenoids from 79 genera terrestrial and marine-derived fungi including macrofungi, Basidiomycetes, in 441 research papers in 2009–2019. Based on the nonterpenoid starting moiety in their biosynthesis pathway, meroterpenoids were classified into four categories (polyketide–terpenoid, indole-, shikimate-, and miscellaneous-) with polyketide–terpenoids (mainly tetraketide-) and shikimate–terpenoids as the primary source. Basidiomycota produced 37.5% of meroterpenoids, mostly shikimate–terpenoids. The genera of Ganoderma, Penicillium, Aspergillus, and Stachybotrys are the four dominant producers. Moreover, about 56% of meroterpenoids display various pronounced bioactivities, including cytotoxicity, enzyme inhibition, antibacterial, anti-inflammatory, antiviral, antifungal activities. It's exciting that several meroterpenoids including antroquinonol and 4-acetyl antroquinonol B were developed into phase II clinically used drugs. We assume that the chemical diversity and therapeutic potential of these fungal meroterpenoids will provide biologists and medicinal chemists with a large promising sustainable treasure-trove for drug discovery.
... In our efforts to characterize new or bioactive molecules from deep-sea-derived Penicillium or Aspergillus strains, 1−4 the fungal strain Penicillium thomii YPGA3 was isolated from the sediments at a depth of 4500 m in the Yap Trench (West Pacific Ocean). A literature study revealed that the species P. thomii is prolific, with previous chemical studies affording a series of new metabolites including structurally complex austalide meroterpenoids, 5,6 rare polyketides, 7−9 eudesmane and guaiane sesquiterpenes, 10,11 a prenylated indole alkaloid, 12 and a novel xanthone dimer derivative. 13 Several of these compounds exhibited significant bioactivity. ...
Twelve new polyketides, including a naphthoqui-none derivative, penithoketone (1), and 11 chromone derivatives, penithochromones A−L (2−12), together with three known compounds (13−15) were isolated from the deep-sea-derived fungus Penicillium thomii YPGA3. The structures of the metabolites were elucidated based on extensive analyses of the spectroscopic data, and the configuration of 1 was resolved by quantum chemical calculations of NMR shifts and ECD spectra and comparisons to experimental data. Compound 1, containing a naphthoquinone-derived moiety substituted with a butenolide unit, represents a new modified naphthoquinone skeleton. Interestingly, the 5,7-dioxygenated chromone derivatives 2−13 possessed different alkyl acid or alkyl ester side chain lengths, and those with side chain lengths of seven carbon atoms were discovered from nature for the first time. The metabolites were evaluated for their cytotoxicity against four cancer cell lines; compounds 1 and 15 were found to be active, with IC 50 values ranging from 4.9 to 9.1 μM. D eep-sea fungi live in extreme environments of high pressure, low oxygen, and no light, necessitating a series of physiological adaptations to survive. These adaptations may lead to modifications to secondary metabolic pathways, increasing the possibility to produce molecules with unique properties, which are distinct from those created by shallow-water or terrestrial fungi. In our efforts to characterize new or bioactive molecules from deep-sea-derived Penicillium or Aspergillus strains, 1−4 the fungal strain Penicillium thomii YPGA3 was isolated from the sediments at a depth of 4500 m in the Yap Trench (West Pacific Ocean). A literature study revealed that the species P. thomii is prolific, with previous chemical studies affording a series of new metabolites including structurally complex austalide meroterpenoids, 5,6 rare poly-ketides, 7−9 eudesmane and guaiane sesquiterpenes, 10,11 a prenylated indole alkaloid, 12 and a novel xanthone dimer derivative. 