alpha-Spinasterol

TRPV1 antagonist; active in vivo CAS# 481-18-5

alpha-Spinasterol

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Chemical structure

alpha-Spinasterol

3D structure

Chemical Properties of alpha-Spinasterol

Cas No. 481-18-5 SDF Download SDF
PubChem ID 5281331 Appearance White powder
Formula C29H48O M.Wt 412.7
Type of Compound Steroids Storage Desiccate at -20°C
Synonyms Bessisterol; Hitodesterol; 5α-Stigmasta 7,22-dien 3β-ol
Solubility Soluble to 10 mM in ethanol with gentle warming
Chemical Name (3S,5S,9R,10S,13R,14R,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
SMILES CCC(C=CC(C)C1CCC2C1(CCC3C2=CCC4C3(CCC(C4)O)C)C)C(C)C
Standard InChIKey JZVFJDZBLUFKCA-FXIAWGAOSA-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 alpha-Spinasterol

1 Amaranthus sp. 2 Anagallis sp. 3 Ardisia sp. 4 Argania sp. 5 Aster sp. 6 Baccharis sp. 7 Bupleurum sp. 8 Chenopodium sp. 9 Citrullus sp. 10 Codonopsis sp. 11 Conyza sp. 12 Costus sp. 13 Cucumis sp. 14 Cucurbita sp. 15 Gypsophila sp. 16 Hedera sp. 17 Impatiens sp. 18 Kalimeris sp. 19 Madhuca sp. 20 Manilkara sp. 21 Maytenus sp. 22 Medicago sp. 23 Menyanthes sp. 24 Mimusops sp. 25 Momordica sp. 26 Ononis sp. 27 Phytolacca sp. 28 Pithecellobium sp. 29 Platycodon sp. 30 Polygala sp. 31 Pueraria sp. 32 Spinacia sp. 33 Trichosanthes sp. 34 Vernonia sp.

Biological Activity of alpha-Spinasterol

DescriptionAlpha-Spinasterol is a novel efficacious and safe antagonist of the TRPV1 receptor with anti-inflammatory and antinociceptive effects.Alpha-Spinasterol has a significant therapeutic potential to modulate the development and/or progression of diabetic nephropathy. It also can prevent TP-induced prostatic hyperplasia and may be beneficial in the management of benign prostatic hyperplasia.
TargetsTRPV | HMG-CoA reductase
In vivo

α-Spinasterol from Melandrium firmum attenuates benign prostatic hyperplasia in a rat model.[Pubmed: 24682042]

Mol Med Rep. 2014 Jun;9(6):2362-6.

Spinasterol, a biologically active compound, exhibits a number of pharmacological activities, including antitumor, antiulcerogenic and anticarcinogenic activity, and originates from the aerial parts of Aster scaber Thunb (Asteraceae). The present study investigated whether alpha-Spinasterol isolated from Melandrium firmum Rohrbach could prevent benign prostatic hyperplasia (BPH) induced by testosterone propionate (TP) in rats.
METHODS AND RESULTS:
Male Wistar rats were randomly divided into four groups of eight rats following castration. A negative control group received subcutaneous injections of corn oil. Treatments were administered orally 1 h prior to TP injection. All the rats were sacrificed at the scheduled termination time and their prostates were removed, cleaned and weighed. The prostate size ratio (prostate weight/rat body weight) was then calculated. Additional histopathological examinations were conducted, and the levels of TP and dihydrotestosterone (DHT) in the serum and prostate were measured. TP significantly increased the prostate size ratio (P<0.01), and DHT and testosterone levels in the serum and prostate. The TP-induced increase was significantly inhibited in alpha-Spinasterol-treated rats when compared with the negative controls (P<0.05). In addition, histopathological examination demonstrated that α-spinasterol treatment suppressed TP-induced prostatic hyperplasia.
CONCLUSIONS:
It is concluded that alpha-Spinasterol can prevent TP-induced prostatic hyperplasia and may be beneficial in the management of BPH.

Anti-inflammatory action of hydroalcoholic extract, dichloromethane fraction and steroid α-spinasterol from Polygala sabulosa in LPS-induced peritonitis in mice.[Pubmed: 24161429]

J Ethnopharmacol. 2014;151(1):144-50.

