A fungal metabolite
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(+)-Macrosphelide A

Item No. 27704

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9R,15R-dihydroxy-4S,10S,16S-trimethyl-1,5,11-trioxacyclohexadeca-7E,13E-diene-2,6,12-trione
CAS Number
172923-77-2
Molecular Formula
C16H22O8
Formula Weight
342.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleDMSO: SolubleMethanol: Soluble
SMILES
O=C(O[C@@H](C)[C@H](O)/C=C/C1=O)C[C@H](C)OC(/C=C/[C@@H](O)[C@H](C)O1)=O
InChi Code
InChI=1S/C16H22O8/c1-9-8-16(21)24-11(3)13(18)5-7-15(20)23-10(2)12(17)4-6-14(19)22-9/h4-7,9-13,17-18H,8H2,1-3H3/b6-4+,7-5+/t9-,10-,11-,12+,13+/m0/s1
InChi Key
MJMMUATWVTYSFD-FTXQSDARSA-N
Origin
Fungus/Paraconiothyrium sporulosum FO-5050
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

    (+)-Macrosphelide A is a fungal metabolite originally isolated from Microsphaeropsis.1 It inhibits adhesion of HL-60 human leukemia cells to human umbilical vein endothelial cells (HUVECs) in a concentration-dependent manner. It also inhibits the growth of SKOV3 ovarian cancer cells in a concentration-dependent manner.2 (+)-Macrosphelide A inhibits the growth of Gram-positive bacteria, including B. subtilis, M. luteus, B. thuringiensis, and S. aureus (MICs = 143, 143, 57, and 57 μg/ml, respectively), but not Gram-negative bacteria or fungi.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ono, M., Nakamura, H., Konno, F., et al. Total syntheses of macrosphelides (+)-A, (−)-A and (+)-E. Tetrahedron-Asymmetr. 11(13), 2753-2764 (2000).

    2. Heo, Y.M., Lee, H., Shin, Y.K., et al. Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative. Molecules 19(10), 15572-15583 (2014).

    3. Tomprefa, N., McQuilken, M.P., Hill, R.A., et al. Antimicrobial activity of Coniothyrium minitans and its macrolide antibiotic macrosphelide A. J. Appl. Microbiol. 106(6), 2048-2056 (2009).