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Tigogenin

$355

  • Brand : BIOFRON

  • Catalogue Number : BF-T1004

  • Specification : 98%

  • CAS number : 77-60-1

  • Formula : C27H44O3

  • Molecular Weight : 416.64

  • PUBCHEM ID : 99516

  • Volume : 20mg

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Catalogue Number

BF-T1004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

416.64

Appearance

White crystal

Botanical Source

Solanum lyratum

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)OC1

Synonyms

5α-Spirostan-3β-ol, (25R)-/TIGOGENIN/Tsosarsasaprgein/(3β,5α,25R)-Spirostan-3-ol/Ticogenin/(25R)-5a-Spirostan-3b-ol/(25R)-5α-Spirostan-3β-ol/Sisalagenin/Trigonegenin B/Spirostan-3-ol, (3β,5α,25R)-

IUPAC Name

(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol

Applications

Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells. PUMID/DOI:17363141 Mol Cell Endocrinol. 2007 May 30;270(1-2):17-22. We investigated the effect of Tigogenin on adipocytic and osteoblastic differentiation in mouse bone marrow stromal cells (BMSCs). 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. 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. 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. PUMID/DOI:17786275 Int J Mol Med. 2007 Oct;20(4):451-60. We conducted our study to assess the antiproliferative and proapoptotic potential of hecogenin and Tigogenin, two saponins which are structurally similar to diosgenin. 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 inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells. PUMID/DOI:17363141 Mol Cell Endocrinol. 2007 May 30;270(1-2):17-22. We investigated the effect of Tigogenin on adipocytic and osteoblastic differentiation in mouse bone marrow stromal cells (BMSCs). 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. 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. 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. PUMID/DOI:17786275 Int J Mol Med. 2007 Oct;20(4):451-60. We conducted our study to assess the antiproliferative and proapoptotic potential of hecogenin and Tigogenin, two saponins which are structurally similar to diosgenin. 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.

Density

1.1±0.1 g/cm3

Solubility

Methanol; Acetontrile

Flash Point

266.2±21.8 °C

Boiling Point

516.6±20.0 °C at 760 mmHg

Melting Point

202-204ºC

InChl

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-/m1/s1

InChl Key

GMBQZIIUCVWOCD-MFRNJXNGSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:77-60-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

17363141

Abstract

We investigated the effect of tigogenin on adipocytic and osteoblastic differentiation in mouse bone marrow stromal cells (BMSCs). 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, tigogeninsignificantly 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. 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.

Title

Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells.

Author

Zhou H1, Yang X, Wang N, Zhang Y, Cai G.

Publish date

2007 May 30