Calystegine B2 | CAS:127414-85-1 | Manufacturer ChemFaces

Calystegine B2

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Description:

Calystegine B2 can inhibit the alpha-galactosidase and enzymes beta-glucosidase activities.

In vitro:

J Nat Prod. 1996 Dec;59(12):1137-42.

Biological activities of the nortropane alkaloid, calystegine B2, and analogs: structure-function relationships.[Pubmed: 8988598 ]

METHODS AND RESULTS:
Calystegines, polyhydroxy nortropane alkaloids, are a recently discovered group of plant secondary metabolites believed to influence rhizosphere ecology as nutritional sources for soil microorganisms and as glycosidase inhibitors. Evidence is presented that calystegines mediate nutritional relationships under natural conditions and that their biological activities are closely correlated with their chemical structures and stereochemistry. Assays using synthetic (+)- and (-)-enantiomers of Calystegine B2 established that catabolism by Rhizobium meliloti, glycosidase inhibition, and allelopathic activities were uniquely associated with the natural, (+)-enantiomer. Furthermore, the N-methyl derivative of Calystegine B2 was not catabolized by R. meliloti, and it inhibited alpha-galactosidase, but not beta-glucosidase, whereas the parent alkaloid inhibits both enzymes.
CONCLUSIONS:
This N-methyl analog therefore could serve to construct a cellular or animal model for Fabry's disease, which is caused by a lack of alpha-galactosidase activity.

In vivo:

J Nat Prod. 1995 Jun;58(6):878-86.

Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity.[Pubmed: 7673932]

METHODS AND RESULTS:
The polyhydroxy alkaloid glycosidase inhibitors swainsonine [1] and Calystegine B2 [6] have been identified as constituents of the seeds of the Australian plant Ipomoea sp. Q6 [aff. calobra] (Weir vine) by gas chromatography-mass spectrometry and by their biological activity as inhibitors of specific glycosidases. This plant, which is known only from a small area of southern Queensland, has been reported to produce a neurological disorder when consumed by livestock. The extract of the seeds showed inhibition of alpha-mannosidase, beta-glucosidase, and alpha-galactosidase, consistent with the presence of 1 and alkaloids of the calystegine class. Histological examination of brain tissue from field cases of sheep and cattle poisoned by Weir vine showed lesions similar to those observed in animals poisoned by the swainsonine-containing poison peas (Swainsona spp.) of Australia and locoweeds (Astragalus and Oxytropis spp.) of North America.
CONCLUSIONS:
These results indicate that Weir vine poisoning is an additional manifestation of the induced lysosomal storage disease, mannosidosis, possibly exacerbated by inhibition of the enzymes beta-glucosidase and alpha-galactosidase by Calystegine B2. This is the first reported example of a single plant species capable of producing structurally distinct glycosidase inhibitors, namely, alkaloids of the indolizidine and nortropane classes.

Calystegine B2 Description

Source:	The root barks of Lycium chinense Mill.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

J Org Chem. 2012 Jan 20;77(2):991-8.

Executing and rationalizing the synthesis of a difluorinated analogue of a ring-expanded calystegine B2.[Pubmed: 22148579 ]

METHODS AND RESULTS:
A difluorinated analogue of a ring-expanded calystegine B(2) and some N-protected species were prepared via microwave-mediated transannular ring-opening of an epoxyketone.
CONCLUSIONS:
The diastereofacial selectivity of the epoxidation reaction, which delivers the key intermediate, and the regioselectivity of the transannular reactions were analyzed by density functional theory (DFT) methods. The epoxidation stereoselectivity arises from simple steric control, whereas the ring-closure reactions are subject to thermodynamic control.

J Org Chem. 2001 Nov 16;66(23):7604-14.

Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors.[Pubmed: 11701011]

A practical synthesis of polyhydroxylated 6-oxa-nor-tropanes incorporating the essential structural features of calystegine B(2) from 5-deoxy-5-thioureido and 5-ureido-L-idofuranose precursors is presented.
METHODS AND RESULTS:
The methodology relies on the ability of pseudoamide-type nitrogen atoms (thiourea, urea, and carbamate) to undergo nucleophilic addition to the masked aldehyde group of the monosaccharide. The generated hemiaminal functionality may further undergo in situ intramolecular glycosidation to give the bicyclic aminoacetal compounds, the whole process being favored by the anomeric effect.
CONCLUSIONS:
A series of derivatives bearing different substituents at nitrogen has been prepared and screened against several glycosidases in comparison with xylonojirimycin-type piperidine analogues. Interestingly, strong and highly specific inhibition of bovine liver beta-glucosidase was observed for 6-oxacalystegine B(2) analogues incorporating aromatic pseudoaglyconic groups. On the basis of these data, a 1-azasugar inhibition mode is proposed for this family of glycomimetics.

Product Name	Calystegine B2
Price:
CAS No.:	127414-85-1
Catalog No.:	CFN00161
Molecular Formula:	C₇H₁₃NO₄
Molecular Weight:	175.18 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	The root barks of Lycium chinense Mill.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Alkaloids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.7084 mL	28.5421 mL	57.0841 mL	114.1683 mL	142.7104 mL
5 mM	1.1417 mL	5.7084 mL	11.4168 mL	22.8337 mL	28.5421 mL
10 mM	0.5708 mL	2.8542 mL	5.7084 mL	11.4168 mL	14.271 mL
50 mM	0.1142 mL	0.5708 mL	1.1417 mL	2.2834 mL	2.8542 mL
100 mM	0.0571 mL	0.2854 mL	0.5708 mL	1.1417 mL	1.4271 mL

CFN00156	2,6-Tropanediol	65356-02-7	157.21	C₈H₁₅NO₂
CFN00157	Erycibelline	107633-95-4	143.18	C₇H₁₃NO₂
CFN00158	8-Azabicyclo[3.2.1]octane-3,6-diol	N/A	143.18	C₇H₁₃NO₂
CFN00159	3,6-Ditigloyloxynortropane	359723-70-9	307.39	C₁₇H₂₅NO₄
CFN00160	Calystegine C2	190957-44-9	191.18	C₇H₁₃NO₅
CFN00161	Calystegine B2	127414-85-1	175.18	C₇H₁₃NO₄
CFN00162	Calystegine B3	178231-95-3	175.18	C₇H₁₃NO₄
CFN00152	8-Azabicyclo[3.2.1]octane-2,3-diol	N/A	143.18	C₇H₁₃NO₂
CFN00154	Baogongteng C	107259-50-7	143.18	C₇H₁₃NO₂
CFN00155	Baogongteng A	74239-84-2	185.22	C₉H₁₅NO₃