N.m.r. assignments, conformation, and absolute configuration of ditryptophenaline and model dioxopiperazines

Maes, Catherine M.; Potgieter, M.; Steyn, Pieter S.

doi:10.1039/p19860000861

Cited by 38 publications

(31 citation statements)

References 3 publications

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“…Ditryptophenaline was previously isolated for the first time from Aspergillus flavus var. columnaris (Maes et al 1986 ). (Shaaban et al 2014 ) tested the crude extract isolated from A. oryzae MMAO1 for their antimicrobial and cytotoxic activities and related the antimicrobial activity to ditryptophenaline with other compounds (as constituents of the extract).…”

Section: Resultsmentioning

confidence: 99%

Biological activities and variation of symbiotic fungi isolated from Coral reefs collected from Red Sea in Egypt

et al. 2020

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Ten specimens of coral reefs were collected from the Red Sea in the Ein El-Sukhna region. Fungal isolation was done using two media, Dextrose Yeast Extract Agar (DYA) and Rose Bengal Agar (RBA). The morphological traits identified 18 fungal isolates belonging to the phyla Ascomycota, Mucoromycota and Deuteromycota. Five genera in three orders have been isolated: Eutrotiales (Aspergillus, Penicillium and Byssochlamys), Mucorales (Rhizopus) and Moniliales (Curvularia). The heat mapping clustering of the isolated fungi declared that Aspergillus and Penicillium were the most frequently isolate fungi in coral reefs. It was found that A. fumigatus colonised eight coral samples with 80% colonisation rate. Moreover, about 50% of the isolated fungal species were specific to one coral reef only such as A.candidus and A.carneus isolated from Isophyllastrea rigida only, A.japonicus and A.ochraceopetaliformis from Glaxaea fascicularis, A.niger van Tieghem from Porites astreoides, A.sydowii, A.terreus and P.waksmanii from Cladocora arbuscula, P.janthinellum from Pterogorgia guadalupensis and Curvularia tuberculata, Byssochlamys spectabilis and Rhizopus oryzae from Acropora humilis. Biological activities (antimicrobial, antioxidant antiradical and cytotoxicity) of the most predominant fungal species were investigated. The antimicrobial activity of coral fungal filtrates were investigated against six pathogenic bacteria including Escherichia coli ATCC11775, Neisseria gonorrhoeae ATCC19424, Pseudomonas aeruginosa ATCC10145, Streptococcus faecalis ATCC19433, Staphylococcus aureus subsp. aureus ATCC25923, Bacillus subtilis subsp. spizizenii ATCC6633 and two pathogenic yeast including Candida albicans ATCC7102 and Candida parapsilosis ATCC22019. Most of these fungal filtrates exhibited moderate to high antibacterial activities against both gram positive and gram negative bacteria, however it showed relatively low bioactivity towards the pathogenic Candida species. Investigating the free radical scavenging activity using DPPH reagent showed low to moderate bioactivities. The highest cytotoxic activity against liver cancer cell line Hep-G2 with an IC 50 values of 18.8 µg/ml was exhibited by Aspergillus ochraceopetaliformis MN083316 and a metabolomics study was done on the ethyl acetate extract of this strain using LC-ESI-MS fingerprints leading to the isolation and purification of compound 1. Using 1D and 2D NMR techniques compound 1 was identified as ditryptophenaline. Compound 1 exhibited a strong antimicrobial, antioxidant activities as well as cytotoxic activities against MCF-7 and HEPG2 with IC 50 values of 5.8 and 7.6 mmole, respectively.The objective of this study, isolation of Coral-reef associated fungi and studying their biological activities to produce the most active secondary metabolite which might possess a novel biological activity. ARTICLE HISTORY

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Section: Resultsmentioning

confidence: 99%

Biological activities and variation of symbiotic fungi isolated from Coral reefs collected from Red Sea in Egypt

et al. 2020

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“…In addition to MS analysis (except for cyclo-L-dimethylallylTrp-L-Phe), the identities of the enzymic products of the cyclic peptides (except for cyclo-L-dimethylallyl-Trp-L-Tyr and cyclo-L-dimethylallyl-Trp-L-Phe) were confirmed by 1 H-NMR analysis (Table 1) and comparison with 1 H-NMR spectra of the non-prenylated cyclic dipeptides (Caballero et al, 1998;Hodge et al, 1988;Maes et al, 1986;Santamaría et al, 1999). In the 1 H-NMR spectra of the enzymic products, signals for a dimethylallyl moiety were found at 3?…”

