Loureirin B

CAS# 119425-90-0

Loureirin B

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Chemical structure

Loureirin B

3D structure

Chemical Properties of Loureirin B

Cas No. 119425-90-0 SDF Download SDF
PubChem ID 189670 Appearance White powder
Formula C18H20O5 M.Wt 316.35
Type of Compound Chalcones Storage Desiccate at -20°C
Synonyms 4'-Hydroxy 2,4,6-trimethoxydihydrochalcone
Solubility DMSO : ≥ 150 mg/mL (474.16 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one
SMILES COC1=CC(=C(C(=C1)OC)CCC(=O)C2=CC=C(C=C2)O)OC
Standard InChIKey ZPFRAPVRYLGYEC-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H20O5/c1-21-14-10-17(22-2)15(18(11-14)23-3)8-9-16(20)12-4-6-13(19)7-5-12/h4-7,10-11,19H,8-9H2,1-3H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Loureirin B

The herbs of Dracaena cochinchinensis

Biological Activity of Loureirin B

DescriptionLoureirin B, a flavonoid extracted from Dracaena cochinchinensis, is an inhibitor of plasminogen activator inhibitor-1 (PAI-1), with an IC50 of 26.10 μM; Loureirin B also inhibits KATP, the phosphorylation of ERK and JNK, and has anti-diabetic activity.Loureirin B inhibits fibroblast proliferation and extracellular matrix deposition in hypertrophic scar via TGF-β/Smad pathway, loureirin B can suppress tetrodotoxin-sensitive (TTX-S) voltage-gated sodium currents in a dose-dependent way.
TargetsTGF-β/Smad | MMP(e.g.TIMP) | GLUT | Calcium Channel | PAI-1 | ERK | JNK
In vitro

Loureirin B inhibits fibroblast proliferation and extracellular matrix deposition in hypertrophic scar via TGF-β/Smad pathway.[Pubmed: 25683490]

Exp Dermatol. 2015 May;24(5):355-60.

The ethanolic extract of Resina Draconis (RDEE) has been reported beneficial to normal wound healing yielding more regularly arranged collagen fibres. Loureirin B, a major component in RDEE, has been supposed to be effective on the prevention and treatment of pathological scars.
METHODS AND RESULTS:
To investigate the therapeutic effects of Loureirin B on hypertrophic scar (HS), fibroblasts from human HS and normal skin (NS) were isolated. Results showed that Loureirin B dose-dependently downregulated both mRNA and protein levels of type I collagen (ColI), type III collagen (ColIII) and α-smooth muscle actin (α-SMA) in HS fibroblasts. Loureirin B also suppressed fibroblast proliferative activity and redistributed cell cycle, but did not affect cell apoptosis. In vivo rabbit ear scar model, Loureirin B significantly improved the arrangement and deposition of collagen fibres, decreased protein levels of ColI, ColIII and α-SMA and suppressed myofibroblast differentiation and scar proliferative activity. In NS fibroblasts, Loureirin B effectively inhibited TGF-β1-induced upregulation of ColI, ColIII and α-SMA levels, myofibroblast differentiation and the activation of Smad2 and Smad3. Loureirin B also affected mRNA levels of major MMPs and TIMPs in TGF-β1-stimulated fibroblasts.
CONCLUSIONS:
Taken together, this study demonstrates that Loureirin B could downregulate the expression of fibrosis-related molecules by regulating MMPs and TIMPs levels, inhibit scar fibroblast proliferation and suppress TGF-β1-induced fibrosis, during which TGF-β1/Smad2/3 pathway is likely involved. These findings suggest that Loureirin B is a potential therapeutic compound for HS treatment.

Effects of dragon's blood resin and its component loureirin B on tetrodotoxin-sensitive voltage-gated sodium currents in rat dorsal root ganglion neurons.[Pubmed: 15493475]

Sci China C Life Sci. 2004 Aug;47(4):340-8.

