Alisol A 24-acetate

Details:

Chemical Properties of Alisol A 24-acetate

Cas No.	18674-16-3
PubChem ID	76336194	Appearance	White powder
Formula	C32H52O6	M.Wt	532.75
Type of Compound	Triterpenoids	Storage	Desiccate at -20°C
Synonyms	Alisol-A 24-acetate; Alisol A 24-monoacetate; Alisol A monoacetate
Solubility	DMSO : ≥ 50 mg/mL (93.85 mM) *"≥" means soluble, but saturation unknown.
Chemical Name	[(3R,4S,6R)-2,4-dihydroxy-6-[(5R,8S,9S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] acetate
SMILES	CC(CC(C(C(C)(C)O)OC(=O)C)O)C1=C2CC(C3C4(CCC(=O)C(C4CCC3(C2(CC1)C)C)(C)C)C)O
Standard InChIKey	WXHUQVMHWUQNTG-JSWHPQHOSA-N
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 Alisol A 24-acetate

The tubers of Alisma plantago-aquatica Linn.

Biological Activity of Alisol A 24-acetate

Description	Alisol A 24-acetate has antibacterial activity, it also has anti-complement activity against the classical pathway of the complement system with IC50 values of 130 microM. Alisol A 24-acetate can effectively prevent bone loss in ovariectomized (OVX) mice, and that it can be considered a potential therapeutic for the treatment of postmenopausal osteoporosis.
Targets	Antifection | NFATc1
In vitro	A sensitive liquid chromatography-mass spectrometry method for simultaneous determination of alisol A and alisol A 24-acetate from Alisma orientale (Sam.) Juz. in rat plasma.[Pubmed: 21107819] Anal Bioanal Chem. 2011 Jan;399(3):1363-9. METHODS AND RESULTS: A liquid chromatography-mass spectrometry (LC-MS) method was developed and validated for the simultaneous determination of alisol A and Alisol A 24-acetate from Alisma orientale (Sam.) Juz. in rat plasma using diazepam as an internal standard. A 200-μl plasma sample was extracted by methyl tert-butyl ether and the separation was performed on Kromasil C(18) column (150 × 4.6 mm, 5 μm) with the mobile phase of acetonitrile (containing 0.1% of formic acid)-water (73:27, v/v) at a flow rate of 0.8 ml/min in a run time of 10 min. The two analytes were monitored with positive electrospray ionization by selected ion monitoring mode. The lower limit of quantitation for both alisol A and Alisol A 24-acetate were 10 ng/ml. The calibration curves were linear in the measured range 10-1,000 ng/ml for alisol A and 10-500 ng/ml for Alisol A 24-acetate. The mean extraction recoveries were above 74.7% for alisol A and above 72.4% for Alisol A 24-acetate from biological matrixes. The intra- and inter-day precision for all concentrations of quality controls was lower than 14.1% (RSD %) for each analyte. The accuracy ranged from -12.3% to 9.8% (RE %) for alisol A, and -8.6% to 14.2% (RE %) for Alisol A 24-acetate. CONCLUSIONS: The method was successfully applied to the study on the pharmacokinetics of alisol A and Alisol A 24-acetate in rat plasma. Anti-complementary activity of protostane-type triterpenes from Alismatis rhizoma.[Pubmed: 12877555] Arch Pharm Res. 2003 Jun;26(6):463-5. Four protostane-type triterpenes, alisol B 23-acetate (1a), alisol C 23-acetate (2a), alisol B (3a), and Alisol A 24-acetate (4a), were isolated from the rhizome of Alismatis plantago-aquatice L. var. orientale Samuelson (Alismataceae) and eleven protostane derivatives (compounds 1-11) were obtained by selective modification from alisol B 23-acetate (1a). METHODS AND RESULTS: These compounds were investigated for their anti-complement activity against the classical pathway of the complement system. Alisol B (3a) and Alisol A 24-acetate (4a) exhibited anti-complement activity with IC50 values of 150 and 130 microM. Among the synthetic derivatives, the tetrahydroxylated protostane triterpene (9) showed moderate inhibitory activity with IC50 value of 97.1 microM. CONCLUSIONS: Introduction of an aldehyde group at C-23 (10; IC50 value, 47.7 microM) showed the most potent inhibitory effect on the complement system in vitro. A new triterpenoid from Alisma orientale and their antibacterial effect.[Pubmed: 23212633] Arch Pharm Res. 2012 Nov;35(11):1919-26. A new triterpenoid, named alisol Q 23-acetate, as well as fourteen known terpenes, alisol B 23-acetate (2), alisol B (3), alismol (4), 10-O-methyl-alismoxide (5), alismoxide (6), 11-deoxyalisol C (7), 13β,17β-epoxyalisol B 23-acetate (8), 4β,12-dihydroxyguaian-6,10-diene (9), alisol C 23-acetate (10), alisolide (11), 16β-methoxyalisol B monoacetate (12), alisol A (13), 16β-hydroxyalisol B 23-acetate (14), Alisol A 24-acetate (15) were isolated from the rhizomes of Alisma orientale. The structures of compounds (1-15) were identified based on 1D and 2D NMR, including (1)H-(1)H COSY, HSQC, HMBC and NOESY spectroscopic analyses. METHODS AND RESULTS: Among these isolates, antibacterial effect of compounds 2, 3, 10, and 15, major constituents of A. orientale was examined. The MIC values of compounds 2, 10, and 15 were 5-10 βg/mL against eight antibiotic resistant strains, which were lower than those from the positive controls (MICs of chloramphenicol and ampicillin were 5-80 μg/mL). CONCLUSIONS: Therefore, compounds 2, 10 and 15 exhibited the potent antibacterial activity.
In vivo	The Protective Effects of Alisol A 24-Acetate from Alisma canaliculatum on Ovariectomy Induced Bone Loss in Vivo.[Pubmed: 26760992 ] Molecules. 2016 Jan 9;21(1):74. Alisma canaliculatum is a herb commonly used in traditional Korean medicine, and has been shown in scientific studies to have antitumor, diuretic hepatoprotective, and antibacterial effects. Recently, the anti-osteoclastogenesis of Alisol A 24-acetate from Alisma canaliculatum was investigated in vitro. However, the influence of Alisol A 24-acetate on osteoporosis in animals has not been investigated. METHODS AND RESULTS: The present study was undertaken to investigate the anti-osteoporotic effect of Alisol A 24-acetate on bone mass in ovariectomized (OVX) mice and to identify the mechanism responsible for its effects. OVX mice were treated daily with 0.5 or 2 μg/g of Alisol A 24-acetate for a period of six weeks. It was found that these administrations significantly suppressed osteoporosis in OVX mice and improved bone morphometric parameters. The serum estradiol, bone alkaline phosphatase levels, regulatory T/Th17 cell numbers were significantly increased by Alisol A 24-acetate as compared with untreated OVX mice. In addition, TRAP activity was inhibited by Alisol A 24-acetate in OVX mice. CONCLUSIONS: These results suggest Alisol A 24-acetate effectively prevents bone loss in OVX mice, and that it can be considered a potential therapeutic for the treatment of postmenopausal osteoporosis.

