Asterriquinol D dimethyl ether
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| Category | Bioactive by-products |
| Catalog number | BBF-04492 |
| CAS | 287117-66-2 |
| Molecular Weight | 428.48 |
| Molecular Formula | C26H24N2O4 |
| Purity | ≥95% |
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Description
Asterriquinol D dimethylether is a fungal metabolite first isolated from Aspergillus terreus as part of the asterriquinone complex. It is cytotoxic to NS-1 mouse myeloma cells with IC50 of 28 μg/ml. It has weak activity against tumor cells and the parasitic protozoan, Tritrichomonas foetus.
Specification
| Synonyms | 3,3'-(2,3,5,6-tetramethoxy-1,4-phenylene)bis-1H-indole |
| Storage | Store at -20°C |
| IUPAC Name | 3-[4-(1H-indol-3-yl)-2,3,5,6-tetramethoxyphenyl]-1H-indole |
| Canonical SMILES | COC1=C(C2=CNC3=C2C=CC=C3)C(OC)=C(OC)C(C4=CNC5=C4C=CC=C5)=C1OC |
| InChI | InChI=1S/C26H24N2O4/c1-29-23-21(17-13-27-19-11-7-5-9-15(17)19)25(31-3)26(32-4)22(24(23)30-2)18-14-28-20-12-8-6-10-16(18)20/h5-14,27-28H,1-4H3 |
| InChI Key | LXKDFRJCVQJIIM-UHFFFAOYSA-N |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Parasites |
| Boiling Point | 568.7±50.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062
José A Pereira, Alice A Ramos, Ângela Inácio, Anake Kijjoa, Nazim Sekeroglu, Artur M S Silva, Eduardo Rocha, Suradet Buttachon, Tida Dethoup, Madalena M M Pinto, Paulo M Costa, Luís Gales, Michael Lee Mar Drugs . 2018 Apr 6;16(4):119. doi: 10.3390/md16040119.
A previously unreportedbis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), sixbis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2″-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungusAspergillus candidusKUFA 0062. Compounds1a,2a-e,3,4,5a-b, and6were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only5aexhibited an inhibitory effect againstS. aureusATCC 29213 andE. faecalisATCC29212 as well as both methicillin-resistantS. aureus(MRSA) and vancomycin-resistant enterococci (VRE) strains. Both1aand5aalso reduced significant biofilm formation inE. coliATCC 25922. Moreover,2band5arevealed a synergistic effect with oxacillin against MRSAS. aureus66/1 while5aexhibited a strong synergistic effect with the antibiotic colistin againstE. coli1410/1. Compound1a,2a-e,3,4,5a-b, and6were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for1a,2a,2d,4,and6, all the compounds showed cytotoxicity against all the cancer cell lines tested.
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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 ╳
