A fungal metabolite
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Butyrolactone V

Item No. 29947

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-2-[[(3S)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl]methyl]-2,5-dihydro-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2-Furancarboxylic acid, methyl ester
CAS Number
1151509-01-1
Molecular Formula
C24H24O8
Formula Weight
440.4
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
OC1=C(C2=CC=C(O)C=C2)[C@@](C(OC)=O)(CC3=CC(C[C@H](O)C(C)(C)O4)=C4C=C3)OC1=O
InChi Code
InChI=1S/C24H24O8/c1-23(2)18(26)11-15-10-13(4-9-17(15)31-23)12-24(22(29)30-3)19(20(27)21(28)32-24)14-5-7-16(25)8-6-14/h4-10,18,25-27H,11-12H2,1-3H3/t18-,24+/m0/s1
InChi Key
NSXYYYUKWBLFQH-MHECFPHRSA-N
Origin
Fungus/Aspergillus terreus
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $174

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    5 mg

    $648

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    Product Description

    Butyrolactone V is a fungal metabolite that has been found in A. terreus and has antiprotozoal, antioxidant, and anticancer activities.1,2,3 It is active against the P. falciparum strain K1 (IC50 = 7.9 µg/ml) and L. amazonensis promastigotes (IC50 = 23.7 µM).2,1 Butyrolactone V (227 and 454.1 µM) is also active against adult S. mansoni worms.1 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) and ABTS (Item No. 27317) radicals with IC50 values of 20.7 and 3.7 µM, respectively, in cell-free assays.3 Butyrolactone V also inhibits proliferation of MDA-MB-231 and MCF-7 breast cancer cells (IC50s = 22.2 and 31.9 µM, respectively).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. de Silva, I.P., Brissow, E., Kellner, F., L.C., et al. Bioactive compounds of Aspergillus terreus—F7, an endophytic fungus from Hyptis suaveolens (L.) Poit. World J. Microbiol. Biotechnol. 33(3), 62 (2017).

    2. Haritakun, R., Rachtawee, P., Chanthaket, R., et al. Butyrolactones from the fungus Aspergillus terreus BCC 4651. Chem. Pharm. Bull. (Tokyo) 58(11), 1545-1548 (2010).

    3. An, X., Pei, Y., Chen, S., et al. Three new butenolides from the fungus Aspergillus sp. CBS-P-2. Molecules 21(10), E1361 (2016).