A fungal metabolite
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Cochlioquinone B

Item No. 25121

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,4aR,6aR,12aR,12bR)-9-[(1S,3S)-1,3-dimethyl-2-oxopentyl]-1,2,3,4a,5,6,6a,12,12a,12b-decahydro-3-(1-hydroxy-1-methylethyl)-6a,12b-dimethyl-pyrano[3,2-a]xanthene-8,11-dione
CAS Number
32450-26-3
Molecular Formula
C28H40O6
Formula Weight
472.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
C[C@]12[C@@](O[C@@H](C(C)(O)C)CC2)([H])CC[C@@]([C@]1([H])C3)(C)OC4=C3C(C=C([C@H](C)C([C@@H](C)CC)=O)C4=O)=O
InChi Code
InChI=1S/C28H40O6/c1-8-15(2)23(30)16(3)17-13-19(29)18-14-20-27(6)11-9-21(26(4,5)32)33-22(27)10-12-28(20,7)34-25(18)24(17)31/h13,15-16,20-22,32H,8-12,14H2,1-7H3/t15-,16-,20+,21+,22+,27+,28+/m0/s1
InChi Key
NTPNSKLZWVYKGK-WWURSIHSSA-N
Origin
Fungus/Bipolaris leersia
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Cochlioquinone is a sesquiterpene metabolite originally isolated from C. miyabeanus.1 It is a phytotoxin that inhibits root growth of finger millet (E. coracana) and rice plants (O. sativa) by 59.9 and 51.7%, respectively, when used at a concentration of 100 ppm.2 Cochlioquinone B inhibits NADH oxidase and NADH-2,3-dimethoxy-5-pentyl-1,4-benzoquinone reductase from bovine heart mitochondria.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Carruthers, J.R., Cerrini, S., Fedeli, W., et al. Structures of cochlioquinones A and B, new metabolites of Cochliobolus miyabeanus: Chemical and X-ray crystallographic determination. J. Chem. Soc. D. 0(3), 164-166 (1971).

    2. Miyagawa, H., Nagai, S., Tsurushima, T., et al. Phytotoxins produced by the plant pathogenic fungus Bipolaris bicolor El-1. Biosci. Biotech. Biochem. 58(6), 1143-1145 (1994).

    3. Lim, C.-H., Ueno, H., Miyoshi, H., et al. Phytotoxic compounds cochlioquinones are inhibitors of mitochondrial NADH-ubiquinone reductase. J. Pest. Scien. 21(2), 213-215 (1996).