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Timosaponin BII

CAS# 136656-07-0

Timosaponin BII

2D Structure

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Timosaponin BII

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Chemical Properties of Timosaponin BII

Cas No. 136656-07-0 SDF Download SDF
PubChem ID 44575945 Appearance White powder
Formula C45H76O19 M.Wt 921.1
Type of Compound Steroids Storage Desiccate at -20°C
Synonyms Prototimosaponin A III
Solubility Soluble in pyridine; sparingly soluble in water
Chemical Name (2R,3R,4S,5S,6R)-2-[(2S)-4-[(1R,2S,4S,7S,8R,9S,12S,13S,16S,18R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-hydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES CC1C2C(CC3C2(CCC4C3CCC5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C)OC1(CCC(C)COC8C(C(C(C(O8)CO)O)O)O)O
Standard InChIKey SORUXVRKWOHYEO-FRUGGTEYSA-N
Standard InChI InChI=1S/C45H76O19/c1-19(18-58-40-37(55)34(52)31(49)27(15-46)60-40)7-12-45(57)20(2)30-26(64-45)14-25-23-6-5-21-13-22(8-10-43(21,3)24(23)9-11-44(25,30)4)59-42-39(36(54)33(51)29(17-48)62-42)63-41-38(56)35(53)32(50)28(16-47)61-41/h19-42,46-57H,5-18H2,1-4H3/t19-,20-,21+,22-,23+,24-,25-,26-,27+,28+,29+,30-,31+,32+,33-,34-,35-,36-,37+,38+,39+,40+,41-,42+,43-,44-,45?/m0/s1
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 Timosaponin BII

The rhizomes of Anemarrhena asphodeloides Bunge

Biological Activity of Timosaponin BII

DescriptionTimosaponin BII has anti-diabetes, antioxidant, anti-inflammatory, and anti-dementia activities, it can significantly reduce the neurotoxicity induced by beta amyloid peptide 25-35 in primary neurons, the mechanism of which may be related with resisting oxidative damage and regulating the cholinergic system.Timosaponin BII can improve the neurological symptoms of cerebral ischemic rat, reduce infarct size, relieve brain water edema, improve hemorheology, reduce inflammatory injury of cerebral ischemia; it could be used in the preparation of a medicament or product for the prevention and treatment of stroke.
TargetsBeta Amyloid | BACE | SOD | AChE
In vitro

Protective effects of timosaponin BII on primary neurons against beta amyloid peptide 25-35.[Reference: WebLink]

Chinese Pharmacological Bulletin, 2009, 25(2):244-7.

To study the protective effects of Timosaponin BII on primary neurons against beta amyloid peptide 25-35 induced toxicity.
METHODS AND RESULTS:
Immunofluorescence was used to identify primary neurons. MTT(tetrazolium salt) assay was used to measure neurons metabolic state. Spectrophotometric method was used to measure the release of LDH (lactate dehydrogenase), the activity of SOD (superoxide dismutase), the activity of AChE (acetylcholine) and the production of MDA(malonaldehyde) in the culture medium.Treatment with beta amyloid peptide 25-35 (20 μmol · L-1) for 24 h caused a significant damage in primary neurons. Timosaponin BII 10-4 10-5 mol · L-1 markedly improved neurons metabolic activity, decresed the release of LDH and the production of MDA, markedly increased the activity of SOD and decresed the activity of AChE.
CONCLUSIONS:
Timosaponin BII could significantly reduce the neurotoxicity induced by beta amyloid peptide 25-35 in primary neurons. The mechanism of which may be related with resisting oxidative damage and regulating the cholinergic system.

In vivo

Anti-diabetic effects of TongGuanWan, a Chinese traditional herbal formula, in C57BL/KsJ-db/db mice.[Pubmed: 22002851]

Planta Med. 2012 Jan;78(1):18-23. doi: 10.1055/s-0031-1280268.