Polygala sabulosa A. W. Bennett is a small herb popularly known as "timutu-pinheirinho" that is widely distributed in southern Brazil and that is used to treat disorders of the bowel and kidney and as a topical anesthetic and expectorant in folk medicine. This study was designed to investigate the anti-inflammatory properties of the hydroalcoholic extract (HEPs), CH2Cl2 fraction and the steroid α-spinasterol obtained from the aerial parts of Polygala sabulosa in a model of acute inflammation induced by intraperitoneal injection of bacterial lipopolysaccharide in mice.
METHODS AND RESULTS:
The anti-inflammatory effect of HEPs (3-300 mg/kg, i.g.), CH2Cl2 fraction (0.003-30 mg/kg, i.g.) and steroid α-spinasterol (0.001-1mg/kg, i.p. or 1-10mg/kg, i.g.), were evaluated in mice subjected to the acute inflammation caused by intraperitoneal (i.p.) injection of lipopolysaccharide (LPS, 0.02 µg/kg). The anti-inflammatory activity of the HEPs, CH2Cl2 fraction and steroid were assessed by determining the total numbers of leukocytes and differential cell counts (neutrophils and mononuclear cells) and levels of pro-inflammatory (IL-1β, TNF-α, IL-6) or anti-inflammatory (IL-10) cytokines in peritoneal fluid. The administration of HEPs (3-300 mg/kg, i.g.) completely inhibited inflammatory cell infiltration (300 mg/kg, i.g.) and it reduced TNF-α (100-300 mg/kg) and IL-1β (100mg/kg) levels in LPS-injected mice. Furthermore, the administration of CH2Cl2 fraction (0.003-30 mg/kg, i.g.) or α-spinasterol (0.001-10mg/kg, by i.p. or i.g.) significantly reduces inflammatory cell infiltration in LPS-injected mice. Moreover, dexamethasone (0.5mg/kg, i.p., used as a positive control) inhibited inflammatory cell infiltration and reduced the levels of TNF-α, IL-1β and IL-6 in LPS-injected mice.
CONCLUSIONS:
Taken together, these results provide the first experimental evidence demonstrating that HEPs have significant anti-inflammatory effects on LPS-induced inflammation. These effects appear to be, at least in part, due to the presence of α-spinasterol. These findings support the widespread use of Polygala sabulosa in popular medicine and demonstrate that this plant has therapeutic potential for the development of phytomedicines with anti-inflammatory properties.

alpha-Spinasterol isolated from the root of Phytolacca americana and its pharmacological property on diabetic nephropathy.[Pubmed: 15326549 ]

Planta Med. 2004 Aug;70(8):736-9.


METHODS AND RESULTS:
Based on an inhibitory activity-guided fractionation for the high glucose-induced proliferation of glomerular mesangial cells (GMCs), chloroform extracts of the roots of Phytolacca americana were found to contain alpha-Spinasterol (C (29)H (48)O), a delta (7)-sterol. This phytosterol proved to be a potent inhibitor (IC (50) = 3.9 x 10 (-12) g/mL, 9.5 pmol/L) of glomerular mesangial cell proliferation caused by high-ambient glucose (5.6 mM vs. 25 mM), and its inhibitory potency was about 1,000 times higher than that of simvastatin, an HMG-CoA reductase inhibitor used as a positive control. alpha-Spinasterol also significantly reduced the increases of serum triglycerides, renal weight and urinary protein excretion in streptozotocin-induced diabetic mice, and these were comparable to the results observed in insulin-treated diabetic mice.
CONCLUSIONS:
Therefore, the results obtained in this study suggest that alpha-Spinasterol has a significant therapeutic potential to modulate the development and/or progression of diabetic nephropathy.

Protocol of alpha-Spinasterol

Kinase Assay

Identification of the plant steroid α-spinasterol as a novel transient receptor potential vanilloid 1 antagonist with antinociceptive properties.[Pubmed: 22837009]

J Pharmacol Exp Ther. 2012 Nov;343(2):258-69.

