S8195

Swainsonine

Name: Swainsonine
Brand: SIGMA
Price: 13685 CZK

from Metarrhizium anisopliae, ≥98% (TLC)

Synonym(s):

(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol

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1 MG

CZK 13,685.00

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About This Item

Empirical Formula (Hill Notation):

C₈H₁₅NO₃

CAS Number:

72741-87-8

Molecular Weight:

173.21

UNSPSC Code:

51102829

NACRES:

NA.85

PubChem Substance ID:

24899779

MDL number:

MFCD00017554

Beilstein/REAXYS Number:

4175740

Key Documents

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Product Name

Swainsonine, from Metarrhizium anisopliae, ≥98% (TLC)

InChI key

FXUAIOOAOAVCGD-DCDLSZRSSA-N

SMILES string

O[C@@H]1CCCN2C[C@@H](O)[C@@H](O)C12

InChI

1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7?,8-/m1/s1

biological source

Metarrhizium anisopliae

assay

≥98% (TLC)

form

lyophilized powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

white to faint yellow

solubility

H₂O: soluble 1 mg/mL

antibiotic activity spectrum

neoplastics

mode of action

enzyme | inhibits

storage temp.

2-8°C

Quality Level

200

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Show Differences

1 of 4

This Item	S9263	SML0789	574775-M
Sigma-Aldrich S8195 Swainsonine	Sigma-Aldrich S9263 Swainsonine	Sigma-Aldrich SML0789 GI254023X	Sigma-Aldrich 574775-M Swainsonine, Swainsona canescens
mode of action enzyme \| inhibits	mode of action -	mode of action -	mode of action -
antibiotic activity spectrum neoplastics	antibiotic activity spectrum -	antibiotic activity spectrum -	antibiotic activity spectrum -
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level 100
form lyophilized powder	form solid	form powder	form solid
assay ≥98% (TLC)	assay ≥95% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (TLC)
solubility H₂O: soluble 1 mg/mL	solubility methanol: 5 mg/mL, clear, colorless to light yellow	solubility DMSO: 15 mg/mL, clear	solubility water: 1 mg/mL, DMSO: 5 mg/mL, chloroform: soluble

Application

Swainsonine is a potent inhibitor of various α-mannosidases, especially of α-mannosidase II. It inhibits glycoprotein processing and also acts as immune modulator.

Swainsonine is an indolizidine alkaloid from the plant Metarrhizium anisopliae that is used as a potent α-mannosidase inhibitor[1]. Product S8195 has been used in chemical inhibition assays of CHO Lec2 cells to inhibit glycosylation [2].

Biochem/physiol Actions

Swainsonine is a potent α-mannosidase inhibitor. It also has antimetastatic, antiproliferative, and immunomodulatory activity [1]. It also inhibits glycoprotein processing.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Packaging

1MG

Preparation Note

Soluble in water, methanol, DMSO

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000342952

0000214491

0000235807

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Terminal N-linked galactose is the primary receptor for adeno-associated virus 9.

Shen Shen et al.

The Journal of biological chemistry, 286(15), 13532-13540 (2011-02-19)

Sialylated glycans serve as cell surface attachment factors for a broad range of pathogens. We report an atypical example, where desialylation increases cell surface binding and infectivity of adeno-associated virus (AAV) serotype 9, a human parvovirus isolate. Enzymatic removal of

The potential importance of swainsonine in therapy for cancers and immunology.

K Olden et al.

Pharmacology & therapeutics, 50(3), 285-290 (1991-01-01)

Swainsonine, an indolizidine alkaloid, was initially used in biomedical research as a tool to investigate the biosynthesis and function of asparagine-linked 'complex' type oligosaccharide moieties of glycoproteins. Recently, swainsonine has generated interest in its potential use as an anticancer agent

Production of the alkaloid swainsonine by a fungal endophyte in the host Swainsona canescens.

Daniel S Grum et al.

Journal of natural products, 76(10), 1984-1988 (2013-09-24)

Legumes belonging to the Astragalus, Oxytropis, and Swainsona genera have been noted by ranchers in the Americas, Asia, and Australia to cause a neurologic disease often referred to as locoism or peastruck. The toxin in these legumes is swainsonine, an

The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages.

H P Broquist

Annual review of nutrition, 5, 391-409 (1985-01-01)

The involvement of slaframine and swainsonine in slobbers syndrome: a review.

W J Croom et al.

Journal of animal science, 73(5), 1499-1508 (1995-05-01)

The history of "slobbers syndrome," a mycotoxicosis associated with Rhizoctonia leguminicola infestation of pastures and stored forages, is discussed. The chemistry and physiological effects of the two known biologically active alkaloids of R. leguminicola, slaframine and swainsonine, are described. Slaframine

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