Using whole-cell patch clamp technique on the membrane of freshly isolated dorsal root ganglion (DRG) neurons, the effects of dragon's blood resin and its important component Loureirin B on tetrodotoxin-sensitive (TTX-S) voltage-gated sodium currents were observed.
METHODS AND RESULTS:
The results show that both blood resin and Loureirin B could suppress TTX-S voltage-gated sodium currents in a dose-dependent way. The peak current amplitudes and the steady-state activation and inactivation curves are also made to shift by 0.05% blood resin and 0.2 mmol/L Loureirin B.
CONCLUSIONS:
These results demonstrate that the effects of blood resin on TTX-S sodium current may contribute to Loureirin B in blood resin. Perhaps the analgesic effect of blood resin is caused partly by Loureirin B directly interfering with the nociceptive transmission of primary sensory neurons.

Protocol of Loureirin B

Kinase Assay

Loureirin B, an essential component of Sanguis Draxonis, inhibits Kv1.3 channel and suppresses cytokine release from Jurkat T cells.[Pubmed: 25937895]

Cell Biosci. 2014 Dec 12;4:78.

Sanguis draxonis (SD), also known as "Dragon's Blood", is a traditional herb medicine that has been used to treat a variety of complications with unknown mechanisms. Recent studies show that SD displays immunosuppressive activities and improves symptoms of type I diabetes in animal models. However, the mechanisms underlying SD's immunosuppressive actions are not completely understood. The voltage-gated Kv1.3 channel plays a critical role in the pathogenesis of autoimmune diseases by regulating the functions of both T cells and B cells.
METHODS AND RESULTS:
Here we investigated the effect of SD and one of its active components Loureirin B (LrB) on Kv1.3. Both SD and LrB inhibited Kv1.3-mediated currents, produced a membrane depolarization, and reduced Ca(2+) influx in Jurkat T cells. In addition, application of LrB inhibited phytohemagglutinin (PHA)-induced IL-2 release from activated Jurkat T cells. Furthermore, point mutations in the selective filter region significantly reduced the inhibitory effect of LrB on Kv1.3.
CONCLUSIONS:
The results of these experiments provide evidence that LrB is a channel blocker of Kv1.3 by interacting with amino acid residues in its selective filter region. Direct inhibition of Kv1.3 in T cells by SD and LrB might be the cellular and molecular basis of SD-mediated immunosuppression.

Cell Research

Protective Effects of Loureirin B on Dysfunction of Pacreatic Islet β Cell Induced by Palmitate.[Reference: WebLink]

Effect of loureirin B on proliferation and extracellular matrix secretion of rat hepatic stellate cells in vitro.[Reference: WebLink]

Shandong Medical Journal, 2012, 52(13):7-9.

To investigate the effects of Loureirin B on proliferation and extracellular matrix secretion of rat hepatic stellate cells in vitro.
METHODS AND RESULTS:
HSC-T6 was cultured in 96-well plates for 24 hours.Then they were incubated with different concentration of Loureirin B for 48 hours.MTT was used for assaying proliferation of HSC.Inhibition rate was calculated.Hyaluronic acid,laminin and collagen type Ⅳ were measured by radioimmunoassay. Addition of Loureirin B into culture medium significantly inhibited HSC proliferation,and the higher concentration of the Loureirin B were,the stronger inhibition rate of the HSC had.It also inhibited hyaluronic acid,laminin and collagen type Ⅳ secretion in different degree.
CONCLUSIONS:
Loureirin B significantly inhibits HSC proliferation and extracellular matrix secretion.

Chinese Journal of Experimental Traditional Medical, 2013, 19(23):254-7.

To study the protective effects and mechanism of Loureirin B on the dysfunctiion of pancreatic islet β cell induced by palmitic acid.
METHODS AND RESULTS:
NIT-1 cells were cultured in medium added palmitic acid,and treated with Loureirin B.Cell apoptosis ratio and content of reactive oxygen species(ROS) were detected by flow cytometry,the expressions of glucose tnansport receptor-2(GLUT2) was examined by semiquantitate reverse transcript PCR.Compared with palmitic acid treated group,survival rate of NIT-1 with Loureirin B(20,10 μmol·L- 1) was increased significantly(P0.05).Loureirin B(20,10,5 μmol·L- 1)scavenged excessive ROS and lowered its concentration significantly(P0.05).Loureirin B(20 μmol·L- 1) was increased the expressions of GLUT2(P0.05),and Loureirin B(20,10,5 μmol·L- 1) was effective on reducing apoptosis ratio induced by palmitic acid(P0.05).
CONCLUSIONS:
Loureirin B can increase the survival rate of NIT-1 cultured in the medium added palmitic acid,scavenge excessive ROS induced by palmitic acid,decrease the cell apoptosis ratio and elevate the expressions of GLUT2.This indicates Loureirin B may accomplish its islet cell protection effects by reducing ROS within cell and reversing glucose metabolism disorder rand other effects induced by forkhead box protein-1(FOXO1) activated by oxidative stress.

