Penicillide
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03208 |
| CAS | 55303-92-9 |
| Molecular Weight | 372.41 |
| Molecular Formula | C21H24O6 |
| Purity | ≥95% |
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Description
Penicillide is an acyl-CoA: cholesterol acyltransferase (ACAT) inhibitor produced by Penicillum asperosporum KY1635. The IC50 for inhibiting ACAT was 22.9 µmol/L.
Specification
| Synonyms | Vermixocin A; AS-186a; 11-hydroxy-3-[(1s)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5h,7h-dibenzo[b,g][1,5]dioxocin-5-one |
| IUPAC Name | 6-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one |
| Canonical SMILES | CC1=CC2=C(C(=C1)O)OC3=C(C(=C(C=C3)C(CC(C)C)O)OC)C(=O)OC2 |
| InChI | InChI=1S/C21H24O6/c1-11(2)7-15(22)14-5-6-17-18(20(14)25-4)21(24)26-10-13-8-12(3)9-16(23)19(13)27-17/h5-6,8-9,11,15,22-23H,7,10H2,1-4H3/t15-/m0/s1 |
| InChI Key | UOWGLBYIKHMCIS-HNNXBMFYSA-N |
Properties
| Appearance | Solid Powder |
| Boiling Point | 606.1°C at 760 mmHg |
| Density | 1.242 g/cm3 |
Reference Reading
1. Enhancement of metabolites productivity of Penicillium pinophilum FKI-5653, by co-culture with Trichoderma harzianum FKI-5655
Tsuyoshi Yamamoto, Mihoko Mori, Kazuro Shiomi, Satoshi Omura, Masato Iwatsuki, Rokuro Masuma, Tadahide Abe, Kenichi Nonaka J Antibiot (Tokyo) . 2011 Dec;64(12):769-74. doi: 10.1038/ja.2011.91.
In the course of discovering new metabolites from co-culture of Penicillium pinophilum FKI-5653 and Trichoderma harzianum FKI-5655, a new compound, designated secopenicillide C, and four known compounds, penicillide, MC-141, pestalasin A and stromemycin were isolated. The production of these compounds, except pestalasin A, was enhanced in co-culture to be two to six times higher than in pure culture of Penicillium pinophilum FKI-5653, which was the producer of these compounds.
2. Secondary Metabolites Produced by an Endophytic Fungus Pestalotiopsis sydowiana and Their 20S Proteasome Inhibitory Activities
Soonok Kim, Sang Hee Shim, Xuekui Xia, Changheng Liu Molecules . 2016 Jul 20;21(7):944. doi: 10.3390/molecules21070944.
Fungal endophytes have attracted attention due to their functional diversity. Secondary metabolites produced by Pestalotiopsis sydowiana from a halophyte, Phragmites communis Trinus, were investigated. Eleven compounds, including four penicillide derivatives (1-4) and seven α-pyrone analogues (5-10) were isolated from cultures of P. sydowiana. The compounds were identified based on spectroscopic data. The inhibitory activities against the 20S proteasome were evaluated. Compounds 1-3, 5, and 9-10 showed modest proteasome inhibition activities, while compound 8 showed strong activity with an IC50 of 1.2 ± 0.3 μM. This is the first study on the secondary metabolites produced by P. sydowiana and their proteasome inhibitory activities. The endophytic fungus P. sydowiana might be a good resource for proteasome inhibitors.
3. AS-186 compounds, new inhibitors of acyl-CoA: cholesterol acyltransferase from Penicillium asperosporum KY1635
K Kuroda, Y Matsuda, Y Saito, K Ando, I Kawamoto, Y Morishita, Y Ikuina J Antibiot (Tokyo) . 1994 Jan;47(1):16-22. doi: 10.7164/antibiotics.47.16.
AS-186a, b, c, d, and g were isolated from the cultured broth of Penicillium asperosporum KY1635 as inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT). IC50 values for the effect of AS-186a, b, c, d, and g against ACAT activity of the microsomes from cholesterol-fed rabbit liver were calculated to be 22.9, 8.2, 11.5, 12.4, and 13.9 microM, respectively. Although AS-186a, and b were identical to penicillide and purpactin A, respectively, AS-186c, d, and g were found to be new compounds.
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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 ╳