Protocol of Alisol A 24-acetate

Cell Research

The Inhibitory Effect of Alisol A 24-Acetate from Alisma canaliculatum on Osteoclastogenesis.[Pubmed: 26273291 ] Int J Endocrinol. 2015;2015:132436. Osteoporosis is a disease that decreases bone mass. The number of patients with osteoporosis has been increasing, including an increase in patients with bone fractures, which lead to higher medical costs. Osteoporosis treatment is all-important in preventing bone loss. One strategy for osteoporosis treatment is to inhibit osteoclastogenesis. Osteoclasts are bone-resorbing multinucleated cells, and overactive osteoclasts and/or their increased number are observed in bone disorders including osteoporosis and rheumatoid arthritis. METHODS AND RESULTS: Bioactivity-guided fractionations led to the isolation of Alisol A 24-acetate from the dried tuber of Alisma canaliculatum. Alisol A 24-acetate inhibited RANKL-mediated osteoclast differentiation by downregulating NFATc1, which plays an essential role in osteoclast differentiation. Furthermore, it inhibited the expression of DC-STAMP and cathepsin K, which are related to cell-cell fusion of osteoclasts and bone resorption, respectively. CONCLUSIONS: Therefore, Alisol A 24-acetate could be developed as a new structural scaffold for inhibitors of osteoclast differentiation in order to develop new drugs against osteoporosis.