The transient receptor potential vanilloid 1 (TRPV1) receptor is relevant to the perception of noxious information and has been studied as a therapeutic target for the development of new analgesics. The goal of this study was to perform in vivo and in vitro screens to identify novel, efficacious, and safe TRPV1 antagonists isolated from leaves of the medicinal plant Vernonia tweedieana Baker.
METHODS AND RESULTS:
All of the fractions and the hydroalcoholic extract produced antinociception in mice during the capsaicin test, but the dichloromethane fraction also had antioedematogenic effect. Among the compounds isolated from the dichloromethane fraction, only alpha-Spinasterol reduced the nociception and edema induced by capsaicin injection. Moreover, α-spinasterol demonstrated good oral absorption and high penetration into the brain and spinal cord of mice. alpha-Spinasterol was able to displace [3H]resiniferatoxin binding and diminish calcium influx mediated by capsaicin. Oral administration of the dichloromethane fraction and alpha-Spinasterol also produced antinociceptive effect in the noxious heat-induced nociception test; however, they did not change the mechanical threshold of naive mice. The treatment with α-spinasterol did not produce antinociceptive effect in mice systemically pretreated with resiniferatoxin. In addition, alpha-Spinasterol and the dichloromethane fraction reduced the edema, mechanical, and heat hyperalgesia elicited by complete Freund's adjuvant paw injection. The dichloromethane fraction and alpha-Spinasterol did not affect body temperature or locomotor activity.
CONCLUSIONS:
In conclusion, alpha-Spinasterol is a novel efficacious and safe antagonist of the TRPV1 receptor with antinociceptive effect.

Animal Research

α-Spinasterol, a TRPV1 receptor antagonist, elevates the seizure threshold in three acute seizure tests in mice.[Pubmed: 25764210]

J Neural Transm (Vienna). 2015 Sep;122(9):1239-47.

alpha-Spinasterol is a plant-derived compound which was reported to act as a selective antagonist for the transient receptor potential vanilloid 1 (TRPV1) receptor. Several studies revealed that the TRPV1 receptors might modulate seizure activity in animal models of seizures and epilepsy.
METHODS AND RESULTS:
The aim of the present study was to investigate the effect of alpha-Spinasterol on the seizure threshold in three acute models of seizures, i.e., in the intravenous (i.v.) pentylenetetrazole (PTZ) seizure test, in the maximal electroshock seizure threshold (MEST) test and in the model of psychomotor seizures induced by 6 Hz stimulation in mice. Our results revealed significant anticonvulsant effect of alpha-Spinasterol in all the used seizure tests. In the i.v. PTZ test, statistically significant elevation was noted in case of the threshold for myoclonic twitches (doses of 0.1-1 mg/kg) and generalized clonus seizures (doses of 0.5 and 1 mg/kg) but not for tonic seizures. The studied TRPV1 antagonist also increased the threshold for tonic hindlimb extension in the MEST (doses of 0.5 and 1 mg/kg) and 6 Hz psychomotor seizure (doses of 0.1 and 0.5 mg/kg) tests in mice. Furthermore, alpha-Spinasterol did not produce any significant impairment of motor coordination (assessed in the chimney test) and muscular strength (investigated in the grip-strength test) and it did not provoke significant changes in body temperature in mice.
CONCLUSIONS:
Based on the results of our study and the fact that alpha-Spinasterol is characterized by good blood-brain permeability, we postulate further investigation of this compound to precisely evaluate mechanism of its anticonvulsant action and opportunity of its usage in clinical practice.

alpha-Spinasterol Dilution Calculator

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Preparing Stock Solutions of alpha-Spinasterol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4231 mL 12.1153 mL 24.2307 mL 48.4614 mL 60.5767 mL
5 mM 0.4846 mL 2.4231 mL 4.8461 mL 9.6923 mL 12.1153 mL
10 mM 0.2423 mL 1.2115 mL 2.4231 mL 4.8461 mL 6.0577 mL
50 mM 0.0485 mL 0.2423 mL 0.4846 mL 0.9692 mL 1.2115 mL
100 mM 0.0242 mL 0.1212 mL 0.2423 mL 0.4846 mL 0.6058 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 alpha-Spinasterol

alpha-Spinasterol isolated from the root of Phytolacca americana and its pharmacological property on diabetic nephropathy.[Pubmed:15326549]

Planta Med. 2004 Aug;70(8):736-9.

Based on an inhibitory activity-guided fractionation for the high glucose-induced proliferation of glomerular mesangial cells (GMCs), chloroform extracts of the roots of Phytolacca americana were found to contain alpha-Spinasterol (C (29)H (48)O), a delta (7)-sterol. This phytosterol proved to be a potent inhibitor (IC (50) = 3.9 x 10 (-12) g/mL, 9.5 pmol/L) of glomerular mesangial cell proliferation caused by high-ambient glucose (5.6 mM vs. 25 mM), and its inhibitory potency was about 1,000 times higher than that of simvastatin, an HMG-CoA reductase inhibitor used as a positive control. alpha-Spinasterol also significantly reduced the increases of serum triglycerides, renal weight and urinary protein excretion in streptozotocin-induced diabetic mice, and these were comparable to the results observed in insulin-treated diabetic mice. Therefore, the results obtained in this study suggest that alpha-Spinasterol has a significant therapeutic potential to modulate the development and/or progression of diabetic nephropathy.

