An anthraquinone with diverse biological activities
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Bostrycin

Item No. 27466

Technical Information
Formal Name
(5S,6R,7S)-5,6,7,8-tetrahydro-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4-anthracenedione
CAS Number
21879-81-2
Synonyms
  • Rhodosporin
Molecular Formula
C16H16O8
Formula Weight
Purity
≥95%
A solid
SMILES
O=C(C(OC)=C1)C2=C(C(O)=C([C@H](O)[C@@H](O)[C@](O)(C)C3)C3=C2O)C1=O
InChi Code
InChI=1S/C16H16O8/c1-16(23)4-5-8(14(21)15(16)22)13(20)9-6(17)3-7(24-2)12(19)10(9)11(5)18/h3,14-15,18,20-23H,4H2,1-2H3/t14-,15+,16-/m0/s1
InChi Key
ZQNOLGRKZRDRQO-XHSDSOJGSA-N
Origin
Fungus/Arthrinium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Bostrycin is an anthraquinone originally isolated from B. alpestre that has diverse biological activities, including antibacterial, antiproliferative, and phytotoxic properties.1,2 It is active against Gram-positive bacteria, including methicillin-resistant S. aureus (MRSA), M. tuberculosis, and C. botulinum.2 Bostrycin inhibits proliferation of A549 lung adenocarcinoma cells when used at concentrations ranging from 10 to 30 µM, as well as halts the cell cycle at the G0/G1 phase and induces apoptosis in A549 cells.3 It is a phytotoxin that induces necrosis of water hyacinth leaves when used at a concentration of approximately 7 µg/ml.4 Bostrycin has been used as a cross-linking agent for protein immobilization that retains bacteriostatic activity when immobilized on nonwoven polypropylene fabric.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Noda, T., Take, T., Otani, M., et alStructure of bostrycin. Tetrahedron Lett. 9(58), 6087-6090 (1968).

    2. Yang, W.J., Yang, C.S., Huang, C.J., et alBostrycin, a novel coupling agent for protein immobilization and prevention of biomaterial-centered infection produced by Nigrospora sp. No. 407. Enzyme Microb. Technol. 50(6-7), 287-292 (2012).

    3. Chen, W.S., Hou, J.N., Guo, Y.B., et alBostrycin inhibits proliferation of human lung carcinoma A549 cells via downregulation of the PI3K/Akt pathway. J. Exp. Clin. Cancer Res. 30(1), 17 (2011).

    4. Charudattan, R., and Rao, K.V. Bostrycin and 4-deoxybostrycin: Two nonspecific phytotoxins produced by Alternaria eichhorniae. Appl. Environ. Microbiol. 43(4), 846-849 (1982).