Loureirin B Dilution Calculator

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Preparing Stock Solutions of Loureirin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1611 mL 15.8053 mL 31.6106 mL 63.2211 mL 79.0264 mL
5 mM 0.6322 mL 3.1611 mL 6.3221 mL 12.6442 mL 15.8053 mL
10 mM 0.3161 mL 1.5805 mL 3.1611 mL 6.3221 mL 7.9026 mL
50 mM 0.0632 mL 0.3161 mL 0.6322 mL 1.2644 mL 1.5805 mL
100 mM 0.0316 mL 0.1581 mL 0.3161 mL 0.6322 mL 0.7903 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Loureirin B

Loureirin B, a flavonoid extracted from Dracaena cochinchinensis, is an inhibitor of plasminogen activator inhibitor-1 (PAI-1), with an IC50 of 26.10 μM; Loureirin B also inhibits KATP, the phosphorylation of ERK and JNK, and has anti-diabetic activity.

In Vitro:Loureirin B enhances the relative mRNA level of Pdx-1 and MafA. Loureirin B (1, 0.1, and 0.01 µM) increases insulin secretion in Ins-1 cells. Loureirin B (0.01 µM) almost causes no toxicity on cells. Loureirin B improves the level of expressions of MafA and Pdx-1 and ATP level. Loureirin B inhibits the KATP current but increases the [Ca2+]i level in Ins-1 cells[1]. Loureirin B inhibits the expression of Col1 and FN, as well as the TGF-β1-mediated up regulation of p-JNK. Loureirin B also inhibits the up regulation of p-ERK that is induced by TGF-β1. Moreover, Loureirin B inhibits the contraction of TGF-β1-stimulated fibroblasts through the down regulation of p-ERK and p-JNK. However, Loureirin B does not suppress the up regulation of p-p38 that is induced by TGF-β1[2]. Loureirin B downregulates both mRNA and protein levels of type I collagen, type III collagen and α-smooth muscle actin in a dose dependent manner in HS fibroblasts. Loureirin B also suppresses fibroblast proliferative activity and redistributes cell cycle, but does not affect cell apoptosis[3].

In Vivo:Loureirin B significantly improves the arrangement and deposition of collagen fibres, decreases protein levels of ColI, ColIII and α-SMA and suppresses myofibroblast differentiation and scar proliferative activity, in a rabbit ear scar model. Loureirin B effectively inhibits TGF-β1-induced upregulation of ColI, ColIII and α-SMA levels, myofibroblast differentiation and the activation of Smad2 and Smad3, in NS fibroblasts[3].

References:
[1]. Sha Y, et al. Loureirin B promotes insulin secretion through inhibition of KATP channel and influx of intracellular calcium. J Cell Biochem. 2017 Aug 17. [2]. He T, et al. Loureirin B Inhibits Hypertrophic Scar Formation via Inhibition of the TGF-β1-ERK/JNK Pathway. Cell Physiol Biochem. 2015;37(2):666-76. [3]. Bai X, et al. Loureirin B inhibits fibroblast proliferation and extracellular matrix deposition in hypertrophic scar via TGF-β/Smad pathway. Exp Dermatol. 2015 May;24(5):355-60. [4]. Yu Jiang, et al. Bioactivity-Guided Fractionation of the Traditional Chinese Medicine Resina Draconis Reveals Loureirin B as a PAI-1 Inhibitor. Evidence-Based Complementary and Alternative Medicine

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References on Loureirin B

Loureirin B, an essential component of Sanguis Draxonis, inhibits Kv1.3 channel and suppresses cytokine release from Jurkat T cells.[Pubmed:25937895]

Cell Biosci. 2014 Dec 12;4:78.

