Meleagrin
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| Category | Antibiotics |
| Catalog number | BBF-04191 |
| CAS | 71751-77-4 |
| Molecular Weight | 433.46 |
| Molecular Formula | C23H23N5O4 |
| Purity | >98% by HPLC |
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Description
Meleagrin is an alkaloid antibiotic isolated from a number of species of penicillium with antitumor, anti-proliferative and antibacterial activity. It inhibits the growth of S. aureus, E. coli and S. pneumoniae. Meleagrin is a class of FabI inhibitor, and a lead c-Met inhibitory entity useful for the control of c-Met-dependent metastatic and invasive breast malignancies.
Specification
| Synonyms | 6-O-Methyloxaline; Meleagrine; (3E,7aR,12aS)-7a-(1,1-Dimethyl-2-propenyl)-7a,12-dihydro-6-hydroxy-3-(1H-imidazol-4-ylmethylene)-12-methoxy-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione; [7aR-(3E,7aR*,12aS*)]-7a-(1,1-Dimethyl-2-propenyl)-7a,12-dihydro-6-hydroxy-3-(1H-imidazol-4-ylmethylene)-12-methoxy-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione |
| Shelf Life | 2 month in rt, long time |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (1S,9R,14E)-11-hydroxy-14-(1H-imidazol-5-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7,10-tetraene-12,15-dione |
| Canonical SMILES | CC(C)(C=C)C12C=C(C(=O)N3C1(NC(=O)C3=CC4=CN=CN4)N(C5=CC=CC=C25)OC)O |
| InChI | InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1 |
| InChI Key | JTJJJLSLKZFEPJ-ZAYCRUKZSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Pale Yellow Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor) |
| Melting Point | 250°C (dec.) |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Slightly soluble in DMSO, Methanol |
Reference Reading
1.The cost of running uphill: linking organismal and muscle energy use in guinea fowl (Numida meleagris).
Rubenson J;Henry HT;Dimoulas PM;Marsh RL J Exp Biol. 2006 Jul;209(Pt 13):2395-408.
Uphill running requires more energy than level running at the same speed, largely due to the additional mechanical work of elevating the body weight. We explored the distribution of energy use among the leg muscles of guinea fowl running on the level and uphill using both organismal energy expenditure (oxygen consumption) and muscle blood flow measurements. We tested each bird under four conditions: (1) rest, (2) a moderate-speed level run at 1.5 m s(-1), (3) an incline run at 1.5 m s(-1) with a 15% gradient and (4) a fast level run at a speed eliciting the same metabolic rate as did running at a 15% gradient at 1.5 m s(-1) (2.28-2.39 m s(-1)). The organismal energy expenditure increased by 30% between the moderate-speed level run and both the fast level run and the incline run, and was matched by a proportional increase in total blood flow to the leg muscles. We found that blood flow increased significantly to nearly all the leg muscles between the moderate-speed level run and the incline run. However, the increase in flow was distributed unevenly across the leg muscles, with just three muscles being responsible for over 50% of the total increase in blood flow during uphill running.
2.[The biosynthesis of low-molecular-weight nitrogen-containing secondary metabolite-alkaloids by the resident strains of Penicillium chrysogenum and Penicillium expansum isolated on the board of the Mir space station ].
Kozlovskiĭ AG;Zhelifonova VP;Adanin VM;Antipova TV;Shnyreva AV;Viktorov AN Mikrobiologiia. 2002 Nov-Dec;71(6):773-7.
The analysis of the absorption spectra of the low-molecular-weight nitrogen-containing secondary metabolites--alkaloids--of 4 Penicillium chrysogenum strains and 6 Penicillium expansum strains isolated on board the Mir space station showed that all these strains synthesize metabolites of alkaloid origin (roquefortine, 3,12-dihydroroquefortine, meleagrin, viridicatin, viridicatol, isorugulosuvin, rugulosuvin B, N-acetyl-tryptamine, and a "yellow metabolite" containing the benzoquinone chromophore).
3.Antioxidant and antimicrobial capacities of ethanolic extract of Pergularia daemia leaves: a possible substitute in diabetic management.
Sarkodie JA;Squire SA;Oppong Bekoe E;Fosu Domozoro CY;Kretchy IA;Ahiagbe MK;Frimpong-Manso S;Oboba Kwakyi NA;Edoh DA;Sakyiama M;Lamptey VK;Affedzi-Obresi S;Duncan JL;Debrah P;N'guessa BB;Asiedu-Gyekye JI;Kwadwo Nyarko A J Complement Integr Med. 2016 Sep 1;13(3):239-245. doi: 10.1515/jcim-2015-0069.
BACKGROUND: ;The leaves of Pergularia daemia Forsk (family Asclepidaceae) provide alternative plant-based treatments for the management of diabetes mellitus and diarrhoea in both humans and indigenous poultry species like the Guinea fowls (Numida meleagris). However, no scientific investigations to validate its usefulness in Ghana have been established. This study therefore sought to investigate the anti-hyperglycaemic activity of the 70 % ethanolic extract of P. daemia using streptozotocin (STZ)-induced diabetic male Sprague-Dawley rats. Additionally, the antioxidant and antimicrobial properties of the extract were investigated.;METHODS: ;The total phenolic content, total flavonoids content, radical scavenging activity and reducing power assays were estimated using Folin-Ciocalteu method, aluminium chloride colorimetric assay, Fe3+ reduction assay and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assays, respectively.;RESULTS: ;The results showed that P. daemia extract caused anti-hyperglycaemic activity in the STZ-induced rats at doses of 30, 60 and 90 mg/kg body weight with significant reduction in blood glucose levels. The phytosterols, saponins, phenols, alkaloids, tannins and triterpenes found in the extract may be responsible for the observed anti-hyperglycaemia and antioxidant activities.
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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 ╳
