MedKoo Cat#: 112085 | Name: Montbretin A
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Montbretin A has antidiabetic activity and inhibits human pancreatic α-amylase and B. fibrisolvens amylase B.

Chemical Structure

Montbretin A
Montbretin A
CAS# 115712-92-0

Theoretical Analysis

MedKoo Cat#: 112085

Name: Montbretin A

CAS#: 115712-92-0

Chemical Formula: C53H64O33

Exact Mass: 1228.3330

Molecular Weight: 1229.06

Elemental Analysis: C, 51.79; H, 5.25; O, 42.96

Price and Availability

Size Price Availability Quantity
1mg USD 400.00 2 Weeks
5mg USD 1,050.00 2 Weeks
10mg USD 1,500.00 2 Weeks
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Related CAS #
No Data
Synonym
Montbretin A; MbA
IUPAC/Chemical Name
((2R,3S,4S,5R,6S)-6-(((2S,3R,4R,5R,6S)-2-((2-(4-(((2S,3R,4R,5R)-3,4-dihydroxy-5-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-3,4-dihydroxy-5-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)methyl (E)-3-(3,4-dihydroxyphenyl)acrylate
InChi Key
FHVDXUPJFGRQLV-OWPXYNISSA-N
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
SMILES Code
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)OC3=C(C=C(C=C3O)C4=C(C(C5=C(C=C(C=C5O4)O)O)=O)O[C@H]6[C@@H]([C@@H]([C@H]([C@@H](O6)C)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)COC(/C=C/C8=CC(O)=C(C=C8)O)=O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM
Solubility
DMF 1.0 0.81
DMSO 2.0 1.63
PBS (pH:7.2) 2.0 1.63
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,229.06 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Williams LK, Zhang X, Caner S, Tysoe C, Nguyen NT, Wicki J, Williams DE, Coleman J, McNeill JH, Yuen V, Andersen RJ, Withers SG, Brayer GD. The amylase inhibitor montbretin A reveals a new glycosidase inhibition motif. Nat Chem Biol. 2015 Sep;11(9):691-6. doi: 10.1038/nchembio.1865. Epub 2015 Jul 27. PMID: 26214255. 2: Sunstrum FG, Liu HL, Jancsik S, Madilao LL, Bohlmann J, Irmisch S. 4-Coumaroyl-CoA ligases in the biosynthesis of the anti-diabetic metabolite montbretin A. PLoS One. 2021 Oct 7;16(10):e0257478. doi: 10.1371/journal.pone.0257478. PMID: 34618820; PMCID: PMC8496819. 3: Yuen VG, Coleman J, Withers SG, Andersen RJ, Brayer GD, Mustafa S, McNeill JH. Glucose lowering effect of montbretin A in Zucker Diabetic Fatty rats. Mol Cell Biochem. 2016 Jan;411(1-2):373-81. doi: 10.1007/s11010-015-2599-4. Epub 2015 Nov 7. PMID: 26547551. 4: Irmisch S, Jancsik S, Man Saint Yuen M, Madilao LL, Bohlmann J. Complete Biosynthesis of the Anti-Diabetic Plant Metabolite Montbretin A. Plant Physiol. 2020 Sep;184(1):97-109. doi: 10.1104/pp.20.00522. Epub 2020 Jul 9. PMID: 32647038; PMCID: PMC7479892. 5: Tysoe CR, Caner S, Calvert MB, Win-Mason A, Brayer GD, Withers SG. Synthesis of montbretin A analogues yields potent competitive inhibitors of human pancreatic α-amylase. Chem Sci. 2019 Oct 18;10(48):11073-11077. doi: 10.1039/c9sc02610j. PMID: 32206255; PMCID: PMC7069248. 6: Irmisch S, Jancsik S, Yuen MMS, Madilao LL, Bohlmann J. Biosynthesis of the anti-diabetic metabolite montbretin A: glucosylation of the central intermediate mini-MbA. Plant J. 2019 Dec;100(5):879-891. doi: 10.1111/tpj.14493. Epub 2019 Sep 16. PMID: 31400245; PMCID: PMC6899944. 7: Maron L. Imitation is the sincerest form of flattery: reconstructing the biosynthesis of montbretin A. Plant J. 2019 Dec;100(5):877-878. doi: 10.1111/tpj.14609. PMID: 31774611. 8: Irmisch S, Ruebsam H, Jancsik S, Man Saint Yuen M, Madilao LL, Bohlmann J. Flavonol Biosynthesis Genes and Their Use in Engineering the Plant Antidiabetic Metabolite Montbretin A. Plant Physiol. 2019 Jul;180(3):1277-1290. doi: 10.1104/pp.19.00254. Epub 2019 Apr 19. PMID: 31004005; PMCID: PMC6752896. 9: Irmisch S, Jo S, Roach CR, Jancsik S, Man Saint Yuen M, Madilao LL, O'Neil- Johnson M, Williams R, Withers SG, Bohlmann J. Discovery of UDP- Glycosyltransferases and BAHD-Acyltransferases Involved in the Biosynthesis of the Antidiabetic Plant Metabolite Montbretin A. Plant Cell. 2018 Aug;30(8):1864-1886. doi: 10.1105/tpc.18.00406. Epub 2018 Jul 2. PMID: 29967287; PMCID: PMC6139687.