Section: Biochemical Properties and Kinetic Parameters Of Ftmpt1mentioning

confidence: 88%

Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus

2005

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A putative prenyltransferase gene, ftmPT1, was identified in the genome sequence of Aspergillus fumigatus. ftmPT1 was cloned and expressed in Escherichia coli, and the protein FtmPT1 was purified to near homogeneity and characterized biochemically. This enzyme was found to catalyse the prenylation of cyclo-L-Trp-L-Pro (brevianamide F) at the C-2 position of the indole nucleus. FtmPT1 is a soluble monomeric protein, which does not contain the usual prenyl diphosphate binding site (N/D)DXXD found in most prenyltransferases, and which does not require divalent metal ions for its enzymic activity. K m values for brevianamide F and dimethylallyl diphosphate were determined as 55 and 74 mM, respectively. The turnover number was 5?57 s "1 . FtmPT1 showed a high substrate specificity towards dimethylallyl diphosphate, but accepted different tryptophan-containing cyclic dipeptides. Together with dimethylallyltryptophan synthase of ergot alkaloid biosynthesis, FtmPT1 belongs to a new group of prenyltransferases with aromatic substrates. INTRODUCTIONTrans-prenyltransferases (Bohlmann et al., 1998;Liang et al., 2002;Sacchettini & Poulter, 1997) are involved in the biosynthesis of terpenoids from C-5 units. These enzymes usually contain one or more prenyl diphosphate binding motifs, (N/D)DXXD, in their sequences (Bohlmann et al., 1998;Liang et al., 2002;Sacchettini & Poulter, 1997). Their enzymic reaction depends strictly on the presence of metal ions such as Mg 2+ or Mn 2+ (Bohlmann et al., 1998;Liang et al., 2002). A special group of prenyltransferases catalyses the attachment of a prenyl moiety to an aromatic nucleus. These enzymes show similar sequence motifs and metal ion requirements to those of the trans-prenyltransferases. Examples of this group are the prenyltransferases involved in the biosynthesis of the primary metabolites ubiquinone (Turunen et al., 2004), menaquinone (Suvarna et al., 1998), tocopherol (Schledz et al., 2001) and plastoquinone (Collakova & DellaPenna, 2001), and the prenyltransferase involved in the formation of the plant secondary metabolite shikonin (Yazaki et al., 2002). All these enzymes are membrane-bound proteins.In contrast, the dimethylallyltryptophan synthase (DMATS) that catalyses the prenylation of tryptophan at position C-4 of the indole nucleus during ergot alkaloid biosynthesis in the fungus Claviceps has been found to be a soluble protein and is active in a metal-free buffer containing EDTA (Cress et al., 1981;Lee et al., 1976;Tsai et al., 1995; Tudzynski et al., 1999). Recently, two further soluble prenyltransferases with aromatic substrates, which are active in the absence of metal ions and contain no (N/D)DXXD motifs, CloQ involved in the biosynthesis of clorobiocin from Streptomyces roseochromogenes (Pojer et al., 2003) and LtxC involved in the biosynthesis of lyngbyatoxins from Lyngbya majuscula (Edwards & Gerwick 2004), have been identified. Very recently, we identified an orthologue of DMATS, FgaPT2, in the genome sequence of Aspergillus fumigatus (Unsöld & Li, 2005). Inte...

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“…The first total synthesis of (–)-ditryptophenaline ( 1 ) was achieved in 1981, through a biomimetic thallium(III)-promoted oxidative dimerization allowing the determination of its absolute stereochemistry [46]. The S configuration at the ring junctions C2/C2’ and C3/C3’, and the two N -methyl-L-phenylalanines involved in the dimeric moiety, were later corroborated by Maes et al [47], through additional NMR assignments and circular dichroism experiments. Relevantly, the early work by Nakagawa and colleagues [46] provided preliminary but relevant clues on the biosynthetic pathway involved in the production of 1 , which was further elucidated by Saruwatari and co-workers [48], suggesting that the cytochrome P450 DtpC is responsible for both pyrroloindole ring formation and the concomitant dimerization through a radical-mediated coupling reaction.…”

Section: Chemistry and Biological Properties Of Marine Diketopipermentioning

confidence: 99%

Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

et al. 2019

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While several marine natural products bearing the 2,5-diketopiperazine ring have been reported to date, the unique chemistry of dimeric frameworks appears to remain neglected. Frequently reported from marine-derived strains of fungi, many naturally occurring diketopiperazine dimers have been shown to display a wide spectrum of pharmacological properties, particularly within the field of cancer and antimicrobial therapy. While their structures illustrate the unmatched power of marine biosynthetic machinery, often exhibiting unsymmetrical connections with rare linkage frameworks, enhanced binding ability to a variety of pharmacologically relevant receptors has been also witnessed. The existence of a bifunctional linker to anchor two substrates, resulting in a higher concentration of pharmacophores in proximity to recognition sites of several receptors involved in human diseases, portrays this group of metabolites as privileged lead structures for advanced pre-clinical and clinical studies. Despite the structural novelty of various marine diketopiperazine dimers and their relevant bioactive properties in several models of disease, to our knowledge, this attractive subclass of compounds is reviewed here for the first time.

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N.m.r. assignments, conformation, and absolute configuration of ditryptophenaline and model dioxopiperazines

Cited by 38 publications

References 3 publications

Biological activities and variation of symbiotic fungi isolated from Coral reefs collected from Red Sea in Egypt

Biological activities and variation of symbiotic fungi isolated from Coral reefs collected from Red Sea in Egypt

Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus

Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers

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