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P4368

Piericidin A from microbial source

Name: Piericidin A from microbial source
Brand: SIGMA

>95% (HPLC), DMSO solution

Synonym(s):

2,6,9,11-Tridecatetraen-4-ol,13-(4-hydrox-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-(all-E)-(4R,5R), 4-Pyridinol,2-(10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy- [R-[R*,R*-(all-E)]]-3-methyl-, Piericidin A1, SN 198E, Shaoguamycin B

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₃₇NO₄

CAS Number:

2738-64-9

Molecular Weight:

415.57

NACRES:

NA.77

PubChem Substance ID:

24898532

UNSPSC Code:

12352200

MDL number:

MFCD01677956

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Quality Level

200

assay

>95% (HPLC)

form

DMSO solution

shipped in

wet ice

storage temp.

2-8°C

SMILES string

COc1nc(C\C=C(/C)C\C=C\C(C)=C\[C@@H](C)[C@@H](O)\C(C)=C\C)c(C)c(O)c1OC

InChI

1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/b12-10+,16-13+,17-15+,18-9+/t19-,22+/m1/s1

InChI key

BBLGCDSLCDDALX-LKGBESRRSA-N

Biochem/physiol Actions

Piericidin A (PA), an insecticidal metabolite of Streptomyces mobaraensis is a potential quorum-sensing inhibitors (QSIs) that can destroy the expression of the virulence genes of Erwinia carotovora subsp. atroseptica (Eca). Hence it may be used as control agents of soft rot disease on potato tubers.

Piericidin A is a potent inhibitor of the mitochondrial and bacterial type I NADH-ubiquinone oxireductase (Complex I). It is considered to bind to the ubiquinone binding sites of the enzyme. Peiricidin A inactivation of complex I completely prevents NADH-induced proton translocation in the NADH-endogenous ubiquinone reductase reaction.

Potent inhibitor of the mitochondrial and bacterial type I NADH-ubiquinone oxireductase (Complex I).

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

185.0 °F - closed cup

flash_point_c

85 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Structure of piericidin A

Takahashi N, et al.

Journal of the American Chemical Society, 87(9), 2066-2068 (1965)

Isolation and characterization of complex I, rotenone-sensitive NADH: ubiquinone oxidoreductase, from the procyclic forms of Trypanosoma brucei.

J Fang et al.

European journal of biochemistry, 268(10), 3075-3082 (2001-05-19)

Additional characterization of complex I, rotenone-sensitive NADH:ubiquinone oxidoreductase, in the mitochondria of Trypanosoma brucei brucei has been obtained. Both proline:cytochrome c reductase and NADH:ubiquinone oxidoreductase of procyclic T. brucei were inhibited by the specific inhibitors of complex I rotenone, piericidin

Three classes of inhibitors share a common binding domain in mitochondrial complex I (NADH:ubiquinone oxidoreductase).

J G Okun et al.

The Journal of biological chemistry, 274(5), 2625-2630 (1999-01-23)

We have developed two independent methods to measure equilibrium binding of inhibitors to membrane-bound and partially purified NADH:ubiquinone oxidoreductase (complex I) to characterize the binding sites for the great variety of hydrophobic compounds acting on this large and complicated enzyme.

Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species.

Romana Fato et al.

Biochimica et biophysica acta, 1787(5), 384-392 (2008-12-09)

We have investigated the production of reactive oxygen species (ROS) by Complex I in isolated open bovine heart submitochondrial membrane fragments during forward electron transfer in presence of NADH, by means of the probe 2',7'-Dichlorodihydrofluorescein diacetate. ROS production by Complex

Inhibition of photosystem II of spinach by the respiration inhibitors piericidin A and thenoyltrifluoroacetone.

Nobuhiro Ikezawa et al.

Bioscience, biotechnology, and biochemistry, 66(9), 1925-1929 (2002-10-29)

The effects of several respiration inhibitors on photosystem II (PS II) were investigated. Among the agents tested, piericidin A and thenoyltrifluoroacetone (TTFA) inhibited the photosynthetic electron transport of spinach as measured from chlorophyll (Chl) fluorescence parameters (Fm'-F)/Fm' and Fv/Fm. Using

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