13 Several of these compounds exhibited significant bioactivity. As deep-sea-derived P. thomii has not been chemically investigated, chromatography of the fermented material of P. thomii YPGA3 was performed, yielding a new naphthoquinone derivative (1) and 11 new 5,7-dioxygenated chromone derivatives (2−12), together with penithochromone L (13), 3,5-dihydroxy-2-methoxy-1,4-naphthalenedione (14), and 2-methoxyjuglone (15). Herein, we report the structure elucidation and the cytotoxicity of the metabolites. ■ RESULTS AND DISCUSSION The molecular formula of penithoketone (1) was determined to be C 18 H 18 O 7 by HRESIMS and NMR data (Table 1), establishing an index of hydrogen deficiency of 10. The 1 H NMR spectrum indicated the presence of a 1,2,3-trisubstituted benzene ring [δ H 6.97 (1H, dd, J = 8.3, 0.8 Hz), 7.60 (1H, dd, J = 8.3, 7.9 Hz), 7.18 (1H, dd, J = 7.9, 0.8 Hz)], a methyl doublet (δ H 0.84, d, J = 7.0 Hz), two methoxys [δ H 3.00 (3H, s), 4.06 (3H, s)], two protons for an oxymethylene [δ H 5.47 (1H, dd, J = 17.9, 1.7 Hz), 4.93 (1H, dd, J = 17.9, 1.7 Hz)], a methine [δ H 3.19 (1H, qd, J = 7.0, 1.4 Hz)], and an olefinic proton [δ H 5.83 (1H, ddd, J = 1.7, 1.7, 1.4 Hz)]. The 13 C NMR spectrum resolved 18 carbon resonances that were classified by HSQC spectrum as a methyl, two methoxys, an oxygenated methylene, five methines, and nine nonprotonated carbons. Analyses of the 2D NMR data revealed that the structure of 1 was partially similar to that of a co-isolated naphthoquinone derivative, 14, possessing a naphthoquinone-derived moiety similar to the structure of 14 and an ethyl-substituted butenolide unit. The obvious distinction between the naphthoquinone-derived moiety and compound 14 was the
... A new austalide-type meroterpenoids, austalide H acid ethyl ester (415) [138], was isolated from the marine algae-derived fungi Penicillium thomii Maire KMM 4645, and compound 415 showed inhibition of the enzyme endo-1,3-β-D-glucanase [138]. Another deep-sea-derived fungus, Penicillium chrysogenum (SCSIO 41001), produced a new merosesquiterpenoid, yaminterritrem C (416), bearing a novel naphtho[2,1-b]pyrano- [3,2e]pyran scaffold [139]. ...
... A new austalide-type meroterpenoids, austalide H acid ethyl ester (415) [138], was isolated from the marine algae-derived fungi Penicillium thomii Maire KMM 4645, and compound 415 showed inhibition of the enzyme endo-1,3-β-D-glucanase [138]. Another deep-sea-derived fungus, Penicillium chrysogenum (SCSIO 41001), produced a new merosesquiterpenoid, yaminterritrem C (416), bearing a novel naphtho[2,1-b]pyrano- [3,2e]pyran scaffold [139]. ...
Marine-derived fungi are a significant source of pharmacologically active metabolites with interesting structural properties, especially terpenoids with biological and chemical diversity. In the past five years, there has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered. In this updated review, we examine the chemical structures and bioactive properties of new terpenes from marine-derived fungi, and the biodiversity of these fungi from 2015 to 2019. A total of 140 research papers describing 471 new terpenoids of six groups (monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and meroterpenes) from 133 marine fungal strains belonging to 34 genera were included. Among them, sesquiterpenes, meroterpenes, and diterpenes comprise the largest proportions of terpenes, and the fungi genera of Penicillium, Aspergillus, and Trichoderma are the dominant producers of terpenoids. The majority of the marine-derived fungi are isolated from live marine matter: marine animals and aquatic plants (including mangrove plants and algae). Moreover, many terpenoids display various bioactivities, including cytotoxicity, antibacterial activity, lethal toxicity, anti-inflammatory activity, enzyme inhibitor activity, etc. In our opinion, the chemical diversity and biological activities of these novel terpenoids will provide medical and chemical researchers with a plenty variety of promising lead compounds for the development of marine drugs.
... Recent research showed that fungal micromycetes isolated from marine sources are interesting as producers of biologically active compounds (BACs) [1][2][3]. A discovery program for BACs in extracts of marine isolates of microscopic fungi produced 11 new meroterpenoid austalides, 8 new 6,6-spiroketals sargassopenillines A-H, and 3 new furoic-acid derivatives from Penicillium thomii KMM 4645, which was isolated from the surface of the seaweed Sargassum miyabei [3][4][5][6]. Several of the austalides had significant inhibitory activity for endo-1,3-E-D-glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis [3,4] although furoic-acid derivatives at nontoxic concentrations inhibited adhesion of CD-1 murine peritoneal macrophages [5]. ...
