Aspergillin PZ
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| Category | Others |
| Catalog number | BBF-00567 |
| CAS | 483305-08-4 |
| Molecular Weight | 401.54 |
| Molecular Formula | C24H35NO4 |
| Purity | >98% |
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Description
Asperillin PZ is an isoindole fungal metabolite produced by Aspergillus awamoli. 0.089 μmol/L can cause the morphological changes of the conidia of Pear spores. It may possess anti-cancer and anti-tumor properties.
Specification
| Synonyms | (1R,2S,5R,5aS,5bS,8R,8aS,9R,11aR,13aR)-2,3,4,5,5a,5b,8,8a,9,10,13,13a-Dodecahydro-2-hydroxy-5,7,8-trimethyl-9-(2-methylpropyl)-1,5-epoxy-1H-cyclohepta[3,4]benz[1,2-d]isoindole-11,12-dione; (+)-Aspergillin PZ; Aspergilline PZ |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2R,3R,6S,7R,8S,11S,14S,15S,16R)-16-hydroxy-1,5,6-trimethyl-8-(2-methylpropyl)-19-oxa-9-azapentacyclo[13.3.1.02,14.03,11.07,11]nonadec-4-ene-10,12-dione |
| Canonical SMILES | CC1C2C(NC(=O)C23C(C=C1C)C4C(CC3=O)C5C(CCC4(O5)C)O)CC(C)C |
| InChI | InChI=1S/C24H35NO4/c1-11(2)8-16-19-13(4)12(3)9-15-20-14(10-18(27)24(15,19)22(28)25-16)21-17(26)6-7-23(20,5)29-21/h9,11,13-17,19-21,26H,6-8,10H2,1-5H3,(H,25,28)/t13-,14+,15-,16+,17-,19+,20+,21+,23+,24-/m1/s1 |
| InChI Key | AQZDMONQDXTWHN-XLFKICHRSA-N |
Properties
| Appearance | Colorless Square Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 598.7±50.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Ethanol, Methanol |
Reference Reading
1. Insights into the Chemical Diversity of Selected Fungi from the Tza Itzá Cenote of the Yucatan Peninsula
Baojie Wan, Marian A López-Lobato, Rodolfo García-Contreras, Anahí Martínez-Cárdenas, Alejandra Prieto-Davó, Rui Ma, Mallique Qader, Shabnam Hematian, Mario Figueroa, Laura Flores-Bocanegra, Carlos A Fajardo-Hernández, Rodrigo Villanueva-Silva, Huzefa A Raja, Firoz Shah Tuglak Khan, Scott G Franzblau ACS Omega . 2022 Mar 28;7(14):12171-12185. doi: 10.1021/acsomega.2c00544.
Cenotes are habitats with unique physical, chemical, and biological features. Unexplored microorganisms from these sinkholes represent a potential source of bioactive molecules. Thus, a series of cultivable fungi (Aspergillusspp. NCA257, NCA264, and NCA276,Stachybotryssp. NCA252, andCladosporiumsp. NCA273) isolated from the cenote Tza Itzá were subjected to chemical, coculture, and metabolomic analyses. Nineteen compounds were obtained and tested for their antimicrobial potential against ESKAPE pathogens,Mycobacterium tuberculosis, and nontuberculous mycobacteria. In particular, phenylspirodrimanes fromStachybotryssp. NCA252 showed significant activity against MRSA, MSSA, and mycobacterial strains. On the other hand, the absolute configuration of the new compound 17-deoxy-aspergillin PZ (1) isolated fromAspergillussp. NCA276 was established via single-crystal X-ray crystallography. Also, the chemical analysis of the cocultures betweenAspergillusandCladosporiumstrains revealed the production of metabolites that were not present or were barely detected in the monocultures. Finally, molecular networking analysis of the LC-MS-MS/MS data for each fungus was used as a tool for the annotation of additional compounds, increasing the chemical knowledge on the corresponding fungal strains. Overall, this is the first systematic chemical study on fungi isolated from a sinkhole in Mexico.
2. Biomimetic Synthesis of (+)-Aspergillin PZ
Lukas Spessert, Nils Winter, Julius R Reyes, Dirk Trauner Angew Chem Int Ed Engl . 2018 Nov 19;57(47):15587-15591. doi: 10.1002/anie.201809703.
The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels-Alder reaction that features high regio- and stereoselectivity. So far, our work has culminated in a biomimetic synthesis of aspergillin PZ, an intricate pentacyclic aspochalasan.
3. Aspergillin PZ, a novel isoindole-alkaloid from Aspergillus awamori
Yuehu Pei, Baomin Feng, Yi Zhang, Huiming Hua, Tao Wang J Antibiot (Tokyo) . 2002 Aug;55(8):693-5. doi: 10.7164/antibiotics.55.693.
Aspergillin PZ was obtained from the fermentation of Aspergillus awamori (Nakazawa) by activity-guided fractionation and purification. Its structure was elucidated on the basis of spectral data, especially by 2D NMR, and finally confirmed by an X-ray analysis. It could induce conidia of P. oryzae to deform moderately.
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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 ╳
