New Cytotoxic Cytochalasans from a Plant-Associated Fungus Chaetomium globosum kz-19.
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ABSTRACT:
SUBMITTER: Li T
PROVIDER: S-EPMC8398356 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:Cytoglobosins H (1) and I (2), together with seven known cytochalasan alkaloids (3-9), were isolated from the deep-sea-derived fungus Chaetomium globosum. The structures of new compounds 1 and 2 were elucidated by extensive 1D and 2D NMR and mass spectroscopic data. All the compounds were evaluated for their antiproliferative activities against MDA-MB-231 human breast cancer cells, LNCaP human prostate cancer cells, and B16F10 mouse melanoma cells. Compound 6 showed significant antiproliferative activity against LNCaP and B16F10 cell lines with IC50 values of 0.62 and 2.78 ?M, respectively. Further testing confirmed that compound 6 inhibited the growth of LNCaP cells by inducing apoptosis.
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Project description:Five metabolites including two new ones, prochaetoviridin A (1) and chaetoindolin A (2), were isolated from the endophytic fungus Chaetomium globosum CDW7. Compounds 1 and 2 were characterized as an isocoumarin and an indole alkaloid derivative, respectively, with their structures elucidated by comprehensive spectroscopic analyses including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), NMR, and circular dichroism (CD) comparison. Compounds 3?5 were identified as chaetoviridin A, chaetoglobosin R, and chaetoglobosin T, respectively. Chaetoviridin A (3) exhibited antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.97 ?g/mL. In vivo test showed that 3 displayed a protective efficacy of 64.3% against rape Sclerotinia rot at the dosage of 200 ?g/mL, comparable to that of carbendazim (69.2%).
| S-EPMC6278401 | biostudies-other
Project description:Two new cytochalasans, Chaetomadrasins A (1) and B (2), along with six known analogues (3-8), were isolated from the solid-state fermented culture of desert soil-derived Chaetomium madrasense 375. Their structures were clarified by comprehensive spectroscopic analyses, and the absolute configurations of Compounds 1 and 2 were confirmed by electronic circular dichroism (ECD) and calculated ECD. For the first time, Chaetomadrasins A (1), which belongs to the chaetoglobosin family, is characterized by the presence of all oxygen atoms in the form of Carbonyl. Chaetomadrasin B (2) represents the first example of chaetoglobosin type cytochalasan characterized by a hydroxy unit and carbonyl group fused to the indole ring. Compounds 1 and 2 displayed moderate cytotoxicity against HepG2 human hepatocellular carcinoma cells.
| S-EPMC6767004 | biostudies-literature
Project description:The following compounds were isolated from acetate extracts of Chaetomium globosum 7951 solid cultures: demethylchaetocochin C (1) and chaetoperazine A (3), two new epipolythiodioxopiperazine (ETP) alkaloids, a novel pyridine benzamide, 4-formyl-N-(3'-hydroxypyridin-2'-yl) benzamide (6), and three known ETP derivatives (2, 4, and 5). The structures of these compounds were determined using extensive spectroscopic data analysis. Compounds 1-3, and 6, inhibited the growth of MCF-7, MDA-MB-231, H460 and HCT-8 cells with an IC50 of 4.5 to 65.0 μM.
| S-EPMC9064350 | biostudies-literature
Project description:The marine ecosystem is an extraordinary reserve of pharmaceutically important, bioactive compounds even in this "synthetic age". Marine algae-associated endophytic fungi have gained prominence as an important source of bioactive compounds. This study was conducted on secondary metabolites of Chaetomium globosum-associated with marine green alga Chaetomorpha media from the Konkan coastline, India. Its ethyl acetate extract (CGEE) exhibited an IC50 value of 7.9?±?0.1 µg/mL on MCF-7 cells. CGEE exhibited G2M phase cell cycle arrest, ROS production and MMP loss in MCF-7 cells. The myco-components in CGEE contributing to the cytotoxicity were found by Gas Chromatography/Mass Spectrometry analyses. Chrysin, a dihydroxyflavone was one of the forty-six myco-components which is commonly found in honey, propolis and passionflower extracts. The compound was isolated and characterized as fungal chrysin using HPLC, UV-Vis spectroscopy, LC-MS, IR and NMR analyses by comparing with standard chrysin. The purified compound exhibited an IC50 value of 49.0?±?0.6 µM while that of standard chrysin was 48.5?±?1.6 µM in MCF-7 cells. It induced apoptosis, G1 phase cell cycle arrest, MMP loss, and ROS production. This is the first report of chrysin from an alternative source with opportunities for yield enhancement.
