Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.

Li, Hou-Jin; Chen, Ting; Xie, Ying Lu; Chen, Wen Dan; Zhu, Xiao Feng; Lan, Wen Jian

doi:10.3390/md11020551

Cited by 32 publications

(47 citation statements)

References 10 publications

(12 reference statements)

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“…Recent studies revealed that the cryptic biosynthetic pathways of fungi can be activated and the chemical diversity of their metabolites can be maximized by alternating their cultivation parameters systematically, such as the components of the media [1,2], co-culture [3,4], feeding precursors [5,6] and the addition of enzyme inhibitors [7,8]. For example, marine fungus Chondrostereum sp., which was isolated from soft coral Sarcophyton tortuosum , grows in different culture media and can produce various novel bioactive hirsutane-type sesquiterpenoids [9,10,11,12]. …”

Section: Introductionmentioning

confidence: 99%

Exploring the Chemodiversity and Biological Activities of the Secondary Metabolites from the Marine Fungus Neosartorya pseudofischeri

Liang

et al. 2014

Marine Drugs

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The production of fungal metabolites can be remarkably influenced by various cultivation parameters. To explore the biosynthetic potentials of the marine fungus, Neosartorya pseudofischeri, which was isolated from the inner tissue of starfish Acanthaster planci, glycerol-peptone-yeast extract (GlyPY) and glucose-peptone-yeast extract (GluPY) media were used to culture this fungus. When cultured in GlyPY medium, this fungus produced two novel diketopiperazines, neosartins A and B (1 and 2), together with six biogenetically-related known diketopiperazines,1,2,3,4-tetrahydro-2,3-dimethyl-1,4-dioxopyrazino[1,2-a]indole (3), 1,2,3,4-tetrahydro-2-methyl-3-methylene-1,4-dioxopyrazino[1,2-a]indole (4), 1,2,3,4-tetrahydro-2-methyl-1,3,4-trioxopyrazino[1,2-a] indole (5), 6-acetylbis(methylthio)gliotoxin (10), bisdethiobis(methylthio)gliotoxin (11), didehydrobisdethiobis(methylthio)gliotoxin (12) and N-methyl-1H-indole-2-carboxamide (6). However, a novel tetracyclic-fused alkaloid, neosartin C (14), a meroterpenoid, pyripyropene A (15), gliotoxin (7) and five known gliotoxin analogues, acetylgliotoxin (8), reduced gliotoxin (9), 6-acetylbis(methylthio)gliotoxin (10), bisdethiobis(methylthio) gliotoxin (11) and bis-N-norgliovictin (13), were obtained when grown in glucose-containing medium (GluPY medium). This is the first report of compounds 3, 4, 6, 9, 10 and 12 as naturally occurring. Their structures were determined mainly by MS, 1D and 2D NMR data. The possible biosynthetic pathways of gliotoxin-related analogues and neosartin C were proposed. The antibacterial activity of compounds 2–14 and the cytotoxic activity of compounds 4, 5 and 7–13 were evaluated. Their structure-activity relationships are also preliminarily discussed.

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Section: Introductionmentioning

confidence: 99%

Exploring the Chemodiversity and Biological Activities of the Secondary Metabolites from the Marine Fungus Neosartorya pseudofischeri

Liang

et al. 2014

Marine Drugs

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“…Incarnal extracted from G. incarnatum and another fungus in Cyphellaceae (Chondrostereum sp.) also shows potent cytotoxicity against several cancer cell lines [8,55]. To further investigate the biosynthesis of terpenoids in G. incarnatum, we mapped 35 proteins to 17 enzymes in the "terpenoid backbone biosynthesis" (KEGG: ko00900) pathway, and 10 proteins to four enzymes in the "sesquiterpenoid and triterpenoid biosynthesis" (KEGG: ko00909) pathway ( Figure 4).…”

Section: Secondary Metabolites and Terpene Pathwaymentioning

confidence: 99%

“…Secretory proteins were predicted using SignalP 3.0 [54]. Transmembrane proteins were predicted by TMHMM [55]. Protein localization signals, excluding those related to the plastid location, were identified using TargetP [56].…”

Section: Secretory Protein Analysis and Pathogenicity-related Genesmentioning

confidence: 99%

Advances in Single Molecule, Real-Time (SMRT) Sequencing

2019

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Infrastructure (NGI) in Sweden. He originally trained as a computer scientist and has worked in the field of next-generation sequencing (NGS) for over a decade. In 2008, he received his doctorate degree in bioinformatics from Uppsala University, Sweden, and to date, has authored over 50 scientific publications in genomics and bioinformatics. His current research is focused on technology development and novel sequencing applications for the study of human health and disease. Ongoing activities include the coordination of data analysis within the SweGen project, a national effort that aims to construct a whole genome map of genetic variation in the Swedish population, as well as the introduction of long-read single-molecule sequencing into clinical routines.

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“…Our primary objective is to search for chemotherapeutic agents for prevalent malignancies with remarkably high incidence in South China, such as nasopharyngeal carcinoma and hepatocellular carcinoma. As a result, we obtained a series of cytotoxic metabolites, for example hirsutanol A [18], incarnal [19], chondrosterins A and J-M [20][21][22], pseudaboydin A [23], xanthocillin X dimethyl ether [24], 7-deacetylpyripyropene A [25], pyripyropene O [25], 13-dehydroxypyripyropene A [25] and 3,3 -cyclohexylidenebis(1H-indole) [26]. As part of our continuous project, culture of the fungus Monascus ruber BB5 with liquid GPY culture medium led to the isolation of three new compounds, monarubins A-C (1, 6 and 13), together with ten known metabolites (2-5 and 7-12) ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

et al. 2020

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Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.

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Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.

Cited by 32 publications

References 10 publications

Exploring the Chemodiversity and Biological Activities of the Secondary Metabolites from the Marine Fungus Neosartorya pseudofischeri

Exploring the Chemodiversity and Biological Activities of the Secondary Metabolites from the Marine Fungus Neosartorya pseudofischeri

Advances in Single Molecule, Real-Time (SMRT) Sequencing

Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

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