Curvulinic acid
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| Category | Mycotoxins |
| Catalog number | BBF-04683 |
| CAS | 19053-94-2 |
| Molecular Weight | 210.18 |
| Molecular Formula | C10H10O5 |
| Purity | >95% by HPLC |
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Description
Curvulinic acid is a phytotoxin isolated from C. siddiqui.
Specification
| Storage | Store at -20°C |
| IUPAC Name | 2-(2-acetyl-3,5-dihydroxyphenyl)acetic acid |
| Canonical SMILES | CC(=O)C1=C(C=C(C=C1O)O)CC(=O)O |
| InChI | InChI=1S/C10H10O5/c1-5(11)10-6(3-9(14)15)2-7(12)4-8(10)13/h2,4,12-13H,3H2,1H3,(H,14,15) |
| InChI Key | JAHPPWGWEUVLMS-UHFFFAOYSA-N |
Properties
| Solubility | Soluble in methanol, DMSO |
Reference Reading
1. Serum Metabonomics Reveals Key Metabolites in Different Types of Childhood Short Stature
Guoyou Chen, Jinming Wang, Yisi Jing, Chunxiang Li, Wenyue Zhang, Shuang Yang, Ye Song, Xin Wang, Jincheng Liu, Dejun Yu, Zhichun Xu Front Pharmacol. 2022 May 5;13:818952. doi: 10.3389/fphar.2022.818952. eCollection 2022.
Nowadays, short stature (SS) in childhood is a common condition encountered by pediatricians, with an increase in not just a few families. Various studies related to the variations in key metabolites and their biological mechanisms that lead to SS have increased our understanding of the pathophysiology of the disease. However, little is known about the role of metabolite variation in different types of childhood SS that influence these biological processes and whether the understanding of the key metabolites from different types of childhood SS would predict the disease progression better. We performed a systematic investigation using the metabonomics method and studied the correlation between the three groups, namely, the control, idiopathic short stature (ISS), and short stature due to growth hormone deficiency (GHD). We observed that three pathways (viz., purine metabolism, sphingolipid signaling pathway, and sphingolipid metabolism) were significantly enriched in childhood SS. Moreover, we reported that two short peptides (Thr Val Leu Thr Ser and Trp Ile Lys) might play a significant role in childhood SS. Various metabolites in different pathways including 9,10-DiHOME, 12-HETE, 12(13)-EpOME, arachidonic acid methyl ester, glycerophospho-N-arachidonoyl ethanolamine, curvulinic acid (2-acetyl-3,5-dihydroxyphenyl acetic acid), nonanoic acid, and N'-(2,4-dimethylphenyl)-N-methylformamidine in human serum were compared between 60 children diagnosed with SS and 30 normal-height children. More investigations in this area may provide insights and enhance the personalized treatment approaches in clinical practice for SS by elucidating pathophysiology mechanisms of experimental verification.
2. Spirocyclic lactams and curvulinic acid derivatives from the endophytic fungus Curvularia lunata and their antibacterial and antifungal activities
Felipe Hilario, Giulia Polinário, Marcelo Rodrigues de Amorim, Victor de Sousa Batista, Nailton Monteiro do Nascimento Júnior, Angela Regina Araújo, Taís Maria Bauab, Lourdes Campaner Dos Santos Fitoterapia. 2020 Mar;141:104466. doi: 10.1016/j.fitote.2019.104466. Epub 2019 Dec 20.
Curvularia lunata, isolated from the capitula of Paepalanthus chiquitensis (Eriocaulaceae), was cultured in potato dextrose broth (PDB) medium. The ethyl acetate extract yielded two new spirocyclic γ-lactams (3 and 4), and five known compounds, namely: triticones E (1) and F (2), 5-O-methylcurvulinic acid (5), curvulinic acid (6) and curvulin (7). Their structures were elucidated by spectroscopic analysis and by the comparison with literature data. Besides, a computational study was used to elucidate the absolute configuration of the C - 3' in the compounds (3) and (4). The extract and the compounds (1 and 2), (6) and (7) were assayed against gram-positive and gram-negative bacteria and fluconazole-resistant yeast. The triticones (1) and (2) showed good antibacterial activity for Escherichia coli, with a minimum inhibitory concentration of 62.5 μg/mL.
3. Penicillium arizonense, a new, genome sequenced fungal species, reveals a high chemical diversity in secreted metabolites
Sietske Grijseels, Jens Christian Nielsen, Milica Randelovic, Jens Nielsen, Kristian Fog Nielsen, Mhairi Workman, Jens Christian Frisvad Sci Rep. 2016 Oct 14;6:35112. doi: 10.1038/srep35112.
A new soil-borne species belonging to the Penicillium section Canescentia is described, Penicillium arizonense sp. nov. (type strain CBS 141311T = IBT 12289T). The genome was sequenced and assembled into 33.7 Mb containing 12,502 predicted genes. A phylogenetic assessment based on marker genes confirmed the grouping of P. arizonense within section Canescentia. Compared to related species, P. arizonense proved to encode a high number of proteins involved in carbohydrate metabolism, in particular hemicellulases. Mining the genome for genes involved in secondary metabolite biosynthesis resulted in the identification of 62 putative biosynthetic gene clusters. Extracts of P. arizonense were analysed for secondary metabolites and austalides, pyripyropenes, tryptoquivalines, fumagillin, pseurotin A, curvulinic acid and xanthoepocin were detected. A comparative analysis against known pathways enabled the proposal of biosynthetic gene clusters in P. arizonense responsible for the synthesis of all detected compounds except curvulinic acid. The capacity to produce biomass degrading enzymes and the identification of a high chemical diversity in secreted bioactive secondary metabolites, offers a broad range of potential industrial applications for the new species P. arizonense. The description and availability of the genome sequence of P. arizonense, further provides the basis for biotechnological exploitation of this species.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
