Sartorymensin, a new indole alkaloid, and new analogues of tryptoquivaline and fiscalins produced by Neosartorya siamensis (KUFC 6349)

Buttachon, Suradet; Chandrapatya, Angsumarn; Manoch, Leka; Silva, Artur M. S.; Gales, Luı́s; Bruyère, Céline; Kiss, Róbert; Kijjoa, Anake

doi:10.1016/j.tet.2012.02.024

Cited by 71 publications

(83 citation statements)

References 19 publications

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“…Subsequently, some tryptoquivaline ( 20 ) analogues; tryptoquivalines F ( 21 ), H ( 22 ), L ( 23 ), and O ( 24 ); fiscalins A ( 25 ) and C ( 26 ); sartorymensin ( 27 ); a quinazolinone‐containing indole; epi‐fiscalins A ( 28 ) and C ( 29 ); neofiscalin A ( 30 ); epi‐neofiscalin A ( 31 ); and 3′‐(4‐oxoquinazolin‐3‐yl)spiro[1H‐indole‐3,5′‐oxolane]‐2,2′‐dione ( 32 ) (Figure ) were isolated from the fungus Neosartorya siamensis (KUFC 6349). Except for alkaloid 27 (IC 50 = 39‒73 μM), all of the compounds showed no in vitro growth inhibitory activity (IC 50 > 100 μM) against U373 (glioblastoma), Hs683a (glioblastoma), A549, MCF‐7, and SK‐MEL‐28 (melanoma) cell lines . Meanwhile, 15β‐hydroxy‐5N‐acetylardeemin ( 33 ) showed greater cytotoxic activity against human HeLa contaminant KB (IC 50 = 61.4 μM) and rat hepatic HSC‐T6 (IC 50 = 88.2 μM) cell lines than its geometric hydroxylated and nonhydroxylated congeners, 16α‐hydroxy‐5N‐acetylardeemin ( 34 ) and 5N‐acetylardeemin ( 35 ) (Figure ), from Aspergillus terreus …”

Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

158

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To follow-up on our prior Part I review, this Part II review summarizes and provides updated literature on novel quinoline and quinazoline alkaloids isolated during the period of 2009-2016, together with the biological activity and the mechanisms of action of these classes of natural products. Over 200 molecules with a broad range of biological activities, including antitumor, antiparasitic and insecticidal, antibacterial and antifungal, cardioprotective, antiviral, anti-inflammatory, hepatoprotective, antioxidant, anti-asthma, antitussive, and other activities, are discussed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

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Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

158

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“…Other fiscalins have now been discovered: epi, neo, etc . 68 Verrucines A and B and anacine have been isolated from Penicillium verrucosum (figure 13c). 69 They likely form via Ant- l -Gln- l -Phe-, Ant- l -Gln- d -Phe- and Ant- l -Gln- d -Leu-thioester intermediates on related trimodular NRPSs with the same double cyclization/release process to yield the characteristic pyrazinoqinazolinone scaffold.…”

Section: Pathways Using Tethered Ant-tripeptidyl Intermediatesmentioning

confidence: 99%

Short Pathways to Complexity Generation: Fungal Peptidyl Alkaloid Multicyclic Scaffolds from Anthranilate Building Blocks

et al. 2013

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Complexity generation in naturally occurring peptide scaffolds can occur either by posttranslational modifications of nascent ribosomal proteins or through post assembly line tailoring of nonribosomal peptides. Short enzymatic pathways utilizing bimodular and trimodular nonribosomal peptide synthetase (NRPS) assembly lines, followed by tailoring oxygenases and/or prenyltransferases, efficiently construct complex fungal peptidyl alkaloid scaffolds in Aspergilli, Neosartorya, and Penicillium species. Use of the nonproteinogenic amino acid anthranilate as chain-initiating building block and chain-terminating intramolecular nucleophile leads efficiently to peptidyl alkaloid scaffolds with two to seven fused rings.

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“…Reexamination of the column fractions left over from our previous work of N. laciniosa (KUFC 7896) [15] led to isolation of a new tryptoquivaline analogue, tryptoquivaline T ( 1d ), whereas reexamination of the nonpolar fractions from the column chromatography of N. siamensis (KUFC 6349) [16] furnished chevalone B ( 6 ) and chevalone C ( 7a ) (Figure 1). The isolated compounds were evaluated, together with sartorypyrone B ( 7b ) previously isolated from N. tsunodae and sartorypyrone A ( 8 ) (Figure 1) previously isolated from N. fischeri , for antibacterial activity against the Gram-positive ( Staphylococcus aureus ATCC 25923 and Bacillus subtilis ATCC 6633) and Gram-negative ( Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) bacteria, as well as multidrug-resistant isolates from the environment.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial and Antibiofilm Activities of Tryptoquivalines and Meroditerpenes Isolated from the Marine-Derived Fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the Soil Fungi N. fischeri and N. siamensis

et al. 2014

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A new meroditerpene, sartorypyrone C (5), was isolated, together with the known tryptoquivalines l (1a), H (1b), F (1c), 3′-(4-oxoquinazolin-3-yl) spiro[1H-indole-3,5′]-2,2′-dione (2) and 4(3H)-quinazolinone (3), from the culture of the marine sponge-associated fungus Neosartorya paulistensis (KUFC 7897), while reexamination of the fractions remaining from a previous study of the culture of the diseased coral-derived fungus N. laciniosa (KUFC 7896) led to isolation of a new tryptoquivaline derivative tryptoquivaline T (1d). Compounds 1a–d, 2, 3, and 5, together with aszonapyrones A (4a) and B (4b), chevalones B (6) and C (7a), sartorypyrones B (7b) and A (8), were tested for their antibacterial activity against four reference strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa), as well as the environmental multidrug-resistant isolates. Only aszonapyrone A (4a) and sartorypyrone A (8) exhibited significant antibacterial activity as well as synergism with antibiotics against the Gram-positive multidrug-resistant strains. Antibiofilm assays of aszonapyrone A (4a) and sartorypyrone A (8) showed that practically no biofilm was formed in the presence of their 2× MIC and MIC. However, the presence of a sub-inhibitory concentration of ½ MIC of 4a and 8 was found to increase the biofilm production in both reference strain and the multidrug-resistant isolates of S. aureus.

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Sartorymensin, a new indole alkaloid, and new analogues of tryptoquivaline and fiscalins produced by Neosartorya siamensis (KUFC 6349)

Cited by 71 publications

References 19 publications

Biologically active quinoline and quinazoline alkaloids part II

Biologically active quinoline and quinazoline alkaloids part II

Short Pathways to Complexity Generation: Fungal Peptidyl Alkaloid Multicyclic Scaffolds from Anthranilate Building Blocks

Antibacterial and Antibiofilm Activities of Tryptoquivalines and Meroditerpenes Isolated from the Marine-Derived Fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the Soil Fungi N. fischeri and N. siamensis

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