An acylated flavonol glycoside with antidiabetic activity
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Montbretin A

Item No. 30651

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[4-[[4-O-(6-deoxy-α-L-mannopyranosyl)-β-D-xylopyranosyl]oxy]-3,5-dihydroxyphenyl]-3-[[O-β-D-glucopyranosyl-(1→2)-O-6-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-β-D-glucopyranosyl-(1→2)-6-deoxy-α-L-mannopyranosyl]oxy]-5,7-dihydroxy-4H-1-benzopyran-4-one
CAS Number
115712-92-0
Synonyms
  • MbA
Molecular Formula
C53H64O33
Formula Weight
1229.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 2 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
267, 329 nm
SMILES
C[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O[C@@H]2CO[C@@H](OC3=C(O)C=C(C4=C(O[C@H]5[C@H](O[C@H]6[C@H](O[C@H]7[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)[C@@H](O)[C@H](O)[C@@H](COC(/C=C/C8=CC(O)=C(O)C=C8)=O)O6)[C@H](O)[C@@H](O)[C@H](C)O5)C(C9=C(O)C=C(O)C=C9O4)=O)C=C3O)[C@H](O)[C@H]2O)O1
InChi Code
InChI=1S/C53H64O33/c1-15-31(62)37(68)42(73)50(77-15)81-28-14-76-49(41(72)35(28)66)83-45-23(59)8-18(9-24(45)60)44-46(36(67)30-22(58)10-19(55)11-25(30)79-44)84-52-47(39(70)32(63)16(2)78-52)86-53-48(85-51-43(74)38(69)33(64)26(12-54)80-51)40(71)34(65)27(82-53)13-75-29(61)6-4-17-3-5-20(56)21(57)7-17/h3-11,15-16,26-28,31-35,37-43,47-60,62-66,68-74H,12-14H2,1-2H3/b6-4+/t15-,16-,26+,27+,28+,31-,32-,33+,34+,35-,37+,38-,39+,40-,41+,42+,43+,47+,48+,49-,50-,51-,52-,53-/m0/s1
InChi Key
FHVDXUPJFGRQLV-OWPXYNISSA-N
Origin
Plant/Crocosmia 'Lucifer'
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Montbretin A is an acylated flavonol glycoside that has been found in C. crocosmiiflora and has antidiabetic activity.1,2,3 It inhibits human pancreatic α-amylase and B. fibrisolvens amylase B (Kis = 8.1 and 1,600 nM, respectively).2 Montbretin A reduces blood glucose levels in Zucker diabetic fatty rats when administered at a dose of 7.4 mg/kg per day.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Asada, Y., Hirayama, Y., and Furuya, T. Acylated flavonols from Crocosmia crocosmiiflora. Phytochemistry 27(5), 1497-1501 (1988).

    2. Williams, L.K., Zhang, X., Caner, S., et al. The amylase inhibitor montbretin A reveals a new glycosidase inhibition motif. Nat. Chem. Biol. 11(9), 691-696 (2015).

    3. Irmisch, S., Jo, S., Roach, C.R., et al. Discovery of UDP-glycosyltransferases and BAHD-acyltransferases involved in the biosynthesis of the antidiabetic plant metabolite montbretin A. Plant Cell 30(8), 1864-1886 (2018).

    4. Yuen, V.G., Coleman, J., Withers, S.G., et al. Glucose lowering effect of montbretin A in Zucker diabetic fatty rats. Mol. Cell Biochem. 411(1-2), 373-381 (2016).