Andrastin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00686 |
| CAS | 174232-42-9 |
| Molecular Weight | 486.60 |
| Molecular Formula | C28H38O7 |
| Purity | ≥95% |
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Description
It is produced by the strain of Penicillum sp. FO-3929. It can inhibit PFTase. IC50 is 24.9 μmol/L.
Specification
| Synonyms | NSC 697452; NSC697452; NSC-697452 |
| IUPAC Name | methyl (3S,5R,8S,9R,10S,13R,14R)-3-acetyloxy-10-formyl-4,4,8,12,13,16-hexamethyl-15,17-dioxo-2,3,5,6,7,9-hexahydro-1H-cyclopenta[a]phenanthrene-14-carboxylate |
| Canonical SMILES | CC1=C[C@]2([H])[C@]([C@@](C(C3C)=O)(C(OC)=O)[C@]1(C)C3=O)(C)CC[C@]4([H])C(C)(C)[C@@H](OC(C)=O)CC[C@]42C=O |
| InChI | InChI=1S/C28H38O7/c1-15-13-19-25(6,28(23(33)34-8)22(32)16(2)21(31)26(15,28)7)11-9-18-24(4,5)20(35-17(3)30)10-12-27(18,19)14-29/h13-14,16,18-20H,9-12H2,1-8H3/t16?,18-,19-,20+,25+,26+,27+,28-/m1/s1 |
| InChI Key | GRBXNADBNJGZRK-GJEDHNSHSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 560.3 °C at 760 mmHg (Predicted) |
| Melting Point | 131-135 °C |
| Density | 1.2 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Cytochrome P450 for Citreohybridonol Synthesis: Oxidative Derivatization of the Andrastin Scaffold
Yudai Matsuda, Zhiyang Quan, Ikuro Abe, Chang Li, Takaaki Mitsuhashi Org Lett . 2016 Jan 15;18(2):296-9. doi: 10.1021/acs.orglett.5b03465.
A biosynthetic gene cluster similar to that for andrastin A (1) was discovered in Emericella variecolor NBRC 32302. Ctr-P450, a cytochrome P450 uniquely present in the cluster, was coexpressed with the andrastin A biosynthetic genes, leading to the production of the antifeedant agent citreohybridonol (4), along with four new andrastin derivatives. The results revealed the unusual multifunctionality of Ctr-P450 and indicated that this approach can be applied for further natural product diversification.
2. Andrastins A-D, Penicillium roqueforti Metabolites consistently produced in blue-mold-ripened cheese
Petur Weihe Dalsgaard, Thomas Ostenfeld Larsen, Kristian Fog Nielsen, Jørn Smedsgaard J Agric Food Chem . 2005 Apr 20;53(8):2908-13. doi: 10.1021/jf047983u.
This is the first finding of andrastins in blue cheese as well as any other sample type. Here, they were produced by the secondary starter culture Penicillium roqueforti. After purification by normal-phase chromatography followed by combined reverse-phase ion-exchange chromatography, the andrastins A-D were detected by liquid chromatography combined with UV and high-resolution mass spectrometry. In 23 representative samples of European blue cheeses, andrastin A was consistently found in quantities between 0.1 and 3.7 microg/g of cheese (median 2.4 microg/g). Assuming the same molar response factors as for andrastin A, the B, C, and D analogues were present in approximately 5-, 3-, and 5-20-fold lower amounts than andrastin A, respectively. The andrastins are protein farnesyltransferase inhibitors and are capable of inhibiting the efflux of anticancer drugs from multidrug-resistant cancer cells. Thus, their presence in common blue cheese suggests a potential for a positive or negative impact on human health.
3. Andrastin A and barceloneic acid metabolites, protein farnesyl transferase inhibitors from Penicillium albocoremium: chemotaxonomic significance and pathological implications
Richard Phipps, Murray H G Munro, Petur W Dalsgaard, Karla Frydenvang, David P Overy, Thomas O Larsen, Carsten Christophersen Mycol Res . 2005 Nov;109(Pt 11):1243-9. doi: 10.1017/s0953756205003734.
A survey of Penicillium albocoremium was undertaken to identify potential taxonomic metabolite markers. One major and four minor metabolites were consistently produced by the 19 strains surveyed on three different media. Following purification and spectral studies, the metabolites were identified as the known protein farnesyl transferase inhibitors andrastin A (1) and barceloneic acid A (2) along with barceloneic acid B (3), barceloneic lactone (4), and methyl barceloneate (5). These compounds are significant taxonomic markers for P. albocoremium; moreover this is the first report of a methyl ester of a barceloneic acid being produced as a secondary metabolite. Tissue extracts created following pathogenicity trials involving P. albocoremium and Allium cepa confirmed the production of these five metabolites in planta. Barceloneic acid B was found to be biologically active against a P388 murine leukemia cell line.
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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 ╳
