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Tiliroside

$178

  • Brand : BIOFRON

  • Catalogue Number : BF-T3017

  • Specification : 99%

  • CAS number : 20316-62-5

  • Formula : C30H26O13

  • Molecular Weight : 594.52

  • PUBCHEM ID : 5320686

  • Volume : 25mg

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Catalogue Number

BF-T3017

Analysis Method

HPLC,NMR,MS

Specification

99%

Storage

2-8°C

Molecular Weight

594.52

Appearance

White crystalline powder

Botanical Source

Leonurus japonicus,Ipomoea batatas,Pulsatilla chinensis,Castanea mollissima,Gnaphalium adnatum

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O

Synonyms

5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-b-D-glucopyranoside/[(2R,3S,4S,5R,6S)-6-{[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]methyl-(2E)-3-(4-hydroxyphenyl)acrylat/Kaempferol-3-Glucoside-6''-p-coumaroyl/tiliroside/[(2R,3S,4S,5R,6S)-6-{[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]methyl (2E)-3-(4-hydroxyphenyl)acrylate/4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-β-D-glucopyranosyl]oxy]-/(2E)-3-(4-Hydroxyphenyl)acrylate de [(2R,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]methyle/trans-tiliroside/6-O-[(2E)-3-(4-Hydroxyphenyl)-2-propenan-1-oyl]-β-D-glucopyranoside de 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yle/5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-β-D-glucopyranoside/6'-O-trans-p-CouMaroylastragalin/5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside/4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-β-D-glucopyranosyl]oxy]-/5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl-6-O-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-β-D-glucopyranoside

IUPAC Name

[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Density

1.7±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

311.9±27.8 °C

Boiling Point

943.9±65.0 °C at 760 mmHg

Melting Point

257-260ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:20316-62-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30815860

Abstract

Osteoporosis is a class of metabolic bone disease caused by complexed ramifications. Overactivation of osteoclasts due to a sudden decreased estrogen level plays a pivotal role for postmenopausal women suffering from osteoporosis. Therefore, inhibiting osteoclast formation and function has become a major direction for the treatment of osteoporosis. Tiliroside (Tle) is a salutary dietary glycosidic flavonoid extracted from Oriental Paperbush flower, which has been reported to have an anti-inflammation effect. However, whether Tle affects the osteoclastogenesis and bone resorption remains unknown. Herein, we demonstrate that Tle prevents bone loss in ovariectomy in mice and inhibits osteoclast differentiation and bone resorption stimulated by receptor activator of nuclear factor-κB ligand (RANKL) in vitro. Molecular mechanism studies reveal that Tle reduces RANKL-induced activation of mitogen-activated protein kinase and T-cell nuclear factor 1 pathways, and osteoclastogenesis-related marker gene expression, including cathepsin K (Ctsk), matrix metalloproteinase 9, tartrate-resistant acid phosphatase (Acp5), and Atp6v0d2. Our research indicates that Tle suppresses osteoclastogenesis and bone loss by downregulating the RANKL-mediated signaling protein activation and expression. In addition, Tle inhibits intracellular reactive oxygen species generation which is related to the formation of osteoclasts. Therefore, Tle might serve as a potential drug for osteolytic disease such as osteoporosis.

KEYWORDS

MAPK; osteoclast differentiation; osteoporosis; tiliroside.

Title

Tiliroside Is a New Potential Therapeutic Drug for Osteoporosis in Mice

Author

Kai Li 1 2 , Yu Xiao 1 2 , Ziyi Wang 3 , Fangsheng Fu 1 , Siyuan Shao 1 , Fangming Song 1 3 , Jinmin Zhao 1 2 , Xixi Lin 1 , Qian Liu 2 , Jiake Xu 1 3

