A mycotoxin
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Fumitremorgin B

Item No. 31173

Technical Information
Formal Name
(5aR,6S,12S,14aS)-1,2,3,5a,6,11,12,14a-octahydro-5a,6-dihydroxy-9-methoxy-11-(3-methyl-2-buten-1-yl)-12-(2-methyl-1-propen-1-yl)-5H,14H-pyrrolo[1",2":4′,5′]pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-5,14-dione
CAS Number
12626-17-4
Synonyms
  • Lanosulin
Molecular Formula
C27H33N3O5
Formula Weight
Purity
≥95%
A solid
SMILES
COC1=CC=C(C(N2C/C=C(C)\C)=C1)C3=C2[C@H](/C=C(C)\C)N(C([C@@]4([H])N5CCC4)=O)[C@]([C@H]3O)(O)C5=O
InChi Code
InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3/t19-,21-,24-,27+/m0/s1
InChi Key
WEIYXEFMCIRZHC-MWGWWEMPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Fumitremorgin B is a mycotoxin originally isolated from A. fumigatus.1,2 It induces tremors in and is lethal to mice (LD50 = 5.4 mg/kg, i.v.). It is also toxic to brine shrimp (LC50 = 13.6 μg/ml).3 Fumitremorgin B inhibits the proliferation of U937 and PC3 cells (IC50s = 14.12 and 43.36 μM, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yamazaki, M., Suzuki, S., and Miyaki, K. Tremorgenic toxins from Aspergillus fumigatus Fres. Chem. Pharm. Bull. (Tokyo) 19(8), 1739-1740 (1971).

    2. Yamazaki, M., and Suzuki, S. Toxicology of tremorgenic mycotoxins, fumitremorgin A and B. Dev. Toxicol. Environ. Sci. 12, 273-282 (1986).

    3. Li, X.-J., Zhang, Q., Zhang, A.-L., et al. Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities. J. Agric. Food Chem. 60(13), 3424-3431 (2012).

    4. Wang, Y., Li, Z.-L., Bai, J., et al. 2,5-diketopiperazines from the marine-derived fungus Aspergillus fumigatus YK-7. Chem. Biodivers. 9(2), 85-93 (2012).