Petromurin C
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| Category | Bioactive by-products |
| Catalog number | BBF-04491 |
| CAS | 194608-29-2 |
| Molecular Weight | 444.48 |
| Molecular Formula | C26H24N2O5 |
| Purity | ≥95% |
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Description
Petromurin C is a metabolite isolated as a component of bis-indolyl benzenoid complex from Aspergillus muricatus. It exhibits antitumor activity.
Specification
| Synonyms | 1H-Indol-5-ol, 3-[4-(1H-indol-3-yl)-2,3,5,6-tetramethoxyphenyl]- |
| Storage | Store at -20°C |
| IUPAC Name | 3-[4-(1H-indol-3-yl)-2,3,5,6-tetramethoxyphenyl]-1H-indol-5-ol |
| Canonical SMILES | COC1=C(C(=C(C(=C1OC)C2=CNC3=CC=CC=C32)OC)OC)C4=CNC5=C4C=C(C=C5)O |
| InChI | InChI=1S/C26H24N2O5/c1-30-23-21(17-12-27-19-8-6-5-7-15(17)19)24(31-2)26(33-4)22(25(23)32-3)18-13-28-20-10-9-14(29)11-16(18)20/h5-13,27-29H,1-4H3 |
| InChI Key | QJQIGLORIRGXRI-UHFFFAOYSA-N |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 610.7±55.0°C at 760 mmHg |
| Melting Point | 240°C (dec.) |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Petromurin C Induces Protective Autophagy and Apoptosis in FLT3-ITD-Positive AML: Synergy with Gilteritinib
Claudia Cerella, Anake Kijjoa, Marc Diederich, Barbora Orlikova-Boyer, Sungmi Song, Christo Christov, You Na Ha Mar Drugs . 2020 Jan 16;18(1):57. doi: 10.3390/md18010057.
Treatment of acute myeloid leukemia (AML) remains inefficient due to drug resistance and relapse, particularly in patients with FMS-like tyrosine kinase 3 (FLT3)-internal tandem duplication (ITD). Marine-derived natural products have recently been used for drug development against AML. We show in this study that petromurin C, which was isolated from the culture extract of the marine-derived fungusAspergillus candidusKUFA0062, isolated from the marine spongeEpipolasissp., induces early autophagy followed by apoptotic cell death via activation of the intrinsic cell death pathway concomitant with mitochondrial stress and downregulation of Mcl-1 in FLT3-ITD mutated MV4-11 cells. Moreover, petromurin C synergized with the clinically-used FLT3 inhibitor gilteritinib at sub-toxic concentrations. Altogether, our results provide preliminary indications that petromurin C provides anti-leukemic effects alone or in combination with gilteritinib.
2. 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 ╳
