Two New Pyripyropenes from the Marine Fungus <i>Fusarium lateritium</i> 2016F18‐1

Cao, Qing; Wei, Jun Hua; Deng, Rong; Feng, Gong Kan; Zhu, Xiao Feng; Lan, Wen Jian; Li, Hou-Jin

doi:10.1002/cbdv.201600298

Cited by 17 publications

(12 citation statements)

References 20 publications

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“…In summary, our chemical analysis of a sponge-derived fungus of the genus Fusarium led to the identification of two new and three known aromatic polyketides (1 and 2, and 3-5, respectively) and two sesquiterpenes (6 and 7). Although secondary metabolites of Fusarium were extensively studied in the past [26][27][28], it is still possible to obtain additional new compounds, implying the existence of unstudied Fusarium species capable of producing unknown metabolites in marine symbiotic environments. Interestingly, 4 and its 5-O-methylated congener were previously reported from the Australian marine crinoid Comatula rotalaria [20].…”

Section: Resultsmentioning

confidence: 99%

Two new aromatic polyketides from a sponge-derived Fusarium

Sibero¹,

Zhou²,

Fukaya³

et al. 2019

Beilstein J. Org. Chem.

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In our natural product screening program from marine fungi, two new aromatic polyketides karimunones A (1) and B (2) and five known compounds (3–7) were isolated from sponge-associated Fusarium sp. KJMT.FP.4.3 which was collected from an Indonesian sponge Xestospongia sp. The structures of these compounds were determined by the analysis of NMR and MS spectroscopic data. The NMR assignment of 1 was assisted by DFT-based theoretical chemical shift calculation. Compound 2 showed antibacterial activity against multidrug resistant Salmonella enterica ser. Typhi with a MIC of 125 µg/mL while 1 was not active.

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Section: Resultsmentioning

confidence: 99%

Two new aromatic polyketides from a sponge-derived Fusarium

Sibero¹,

Zhou²,

Fukaya³

et al. 2019

Beilstein J. Org. Chem.

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“…The in vitro cytotoxicities of compounds 1 – 3 were determined by MTS (3‐(4,5‐dimethylthiazol‐2‐yl)‐5(3‐carboxymethoxyphenyl)‐2‐(4‐sulfopheny)‐2 H ‐tetrazolium) assay . Three human cancer cell lines (NCI‐H1975, HepG2, and MCF‐7) were selected for the assay.…”

Section: Methodsmentioning

confidence: 99%

New Bioactive Macrocyclic Diterpenoids from Euphorbia helioscopia

Jin

Luo

Liu

et al. 2017

Chemistry & Biodiversity

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Three new macrocyclic diterpenoids, euphoscopoids A - C (1 - 3), including two new jatrophanes and a new lathyrane, were isolated from the whole plant of Euphorbia helioscopia. Their structures were elucidated by spectroscopic methods. Antifeedant and cytotoxic activities of these isolates were evaluated. All compounds showed significant antifeedant activity against a generalist plant-feeding insect, Helicoverpa armigera, with EC values ranging from 2.05 to 4.34 μg/cm . In addition, compound 2 showed moderate cytotoxicity against tumor cell lines NCI-H1975, HepG2, and MCF-2, while compounds 1 and 3 were not active at 80 μm. The results suggested not only the defensive function of macrocyclic diterpenoids in E. helioscopia against insect herbivores, but also their potential applications as new natural insect antifeedants.

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“…Pyripyropenes are meroterpenoids first isolated from Aspergillus fumigatus by the Ōmura group [ 17 ]. To date, only 25 pyripyropenes bearing different substitution (hydroxyl, acetoxyl, or propionyloxy groups) at C-1, C-7, C-11 and C-13 of the terpenoid moiety have been obtained from natural sources, with pyripyropenes A–R from A. fumigatus FO-1289 and its mutant [ 17 , 32 , 33 ], pyripyropenes S–T from A. similanensis [ 34 , 35 ], 1-deacetylpyripyropene A, 11-deacetylpyripyropene O and 13-dehydroxy-1,11-deacetylpyripyropene A from Fusarium lateritium [ 36 ], 7-deacetylpyripyropene A ( 3 ) and 13-dehydroxylpyripyropene A from N. pseudofischeri [ 16 ]. Pyripyropenes, in particular pyripyropene A ( 4 ), were discovered as a highly potent selective inhibitor of the ACAT-2 isoform, which was considered a new therapeutic target for the treatment and prevention of hypercholesterolemia and atherosclerosis [ 14 ].…”

Section: Discussionmentioning

confidence: 99%

Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

et al. 2018

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The One Strain Many Compounds (OSMAC) method was applied to explore the chemical diversities of secondary metabolites produced by Neosartorya fischeri NRRL 181. Four pyripyropenes 1–4, eight steroids 5–11, and four prenylated indole alkaloids 12–15, were obtained from the fungus cultured in petri dishes containing potato dextrose agar (PDA). 1,7,11-trideacetylpyripyropene A (1) and 1,11-dideacetyl pyripyropene A (2) were obtained and spectroscopically characterized (1D, 2D NMR, and HR-ESI-MS) from a natural source for the first time. It offered a sustainable source of these two compounds, which were usually used as starting materials in preparing pyripyropene derivatives. In addition, as compared with all the other naturally occurring pyripyropenes, 1 and 2 possessed unique acetylation patterns that did not follow the established late-step biosynthetic rules of pyripyropenes. The natural occurrence of 1 and 2 in the fungus implied that the timing and order of hydroxylation and acetylation in the late-step biosynthetic pathway of pyripyropenes remained to be revealed. The isolation and identification of 1–15 indicated that the OSMAC method could remarkably alter the metabolic profile and enrich the chemical diversities of fungal metabolites. Compounds 1–4 exhibited no obvious cytotoxicity against the triple-negative breast cancer cell line MDA-MB-231 as compared with taxol.

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Two New Pyripyropenes from the Marine Fungus Fusarium lateritium 2016F18‐1

Cited by 17 publications

References 20 publications

Two new aromatic polyketides from a sponge-derived Fusarium

Two new aromatic polyketides from a sponge-derived Fusarium

New Bioactive Macrocyclic Diterpenoids from Euphorbia helioscopia

Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

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