Oxaline and neoxaline.

Konda, Yaeko; Onda, Masayuki; Hirano, A.; Ōmura, Satoshi

doi:10.1248/cpb.28.2987

Cited by 41 publications

(19 citation statements)

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“…We compared 19 A. japonicus and A. aculeatus strains by using three different approaches; we compared sequences of the ITS1-5.8S rRNA gene-ITS2 region, RFLPs of nuclear DNA, and secondary-metabolite profiles. A. aculeatus has been reported to produce the secondary metabolites emodin, secalonic acids D and F (2, 18), aculeasins (22,28), and okaramins A, B, H, and I (13), while in A. japonicus festuclavine and cycloclavine (8), E-64 (10,11), and neoxaline (14,16) have been identified. By combining RFLP analysis of nuclear DNA, DNA sequencing, and secondary-metabolite profile analysis we could discriminate between isolates of these two taxa and improved the method by which strains of black aspergilli are identified.…”

mentioning

confidence: 99%

Combined Molecular and Biochemical Approach Identifies Aspergillus japonicus and Aspergillus aculeatus as Two Species

Pařenicová

Skouboe

Frisvad

et al. 2001

Appl Environ Microbiol

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We examined nine Aspergillus japonicus isolates and 10 Aspergillus aculeatus isolates by using molecular and biochemical markers, including DNA sequences of the ITS1-5.8S rRNA gene-ITS2 region, restriction fragment length polymorphisms (RFLP), and secondary-metabolite profiles. The DNA sequence of the internal transcribed spacers (ITS1 and ITS2) and the 5.8S rRNA gene could not be used to distinguish between A. japonicus and A. aculeatus but did show that these two taxa are more closely related to each other than to other species of black aspergilli. Aspergillus niger pyruvate kinase (pkiA) and pectin lyase A (pelA) and Agaricus bisporus 28S rRNA genes, which were used as probes in the RFLP analysis, revealed clear polymorphism between these two taxa. The A. niger pkiA and pelA probes placed six strains in an A. japonicus group and 12 isolates in an A. aculeatus group, which exhibited intraspecific variation when they were probed with the pelA gene. The secondary-metabolite profiles supported division of the isolates into the two species and differed from those of other black aspergilli. The strains classified as A. japonicus produced indole alkaloids and a polar metabolite, while the A. aculeatus isolates produced neoxaline, okaramins, paraherquamidelike compounds, and secalonic acid. A. aculeatus CBS 114.80 showed specific RFLP patterns for all loci examined. The secondary-metabolite profile of strain CBS 114.80 also differed from those of A. japonicus and A. aculeatus. Therefore, this strain probably represents a third taxon. This study provides unambiguous criteria for establishing the taxonomic positions of isolates of black aspergilli, which are important in relation to industrial use and legal protection of these organisms.Representatives of the black aspergilli are commonly used by the fermentation industry to produce extracellular enzymes and metabolites such as citric acid. It is important to clearly establish the taxonomic positions of such Aspergillus isolates due to the use of their products in the food and feed industry and for legal protection purposes. Traditionally, morphological criteria like color, shape, size, and ornamentation of conidia have been used to classify such strains (1,17,23,27,31,32).However, the black aspergilli also vary significantly in their morphological and physiological characteristics. Therefore, unambiguous identification of an isolate requires molecular and biochemical identification techniques. The major taxonomic efforts with the black aspergilli have focused on the Aspergillus niger aggregate (20,21,26,(34)(35)(36). Using mitochondrial DNA (mtDNA) and nuclear DNA restriction fragment length polymorphisms (RFLPs) and randomly amplified polymorphic DNA patterns, workers have proposed that the strains of the A. niger aggregate (1) should be divided into four taxa: A. niger, Aspergillus tubingensis (20), Aspergillus brasiliensis (35), and Aspergillus foetidus (26). Similar studies have been carried out with isolates of Aspergillus carbonarius (15,25) and with isolates of...

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mentioning

confidence: 99%

Combined Molecular and Biochemical Approach Identifies Aspergillus japonicus and Aspergillus aculeatus as Two Species

Pařenicová

Skouboe

Frisvad

et al. 2001

Appl Environ Microbiol

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“…All spectral data of synthetic 1 were identical with reported values, except for optical rotation 3. 4 The optical rotation value of 1 was variable, changing from +2.1 to +36.5. The contaminating acid might significantly influence this value because neoxaline contains basic nitrogen.…”

Section: Resultsmentioning

confidence: 63%

“…After accomplishing a scalable and concise synthetic route to access neoxaline ( 1 ), we next envisioned the total synthesis of related natural products, oxaline ( 3 ), glandicolin B ( 5 ), and meleagrin A ( 6 ) (Scheme ). Total synthesis of 6 was achieved by Albright–Goldman oxidation38 of 1 followed by hydrolysis of the acetoxy group 4. Initially, the 1 H NMR spectra of synthetic 6 was not identical to reported data for naturally occurring meleagrin A ( 6 ) 6b.…”

