Epicoccamide
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| Category | Others |
| Catalog number | BBF-04239 |
| CAS | 606139-26-8 |
| Molecular Weight | 557.72 |
| Molecular Formula | C29H51NO9 |
| Purity | >98% by HPLC |
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Description
It is an ornate linear fatty acid with an acyl tetronic acid terminus and glycosidic alkyl terminus. It is originally isolated from epicoccum purpurascens. It is non-cytotoxic, unlike the weak activity shown by related analogues Epicoccamides B, C and D.
Specification
| Synonyms | 5-hydroxy-1,2-dimethyl-4-(2-methyl-16-(((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexadecanoyl)-1,2-dihydro-3H-pyrrol-3-one; 1,2-Dihydro-5-hydroxy-4-[16-(β-D-mannopyranosyloxy)-2-methyl-1-oxohexadecyl]-1,2-dimethyl-3H-pyrrol-3-one |
| Storage | Store at -20°C |
| IUPAC Name | 3-[1-hydroxy-2-methyl-16-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexadecylidene]-1,5-dimethylpyrrolidine-2,4-dione |
| Canonical SMILES | CC1C(=O)C(=C(C(C)CCCCCCCCCCCCCCOC2C(C(C(C(O2)CO)O)O)O)O)C(=O)N1C |
| InChI | InChI=1S/C29H51NO9/c1-19(23(32)22-24(33)20(2)30(3)28(22)37)16-14-12-10-8-6-4-5-7-9-11-13-15-17-38-29-27(36)26(35)25(34)21(18-31)39-29/h19-21,25-27,29,31-32,34-36H,4-18H2,1-3H3/t19?,20?,21-,25-,26+,27+,29-/m1/s1 |
| InChI Key | GLMMQSHEMIVRFP-XIECNSLGSA-N |
| Source | Epicoccum sp. |
Properties
| Appearance | Amorphous Powder |
| Boiling Point | 703.2±60.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Epicoccamide, a novel secondary metabolite from a jellyfish-derived culture of Epicoccum purpurascens
Anthony D Wright, Gabriele M König, Claudia Osterhage Org Biomol Chem . 2003 Feb 7;1(3):507-10. doi: 10.1039/b208588g.
From the inner tissue of the jellyfish Aurelia aurita a marine strain of the fungus Epicoccum purpurascens was obtained. After mass cultivation the fungus was investigated for its secondary metabolite content and found to contain the new, and most unusual tetramic acid derivative, epicoccamide (1). Epicoccamide is quite unusual since it is composed of three biosynthetically distinct subunits; glycosidic, fatty acid and tetramic acid (amino acid). The structure of the new compound was elucidated using spectroscopic methods, mainly 1D and 2D NMR, ESI-MS, and chemical degradations.
2. Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079
Peter Proksch, Zhen Liu, Werner E G Müller, Michael Feldbrügge, Harwoko Harwoko, Rainer Kalscheuer, Marian Frank, Attila Mándi, Elena Ancheeva, Jungho Lee, Georgios Daletos, Tibor Kurtán, Rudolf Hartmann Fitoterapia . 2020 Oct;146:104698. doi: 10.1016/j.fitote.2020.104698.
Three new flavipin-derived alkaloids, azacoccones F-H (1-3), along with six known compounds (4-9) were isolated from the endophytic fungus Epicoccum nigrum MK214079 associated with leaves of Salix sp. The structures of the new compounds were established by analysis of their 1D/2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data. The absolute configuration of azacoccones F-H (1-3) was determined by comparison of experimental electronic circular dichroism (ECD) data with reported ones and biogenetic considerations. Epicocconigrone A (4), epipyrone A (5), and epicoccolide B (6) exhibited moderate antibacterial activity against Staphylococcus aureus ATCC 29213 with minimal inhibitory concentration (MIC) values ranging from 25 to 50 μM. Furthermore, epipyrone A (5) and epicoccamide A (7) displayed mild antifungal activity against Ustilago maydis AB33 with MIC values of 1.6 and 1.8 mM, respectively. Epicorazine A (8) showed pronounced cytotoxicity against the L5178Y mouse lymphoma cell line with an IC50value of 1.3 μM.
3. Total synthesis and absolute configuration of epicoccamide D, a naturally occurring mannosylated 3-acyltetramic acid
Rainer Schobert, Sebastian Loscher Chemistry . 2013 Aug 5;19(32):10619-24. doi: 10.1002/chem.201301914.
The endofungal metabolite epicoccamide D was synthesised in eighteen steps and 17 % yield as the first member of the family of natural glycotetramic acids. The modular character of the synthesis opens access also to analogues featuring different sugars and spacers. It comprises several high-yielding key steps. The β-D-mannosyl group was introduced by using an α-D-glucosyl imidate donor with subsequent oxidative-reductive epimerisation at C-2'. The pyrrolidine ring was closed quantitatively by a Lacey-Dieckmann condensation of an N-(β-ketoacyl)-N-methyl alaninate. The resulting 3-[ω-(β-D-mannosyl)octadec-2-enoyl]tetramic acid was hydrogenated in the presence of the rhodium catalyst (R,R)-[Rh(Et-DUPHOS)][BF4 ] to establish the (7S)-stereocentre. This was possible only after blocking the acyltetramic acid as a BF2 -chelate to prevent capture of the metal catalyst. We also assigned the hitherto unknown configuration of the natural product as being 5S,7S by comparison of its (13) C NMR spectroscopic and optical rotation data with those of our two synthetic 5S,7R/S-diasteromers.
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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 ╳
