Tigogenin | CAS:77-60-1 | Manufacturer ChemFaces

Tigogenin

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Description:

Tigogenin is one of steroidal sapogenins which is widely used for synthesizing steroid drugs. It might have protective effect on bone and be helpful in preventing the development of osteoporosis.Tigogenin induces apoptosis, associated with overexpression of COX-2 correlated with overproduction of endogenous PGE2. Tigogenin inhibited of PPARgamma and via p38 MAPK pathway.

Targets:

COX | PGE | PPAR | p38MAPK

In vitro:

Int J Mol Med. 2007 Oct;20(4):451-60.

Inhibition of human rheumatoid arthritis synovial cell survival by hecogenin and tigogenin is associated with increased apoptosis, p38 mitogen-activated protein kinase activity and upregulation of cyclooxygenase-2.[Pubmed: 17786275]

We conducted our study to assess the antiproliferative and proapoptotic potential of hecogenin and Tigogenin, two saponins which are structurally similar to diosgenin.
METHODS AND RESULTS:
We particularly focused our attention on mitogen-activated protein kinase (MAPK) activation in relation to apoptosis but also with the COX-2 expression and activity. Rheumatoid arthritis (RA) synoviocytes were isolated from fresh synovial biopsies obtained from five RA patients undergoing hip arthroplasty. Measurement of cell proliferation was determined using the MTT assay. Apoptosis was evaluated by studying caspase-8, caspase-9 and caspase-3 activities but also by quantification of DNA fragmentation. Quantification of human phospho-MAPKs was realized by ELISA. COX-2 expression was demonstrated by Western blot analysis and COX-2 activity by assay of endogenous prostaglandin E2 (PGE2) production. Tigogenin was more effective than hecogenin in inducing apoptosis in human RA fibroblast-like synoviocytes (FLS) which was caspase dependent but poly(ADP-ribose) polymerase independent and characterized by DNA fragmentation. Our results demonstrated hecogenin- and Tigogenin-induced apoptosis through activation of p38 without affecting the JNK and ERK pathways. Indeed, pretreatment with a p38 inhibitor decreased saponin-induced apoptosis with a significant decrease in DNA fragmentation. Furthermore, the rate of apoptosis induced by hecogenin or Tigogenin was associated with overexpression of COX-2 correlated with overproduction of endogenous PGE2.
CONCLUSIONS:
These new results provide strong evidence that a family of structurally similar plant steroids is capable of inducing apoptosis in human RA FLS with different rates and different signalling pathways. This study also confirms the discussed appearance of the downregulation or upregulation of COX-2 in cell apoptosis as a function of cell type.

Tigogenin Description

Source:	The herbs of Agave sisalana Perrine
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.

Cell Research:

Mol Cell Endocrinol. 2007 May 30;270(1-2):17-22.

Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells.[Pubmed: 17363141]

We investigated the effect of Tigogenin on adipocytic and osteoblastic differentiation in mouse bone marrow stromal cells (BMSCs).
METHODS AND RESULTS:
Tigogenin enhanced the proliferation of BMSCs significantly. Tigogenin treatment reduced the adipogenic induction of lipid accumulation, visfatin secretion, and the expressions of peroxisome proliferation-activated receptor (PPAR)gamma2 and adipocyte fatty acid-binding protein (ap)2. Moreover, Tigogenin had no effect on the mitotic clonal expansion. On the other hand, Tigogenin significantly elevated alkaline phosphatase (ALP) activity and the expressions of Cbfa1, collagen type I (COL I) and osteocalcin (OCN), as well as the content of matrix calcium in BMSCs. Further, SB-203580 antagonized the Tigogenin-promoted osteogenesis.
CONCLUSIONS:
These observations suggested that Tigogenin may modulate differentiation of BMSCs to cause a lineage shift away from the adipocytes and toward the osteoblasts, which is at least mediated by inhibition of PPARgamma and via p38 MAPK pathway, and is a potential drug preventing the development of osteoporosis and the related disorders.

Structure Identification:

Carbohydr Res. 2014 Jan 13;383:21-6.

Efficient one-pot synthesis of tigogenin saponins and their antitumor activities.[Pubmed: 24239606]

CONCLUSIONS:
An efficient synthesis of naturally occurring Tigogenin triglycoside 1a and its three derivatives 1b-d bearing different carbohydrate moieties, as well as their antitumor activities, is described. Partially protected thiogalactosides bearing unprotected 2,4-OH or 4-OH groups were used to facilitate regioselective reactions for one-pot sequential multi-step glycosylation, which has significantly simplified the target molecule synthesis.
CONCLUSIONS:
The synthetic saponins 1a-d exhibited much higher anti-tumor activities than the positive control cisplatin against the human epithelial cervical cancer cell (HeLa) as evaluated by CCK-8 assay.

Product Name	Tigogenin
Price:	$80 / 20mg
CAS No.:	77-60-1
Catalog No.:	CFN98501
Molecular Formula:	C₂₇H₄₄O₃
Molecular Weight:	416.64 g/mol
Purity:	>=98%
Type of Compound:	Steroids
Physical Desc.:	Powder
Source:	The herbs of Agave sisalana Perrine
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	Anticancer Compound Library Anti-osteoporosis Compound Library Steroids Compound Library PPAR Inhibitor Library PGE Inhibitor Library p38MAPK Inhibitor Library COX Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.4002 mL	12.0008 mL	24.0015 mL	48.0031 mL	60.0038 mL
5 mM	0.48 mL	2.4002 mL	4.8003 mL	9.6006 mL	12.0008 mL
10 mM	0.24 mL	1.2001 mL	2.4002 mL	4.8003 mL	6.0004 mL
50 mM	0.048 mL	0.24 mL	0.48 mL	0.9601 mL	1.2001 mL
100 mM	0.024 mL	0.12 mL	0.24 mL	0.48 mL	0.6 mL

CFN99779	Sarsasapogenin	126-19-2	416.64	C₂₇H₄₄O₃
CFN98501	Tigogenin	77-60-1	416.64	C₂₇H₄₄O₃
CFN91164	Tigogenin acetate	2530-07-6	458.7	C₂₉H₄₆O₄
CFN99515	Diosgenin	512-04-9	414.63	C₂₇H₄₂O₃
CFN90706	Pennogenin	507-89-1	430.62	C₂₇H₄₂O₄
CFN98586	Hecogenin	467-55-0	430.62	C₂₇H₄₂O₄
CFN91702	(25R)-Spirost-4-ene-3,12-dione	6875-60-1	426.6	C₂₇H₃₈O₄
CFN93779	Gitogenin	511-96-6	432.6	C₂₇H₄₄O₄
CFN91558	Chlorogenin	562-34-5	432.6	C₂₇H₄₄O₄