Section: Resultsmentioning

confidence: 96%

“…Neoxaline ( 1 ) was isolated from a culture broth of Aspergillus japonicus Fg‐551 through our chemical screening in 1979 (Figure 1). 3 It possesses a unique indoline spiroaminal framework, as well as the sterically bulky reverse prenyl group and ( E )‐dehydrohistidine 4. We have identified the anticancer activity of 1 , which results from inhibition of cell proliferation and arrest of the cell cycle during the M phase 5.…”

Section: Introductionmentioning

confidence: 99%

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Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework

Yamada

Ideguchi-Matsushita

Hirose

et al. 2015

Chemistry A European J

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The total synthesis of the indole alkaloids, neoxaline, oxaline and meleagrin A, all containing a unique indoline spiroaminal framework, was accomplished through the stereoselective introduction of a reverse prenyl group to the congested benzylic carbon of furoindoline, a two-pot transformation of indoline (containing three nitrogen atoms at appropriate positions) to the featured indoline spiroaminal framework, and elimination of carbonate assisted by the adjacent imidazole moiety to construct the (E)-dehydrohistidine. The absolute stereochemistry of neoxaline was elucidated through our total synthesis. In addition, we evaluated the bioactivity, especially the anti-infectious properties, of neoxaline and oxaline, and of some synthetic intermediates.

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“…Reaction of 4-methoxycyclohexanone (27) and 4-hydrazinopyrid-2-one (28) produced a pyridylhydrazone (29), which gave 8-methoxy-1-oxo-5H-pyrido [4,3-b]indole (30) upon refluxing in diphenylether under a N 2 atmosphere with subsequent dehydrogenation in the presence of 10% Pd/C (Scheme 6) [64]. (33) can also be obtained by refluxing phenylhydrazine (31) and 4-hydroxy-5-methylpyrid-2-one (32) in diphenylether under an Ar atmosphere (Scheme 7) [65].…”

Section: Thermal Cyclization Of Pyridyl-4-hydrazones Of Cyclohexanonementioning

confidence: 99%

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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The main trends in the development of the chemistry of a-, g-, and d-carbolines are generalized. Syntheses of carbolines based on pyridine derivatives (including the Fischer synthesis, Graebe-Ullmann reaction, thermal decomposition of azides, photochemical cyclization of anilinopyridines, arylation of substituted pyridines and piperidones, etc.) and based on indole derivatives are described. Published data about the biological activity of compounds belonging to these series are summarized.Four classes of pyridoindoles, i.e., carbolines (1 -4), are known. Of these, b-carbolines (2) have been studied most completely. Numerous studies, including several reviews [1 -3], have addressed the synthesis and various properties of this class of compounds. The properties of the other carbolines have been studied in less detail, e.g., their syntheses and chemical and physicochemical properties have not yet been discussed and compared in the literature.A detailed comparison seems especially important because precisely such an analysis can expose the basic features that make these classes chemically and biologically significant. This is especially important during research directed at the discovery of new biologically active compounds. Because the large volume of literature dedicated to b-carbolines makes it practically impossible to discuss it in a single review, the present review is limited to a comparison of the other carbolines only, the syntheses of which have been discussed much less in the literature. We intend to discuss the main trends in the development of the chemistry of a-, g-, and d-carbolines without pretending to include all literature in its entirety in order to compare the potential of finding novel effective drugs in these series. We discuss first reviews dedicated to pyridoindoles [2 -5], including a rather recent review of g-carbolines [6]. Then we switch to chemical approaches to the synthesis of selected carboline derivatives, noting briefly publications on their biological properties.Pyridoindoles (carbolines), including pyrido[4,3-b]indoles (g-carbolines), some of which exhibit a broad spectrum of biological activity, are definitely interesting. Drugs of this class already exist, e.g., neuroleptic carbidine 5 (Carbidinum or Stobadine) and dimebon antihistamine drugs 6 (Dimebonum) and diazoline 7 (Diazolinum or Omeril) [7,8]. Furthermore, dimebon exhibited pronounced anti-NMDA (N-methyl-D-asparate, ED 50 = 42 mg/kg i.p.) and anticalcium activity (blocks calcium channels, IC 50 = 57 mM) and inhibited acetylcholinesterase (ACE) and butyrylcholinesterase (BuCE) (IC 50 = 42 and 7.9 mM, respectively) in in vitro tests. It also had pronounced cognitive-stimulant properties in in vivo tests for a neurotoxic 654 0091-150X/11/4412-0654

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Oxaline and neoxaline.

Cited by 41 publications

References 0 publications

Combined Molecular and Biochemical Approach Identifies Aspergillus japonicus and Aspergillus aculeatus as Two Species

Combined Molecular and Biochemical Approach Identifies Aspergillus japonicus and Aspergillus aculeatus as Two Species

Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

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