A fungal metabolite
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Isomer(s)
29940Aszonapyrone A
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Chevalone C

Item No. 25084

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,4aR,4bR,6aS,12aS,12bR,14aR)-2-(acetyloxy)-2,3,4,4a,4b,5,6,6a,12,12a,12b,13,14,14a-tetradecahydro-1,1,4a,6a,9,12b-hexamethyl-1H,11H-phenanthro[2,1-b]pyrano[3,2-e]pyran-11-one
CAS Number
1318025-77-2
Molecular Formula
C28H40O5
Formula Weight
456.6
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
CC(OC1=C2C[C@]3([H])[C@@](CC[C@@]4([H])[C@@]3(C)CC[C@]5([H])[C@]4(C)CC[C@H](OC(C)=O)C5(C)C)(C)O1)=CC2=O
InChi Code
InChI=1S/C28H40O5/c1-16-14-19(30)18-15-22-27(6)11-8-20-25(3,4)23(32-17(2)29)10-12-26(20,5)21(27)9-13-28(22,7)33-24(18)31-16/h14,20-23H,8-13,15H2,1-7H3/t20-,21+,22-,23-,26-,27+,28-/m0/s1
InChi Key
ASOIHOGDYISNRH-GPTGPEQGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $222

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    5 mg

    $827

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    Product Description

    Chevalone C is a meroterpenoid fungal metabolite originally isolated from E. chevalieri.1 It is active against M. tuberculosis H37Ra (MIC = 6.3 μg/ml) and is cytotoxic to BC1 human breast cancer cells (IC50 = 8.7 μg/ml). Chevalone C inhibits the growth of multidrug-resistant isolates of E. coli, S. aureus, and E. faecium in a disc diffusion assay when used at a concentration of 15 μg/disc.2 It also induces cell death in HCT116 colorectal carcinoma cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kanokmedhakul, K., Kanokmedhakul, S., Suwannatrai, R., et al. Bioactive meroterpenoids and alkaloids from the fungus Eurotium chevalieri. Tetrahedron 67(30), 5461-5468 (2011).

    2. Gomes, N.M., Bessa, L.J., Buttachon, S., et al. Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis. Mar. Drugs 12(2), 822-839 (2014).

    3. Prata-Sena, M., Ramos, A.A., Buttachon, S., et al. Cytotoxic activity of secondary metabolites from marine-derived fungus Neosartorya siamensis in human cancer cells. Phytother. Res. 30(11), 1862-1871 (2016).