Anti-inflammatory action of hydroalcoholic extract, dichloromethane fraction and steroid alpha-spinasterol from Polygala sabulosa in LPS-induced peritonitis in mice.[Pubmed:24161429]

J Ethnopharmacol. 2014;151(1):144-50.

ETHNOPHARMACOLOGICAL RELEVANCE: Polygala sabulosa A. W. Bennett is a small herb popularly known as "timutu-pinheirinho" that is widely distributed in southern Brazil and that is used to treat disorders of the bowel and kidney and as a topical anesthetic and expectorant in folk medicine. This study was designed to investigate the anti-inflammatory properties of the hydroalcoholic extract (HEPs), CH2Cl2 fraction and the steroid alpha-Spinasterol obtained from the aerial parts of Polygala sabulosa in a model of acute inflammation induced by intraperitoneal injection of bacterial lipopolysaccharide in mice. MATERIALS AND METHODS: The anti-inflammatory effect of HEPs (3-300 mg/kg, i.g.), CH2Cl2 fraction (0.003-30 mg/kg, i.g.) and steroid alpha-Spinasterol (0.001-1mg/kg, i.p. or 1-10mg/kg, i.g.), were evaluated in mice subjected to the acute inflammation caused by intraperitoneal (i.p.) injection of lipopolysaccharide (LPS, 0.02 microg/kg). The anti-inflammatory activity of the HEPs, CH2Cl2 fraction and steroid were assessed by determining the total numbers of leukocytes and differential cell counts (neutrophils and mononuclear cells) and levels of pro-inflammatory (IL-1beta, TNF-alpha, IL-6) or anti-inflammatory (IL-10) cytokines in peritoneal fluid. RESULTS: The administration of HEPs (3-300 mg/kg, i.g.) completely inhibited inflammatory cell infiltration (300 mg/kg, i.g.) and it reduced TNF-alpha (100-300 mg/kg) and IL-1beta (100mg/kg) levels in LPS-injected mice. Furthermore, the administration of CH2Cl2 fraction (0.003-30 mg/kg, i.g.) or alpha-Spinasterol (0.001-10mg/kg, by i.p. or i.g.) significantly reduces inflammatory cell infiltration in LPS-injected mice. Moreover, dexamethasone (0.5mg/kg, i.p., used as a positive control) inhibited inflammatory cell infiltration and reduced the levels of TNF-alpha, IL-1beta and IL-6 in LPS-injected mice. CONCLUSIONS: Taken together, these results provide the first experimental evidence demonstrating that HEPs have significant anti-inflammatory effects on LPS-induced inflammation. These effects appear to be, at least in part, due to the presence of alpha-Spinasterol. These findings support the widespread use of Polygala sabulosa in popular medicine and demonstrate that this plant has therapeutic potential for the development of phytomedicines with anti-inflammatory properties.

alpha-Spinasterol, a TRPV1 receptor antagonist, elevates the seizure threshold in three acute seizure tests in mice.[Pubmed:25764210]

J Neural Transm (Vienna). 2015 Sep;122(9):1239-47.

alpha-Spinasterol is a plant-derived compound which was reported to act as a selective antagonist for the transient receptor potential vanilloid 1 (TRPV1) receptor. Several studies revealed that the TRPV1 receptors might modulate seizure activity in animal models of seizures and epilepsy. The aim of the present study was to investigate the effect of alpha-Spinasterol on the seizure threshold in three acute models of seizures, i.e., in the intravenous (i.v.) pentylenetetrazole (PTZ) seizure test, in the maximal electroshock seizure threshold (MEST) test and in the model of psychomotor seizures induced by 6 Hz stimulation in mice. Our results revealed significant anticonvulsant effect of alpha-Spinasterol in all the used seizure tests. In the i.v. PTZ test, statistically significant elevation was noted in case of the threshold for myoclonic twitches (doses of 0.1-1 mg/kg) and generalized clonus seizures (doses of 0.5 and 1 mg/kg) but not for tonic seizures. The studied TRPV1 antagonist also increased the threshold for tonic hindlimb extension in the MEST (doses of 0.5 and 1 mg/kg) and 6 Hz psychomotor seizure (doses of 0.1 and 0.5 mg/kg) tests in mice. Furthermore, alpha-Spinasterol did not produce any significant impairment of motor coordination (assessed in the chimney test) and muscular strength (investigated in the grip-strength test) and it did not provoke significant changes in body temperature in mice. Based on the results of our study and the fact that alpha-Spinasterol is characterized by good blood-brain permeability, we postulate further investigation of this compound to precisely evaluate mechanism of its anticonvulsant action and opportunity of its usage in clinical practice.