Publish date

2019 Feb 27

PMID

29508282

Abstract

Hyperactivated microglia plays a key role in regulating neuroinflammatory responses which cause damage to neurons. In recent years, substantial attention has been paid in identifying new strategies to abrogate neuroinflammation. Tiliroside, a natural dietary glycosidic flavonoid, is known to inhibit neuroinflammation. This study was aimed at investigating the molecular mechanisms involved in the inhibition of neuroinflammation and neurotoxicity by tiliroside. The effects of tiliroside on Nrf2 and SIRT1 activities in BV2 microglia and HT22 hippocampal neurons were investigated using immunoblotting and DNA binding assays. The roles of Nrf2 and SIRT1 in the anti-inflammatory activity of tiliroside were further investigated using RNA interference experiments. HT22 neuronal viability was determined by XTT, calcium influx, DNA fragmentation assays. The effect of tiliroside on MAP2 protein expression in HT22 neurons was investigated using western blotting and immunofluorescence. We also studied the impact of tiliroside on DNA fragmentation and ROS generation in APPSwe-transfected 3D neuronal stem cells. Results show that tiliroside increased protein levels of Nrf2, HO-1 and NQO1, indicating an activation of the Nrf2 protective mechanisms in the microglia. Furthermore, transfection of BV2 cells with Nrf2 siRNA resulted in the loss of anti-inflammatory activity by tiliroside. Tiliroside reduced protein levels of acetylated-NF-κB-p65, and increased SIRT1 in LPS/IFNγ-activated BV2 microglia. RNAi experiments revealed that inhibition of neuroinflammation by tiliroside was not affected by silencing SIRT1 gene. Results of neurotoxicity experiments revealed that neuroinflammation-induced toxicity, DNA fragmentation, ROS generation and calcium accumulation in HT22 neurons were significantly reduced by tiliroside treatment. In addition, the compound also protected differentiated human neural progenitor cells by blocking ROS generation and DNA fragmentation. Overall, this study has established that tiliroside protected BV2 microglia from LPS/IFNγ-induced neuroinflammation and HT22 neuronal toxicity by targeting Nrf2 antioxidant mechanisms. The compound also produced inhibition of NF-κB acetylation through activation of SIRT1, as well as increasing SIRT1 activity in mouse hippocampal neurons. Results from this study have further established the mechanisms involved in the anti-neuroinflammatory and neuroprotective activities of tiliroside.

KEYWORDS

MAPK; osteoclast differentiation; osteoporosis; tiliroside.

Title

Activation of Nrf2 Pathway Contributes to Neuroprotection by the Dietary Flavonoid Tiliroside

Author

Ravikanth Velagapudi 1 2 , Abdelmeneim El-Bakoush 3 , Olumayokun A Olajide 4

Publish date

2018 Oct

PMID

30300355

Abstract

The activation of peroxisomeproliferator-activated receptor (PPAR) α can stimulate the expression of ceramide-related enzymes, and a major component of strawberry seed extract (SSE) tiliroside enhances the expression of PPARα. We determined whether SSE and tiliroside may stimulate ceramide synthesis in the stratum corneum (SC) of the human epidermal equivalents (HEEs) culture model. Treatment with SSE at 1.0 and 3.0 μg/mL elicited a significant increase in the total ceramide content in the SC, which was accompanied by a significant increase in almost all ceramide species except for ceramide [EOS] and [AP]. Treatment with tiliroside at 0.3 μg/mL slightly accentuated the total ceramide content in the SC together with a significant increase in the ceramide [NS, NDS] content. Messenger RNA analysis demonstrated that SSE at 1 or 3 μg/mL significantly stimulated the gene expression of serine palmitoyltransferase (SPT) 2, ceramide synthase (CerS) 3, glucosylceramide synthase (GCS), and β-glucocerebrosidase (GBA) but not of SPT1, sphingomyelin synthase (SMS) 1/2 and acid sphingomyelinase (ASM). In contrast, tiliroside elicited significant increases in the gene expression levels of GCS and GBA only at 0.3 and/or 0.1 μg/mL. Western blotting analysis revealed that both SSE and tiliroside enhanced the protein expression levels of GCS and GBA but not of SPT2 at 1 or 3 and 0.1 or 0.3 μg/mL, respectively. These findings suggested that both SSE and tiliroside have a distinct potential to stimulate the level of ceramide [NS, NDS] in the SC by enhancing the expression of GCS and GBA. The higher stimulatory effect with SSE than tiliroside on SC ceramide synthesis correlates with the significant increase observed with SSE but not tiliroside in the gene expression levels of SPT2 and CerS3. Therefore, it is anticipated that SSE is effective in improving skin barrier function and moisture retention in several ceramide-deficit skin conditions, including surfactant-induced roughened skin, xerosis, and atopic dermatitis.

Title

Strawberry Seed Extract and Its Major Component, Tiliroside, Promote Ceramide Synthesis in the Stratum Corneum of Human Epidermal Equivalents

Author

Shogo Takeda 1 , Hiroshi Shimoda 1 , Toru Takarada 1 , Genji Imokawa 2 3

Publish date

2018 Oct 9


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