Acremonidin A
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| Category | Antibiotics |
| Catalog number | BBF-00016 |
| CAS | |
| Molecular Weight | 614.56 |
| Molecular Formula | C33H26O12 |
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Description
Acremonidins A to approximately E (1 to approximately 5) were produced by fermentation of Acremonium sp. LL-Cyan 416, in heterogeneous phases. Acremonidins A showed moderate activity against Gram-positive bacteria, including the methicillin-resistant staphylococci and vancomycin-resistant enterococci.
Specification
| IUPAC Name | methyl 2-[(1R,2S,12S)-2-acetyloxy-7,9,14,16-tetrahydroxy-5-methyl-11-oxopentacyclo[10.7.2.01,10.03,8.013,18]henicosa-3(8),4,6,9,13,15,17,20-octaene-15-carbonyl]-3,6-dihydroxybenzoate |
| Canonical SMILES | CC1=CC2=C(C(=C1)O)C(=C3C(=O)C4C=CC3(C2OC(=O)C)CC5=CC(=C(C(=C45)O)C(=O)C6=C(C=CC(=C6C(=O)OC)O)O)O)O |
| InChI | InChI=1S/C33H26O12/c1-12-8-16-22(19(37)9-12)30(42)26-27(39)15-6-7-33(26,31(16)45-13(2)34)11-14-10-20(38)25(28(40)21(14)15)29(41)23-17(35)4-5-18(36)24(23)32(43)44-3/h4-10,15,31,35-38,40,42H,11H2,1-3H3/t15-,31-,33-/m0/s1 |
| InChI Key | OFAIMNXQEZOWPU-RXKIPKFJSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
Reference Reading
1. Absolute configuration of acremoxanthone C, a potent calmodulin inhibitor from Purpureocillium lilacinum
Abraham Madariaga-Mazón, Martín González-Andrade, María Del Carmen González, Anthony E Glenn, Carlos M Cerda-García-Rojas, Rachel Mata J Nat Prod. 2013 Aug 23;76(8):1454-60. doi: 10.1021/np4002477. Epub 2013 Jul 22.
Bioassay-guided fractionation of an extract prepared from the culture medium and mycelium of Purpureocillium lilacinum allowed the isolation of two calmodulin (CaM) inhibitors, namely, acremoxanthone C (1) and acremonidin A (2). The absolute configuration of 1 was established as 2R, 3R, 1'S, 11'S, and 14'R through extensive NMR spectroscopy and molecular modeling calculations at the DFT B3LYP/DGDZVP level, which included the comparison between theoretical and experimental specific rotation, ³J(C,H), and ³J(H,H) values. Compounds 1 and 2 bind to the human calmodulin (hCaM) biosensor hCaM M124C-mBBr, with dissociation constants (Kd) of 18.25 and 19.40 nM, respectively, 70-fold higher than that of chlorpromazine (Kd = 1.24 μM), used as positive control. Docking analysis using AutoDock 4.2 predicted that 1 and 2 bind to CaM at a similar site to that which KAR-2 binds, which is unusual. Furthermore, a novel, sensible, and specific fluorescent biosensor of hCaM, i.e., hCaM T110C-mBBr, was constructed; this device is labeled at a site where classical inhibitors do not interact and was successfully applied to measure the interaction of 1 with CaM. This is the first report of xanthone-anthraquinone heterodimers in species of Paecilomyces or Purpureocillium genera.
2. Acremonidin E produced by Penicillium sp. SNF123, a fungal endophyte of Panax ginseng, has antimelanogenic activities
Kyuri Kim, Hae-In Jeong, Inho Yang, Sang-Jip Nam, Kyung-Min Lim J Ginseng Res. 2021 Jan;45(1):98-107. doi: 10.1016/j.jgr.2019.11.007. Epub 2019 Nov 21.
Background: Ginseng extracts and ginseng-fermented products are widely used as functional cosmetic ingredients for their whitening and antiwrinkle effects. Recently, increasing attention has been given to bioactive metabolites isolated from endophytic fungi. However, little is known about the bioactive metabolites of the fungi associated with Panax ginseng Meyer. Methods: An endophytic fungus, Penicillium sp. SNF123 was isolated from the root of P. ginseng, from which acremonidin E was purified. Acremonidin E was tested on melanin synthesis in the murine melanoma cell line B16F10, in the human melanoma cell line MNT-1, and in a pigmented 3D-human skin model, Melanoderm. Results: Acremonidin E reduced melanogenesis in α-melanocyte-stimulating hormone (α-MSH)-stimulated B16F10 cells with minimal cytotoxicity. qRT-PCR analysis demonstrated that acremonidin E downregulated melanogenic genes, including tyrosinase and tyrosinase-related protein 1 (TRP-1), while their enzymatic activities were unaffected. The antimelanogenic effects of acremonidin E were further confirmed in MNT-1 and a pigmented 3D human epidermal skin model, Melanoderm. Immunohistological examination of the Melanoderm further confirmed the regression of both melanin synthesis and melanocyte activation in the treated tissue. Conclusion: This study demonstrates that acremonidin E, a bioactive metabolite derived from a fungal endophyte of P. ginseng, can inhibit melanin synthesis by downregulating tyrosinase, illuminating the potential utility of microorganisms associated with P. ginseng for cosmetic ingredients.
3. Role of bioactive metabolites from Acremonium camptosporum associated with the marine sponge Aplysina fulva
Thamires Martins, Claudia Schinke, Sonia C N Queiroz, Patrícia A de C Braga, Fábio S P Silva, Itamar S Melo, Felix G R Reyes Chemosphere. 2021 Jul;274:129753. doi: 10.1016/j.chemosphere.2021.129753. Epub 2021 Jan 22.
Acremonium camptosporum, a fungus associated with the marine sponge Aplysina fulva, was collected from the isolated mid-Atlantic Saint Peter and Saint Paul Archipelago, Brazil, and was found to produce secondary metabolites that displayed antibacterial activities. Mass spectra data obtained by UPLC-ESI-MS/MS analyses of these extracts were compared to several databases and revealed the presence of several different cytotoxic acremonidins and acremoxanthones. The close association between the sponge and the fungi with its compounds could be of strategic importance in defending both from the high predation pressure and spatial competition in the warm-water scarps of the islands.
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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 ╳
