AGI-B4
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| Category | Others |
| Catalog number | BBF-03194 |
| CAS | 1313588-44-1 |
| Molecular Weight | 318.28 |
| Molecular Formula | C16H14O7 |
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Description
AGI-B4 is a substance produced by Aspergillus sp. Y80118 that inhibits the growth of endothelial cells. It inhibits the proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor (VEGF), basic fibroblast growth factor (bFGF) and endothelial cell growth factor (ECGS) with IC50 of 1.4 µmol/ L, 2.8 µmol/L and 6.2 µmol/L.
Specification
| Synonyms | (7R,8R)-AGI-B4 |
| IUPAC Name | methyl (1R,2R)-2,8-dihydroxy-6-(hydroxymethyl)-9-oxo-1,2-dihydroxanthene-1-carboxylate |
| Canonical SMILES | COC(=O)C1C(C=CC2=C1C(=O)C3=C(C=C(C=C3O2)CO)O)O |
| InChI | InChI=1S/C16H14O7/c1-22-16(21)13-8(18)2-3-10-14(13)15(20)12-9(19)4-7(6-17)5-11(12)23-10/h2-5,8,13,17-19H,6H2,1H3/t8-,13+/m1/s1 |
| InChI Key | MPAKYMOQGZITTQ-OQPBUACISA-N |
Properties
| Appearance | Yellow Powder |
| Boiling Point | 624.2±55.0°C at 760 mmHg |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1. α-Glucosidase and PTP-1B Inhibitors from Malbranchea dendritica
Daniela Rebollar-Ramos, Berenice Ovalle-Magallanes, Juan Francisco Palacios-Espinosa, Martha Lydia Macías-Rubalcava, Huzefa A Raja, Martín González-Andrade, Rachel Mata ACS Omega. 2021 Aug 25;6(35):22969-22981. doi: 10.1021/acsomega.1c03708. eCollection 2021 Sep 7.
An extract from a PDB static culture of Malbranchea dendritica exhibited α-glucosidase and PTP-1B inhibitory activities. Fractionation of the active extract led to the isolation of gymnoascolide A (1), a γ-butenolide, and xanthones sydowinin A (2), sydowinin B (3), and AGI-B4 (4), as well as orcinol (5). Compound 1 exhibited important inhibitory activity against yeast α-glucosidase (IC50 = 0.556 ± 0.009 mM) in comparison to acarbose (IC50 = 0.403 ± 0.010 mM). Kinetic analysis revealed that 1 is a mixed-type inhibitor. Furthermore, compound 1 significantly reduced the postprandial peak in mice during a sucrose tolerance test at the doses of 5.16 and 10 mg/kg. Compound 1 was reduced with Pd/C to yield a mixture of enantiomers 1a and 1b; the mixture showed similar activity against α-glucosidase (IC50 = 0.396 ± 0.003 mM) and kinetic behavior as the parent compound but might possess better drug-likeness properties according to SwissADME and Osiris Property Explorer tools. Docking analysis with yeast α-glucosidase (pdb: 3A4A) and the C-terminal subunit of human maltase-glucoamylase (pdb: 3TOP) predicted that 1, 1a, and 1b bind to an allosteric site of the enzymes. Compounds 1-5 were evaluated against PTP-1B, but only xanthone 3 moderately inhibited in a noncompetitive fashion the enzyme with an IC50 of 0.081 ± 0.004 mM. This result was consistent with that of docking analysis, which revealed that 3 might bind to an allosteric site of the enzyme. From the inactive barley-based semisolid culture of M. dendritica, the natural pigment erythroglaucin (6) and the nucleosides deoxyadenosine (7), adenosine (8), thymidine (9), and uridine (10) were also isolated and identified.
2. Anti-inflammatory dihydroxanthones from a Diaporthe species
Markus Rohr, Anna Maria Kiefer, Ulrich Kauhl, Jonathan Groß, Till Opatz, Gerhard Erkel Biol Chem. 2021 Aug 2;403(1):89-101. doi: 10.1515/hsz-2021-0192. Print 2022 Jan 26.
In a search for anti-inflammatory compounds from fungi inhibiting the promoter activity of the small chemokine CXCL10 (Interferon-inducible protein 10, IP-10) as a pro-inflammatory marker gene, the new dihydroxanthone methyl (1R, 2R)-1,2,8-trihydroxy-6-(hydroxymethyl)-9-oxo-2,9-dihydro-1H-xanthene-1-carboxylate (2) and the previously described dihydroxanthone AGI-B4 (1) were isolated from fermentations of a Diaporthe species. The structures of the compounds were elucidated by a combination of one- and two-dimensional NMR spectroscopy, mass spectrometry, and calculations using density functional theory (DFT). Compounds 1 and 2 inhibited the LPS/IFNγ induced CXCL10 promoter activity in transiently transfected human MonoMac6 cells in a dose-dependent manner with IC50 values of 4.1 µM (±0.2 µM) and 1.0 µM (±0.06 µM) respectively. Moreover, compounds 1 and 2 reduced mRNA levels and synthesis of pro-inflammatory mediators such as cytokines and chemokines in LPS/IFNγ stimulated MonoMac6 cells by interfering with the Stat1 and NFκB pathway.
3. Bioactive metabolites from a marine-derived strain of the fungus Neosartorya fischeri
Qing-Wei Tan, Ming-An Ouyang, Shuo Shen, Wei Li Nat Prod Res. 2012;26(15):1402-7. doi: 10.1080/14786419.2011.592834. Epub 2011 Sep 15.
Two new compounds named fischeacid and fischexanthone, together with eight known compounds, were obtained from the culture of a marine-derived fungus Neosartorya fischeri strain 1008F₁. The structures of the new compounds were elucidated based on the spectroscopic data. Bioassays indicated that AGI-B4 and 3,4-dihydroxybenzoic acid showed potent inhibitory effect on the replication of tobacco mosaic virus, and AGI-B4 also possessed an inhibition of the cell proliferation of human gastric cancer cell line SGC-7901 and hepatic cancer cells BEL-7404.
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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 ╳
