Pyripyropene B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02098 |
| CAS | 151519-44-7 |
| Molecular Weight | 597.65 |
| Molecular Formula | C32H39NO10 |
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Description
Pyripyropene B is a powerful acyl-CoA: cholesterol acyltransferase 2 (ACAT2) inhibitor produced by the fungus Aspergillus fumigatus FO 1289. It inhibits acyl-CoA: cholesterol acyltransferase with an IC50 of 117 nmol/L.
Specification
| Synonyms | 2H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-11-one,3,6-bis(acetyloxy)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-4-[(1-oxopropoxy)methyl]-9-(3-pyridinyl)-,(3S,4R,4aR,6S,6aS,12R,12aS,12bS)- |
| IUPAC Name | (5,9-diacetyloxy-18-hydroxy-2,6,10-trimethyl-16-oxo-14-pyridin-3-yl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-6-yl)methyl propanoate |
| Canonical SMILES | CCC(=O)OCC1(C(CCC2(C1CC(C3(C2C(C4=C(O3)C=C(OC4=O)C5=CN=CC=C5)O)C)OC(=O)C)C)OC(=O)C)C |
| InChI | InChI=1S/C32H39NO10/c1-7-25(36)39-16-31(5)22-14-24(41-18(3)35)32(6)28(30(22,4)11-10-23(31)40-17(2)34)27(37)26-21(43-32)13-20(42-29(26)38)19-9-8-12-33-15-19/h8-9,12-13,15,22-24,27-28,37H,7,10-11,14,16H2,1-6H3 |
| InChI Key | HQJYCJFUVSNJFK-UHFFFAOYSA-N |
Reference Reading
1. Pyripyropenes, novel inhibitors of acyl-CoA:cholesterol acyltransferase produced by Aspergillus fumigatus. I. Production, isolation, and biological properties
H Tomoda, Y K Kim, H Nishida, R Masuma, S Omura J Antibiot (Tokyo). 1994 Feb;47(2):148-53. doi: 10.7164/antibiotics.47.148.
Aspergillus fumigatus FO-1289, a soil isolate, was found to produce a series of novel inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT). Four active compounds, named pyripyropenes A, B, C and D, were isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography, ODS column chromatography and preparative HPLC. Pyripyropenes A, B, C and D show very potent ACAT inhibitory activity in an enzyme assay system using rat liver microsomes with IC50 values of 58, 117, 53 and 268 nM, respectively.
2. Pyripyropenes, fungal sesquiterpenes conjugated with alpha-pyrone and pyridine moieties, exhibits anti-angiogenic activity against human umbilical vein endothelial cells
Asami Hayashi, Masayoshi Arai, Mayumi Fujita, Motomasa Kobayashi Biol Pharm Bull. 2009 Jul;32(7):1261-5. doi: 10.1248/bpb.32.1261.
In the course of our search for anti-angiogenic substances, pyripyropenes A (1), B (2), and D (3) were re-discovered as selective anti-proliferative substances against human umbilical vein endothelial cells (HUVECs) from a marine-derived fungus of Aspergillus sp. Pyripyropenes showed potent anti-proliferative activity against HUVECs with IC(50) values of the range of 0.1-1.8 muM, which were cytostatic at 0.05 to 20 muM. The selective index was more than 55-fold in comparison with those of several tumor cell lines. Compound 1 inhibited vascular endothelial growth factor (VEGF)-induced migration and tubular formation of HUVECs, while 1 showed no effect on the VEGF-induced phosphorylations of extracellular signal-regulated kinase (ERK)1/2, p38, and Akt. Pyripyropenes were originally isolated as an inhibitor of acyl-CoA: cholesterol acyltransferase (ACAT-2). While, the expression level of ACATs between HUVECs and other tumor cell lines did not correspond to the selective index of the anti-proliferative activity of compound 1. Moreover, ACATs inhibitor, 2,2-dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide (CI-976), showed growth inhibitory activity with only poor selectivity (2.4-fold) between HUVECs and human epidermoid carcinoma KB3-1 cells.
3. Pyripyropenes, novel inhibitors of acyl-CoA:cholesterol acyltransferase produced by Aspergillus fumigatus. II. Structure elucidation of pyripyropenes A, B, C and D
Y K Kim, H Tomoda, H Nishida, T Sunazuka, R Obata, S Omura J Antibiot (Tokyo). 1994 Feb;47(2):154-62. doi: 10.7164/antibiotics.47.154.
The structures of pyripyropenes A, B, C and D, novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors, were determined mainly by spectroscopic studies including various NMR measurements. Pyripyropenes have a common structure which consists of pyridine, alpha-pyrone and sesquiterpene moieties. One of the three O-acetyl residues in the sesquiterpene moiety of pyripyropene A is replaced with an O-propionyl residue in pyripyropenes B, C and D.
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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 ╳
