Andrastin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00464 |
| CAS | |
| Molecular Weight | 488.61 |
| Molecular Formula | C28H40O7 |
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Description
It is produced by the strain of Penicillum sp. FO-3929. It can inhibit PFTase. IC50 is 47.1 μmol/L.
Specification
| Synonyms | CHEBI:142862; methyl (3beta,5beta,8alpha,9beta,10alpha,13alpha)-3-(acetyloxy)-15,19-dihydroxy-4,4,8,12,16-pentamethyl-17-oxoandrosta-11,15-diene-14-carboxylate; methyl 3beta-(acetyloxy)-15,19-dihydroxy-4,4,8,12,16-pentamethyl-17-oxo-5beta,8alpha,9beta,10alpha,13alpha-androsta-11,15-diene-14-carboxylate |
| IUPAC Name | methyl (3S,5S,8S,9R,10S,13R,14R)-3-acetyloxy-17-hydroxy-10-(hydroxymethyl)-4,4,8,12,13,16-hexamethyl-15-oxo-2,3,5,6,7,9-hexahydro-1H-cyclopenta[a]phenanthrene-14-carboxylate |
| Canonical SMILES | CC1=CC2C(CCC3C2(CCC(C3(C)C)OC(=O)C)CO)(C4(C1(C(=C(C4=O)C)O)C)C(=O)OC)C |
| InChI | InChI=1S/C28H40O7/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/h13,18-20,29,31H,9-12,14H2,1-8H3/t18-,19-,20+,25+,26+,27+,28-/m1/s1 |
| InChI Key | DZXRNRBENGRMTG-OXILWVMOSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 136-139 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Andrastins A-D, Penicillium roqueforti Metabolites consistently produced in blue-mold-ripened cheese
Kristian Fog Nielsen, Petur Weihe Dalsgaard, Jørn Smedsgaard, Thomas Ostenfeld Larsen 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.
2. Andrastins A-C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. I. Producing strain, fermentation, isolation, and biological activities
S Omura, J Inokoshi, R Uchida, K Shiomi, R Masuma, T Kawakubo, H Tanaka, Y Iwai, S Kosemura, S Yamamura J Antibiot (Tokyo). 1996 May;49(5):414-7. doi: 10.7164/antibiotics.49.414.
New protein farnesyltransferase inhibitors, andrastins A-C, have been discovered in the cultured broth of Penicillium sp. FO-3929. Andrastins extracted from broth supernatant were purified by silica gel chromatography, ODS chromatography and HPLC. The IC50 of andrastins A, B, and C against protein farnesyltransferase were 24.9, 47.1, and 13.3 microM, respectively.
3. Andrastins A-C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. II. Structure elucidation and biosynthesis
R Uchida, K Shiomi, J Inokoshi, T Sunazuka, H Tanaka, Y Iwai, H Takayanagi, S Omura J Antibiot (Tokyo). 1996 May;49(5):418-24. doi: 10.7164/antibiotics.49.418.
The structures of new protein farnesyltransferase inhibitors, andrastins A-C, were elucidated. The cyclopentane ring of andrastins exhibited keto-enol tautomerism, which made the structure hard to elucidate. Therefore, the structure of andrastin A was elucidated by INADEQUATE and 13C-13C couplings using 13C-labeled andrastin A. The absolute configuration of the p-bromobenzoyl derivative of andrastin A was elucidated by X-ray crystallographic analysis and its skeleton was shown to be ent-5 alpha,14 beta-androstane. The biosynthesis of andrastin A was also studied by the incorporation of 13C-labeled acetates. Though the andrastins had a common androstane skeleton, they were biosynthesized from a sesquiterpene and a tetraketide.
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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 ╳
