Phenylpyropene A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02396 |
| CAS | 189564-20-3 |
| Molecular Weight | 582.64 |
| Molecular Formula | C32H38O10 |
| Purity | >95% |
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Description
It is produced by the strain of Penicillum griseofulvum F 1959. It can inhibit ACAT activity with IC50 of 0.8 μmol/L.
Specification
| Synonyms | (3S)-3alpha,6alpha-Diacetoxy-4beta-(acetoxymethyl)-4,6aalpha,12balpha-trimethyl-9-phenyl-12alpha-hydroxy-1,3,4,4abeta,5,6,6a,12,12abeta,12b-decahydro-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one; (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,6-bis(acetyloxy)-4-[(acetyloxy)methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-9-phenyl-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one |
| Storage | Store at -20°C |
| IUPAC Name | [(1S,2S,5S,6R,7R,9S,10S,18R)-5,9-diacetyloxy-18-hydroxy-2,6,10-trimethyl-16-oxo-14-phenyl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-6-yl]methyl acetate |
| Canonical SMILES | CC(=O)OCC1(C(CCC2(C1CC(C3(C2C(C4=C(O3)C=C(OC4=O)C5=CC=CC=C5)O)C)OC(=O)C)C)OC(=O)C)C |
| InChI | InChI=1S/C32H38O10/c1-17(33)38-16-31(5)23-15-25(40-19(3)35)32(6)28(30(23,4)13-12-24(31)39-18(2)34)27(36)26-22(42-32)14-21(41-29(26)37)20-10-8-7-9-11-20/h7-11,14,23-25,27-28,36H,12-13,15-16H2,1-6H3/t23-,24+,25+,27+,28-,30+,31+,32-/m1/s1 |
| InChI Key | QHPKCPGUVVWHPW-QQJWEHFTSA-N |
Properties
| Appearance | White Powder |
| Solubility | Soluble in Methanol |
Reference Reading
1. Inhibition of diacylglycerol acyltransferase by phenylpyropenes produced by Penicillium griseofulvum F1959
Yong Seok Choi, Jung-Ho Choi, Hyun Sun Lee, Koanhoi Kim, Young Kook Kim, Seung Woong Lee, Mun-Chual Rho J Microbiol Biotechnol . 2008 Nov;18(11):1785-8. doi: 10.4014/jmb.0800.079.
Phenylpyropenes A, B, and C, isolated from Penicillium griseofulvum F1959, inhibited DGAT in rat liver microsomes with IC50 values of 78.7+/-1.6, 21.7+/-0.2, and 11.04+/-0.2 mM, respectively. In addition, a kinetic analysis using a Lineweaver-Burk plot revealed that phenylpyropene C was a noncompetitive inhibitor of DGAT. The apparent Michaelis constant (Km) value and inhibition constant (Ki) value were calculated to be 8 mM and 10.4 mM, respectively. Moreover, phenylpyropene C inhibited triglyceride formation in HepG2 cells.
2. Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri
Chi-Keung Lam, Jun Xu, Wen-Jian Lan, Guo-Hua Zhong, Wan-Ling Liang, De-Po Yang, Sheng-Jiao Fu, Hou-Jin Li, Meng-Yang Xu Mar Drugs . 2016 Jan 13;14(1):18. doi: 10.3390/md14010018.
The marine fungus Neosartorya pseudofischeri was isolated from Acanthaster planci from the South China Sea. In a preliminary bioactivity screening, the crude methanol extract of the fungal mycelia showed significant inhibitory activity against the Sf9 cell line from the fall armyworm Spodoptera frugiperda. Five novel compounds, including 5-olefin phenylpyropene A (1), 13-dehydroxylpyripyropene A (4), deacetylsesquiterpene (7), 5-formyl-6-hydroxy-8-isopropyl-2- naphthoic acid (9) and 6,8-dihydroxy-3-((1E,3E)-penta-1,3-dien-1-yl)isochroman-1-one (10), together with eleven known compounds, phenylpyropene A (2) and C (3), pyripyropene A (5), 7-deacetylpyripyropene A (6), (1S,2R,4aR,5R,8R,8aR)-1,8a-dihydroxy-2-acetoxy-3,8-dimethyl-5- (prop-1-en-2-yl)-1,2,4a, 5,6,7,8,8a-octahydronaphthalene (8), isochaetominine C (11), trichodermamide A (12), indolyl-3-acetic acid methyl ester (13), 1-acetyl-β-carboline (14), 1,2,3,4-tetrahydro-6-hydroxyl-2-methyl-l,3,4-trioxopyrazino[l,2-a]-indole (15) and fumiquinazoline F (16), were obtained. The structures of these compounds were determined mainly by MS and NMR data. The absolute configuration of 9 was assigned by the single-crystal X-ray diffraction studies. Compounds 1-11 and 15 showed significant cytotoxicity against the Sf9 cells from S. frugiperda.
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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 ╳