Sanguis draxonis (SD), also known as "Dragon's Blood", is a traditional herb medicine that has been used to treat a variety of complications with unknown mechanisms. Recent studies show that SD displays immunosuppressive activities and improves symptoms of type I diabetes in animal models. However, the mechanisms underlying SD's immunosuppressive actions are not completely understood. The voltage-gated Kv1.3 channel plays a critical role in the pathogenesis of autoimmune diseases by regulating the functions of both T cells and B cells. Here we investigated the effect of SD and one of its active components Loureirin B (LrB) on Kv1.3. Both SD and LrB inhibited Kv1.3-mediated currents, produced a membrane depolarization, and reduced Ca(2+) influx in Jurkat T cells. In addition, application of LrB inhibited phytohemagglutinin (PHA)-induced IL-2 release from activated Jurkat T cells. Furthermore, point mutations in the selective filter region significantly reduced the inhibitory effect of LrB on Kv1.3. The results of these experiments provide evidence that LrB is a channel blocker of Kv1.3 by interacting with amino acid residues in its selective filter region. Direct inhibition of Kv1.3 in T cells by SD and LrB might be the cellular and molecular basis of SD-mediated immunosuppression.

Effects of dragon's blood resin and its component loureirin B on tetrodotoxin-sensitive voltage-gated sodium currents in rat dorsal root ganglion neurons.[Pubmed:15493475]

Sci China C Life Sci. 2004 Aug;47(4):340-8.

Using whole-cell patch clamp technique on the membrane of freshly isolated dorsal root ganglion (DRG) neurons, the effects of dragon's blood resin and its important component Loureirin B on tetrodotoxin-sensitive (TTX-S) voltage-gated sodium currents were observed. The results show that both blood resin and Loureirin B could suppress TTX-S voltage-gated sodium currents in a dose-dependent way. The peak current amplitudes and the steady-state activation and inactivation curves are also made to shift by 0.05% blood resin and 0.2 mmol/L Loureirin B. These results demonstrate that the effects of blood resin on TTX-S sodium current may contribute to Loureirin B in blood resin. Perhaps the analgesic effect of blood resin is caused partly by Loureirin B directly interfering with the nociceptive transmission of primary sensory neurons.

Loureirin B inhibits fibroblast proliferation and extracellular matrix deposition in hypertrophic scar via TGF-beta/Smad pathway.[Pubmed:25683490]

Exp Dermatol. 2015 May;24(5):355-60.

The ethanolic extract of Resina Draconis (RDEE) has been reported beneficial to normal wound healing yielding more regularly arranged collagen fibres. Loureirin B, a major component in RDEE, has been supposed to be effective on the prevention and treatment of pathological scars. To investigate the therapeutic effects of Loureirin B on hypertrophic scar (HS), fibroblasts from human HS and normal skin (NS) were isolated. Results showed that Loureirin B dose-dependently downregulated both mRNA and protein levels of type I collagen (ColI), type III collagen (ColIII) and alpha-smooth muscle actin (alpha-SMA) in HS fibroblasts. Loureirin B also suppressed fibroblast proliferative activity and redistributed cell cycle, but did not affect cell apoptosis. In vivo rabbit ear scar model, Loureirin B significantly improved the arrangement and deposition of collagen fibres, decreased protein levels of ColI, ColIII and alpha-SMA and suppressed myofibroblast differentiation and scar proliferative activity. In NS fibroblasts, Loureirin B effectively inhibited TGF-beta1-induced upregulation of ColI, ColIII and alpha-SMA levels, myofibroblast differentiation and the activation of Smad2 and Smad3. Loureirin B also affected mRNA levels of major MMPs and TIMPs in TGF-beta1-stimulated fibroblasts. Taken together, this study demonstrates that Loureirin B could downregulate the expression of fibrosis-related molecules by regulating MMPs and TIMPs levels, inhibit scar fibroblast proliferation and suppress TGF-beta1-induced fibrosis, during which TGF-beta1/Smad2/3 pathway is likely involved. These findings suggest that Loureirin B is a potential therapeutic compound for HS treatment.

Description

Loureirin B, a flavonoid extracted from Dracaena cochinchinensis, is an inhibitor of plasminogen activator inhibitor-1 (PAI-1), with an IC50 of 26.10 μM; Loureirin B also inhibits KATP, the phosphorylation of ERK and JNK, and has anti-diabetic activity.

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