| S-EPMC7603332 | biostudies-literature
Project description:Three new azaphilone alkaloids containing glutamine residues, namely N-glutarylchaetoviridins A-C (1-3), together with two related compounds (4 and 5) were isolated from the extract of Chaetomium globosum HDN151398, a fungus isolated from a deep-sea sediment sample collected in South China Sea. Their structures were elucidated on the basis of extensive 1D and 2D NMR as well as HRESIMS spectroscopic data and chemical analysis. N-glutarylchaetoviridins A-C (1-3) represent the first class of chaetoviridins characterized by embedded glutamate residues. Amino acids incubation experiments produced five azaphilone laden different amino acids residues (6-10) which indicated that this method can enhanced the structural diversity of this strain by culturing with amino acids. Cytotoxicity of the isolated compounds were evaluated against a panel of human cancer cell lines.
| S-EPMC6562794 | biostudies-literature
Project description:BackgroundEndophytic fungi have proven to be a rich source of novel natural products with a wide-array of biological activities and higher levels of structural diversity.ResultsChemical investigation on the liquid- and solid-state fermented products of Chaetomium globosum Km1226 isolated from the littoral medicinal herb Atriplex maximowicziana Makino resulted in the isolation of compounds 1-14. Their structures were determined by spectroscopic analysis as three previously undescribed C13-polyketides, namely aureonitol C (1), mollipilins G (2), and H (3), along with eleven known compounds 4-14. Among these, mollipilin A (5) exhibited significant nitric oxide production inhibitory activity in LPS-induced BV-2 microglial cells with an IC50 value of 0.7 ± 0.1 µM, and chaetoglobosin D (10) displayed potent anti-angiogenesis property in human endothelial progenitor cells (EPCs) with an IC50 value of 0.8 ± 0.3 µM.ConclusionsThree previously unreported compounds 1-3 were isolated and identified. Mollipilin A (5) and chaetoglobosin D (10) could possibly be developed as anti-inflammatory and anti-angiogenic lead drugs, respectively.
| S-EPMC10686906 | biostudies-literature
Project description:Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium globosum C2F17. Their structures were accomplished by extensive spectroscopic analysis combined with single-crystal X-ray crystallography and ECD calculations. Meanwhile, the structures and absolute configurations of the previously reported compounds 6, 12, and 13 were confirmed by single-crystal X-ray analysis for the first time. Chaetoglobosins E (6) and Fex (11) showed significant cytotoxicity against a panel of cancer cell lines, K562, A549, Huh7, H1975, MCF-7, U937, BGC823, HL60, Hela, and MOLT-4, with the IC50 values ranging from 1.4 ?M to 9.2 ?M.
| S-EPMC7179451 | biostudies-literature
Project description:Onychomycosis is usually caused by dermatophytes, but some nondermatophytic molds and yeasts are also associated with invasion of nails. The genus Chaetomium is a dematiaceous nondermatophytic mold found in soil and plant debris as a saprophytic fungus. We report the first Korean case of onychomycosis caused by Chaetomium globosum in a 35-year-old male. The patient showed brownish-yellow discoloration and subungual hyperkeratosis on the right toenails (1st and 5th) and left toenails (1st and 4th). Direct microscopic examination of scraping on the potassium hydroxide preparation revealed septate hyphae and repeated cultures on Sabouraud's dextrose agar (SDA) without cycloheximide slants showed the same fast-growing colonies, which were initially velvety white then turned to dark gray to brown. However, there was no growth of colony on SDA with cycloheximide slants. Brown-colored septated hyphae, perithecia and ascospores were shown in the slide culture. The DNA sequence of internal transcribed spacer region of the clinical sample was a 100% match to that of C. globosum strain ATCC 6205 (GenBank accession number EF524036.1). We confirmed C. globosum by KOH mount, colony, and light microscopic morphology and DNA sequence analysis. The patient was treated with 250 mg oral terbinafine daily and topical amorolfine 5% nail lacquer for 3 months.
| S-EPMC3662921 | biostudies-literature
Project description:Chemical investigation on the methanol extract of Chaetomium globosum TW1-1, a fungus isolated from the common pillbug (Armadillidium vulgare), has resulted in the isolation of nine new highly oxygenated cytochalasan alkaloids, armochaetoglobins S-Z (1 and 3-9) and 7-O-acetylarmochaetoglobin S (2), together with eight structurally related known analogues (10-17). Their structures and absolute configurations were elucidated by spectroscopic analyses. Among them, compound 2 presents to be the first member of chaetoglobosin family with an acetyl group, and compounds 3 represents the first chaetoglobosin characterized by an 2',3'-epoxy-indole moiety. The discovery of these new compounds revealed the largely untapped chemical diversity of cytochalasans and enriched their chemical research. Compounds 1-9 were evaluated for their cytotoxic activities against five human cancer cell lines, and compounds 8 and 9 exhibited significant cytotoxic activities with IC50 values ranging from 10.45 to 30.42??M.
| S-EPMC4703973 | biostudies-literature