alpha-Spinasterol from Melandrium firmum attenuates benign prostatic hyperplasia in a rat model.[Pubmed:24682042]

Mol Med Rep. 2014 Jun;9(6):2362-6.

Spinasterol, a biologically active compound, exhibits a number of pharmacological activities, including antitumor, antiulcerogenic and anticarcinogenic activity, and originates from the aerial parts of Aster scaber Thunb (Asteraceae). The present study investigated whether alpha-Spinasterol isolated from Melandrium firmum Rohrbach could prevent benign prostatic hyperplasia (BPH) induced by testosterone propionate (TP) in rats. Male Wistar rats were randomly divided into four groups of eight rats following castration. A negative control group received subcutaneous injections of corn oil. Treatments were administered orally 1 h prior to TP injection. All the rats were sacrificed at the scheduled termination time and their prostates were removed, cleaned and weighed. The prostate size ratio (prostate weight/rat body weight) was then calculated. Additional histopathological examinations were conducted, and the levels of TP and dihydrotestosterone (DHT) in the serum and prostate were measured. TP significantly increased the prostate size ratio (P<0.01), and DHT and testosterone levels in the serum and prostate. The TP-induced increase was significantly inhibited in alpha-Spinasterol-treated rats when compared with the negative controls (P<0.05). In addition, histopathological examination demonstrated that alpha-Spinasterol treatment suppressed TP-induced prostatic hyperplasia. It is concluded that alpha-Spinasterol can prevent TP-induced prostatic hyperplasia and may be beneficial in the management of BPH.

Identification of the plant steroid alpha-spinasterol as a novel transient receptor potential vanilloid 1 antagonist with antinociceptive properties.[Pubmed:22837009]

J Pharmacol Exp Ther. 2012 Nov;343(2):258-69.

The transient receptor potential vanilloid 1 (TRPV1) receptor is relevant to the perception of noxious information and has been studied as a therapeutic target for the development of new analgesics. The goal of this study was to perform in vivo and in vitro screens to identify novel, efficacious, and safe TRPV1 antagonists isolated from leaves of the medicinal plant Vernonia tweedieana Baker. All of the fractions and the hydroalcoholic extract produced antinociception in mice during the capsaicin test, but the dichloromethane fraction also had antioedematogenic effect. Among the compounds isolated from the dichloromethane fraction, only alpha-Spinasterol reduced the nociception and edema induced by capsaicin injection. Moreover, alpha-Spinasterol demonstrated good oral absorption and high penetration into the brain and spinal cord of mice. alpha-Spinasterol was able to displace [3H]resiniferatoxin binding and diminish calcium influx mediated by capsaicin. Oral administration of the dichloromethane fraction and alpha-Spinasterol also produced antinociceptive effect in the noxious heat-induced nociception test; however, they did not change the mechanical threshold of naive mice. The treatment with alpha-Spinasterol did not produce antinociceptive effect in mice systemically pretreated with resiniferatoxin. In addition, alpha-Spinasterol and the dichloromethane fraction reduced the edema, mechanical, and heat hyperalgesia elicited by complete Freund's adjuvant paw injection. The dichloromethane fraction and alpha-Spinasterol did not affect body temperature or locomotor activity. In conclusion, alpha-Spinasterol is a novel efficacious and safe antagonist of the TRPV1 receptor with antinociceptive effect.

Description

α-Spinasterol, isolated from Spinacia oleracea, has antibacterial activity. α-Spinasterol is a transient receptor potential vanilloid 1 (TRPV1) antagonist, has anti-inflammatory, antidepressant, antioxidant and antinociceptive effects. α-Spinasterol inhibits COX-1 andCOX-2 activities with IC50 values of 16.17 μM and 7.76 μM, respectively.

Keywords:

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