In the present study, the anti-diabetic effects of a traditional Chinese medicinal formula extract, TongGuanWan, were investigated in type 2 diabetic animals.
METHODS AND RESULTS:
It was orally administered to C57BL/KsJ-db/db mice once a day for 4 weeks at the doses of 62, 125, and 250 mg/kg body weight. TongGuanWan significantly lowered the blood glucose and glycosylated haemoglobin levels as well as improved the glucose tolerance in db/db mice. The serum triglyceride levels in the db/db mice were significantly decreased, whereas the high-density lipoprotein cholesterol levels were significantly increased, after treatment with this herbal formula. TongGuanWan also markedly decreased the animals' body weights compared to those of the control db/db group but did not alter food intake. The effects of TongGuanWan were compared to those of the drug rosiglitazone. In addition, five main constituents of TongGuanWan, mangiferin, berberine, cinnamic aldehyde, Timosaponin BII, and timosaponin AIII, were quantified using high performance liquid chromatography coupled with a diode array and an evaporative light scattering detector (HPLC-DAD-ELSD).
CONCLUSIONS:
These results suggest that TongGuanWan may be useful for the treatment of type 2 diabetes.

Use of Timosaponin BII in the Preparation Of A Medicament or Product for the Prevention and Treatment of Stroke[Reference: WebLink]

US20090075912[P]. 2009.

The invention disclosed the use of Timosaponin BII in the preparation of a medicament or product for the prevention and treatment of stroke. The experiments prove that Timosaponin BII can improve the neurological symptoms of cerebral ischemic rat, reduce infarct size, relieve brain water edema, improve hemorheology, reduce inflammatory injury of cerebral ischemia.

Protocol of Timosaponin BII

Kinase Assay

Timosaponin-BII inhibits the up-regulation of BACE1 induced by ferric chloride in rat retina.[Pubmed: 23082924]

BMC Complement Altern Med. 2012 Oct 22;12:189.

Our previous studies indicated that oxidative stress up-regulated the expression of β-amyloid precursor protein cleavage enzyme-1 (BACE1) in rat retina. Pharmacological reports have shown Timosaponin BII, a purified extract originating from Chinese medical herb Rhizoma Anemarrhenae, is characterized as an antioxidant.
METHODS AND RESULTS:
Our present study aimed to determine whether Timosaponin BII affected the expression of BACE1, β-amyloid precursor protein cleavage production of Aβ1-40 and β-C-terminal fragment (β-CTF) in rat retina, which were pre-treated with the oxidizing agent (solution of FeCl₃). Few distinctions of BACE1 distribution were observed among all groups (normal control group, model group, Timosaponin BII treated and vehicle control groups). Rat retinas in model group and vehicle control group manifested an apparent up-regulation of BACE1 expression. Meanwhile, the level of malonaldehyde (MDA), Aβ1-40 and β-CTF were increased. However, when comparing with the vehicle control group, the retinas in Timosaponin BII treated group showed significantly less BACE1 (p<0.05) and accumulated less Aβ1-40 or β-CTF (p<0.05). It also showed significantly decreased level of MDA (p<0.05) and prolonged partial thromboplastin time (p<0.05).
CONCLUSIONS:
Our data suggested that Timosaponin BII remarkably inhibited the up-regulation of BACE1 and reduced the over-production of β-CTF and Aβ in rat retina, which was induced by FeCl₃. The mechanism of Timosaponin BII on BACE1 expression may be related to its antioxidant property.

Structure Identification
J Asian Nat Prod Res. 2010 Nov;12(11):955-61.

Hydrolysis of timosaponin BII by the crude enzyme from Aspergillus niger AS 3.0739.[Pubmed: 21061217 ]

Timosaponin BII (1), a steroidal saponin showing potential anti-dementia activity, was regioselectively hydrolyzed into its deglycosyl derivatives by the crude enzyme from Aspergillus niger AS 3.0739. Three biotransformation products, Timosaponin BII-a (2), Timosaponin BII-b (3), and Timosaponin BII-c (4), were purified and their structures were elucidated on the basis of 1D NMR, 2D NMR, FAB-MS, and HR-ESI-MS spectral data. Compounds 2 and 3 are new compounds.

