Altechromone A

Altechromone A

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Altechromone A
Category Bioactive by-products
Catalog number BBF-04453
CAS 38412-47-4
Molecular Weight 190.19
Molecular Formula C11H10O3
Purity 98.0%

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Description

Altechromone A is produced from Alternaria brassicicola ML-P08. Altechromone A shows antimicrobial activity against Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens and Candida albicans with the MICs of 3.9, 3.9, 1.8, and 3.9 ug/ml, respectively.

Specification

Synonyms 7-Hydroxy-2,5-dimethylchromone; 7-Hydroxy-2,5-dimethyl-4H-1-benzopyran-4-one
Storage Store at 2-8°C
IUPAC Name 7-hydroxy-2,5-dimethylchromen-4-one
Canonical SMILES CC1=CC(=CC2=C1C(=O)C=C(O2)C)O
InChI InChI=1S/C11H10O3/c1-6-3-8(12)5-10-11(6)9(13)4-7(2)14-10/h3-5,12H,1-2H3
InChI Key CRNGFKXWIYTEPH-UHFFFAOYSA-N

Properties

Appearance Crystal
Antibiotic Activity Spectrum Gram-negative bacteria; Yeast
Boiling Point 374.3±42.0°C at 760 mmHg
Melting Point 258-260°C
Density 1.3±0.1 g/cm3
Solubility Soluble in Methanol, Acetone

Reference Reading

1. Morphological and chemical characterization of Alternaria populations from apple fruit
María Agustina Pavicich, Kristian Fog Nielsen, Andrea Patriarca Int J Food Microbiol. 2022 Oct 16;379:109842. doi: 10.1016/j.ijfoodmicro.2022.109842. Epub 2022 Jul 20.
Alternaria is a frequent contaminant of apple fruit, causing severe economic losses. It can produce external lesions and mouldy core, characterised by a rotten area in the apple core. In the present study, morphological and chemical characterization of Alternaria from apples was performed, evaluating differences related to agricultural practices and type of disease. A low morphological diversity was observed; most of the isolates were identified as A. tenuissima sp.-grp. (95 %). A. arborescens sp.-grp. and A. gaisen sp.-grp. were present in a proportion of 1 %, and 3 % of the isolates showed intermediate characteristics between these sp.-grps. and were identified as Alternaria sp. The chemical diversity was greater; 27 secondary metabolites were produced by the apple isolates. The most frequents were altertoxin-I (85 %), altechromone A (76 %), tentoxin (69 %), and tenuazonic acid (68 %). The alternariols were produced in a lower frequency when comparing with isolates from other crops; alternariol, 58 % and alternariol monomethyl ether, 57 %. The predominant secondary metabolite profile included compounds from different chemical families, such as dibenzopyrones, tetramic acids, perylene quinones, and cyclic tetrapeptides. A wider metabolomic capacity was observed in isolates from conventional apples when compared to those from organic fruit, with the predominance of strong producers of altertoxins and alternariols. The isolates from mouldy core showed higher ability to produce metabolites from different chemical families than those from external lesions. The wide chemical diversity of the Alternaria apple population should be considered to assess the health risk associated with apple by-products.
2. Structural revision and synthesis of altechromone A
P Königs, B Rinker, L Maus, M Nieger, J Rheinheimer, S R Waldvogel J Nat Prod. 2010 Dec 27;73(12):2064-6. doi: 10.1021/np1005604. Epub 2010 Nov 17.
The chromone "altechromone A" was synthesized as a substructure in the course of natural product synthesis. Its architecture was verified by X-ray analysis, but spectroscopic data showed a strong deviation from the reported data. By comparison with the synthesized isomers the structure of altechromone A was revised.
3. Secondary metabolite profiles of small-spored Alternaria support the new phylogenetic organization of the genus
Andrea Patriarca, Lucía da Cruz Cabral, María Agustina Pavicich, Kristian Fog Nielsen, Birgitte Andersen Int J Food Microbiol. 2019 Feb 16;291:135-143. doi: 10.1016/j.ijfoodmicro.2018.11.022. Epub 2018 Nov 23.
The group of the small-spored Alternaria species is particularly relevant in foods due to its high frequency and wide distribution in different crops. These species are responsible for the accumulation of mycotoxins and bioactive secondary metabolites in food. The taxonomy of the genus has been recently revised with particular attention on them; several morphospecies within this group cannot be segregated by phylogenetic methods, and the most recent classifications proposed to elevate several phylogenetic species-groups to the taxonomic status of section. The purpose of the present study was to compare the new taxonomic revisions in Alternaria with secondary metabolite profiles with special focus on sections Alternaria and Infectoriae and food safety. A total of 360 small-spored Alternaria isolates from Argentinean food crops (tomato fruit, pepper fruit, blueberry, apple, wheat grain, walnut, pear, and plum) was morphologically identified to species-group according to Simmons (2007), and their secondary metabolite profile was determined. The isolates belonged to A. infectoria sp.-grp. (19), A. tenuissima sp.-grp. (262), A. arborescens sp.-grp. (40), and A. alternata sp.-grp. (7); 32 isolates, presenting characteristics overlapping between the last three groups, were classified as Alternaria sp. A high chemical diversity was observed; 78 different metabolites were detected, 31 of them of known chemical structure. The isolates from A. infectoria sp.-grp. (=Alternaria section Infectoriae) presented a specific secondary metabolite profile, different from the other species-groups. Infectopyrones, novae-zelandins and phomapyrones were the most frequent metabolites produced by section Infectoriae. Altertoxin-I and alterperylenol were the only compounds that these isolates produced in common with members of section Alternaria. None of the well-known Alternaria toxins, considered relevant in foods, namely alternariol (AOH), alternariol monomethyl ether (AME), tenuazonic acid (TeA), tentoxin (TEN) or altenuene (ALT), were produced by isolates of this section. On the other hand, strains from section Alternaria (A. tenuissima, A. arborescens, and A. alternata sp.-grps.) shared a common metabolite profile, indistinguishable from each other. AOH, AME, ALT, TEN, and TeA were the most frequently mycotoxins produced, together with pyrenochaetic acid A and altechromone A. Alternaria section Alternaria represents a substantial risk in food, since their members in all types of crops are able to produce the toxic metabolites.

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