Phenylpyropene B

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Category Enzyme inhibitors
Catalog number BBF-02397
CAS 556013-83-3
Molecular Weight 508.60
Molecular Formula C30H36O7

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Description

It is produced by the strain of Penicillum griseofulvum F 1959. It can inhibit ACAT activity with IC50 of 12.8 μmol/L.

Specification

IUPAC Name [(1R,2S,5S,6R,7R,10R)-5-acetyloxy-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(C2CCC3(C(C2(CCC1OC(=O)C)C)CC4=C(O3)C=C(OC4=O)C5=CC=CC=C5)C)C
InChI InChI=1S/C30H36O7/c1-18(31)34-17-29(4)24-11-14-30(5)25(28(24,3)13-12-26(29)35-19(2)32)15-21-23(37-30)16-22(36-27(21)33)20-9-7-6-8-10-20/h6-10,16,24-26H,11-15,17H2,1-5H3/t24-,25-,26+,28+,29+,30-/m1/s1
InChI Key CBPHTUXBOQCTIG-UEHVIBGPSA-N

Properties

Appearance White Powder
Solubility Soluble in Methanol

Reference Reading

1. Inhibition of diacylglycerol acyltransferase by phenylpyropenes produced by Penicillium griseofulvum F1959
Seung Woong Lee, Mun-Chual Rho, Jung-Ho Choi, Koanhoi Kim, Yong Seok Choi, Hyun Sun Lee, Young Kook Kim 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.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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