Preparing Stock Solutions of Alisol A 24-acetate

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	1.8771 mL	9.3853 mL	18.7705 mL	37.5411 mL	46.9263 mL
5 mM	0.3754 mL	1.8771 mL	3.7541 mL	7.5082 mL	9.3853 mL
10 mM	0.1877 mL	0.9385 mL	1.8771 mL	3.7541 mL	4.6926 mL
50 mM	0.0375 mL	0.1877 mL	0.3754 mL	0.7508 mL	0.9385 mL
100 mM	0.0188 mL	0.0939 mL	0.1877 mL	0.3754 mL	0.4693 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.

References on Alisol A 24-acetate

Stability and structure studies on alisol a 24-acetate.[Pubmed:18175972]

Chem Pharm Bull (Tokyo). 2008 Jan;56(1):41-5.

Alisol A 24-acetate is one of the main active triterpenoid compounds isolated from Rhizoma Alismatis, which is a famous Traditional Chinese Medicine, and has been determined for the quality control of this crude drug. In this study, Alisol A 24-acetate was found to be unstable in solvents and its stability in different solvents was investigated in detail. The results showed that Alisol A 24-acetate and 23-acetate inter-transformed in solvents and the transformation rate was more rapid in protic solvents than in aprotic solvents. Moreover, both Alisol A 24-acetate and 23-acetate were deacetylated to yield alisol A when kept in methanol for a long time. This is the first report on the structural transformation between Alisol A 24-acetate, alisol A 23-acetate and alisol A. In addition, the single crystal X-ray structure of Alisol A 24-acetate and the NMR data of alisol A 23-acetate were also reported for the first time.

Anti-complementary activity of protostane-type triterpenes from Alismatis rhizoma.[Pubmed:12877555]

Arch Pharm Res. 2003 Jun;26(6):463-5.

Four protostane-type triterpenes, alisol B 23-acetate (1a), alisol C 23-acetate (2a), alisol B (3a), and Alisol A 24-acetate (4a), were isolated from the rhizome of Alismatis plantago-aquatice L. var. orientale Samuelson (Alismataceae) and eleven protostane derivatives (compounds 1-11) were obtained by selective modification from alisol B 23-acetate (1a). These compounds were investigated for their anti-complement activity against the classical pathway of the complement system. Alisol B (3a) and Alisol A 24-acetate (4a) exhibited anti-complement activity with IC50 values of 150 and 130 microM. Among the synthetic derivatives, the tetrahydroxylated protostane triterpene (9) showed moderate inhibitory activity with IC50 value of 97.1 microM. Introduction of an aldehyde group at C-23 (10; IC50 value, 47.7 microM) showed the most potent inhibitory effect on the complement system in vitro.

The Inhibitory Effect of Alisol A 24-Acetate from Alisma canaliculatum on Osteoclastogenesis.[Pubmed:26273291]

Int J Endocrinol. 2015;2015:132436.

Osteoporosis is a disease that decreases bone mass. The number of patients with osteoporosis has been increasing, including an increase in patients with bone fractures, which lead to higher medical costs. Osteoporosis treatment is all-important in preventing bone loss. One strategy for osteoporosis treatment is to inhibit osteoclastogenesis. Osteoclasts are bone-resorbing multinucleated cells, and overactive osteoclasts and/or their increased number are observed in bone disorders including osteoporosis and rheumatoid arthritis. Bioactivity-guided fractionations led to the isolation of Alisol A 24-acetate from the dried tuber of Alisma canaliculatum. Alisol A 24-acetate inhibited RANKL-mediated osteoclast differentiation by downregulating NFATc1, which plays an essential role in osteoclast differentiation. Furthermore, it inhibited the expression of DC-STAMP and cathepsin K, which are related to cell-cell fusion of osteoclasts and bone resorption, respectively. Therefore, Alisol A 24-acetate could be developed as a new structural scaffold for inhibitors of osteoclast differentiation in order to develop new drugs against osteoporosis.

The Protective Effects of Alisol A 24-Acetate from Alisma canaliculatum on Ovariectomy Induced Bone Loss in Vivo.[Pubmed:26760992]

Molecules. 2016 Jan 9;21(1):74.