Timosaponin BII Dilution Calculator

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Preparing Stock Solutions of Timosaponin BII

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.0857 mL 5.4283 mL 10.8566 mL 21.7132 mL 27.1415 mL
5 mM 0.2171 mL 1.0857 mL 2.1713 mL 4.3426 mL 5.4283 mL
10 mM 0.1086 mL 0.5428 mL 1.0857 mL 2.1713 mL 2.7141 mL
50 mM 0.0217 mL 0.1086 mL 0.2171 mL 0.4343 mL 0.5428 mL
100 mM 0.0109 mL 0.0543 mL 0.1086 mL 0.2171 mL 0.2714 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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References on Timosaponin BII

Anti-diabetic effects of TongGuanWan, a Chinese traditional herbal formula, in C57BL/KsJ-db/db mice.[Pubmed:22002851]

Planta Med. 2012 Jan;78(1):18-23.

In the present study, the anti-diabetic effects of a traditional Chinese medicinal formula extract, TongGuanWan, were investigated in type 2 diabetic animals. It was orally administered to C57BL/KsJ-db/db mice once a day for 4 weeks at the doses of 62, 125, and 250 mg/kg body weight. TongGuanWan significantly lowered the blood glucose and glycosylated haemoglobin levels as well as improved the glucose tolerance in db/db mice. The serum triglyceride levels in the db/db mice were significantly decreased, whereas the high-density lipoprotein cholesterol levels were significantly increased, after treatment with this herbal formula. TongGuanWan also markedly decreased the animals' body weights compared to those of the control db/db group but did not alter food intake. The effects of TongGuanWan were compared to those of the drug rosiglitazone. In addition, five main constituents of TongGuanWan, mangiferin, berberine, cinnamic aldehyde, Timosaponin BII, and timosaponin AIII, were quantified using high performance liquid chromatography coupled with a diode array and an evaporative light scattering detector (HPLC-DAD-ELSD). These results suggest that TongGuanWan may be useful for the treatment of type 2 diabetes.

Timosaponin-BII inhibits the up-regulation of BACE1 induced by ferric chloride in rat retina.[Pubmed:23082924]

BMC Complement Altern Med. 2012 Oct 22;12:189.

UNLABELLED: BACKGROUND: Our previous studies indicated that oxidative stress up-regulated the expression of beta-amyloid precursor protein cleavage enzyme-1 (BACE1) in rat retina. Pharmacological reports have shown Timosaponin-BII, a purified extract originating from Chinese medical herb Rhizoma Anemarrhenae, is characterized as an antioxidant. Our present study aimed to determine whether Timosaponin-BII affected the expression of BACE1, beta-amyloid precursor protein cleavage production of Abeta1-40 and beta-C-terminal fragment (beta-CTF) in rat retina, which were pre-treated with the oxidizing agent (solution of FeCl(3)). RESULTS: Few distinctions of BACE1 distribution were observed among all groups (normal control group, model group, Timosaponin-BII treated and vehicle control groups). Rat retinas in model group and vehicle control group manifested an apparent up-regulation of BACE1 expression. Meanwhile, the level of malonaldehyde (MDA), Abeta1-40 and beta-CTF were increased. However, when comparing with the vehicle control group, the retinas in Timosaponin-BII treated group showed significantly less BACE1 (p<0.05) and accumulated less Abeta1-40 or beta-CTF (p<0.05). It also showed significantly decreased level of MDA (p<0.05) and prolonged partial thromboplastin time (p<0.05). CONCLUSION: Our data suggested that Timosaponin-BII remarkably inhibited the up-regulation of BACE1 and reduced the over-production of beta-CTF and Abeta in rat retina, which was induced by FeCl(3). The mechanism of Timosaponin-BII on BACE1 expression may be related to its antioxidant property.

Hydrolysis of timosaponin BII by the crude enzyme from Aspergillus niger AS 3.0739.[Pubmed:21061217]

J Asian Nat Prod Res. 2010 Nov;12(11):955-61.

Timosaponin BII (1), a steroidal saponin showing potential anti-dementia activity, was regioselectively hydrolyzed into its deglycosyl derivatives by the crude enzyme from Aspergillus niger AS 3.0739. Three biotransformation products, Timosaponin BII-a (2), Timosaponin BII-b (3), and Timosaponin BII-c (4), were purified and their structures were elucidated on the basis of 1D NMR, 2D NMR, FAB-MS, and HR-ESI-MS spectral data. Compounds 2 and 3 are new compounds.

Description

Timosaponin BII is an antioxidant and an anti-inflammatory agent.

Keywords:

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