Indole-benzodiazepine-2,5-dione Derivatives from <i>Neosartorya Fischeri</i>

Shan, Wei‐Guang; Wang, Shilei; Ying, You‐Min; Ma, Lie‐Feng; Zhan, Zha‐Jun

doi:10.3184/174751914x14140034695581

Cited by 8 publications

(14 citation statements)

References 11 publications

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“…By comparing the 1 H, 13 C NMR and MS data with the literature values, the known compounds were identified as, fumiquinazoline C ( 3 ) [ 19 ], fumiquinazoline G ( 4 ) [ 19 ], epi-aszonalenin A ( 5 ) [ 9 , 20 ], helvolic acid ( 7 ) [ 21 , 22 ], 22- O -acetylisocyclocitrinol A ( 8 ) [ 23 , 24 ]. The stereo-genic carbons of 3 and 8 were determined by an X-ray crystallographic analysis.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Novel Indole Alkaloids and Steroids from Deep Sea-Derived Fungus Aspergillus fumigatus SCSIO 41012

et al. 2018

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Two new alkaloids, fumigatosides E (1) and F (2), and a new natural product, 3, 7-diketo-cephalosporin P1 (6) along with five known compounds (3–5, 7, 8) were isolated from deep-sea derived fungal Aspergillus fumigatus SCSIO 41012. Their structures were determined by extensive spectroscopic data analysis, including 1D, 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS), and comparison between the calculated and experimental electronic circular dichroism (ECD) spectra. In addition, all compounds were tested for antibacterial and antifungal inhibitory activities. Compound 1 showed significant antifungal activity against Fusarium oxysporum f. sp. momordicae with MIC at 1.56 µg/mL. Compound 4 exhibited significant higher activity against S. aureus (16,339 and 29,213) with MIC values of 1.56 and 0.78 µg/mL, respectively, and compound 2 exhibited significant activity against A. baumanii ATCC 19606 with a MIC value of 6.25 µg/mL.

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Section: Resultsmentioning

confidence: 99%

Bioactive Novel Indole Alkaloids and Steroids from Deep Sea-Derived Fungus Aspergillus fumigatus SCSIO 41012

et al. 2018

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“…Compound 8 was isolated from a culture extract of: N. pseudofischeri IFM 52672, which was cultured in moist rice [ 24 ]; N. ficheri KUFC6344, isolated from coastal forest soil at Samaesarn island, Chonburi Province, Thailand, and cultured in a cooked rice solid medium [ 25 ]; N. fischeri CGMCC3.5378, obtained from the Chinese Academy of Science, and cultured in a solid medium containing moist corn germ [ 26 ]; N. fischeri JS0553, an endophytic fungus isolated from the plant Glehnia littoralis (family Apiaceae), which was collected in a swamp area of Suncheon, South Korea, and cultured in a solid rice medium [ 27 ]; N. tatenoi KKU-2NK23, collected from forest soil in Khon Kaen province, Thailand, and cultured in a liquid medium containing potato dextrose broth [ 28 ]; the marine-derived N. takakii KUFC 7898, isolated from the alga Amphiroa sp., which was collected in Samaesarn Island in the Gulf of Thailand and cultured in a cooked rice solid medium [ 29 ], the marine-derived N. glabra , isolated from a marine sponge Mycale sp., which was collected from the coral reef of Samaesarn Island, in the Gulf of Thailand, and cultured in a cooked rice solid medium [ 23 ]; and the marine sponge-associated N. fenelliae KUFA 0811, isolated from the marine sponge Clathria reinwardtii, which was collected from Samaesarn Island in the Gulf of Thailand and cultured in a cooked rice solid medium [ 30 ]. Compound 9a was reported only from N. ficheri KUFC6344 [ 25 ], N. fischeri CGMCC3.5378 [ 26 ], an endophytic fungus, N. fischeri JS0553 [ 27 ], and N. fischeri TJ 403-CA8 [ 20 ], whereas the unreported 6-hydroxyacetylaszonalenin ( 9b ) ( Figure 2 ) was also isolated from a culture extract of the insect-derived N. fischeri TJ403-CA8 [ 20 ]. The indole 6-Hydroxyaszonalenin ( 10 ) ( Figure 2 ) was also isolated from a culture extract of N. fischeri CGMCC3.5378 [ 26 ] and the insect-derived N. fischeri TJ 403-CA8 [ 20 ], whereas 1-formyl-5-hydroxyaszonalenin ( 11 ) ( Figure 2 ) was obtained from a culture extract of N. fischeri KUFC 6344 [ 25 ].…”

