14-Norpseurotin A
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| Category | Others |
| Catalog number | BBF-04472 |
| CAS | 1031727-34-0 |
| Molecular Weight | 417.41 |
| Molecular Formula | C21H23NO8 |
| Purity | ≥98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04472 | 1 mg | $629 | In stock |
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Add to cartDescription
14-Norpseurotin A is a natural compound isolated from the cultures of Aspergillus fumigatus.
Specification
| Synonyms | 1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione, 8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-penten-1-yl]-9-hydroxy-8-methoxy-3-methyl-, (5S,8S,9R)- |
| Storage | Store at -20°C |
| IUPAC Name | (5S,8S,9R)-8-benzoyl-2-[(Z,1S,2S)-1,2-dihydroxypent-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione |
| Canonical SMILES | CC=CC(C(C1=C(C(=O)C2(O1)C(C(NC2=O)(C(=O)C3=CC=CC=C3)OC)O)C)O)O |
| InChI | InChI=1S/C21H23NO8/c1-4-8-13(23)14(24)15-11(2)16(25)20(30-15)18(27)21(29-3,22-19(20)28)17(26)12-9-6-5-7-10-12/h4-10,13-14,18,23-24,27H,1-3H3,(H,22,28)/b8-4-/t13-,14-,18+,20+,21+/m0/s1 |
| InChI Key | FCGCMRDADMTJIM-LFDIKFNASA-N |
Properties
| Appearance | Powder |
| Boiling Point | 750.5±60.0°C (Predicted) |
| Density | 1.44±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO, Acetone |
Reference Reading
1. Angiogenesis Inhibitors and Anti-Inflammatory Agents from Phoma sp. NTOU4195
Ming-Shian Lee, Shih-Wei Wang, Guei-Jane Wang, Ka-Lai Pang, Ching-Kuo Lee, Yueh-Hsiung Kuo, Hyo-Jung Cha, Ruo-Kai Lin, Tzong-Huei Lee J Nat Prod. 2016 Dec 23;79(12):2983-2990. doi: 10.1021/acs.jnatprod.6b00407. Epub 2016 Dec 15.
Seven new polyketides, phomaketides A-E (1-5) and pseurotins A3 (6) and G (7), along with the known compounds FR-111142, pseurotins A, A1, A2, D, and F2, 14-norpseurotin A, α-carbonylcarbene, tyrosol, cyclo(-l-Pro-l-Leu), and cyclo(-l-Pro-l-Phe), were purified from the fermentation broth and mycelium of the endophytic fungal strain Phoma sp. NTOU4195 isolated from the marine red alga Pterocladiella capillacea. The structures were established through interpretation of spectroscopic data. The antiangiogenic and anti-inflammatory effects of 1-7 and related analogues were evaluated using human endothelial progenitor cells (EPCs) and lipopolysaccharide (LPS)-activated murine macrophage RAW264.7 cells, respectively. Of the compounds tested, compound 1 exhibited the most potent antiangiogenic activity by suppressing the tube formation of EPCs with an IC50 of 8.1 μM, and compound 3 showed the most selective inhibitory activity of LPS-induced NO production in RAW264.7 macrophages with an IC50 value of 8.8 μM.
2. Bioactive alkaloids from endophytic Aspergillus fumigatus
Hui Ming Ge, Zhi Guo Yu, Jie Zhang, Jun Hua Wu, Ren Xiang Tan J Nat Prod. 2009 Apr;72(4):753-5. doi: 10.1021/np800700e.
Two new alkaloids, named 9-deacetylfumigaclavine C (1) and 9-deacetoxyfumigaclavine C (2), along with 12 known compounds (3-14), were isolated from the culture of Aspergillus fumigatus. The structures of the new compounds were elucidated by comprehensive spectroscopic analyses. Compound 2 showed selectively potent cytotoxicity against human leukemia cells (K562) with an IC(50) value of 3.1 microM, which was comparable to that of doxorubicin hydrochloride, a presently prescribed drug for the treatment of leukemia. Furthermore, 14-norpseurotin (4) significantly induced neurite outgrowth of rat pheochromocytoma cells (PC12) at a 10.0 microM concentration.
3. Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. strain F1544
Sergio Martínez-Luis, Lilia Cherigo, Elizabeth Arnold, Carmenza Spadafora, William H Gerwick, Luis Cubilla-Rios Nat Prod Commun. 2012 Feb;7(2):165-8.
With the combined goal of finding the best anti-parasitic and anti-cancer activities as well as isolating the bioactive agents and studying their structures and biological properties, we proceeded to perform a small-scale cultivation of Aspergillus sp. strain F1544 using Potato Dextrose, Malt Extract, Czapek Dox and Eight Vegetables media. From the more promising extracts (obtaining using potato dextrose and czapek dox media in large scale) of this fungus, we isolated the five compounds: pseurotin A (1), 14-norpseurotin A (2), FD-838 (3), and pseurotin D (4), and fumoquinone B (5). All compounds showed good antileishmanial and moderate anticancer 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 ╳
