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S8534

Sigma-Aldrich

Sarsasapogenin

≥98%

Synonym(s):

(25S)-Spirostan-3β-ol, Parigenin

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About This Item

Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
126-19-2
Molecular Weight:
416.64
EC Number:
204-776-3
MDL number:
MFCD00270414
UNSPSC Code:
12352200
PubChem Substance ID:
24899798
NACRES:
NA.25

Assay

≥98%

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

C[C@H]1CC[C@@]2(OC1)O[C@H]3C[C@H]4[C@@H]5CC[C@@H]6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C

InChI

1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18+,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

InChI key

GMBQZIIUCVWOCD-WWASVFFGSA-N

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General description

Sarsasapogenin also known as Sarsagenin or Parigenin, is a steroidal saponin and is the main constituent of Anemarrhena asphodeloides Bunge.

Application

Sarsasapogenin has been used as a synthetic saponin treatment to U-2 OS cells to test its effects in reducing osteosarcoma cell viability and down-regulating YAP and TAZ proteins.

Biochem/physiol Actions

Sarsasapogenin is a well-known multi-target directed ligand (MTDL) for Alzheimer′s disease. It elicits anti-inflammatory, antioxidant, anti-arthritis, anti-asthma, anti-amyloidogenic, neuroprotective, anti-depressant, and anti-cancer properties. SAR also improves learning and memory ability, loss of neurons in type-1 diabetic rats and protects against diabetic encephalopathy. It is also a therapeutic target for treating ulcerative colitis (UC). SAR as an anti-inflammatory agent improves insulin resistance and adipose tissue inflammation in high-fat diet (HFD)-fed mice.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Deepa S Mandlik et al.
Immunopharmacology and immunotoxicology, 43(5), 571-583 (2021-08-03)
Ulcerative colitis (UC) is a chronic inflammatory bowel condition considered by oxido-nitrosative stress and the release of pro-inflammatory cytokines that affects the mucosal lining of the colon. Sarsasapogenin (SG), as an active component, has been found in many plants, and
Yan-Yan Yu et al.
Acta pharmacologica Sinica, 42(2), 272-281 (2020-07-24)
Insulin resistance is a major cause of type 2 diabetes and metabolic syndrome. Macrophage infiltration into obese adipose tissue promotes inflammatory responses that contribute to the pathogenesis of insulin resistance. Suppression of adipose tissue inflammatory responses is postulated to increase
Priya Kashyap et al.
Steroids, 153, 108529-108529 (2019-11-02)
Alzheimer's disease (AD) is multi-factorial disorder characterized by impaired memory and cognition deficit. AD is characterized by impaired cholinergic transmission, extracellular amyloid beta deposits, neurofibrillary tangles and oxidative stress. A multi-target directed ligand (MTDL) approach is required to devise a
Maria Ferraiuolo et al.
Cancer letters, 433, 18-32 (2018-06-23)
Osteosarcoma (OS) is the most aggressive type of primary solid tumor that develops in bone. Whilst conventional chemotherapy can improve survival rates, the outcome for patients with metastatic or recurrent OS remains poor, so novel treatment agents and strategies are
Dorota Czajkowska et al.
Steroids, 74(13-14), 1073-1079 (2009-09-15)
Syntheses of "glycospirostanes" from 3beta-hydroxy-23,24-dinor-5alpha-cholano-22,16-lactone and 3alpha-hydroxy-23,24-dinor-5beta-cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivative. Further elaboration of the six-membered ring F consisted of allylic hydroxylation with SeO(2) followed by OsO(4) dihydroxylation
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