Section: Secondary Metabolites Produced By the Cultures Of Fungi Of T...mentioning

confidence: 99%

“…Compound 9a was reported only from N. ficheri KUFC6344 [ 25 ], N. fischeri CGMCC3.5378 [ 26 ], an endophytic fungus, N. fischeri JS0553 [ 27 ], and N. fischeri TJ 403-CA8 [ 20 ], whereas the unreported 6-hydroxyacetylaszonalenin ( 9b ) ( Figure 2 ) was also isolated from a culture extract of the insect-derived N. fischeri TJ403-CA8 [ 20 ]. The indole 6-Hydroxyaszonalenin ( 10 ) ( Figure 2 ) was also isolated from a culture extract of N. fischeri CGMCC3.5378 [ 26 ] and the insect-derived N. fischeri TJ 403-CA8 [ 20 ], whereas 1-formyl-5-hydroxyaszonalenin ( 11 ) ( Figure 2 ) was obtained from a culture extract of N. fischeri KUFC 6344 [ 25 ].…”

Section: Secondary Metabolites Produced By the Cultures Of Fungi Of T...mentioning

confidence: 99%

Bioactive Compounds from Terrestrial and Marine-Derived Fungi of the Genus Neosartorya †

et al. 2022

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Fungi comprise the second most species-rich organism group after that of insects. Recent estimates hypothesized that the currently reported fungal species range from 3.5 to 5.1 million types worldwide. Fungi can grow in a wide range of habitats, from the desert to the depths of the sea. Most develop in terrestrial environments, but several species live only in aquatic habitats, and some live in symbiotic relationships with plants, animals, or other fungi. Fungi have been proved to be a rich source of biologically active natural products, some of which are clinically important drugs such as the β-lactam antibiotics, penicillin and cephalosporin, the immunosuppressant, cyclosporine, and the cholesterol-lowering drugs, compactin and lovastatin. Given the estimates of fungal biodiversity, it is easy to perceive that only a small fraction of fungi worldwide have ever been investigated regarding the production of biologically valuable compounds. Traditionally, fungi are classified primarily based on the structures associated with sexual reproduction. Thus, the genus Neosartorya (Family Trichocomaceae) is the telemorphic (sexual state) of the Aspergillus section known as Fumigati, which produces both a sexual state with ascospores and an asexual state with conidiospores, while the Aspergillus species produces only conidiospores. However, according to the Melbourne Code of nomenclature, only the genus name Aspergillus is to be used for both sexual and asexual states. Consequently, the genus name Neosartorya was no longer to be used after 1 January 2013. Nevertheless, the genus name Neosartorya is still used for the fungi that had already been taxonomically classified before the new rule was in force. Another aspect is that despite the small number of species (23 species) in the genus Neosartorya, and although less than half of them have been investigated chemically, the chemical diversity of this genus is impressive. Many chemical classes of compounds, some of which have unique scaffolds, such as indole alkaloids, peptides, meroterpenes, and polyketides, have been reported from its terrestrial, marine-derived, and endophytic species. Though the biological and pharmacological activities of a small fraction of the isolated metabolites have been investigated due to the available assay systems, they exhibited relevant biological and pharmacological activities, such as anticancer, antibacterial, antiplasmodial, lipid-lowering, and enzyme-inhibitory activities.

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“…In our previous endeavor at discovering novel structures from fungi, we focused on two N. fischeri strains, i.e., N. fischeri CGMCC 3.5378 and N. fischeri NRRL181. In-depth studies on the secondary metabolites of N. fischeri CGMCC 3.5378 led to the isolation of five new prenylated indole alkaloids cultured on wheat bran [ 10 , 11 ] and moist corn [ 12 ], while the preliminary studies on N. fischeri NRRL181 furnished two new fumiquinazolines and a known compound pyripyropene A [ 13 ]. The promising bioactivities and rare natural occurrence of pyripyropenes [ 14 , 15 ] encouraged us to explore the chemical diversities of this kind of natural products.…”

Section: Introductionmentioning

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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Indole-benzodiazepine-2,5-dione Derivatives from Neosartorya Fischeri

Cited by 8 publications

References 11 publications

Bioactive Novel Indole Alkaloids and Steroids from Deep Sea-Derived Fungus Aspergillus fumigatus SCSIO 41012

Bioactive Novel Indole Alkaloids and Steroids from Deep Sea-Derived Fungus Aspergillus fumigatus SCSIO 41012

Bioactive Compounds from Terrestrial and Marine-Derived Fungi of the Genus Neosartorya †

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

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