Alisma canaliculatum is a herb commonly used in traditional Korean medicine, and has been shown in scientific studies to have antitumor, diuretic hepatoprotective, and antibacterial effects. Recently, the anti-osteoclastogenesis of Alisol A 24-acetate from Alisma canaliculatum was investigated in vitro. However, the influence of Alisol A 24-acetate on osteoporosis in animals has not been investigated. The present study was undertaken to investigate the anti-osteoporotic effect of Alisol A 24-acetate on bone mass in ovariectomized (OVX) mice and to identify the mechanism responsible for its effects. OVX mice were treated daily with 0.5 or 2 mug/g of Alisol A 24-acetate for a period of six weeks. It was found that these administrations significantly suppressed osteoporosis in OVX mice and improved bone morphometric parameters. The serum estradiol, bone alkaline phosphatase levels, regulatory T/Th17 cell numbers were significantly increased by Alisol A 24-acetate as compared with untreated OVX mice. In addition, TRAP activity was inhibited by Alisol A 24-acetate in OVX mice. These results suggest Alisol A 24-acetate effectively prevents bone loss in OVX mice, and that it can be considered a potential therapeutic for the treatment of postmenopausal osteoporosis.

A sensitive liquid chromatography-mass spectrometry method for simultaneous determination of alisol A and alisol A 24-acetate from Alisma orientale (Sam.) Juz. in rat plasma.[Pubmed:21107819]

Anal Bioanal Chem. 2011 Jan;399(3):1363-9.

A liquid chromatography-mass spectrometry (LC-MS) method was developed and validated for the simultaneous determination of alisol A and Alisol A 24-acetate from Alisma orientale (Sam.) Juz. in rat plasma using diazepam as an internal standard. A 200-mul plasma sample was extracted by methyl tert-butyl ether and the separation was performed on Kromasil C(18) column (150 x 4.6 mm, 5 mum) with the mobile phase of acetonitrile (containing 0.1% of formic acid)-water (73:27, v/v) at a flow rate of 0.8 ml/min in a run time of 10 min. The two analytes were monitored with positive electrospray ionization by selected ion monitoring mode. The lower limit of quantitation for both alisol A and Alisol A 24-acetate were 10 ng/ml. The calibration curves were linear in the measured range 10-1,000 ng/ml for alisol A and 10-500 ng/ml for Alisol A 24-acetate. The mean extraction recoveries were above 74.7% for alisol A and above 72.4% for Alisol A 24-acetate from biological matrixes. The intra- and inter-day precision for all concentrations of quality controls was lower than 14.1% (RSD %) for each analyte. The accuracy ranged from -12.3% to 9.8% (RE %) for alisol A, and -8.6% to 14.2% (RE %) for Alisol A 24-acetate. The method was successfully applied to the study on the pharmacokinetics of alisol A and Alisol A 24-acetate in rat plasma.

A new triterpenoid from Alisma orientale and their antibacterial effect.[Pubmed:23212633]

Arch Pharm Res. 2012 Nov;35(11):1919-26.

A new triterpenoid, named alisol Q 23-acetate, as well as fourteen known terpenes, alisol B 23-acetate (2), alisol B (3), alismol (4), 10-O-methyl-alismoxide (5), alismoxide (6), 11-deoxyalisol C (7), 13beta,17beta-epoxyalisol B 23-acetate (8), 4beta,12-dihydroxyguaian-6,10-diene (9), alisol C 23-acetate (10), alisolide (11), 16beta-methoxyalisol B monoacetate (12), alisol A (13), 16beta-hydroxyalisol B 23-acetate (14), Alisol A 24-acetate (15) were isolated from the rhizomes of Alisma orientale. The structures of compounds (1-15) were identified based on 1D and 2D NMR, including (1)H-(1)H COSY, HSQC, HMBC and NOESY spectroscopic analyses. Among these isolates, antibacterial effect of compounds 2, 3, 10, and 15, major constituents of A. orientale was examined. The MIC values of compounds 2, 10, and 15 were 5-10 betag/mL against eight antibiotic resistant strains, which were lower than those from the positive controls (MICs of chloramphenicol and ampicillin were 5-80 mug/mL). Therefore, compounds 2, 10 and 15 exhibited the potent antibacterial activity.

Description

Alisol A 24-acetate is a natural product.

Keywords:

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