Diacetylcercosporin
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| Category | Bioactive by-products |
| Catalog number | BBF-04238 |
| CAS | 62574-06-5 |
| Molecular Weight | 618.58 |
| Molecular Formula | C33H30O12 |
| Purity | >95% by HPLC |
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Description
It is a minor hydrophobic analogue of cercosporin produced by several species of the fungal genera, cercospora and septoria. It has moderate in vitro activity against leishmania and chloroquine-sensitive strains of plasmodium falciparum. It exhibits antitumor activity.
Specification
| Synonyms | [S-(R*,R*)]-8,9-bis[2-(acetyloxy)propyl]-5,12-dihydroxy-7,10-dimethoxy-perylo[1,12-def]-1,3-dioxepin-6,11-dione; 2',2''-Diacetylcercosporin |
| Storage | Store at -20°C |
| IUPAC Name | [(2S)-1-[21-[(2S)-2-acetyloxypropyl]-7,19-dihydroxy-6,20-dimethoxy-9,17-dioxo-12,14-dioxahexacyclo[13.8.0.02,11.03,8.04,22.018,23]tricosa-1,3(8),4,6,10,15,18(23),19,21-nonaen-5-yl]propan-2-yl] acetate |
| Canonical SMILES | CC(CC1=C2C3=C(C(=C(C4=C3C5=C6C2=C(C(=O)C=C6OCOC5=CC4=O)C(=C1OC)O)O)OC)CC(C)OC(=O)C)OC(=O)C |
| InChI | InChI=1S/C33H30O12/c1-12(44-14(3)34)7-16-22-23-17(8-13(2)45-15(4)35)33(41-6)31(39)25-19(37)10-21-27(29(23)25)26-20(42-11-43-21)9-18(36)24(28(22)26)30(38)32(16)40-5/h9-10,12-13,38-39H,7-8,11H2,1-6H3/t12-,13-/m0/s1 |
| InChI Key | JQHGSMOYNPGRFL-STQMWFEESA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 895.5±65.0°C at 760 mmHg |
| Melting Point | 80-82°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol |
Reference Reading
1. Antiprotozoal and antimicrobial compounds from the plant pathogen Septoria pistaciarum
Stephen O Duke, N P Dhammika Nanayakkara, Babu L Tekwani, Daneel Ferreira, Melissa Jacob, Mallika Kumarihamy, Shabana I Khan J Nat Prod . 2012 May 25;75(5):883-9. doi: 10.1021/np200940b.
Four new 1,4-dihydroxy-5-phenyl-2-pyridinone alkaloids, 17-hydroxy-N-(O-methyl)septoriamycin A (1), 17-acetoxy-N-(O-methyl)septoriamycin A (2), 13-(S)-hydroxy-N-(O-methyl)septoriamycin A (3), and 13-(R)-hydroxy-N-(O-methyl)septoriamycin A (4), together with the known compounds (+)-cercosporin (5), (+)-14-O-acetylcercosporin (6), (+)-di-O-acetylcercosporin (7), lumichrome, and brassicasterol, were isolated from an ethyl acetate extract of a culture medium of Septoria pistaciarum. Methylation of septoriamycin A (8) with diazomethane yielded three di-O-methyl analogues, two of which existed as mixtures of rotamers. We previously reported antimalarial activity of septoriamycin A. This compound also exhibited significant activity against Leishmania donovani promastigotes. Compounds 5-7 showed moderate in vitro activity against L. donovani promastigotes and chloroquine-sensitive (D6) and -resistant (W2) strains of Plasmodium falciparum, whereas compound 5 was fairly active against methicillin-sensitive and methicillin-resistant strains of Staphylococcus aureus. Compounds 5-7 also displayed moderate phytotoxic activity against both a dicot (lettuce, Lactuca sativa) and a monocot (bentgrass, Agrostis stolonifera) and cytotoxicity against a panel of cell lines.
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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 ╳
