A fungal metabolite
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Phenylpyropene A

Item No. 29594

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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
CAS Number
189564-20-3
Molecular Formula
C32H38O10
Formula Weight
582.6
Purity
≥95%
Formulation
Residue
SMILES
O=C1C2=C(O[C@@]([C@@H](OC(C)=O)C[C@]3([H])[C@]4(C)CC[C@H](OC(C)=O)[C@@]3(C)COC(C)=O)(C)[C@]4([H])[C@H]2O)C=C(C5=CC=CC=C5)O1
InChi Code
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
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $215

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    5 mg

    $966

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    Product Description

    Phenylpyropene A is a fungal metabolite originally isolated from P. griseofulvum that has enzyme inhibitory and insecticidal activities.1,2,3 It inhibits acyl-coenzyme A:cholesterol acyltransferase (ACAT; IC50 = 0.8 μM).1 Phenylpyropene A inhibits diacylglycerol acyltransferase (DGAT) in rat liver microsomes (IC50 = 78.7 μM). It induces mortality in 100% of M. persicae when used at a concentration of 5 ppm.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kwon, O.E., Rho, M.C., Song, H.Y., et al. Phenylpyropene A and B, new inhibitors of acyl-CoA: Cholesterol acyltransferase produced by Penicillium griseofulvum F1959. J. Antibiot. (Tokyo) 55(11), 1004-1008 (2002).

    2. Lee, S.W., Rho, M.C., Choi, J.H., et al. Inhibition of diacylglycerol acyltransferase by phenylpyropenes produced by Penicillium griseofulvum F1959. J. Microbiol. Biotechnol. 18(11), 1785-1788 (2008).

    3. Horikoshi, R., Goto, K., Mitomi, M., et al. Identification of pyripyropene A as a promising insecticidal compound in a microbial metabolite screening. J. Antibiot. (Tokyo) 70(3), 272-276 (2017).