... A discovery program for BACs in extracts of marine isolates of microscopic fungi produced 11 new meroterpenoid austalides, 8 new 6,6-spiroketals sargassopenillines A-H, and 3 new furoic-acid derivatives from Penicillium thomii KMM 4645, which was isolated from the surface of the seaweed Sargassum miyabei [3][4][5][6]. Several of the austalides had significant inhibitory activity for endo-1,3-E-D-glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis [3,4] although furoic-acid derivatives at nontoxic concentrations inhibited adhesion of CD-1 murine peritoneal macrophages [5]. New eudesmane-type sesquiterpenoids thomimarine A-D from P. thomii KMM 4667 isolated from the rhizome of the seagrass Zostera marina induced statistically significant reduction of reactive oxygen species (ROSs) in murine RAW 264.7 macrophages stimulated by lipopolysaccharide (LPS) [6]. ...
... The austalides are a family of related meroterpenoid metabolites that were isolated for the first time from maize cultures of A. ustus 59 . Recently, it was reported that they also were produced by P. thomii KMM 4645 and P. lividum 60 . ...
A new soil-borne species belonging to the Penicillium section Canescentia is described, Penicillium arizonense sp. nov. (type strain CBS 141311T = IBT 12289T). The genome was sequenced and assembled into 33.7 Mb containing 12,502 predicted genes. A phylogenetic assessment based on marker genes confirmed the grouping of P. arizonense within section Canescentia. Compared to related species, P. arizonense proved to encode a high number of proteins involved in carbohydrate metabolism, in particular hemicellulases. Mining the genome for genes involved in secondary metabolite biosynthesis resulted in the identification of 62 putative biosynthetic gene clusters. Extracts of P. arizonense were analysed for secondary metabolites and austalides, pyripyropenes, tryptoquivalines, fumagillin, pseurotin A, curvulinic acid and xanthoepocin were detected. A comparative analysis against known pathways enabled the proposal of biosynthetic gene clusters in P. arizonense responsible for the synthesis of all detected compounds except curvulinic acid. The capacity to produce biomass degrading enzymes and the identification of a high chemical diversity in secreted bioactive secondary metabolites, offers a broad range of potential industrial applications for the new species P. arizonense. The description and availability of the genome sequence of P. arizonense, further provides the basis for biotechnological exploitation of this species.
Phthalides, an important class of bioactive natural products, are widely distributed in plants, fungi, lichens, and liverworts. Amon them, n-butylphthalide, a phthalide monomer, has been approved to cure ischemic stroke. Owing to their good bioactivities in anti-microbial, anti-inflammatory, anti-tumor, anti-diabetic, and other aspects, a large number of researches have been conducted on phthalides from nature materials. In recent years, hundreds of novel natural phthalides were obtained. This review provides profiles of the advances in the distribution, chemistry, and biological activities of natural phthalides in 2016–2022.
Austalides, a series of natural meroterpenoids, were mainly isolated from marine-derived fungal genera Aspergillus and Penicillium. To date, a total of 38 austalides have been reported, which are divided into five subclasses including 5/6/6/6 tetracyclic, 5/6/6/6/6 pentacyclic, 5/6/6/6/7 pentacyclic, 5/6/6/6/6/5 hexacyclic, and 5/6/6/6/5/6/5 heptacyclic types. Biogenetically, austalides are derived from 6-[(2E,6E) farnesyl]-5,7-dihydroxy-4-methylphthalide, and have been found to possess diversified bioactivities such as antitumor, anti-inflammatory, antimicrobial, antiviral, antifouling, promoter enhancement, as well as α-glucosidase, AP-1 transcription factor, endo-1,3-β-d-glucanase and osteoclast diff ;erentiation inhibitory effects. Their unusual molecular frameworks and diverse biological activities have also attracted great interest of synthetic scientists to synthesize them. This review describes the research progress on the chemical structures, bioactivities and synthesis of austalides since 1981, and aim to provide a scientific basis for the discovery and utilization of austalides.
Five previously undescribed compounds, including four azaphilones chermesinones D-G (1-4), one new isocoumarin derivative 6,8-dihydroxy-3-methoxy-3,7-dimethylisochroman-1-one (8), together with four known compounds were isolated from the marine-derived fungus Penicillium chermesinum FS625. Their structures were well established by comprehensive spectroscopic analysis. The absolute configurations of all the new compounds were successfully determined by the X-ray crystallography analysis or electronic circular dichroism (ECD) calculations, and confirmed by their biosynthetic pathways. Compounds 1-9 were evaluated for in vitro cytotoxicity and anti-inflammatory activity. Compounds 2-3, 5, and 7 showed weak inhibitory activity toward nitric oxide (NO) production in LPS-induced RAW 264.7 macrophages with IC50 values in the range of 69.65-95.84 µM.
