Paraherquamide E
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| Category | Antibiotics |
| Catalog number | BBF-04576 |
| CAS | 125600-53-5 |
| Molecular Weight | 477.60 |
| Molecular Formula | C28H35N3O4 |
| Purity | >99% by HPLC |
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Description
A member of the paraherquamide family which causes a potent non-toxic paralysis of nematode. It is a fungal metabolite originally isolated from Penicillium charlesii with anthelmintic and insecticidal activities.
Specification
| Synonyms | Antibiotic VM 54159; VM 54159; 14-Deoxyparaherquamide A; (1'S,5'aS,7'R,8'aS,9'aR)-2',3',8'a,9'-tetrahydro-1',4,4,8',8',11'-hexamethyl-spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-9,10'(10H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1'S,6'S,7'R,8R,9'S)-4,4,6',10',10',13'-hexamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,11'-3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane]-9,14'-dione |
| Canonical SMILES | CC1CCN2C13CC4C(C5(CC4(C2)N(C3=O)C)C6=C(C7=C(C=C6)OC(C=CO7)(C)C)NC5=O)(C)C |
| InChI | InChI=1S/C28H35N3O4/c1-16-9-11-31-15-26-14-27(25(4,5)19(26)13-28(16,31)23(33)30(26)6)17-7-8-18-21(20(17)29-22(27)32)34-12-10-24(2,3)35-18/h7-8,10,12,16,19H,9,11,13-15H2,1-6H3,(H,29,32)/t16-,19-,26+,27+,28+/m0/s1 |
| InChI Key | XNXXZRQPTAQILV-PYGUQFFJSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 650.1±55.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Evidence of multiple mechanisms of avermectin resistance in haemonchus contortus--comparison of selection protocols
C A Kerr, E Lacey, J H Gill, W L Shoop Int J Parasitol . 1998 May;28(5):783-9. doi: 10.1016/s0020-7519(98)00015-0.
Three isolates of Haemonchus contortus selected for avermectin resistance in sheep were compared in three in vitro pharmacological tests previously shown to discriminate between field isolates of H. contortus resistant and susceptible to the avermectins. Two isolates, F7-A and IVC, were selected for avermectin resistance in the laboratory from a reference susceptible isolate using suboptimal doses of ivermectin (LD95) for 7 and 16 generations, respectively. In these isolates avermectin resistance was not associated with a decreased sensitivity to avermectin inhibition of larval development or L3 motility but was associated with an increased sensitivity to paraherquamide. The third isolate, Warren, was derived from an overwhelmingly avermectin-susceptible, mixed species field isolate in a single generation by propagating the small number of survivors of a 0.2 mg/kg ivermectin treatment (i.e. 10 x LD95). This isolate, like previously characterised avermectin-resistant H. contortus isolates derived from the field in South Africa and Australia, showed a markedly reduced sensitivity to avermectin inhibition of larval development and L3 motility, as well as an increased sensitivity to paraherquamide. These results suggest that avermectin resistance can manifest itself in different ways and that the two selection protocols used to generate the F7-A, IVC and Warren isolates have resulted in the selection of different resistance phenotypes.
2. Insecticidal activity of Paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae
Jaime Primo, Ildefonso Ayala, Pilar Moya, M Carmen González, Letizia Ciavatta, M Pilar López-Gresa J Agric Food Chem . 2006 Apr 19;54(8):2921-5. doi: 10.1021/jf0530998.
Paraherquamide H (1) and paraherquamide I (2), two new compounds of the paraherquamide (PHQ) family, together with the already known paraherquamide A (3), paraherquamide B (4), paraherquamide E (5), VM55596 (N-oxide paraherquamide) (6), paraherquamide VM55597 (7), and five known diketopiperazines (8-12) have been isolated from the culture broth of Penicillium cluniae Quintanilla. The structure of 1 and 2, on the basis of NMR and MS analysis, was established. It is worth noticing that, in both cases, an unusual oxidative substitution in C-16 was found, which had only previously been detected in PHQ 7. Isolated compounds were tested for insecticidal activity against the hemipteran Oncopeltus fasciatus Dallas. Mortality data have allowed preliminary structure activity relationships to be proposed. The most potent product was 5 with a LD(50) of 0.089 microg/nymph.
3. Itaconic acid derivatives and diketopiperazine from the marine-derived fungus Aspergillus aculeatus CRI322-03
Chairut Kasettrathat, Thammarat Aree, Udofot J Ekpe, Prasat Kittakoop, Suthep Wiyakrutta, Bassey S Antia, Somsak Ruchirawat, Okon D Ekpa, Chulabhorn Mahidol Phytochemistry . 2011 Jun;72(8):816-20. doi: 10.1016/j.phytochem.2011.02.013.
Three metabolites, pre-aurantiamine (1), (-)-9-hydroxyhexylitaconic acid (4) and (-)-9-hydroxyhexylitaconic acid-4-methyl ester (5), together with two known compounds, paraherquamide E (6) and secalonic acid D (7), were isolated from the marine-derived fungus, Aspergillus aculeatus.
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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 ╳
