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Curculigoside

CAS# 85643-19-2

Curculigoside

2D Structure

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Curculigoside

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Chemical Properties of Curculigoside

Cas No. 85643-19-2 SDF Download SDF
PubChem ID 158845 Appearance White-off white powder
Formula C22H26O11 M.Wt 466.4
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms Curculigoside A
Solubility Sparingly soluble in water
Chemical Name [5-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl 2,6-dimethoxybenzoate
SMILES COC1=C(C(=CC=C1)OC)C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)O
Standard InChIKey SJJRKHVKAXVFJQ-QKYBYQKWSA-N
Standard InChI InChI=1S/C22H26O11/c1-29-14-4-3-5-15(30-2)17(14)21(28)31-10-11-8-12(24)6-7-13(11)32-22-20(27)19(26)18(25)16(9-23)33-22/h3-8,16,18-20,22-27H,9-10H2,1-2H3/t16-,18-,19+,20-,22-/m1/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 Curculigoside

The rhizomes of Curculigo orchioides Gaertn.

Biological Activity of Curculigoside

DescriptionCurculigoside has potent antioxidant, anti-osteoporotic, immunomodulatory, and neuroprotective effects. Curculigoside can improve cognitive function in aged animals, possibly by decreasing the activity of AchE in the cerebra and inhibiting the expression of BACE1 in the hippocampus. Curculigoside exhibits potent inhibitory activity against matrix metalloproteinase-1 in cultured human skin fibroblasts, and increases the levels of ALP and Runx2 in osteoblasts under oxidative stress via anti-oxidative character.
TargetsWnt/β-catenin | NF-kB | BACE | AChR | Caspase | p53 | ROS | NO | NMDAR | Bcl-2/Bax
In vitro

Curculigoside improves osteogenesis of human amniotic fluid-derived stem cells.[Pubmed: 24007307 ]

Stem Cells Dev. 2014 Jan 15;23(2):146-54.

Curculigoside, a phenolic glycoside, is the main active compound of Curculigo orchioides (Amaryllidaceae, rhizome). C. orchioides is a traditional Chinese herbal medicine and has been commonly used to treat orthopedic disorders and bone healing in Asia. This study evaluated the effect of Curculigoside on osteogenic differentiation of human amniotic fluid-derived stem cells (hAFSCs).
METHODS AND RESULTS:
The results showed that Curculigoside stimulated alkaline phosphatase activity and calcium deposition of hAFSCs during osteogenic differentiation in a dose-dependent manner (1-100 μg/mL), while the effects were reduced at the higher concentration of 200 μg/mL. From reverse transcriptase-polymerase chain reaction analysis, the osteogenic genes osteopontin (OPN) and Collagen I were upregulated with Curculigoside treatment (1-100 μg/mL). Concurrently, the ratio of osteoprotegerin (OPG) to receptor activator of nuclear factor kappa-B ligand (RANKL) was increased, indicating the inhibition of osteoclastogenesis by Curculigoside. Moreover, the role of Wnt/β-catenin signaling during Curculigoside treatment was revealed by the upregulation of β-catenin and Cyclin D1.
CONCLUSIONS:
In summary, Curculigoside improved osteogenesis and inhibited osteoclastogenesis of hAFSCs, suggesting its potential use to regulate hAFSC osteogenic differentiation for treating bone disorders.

Curculigoside attenuates human umbilical vein endothelial cell injury induced by H2O2.[Pubmed: 20713149]

J Ethnopharmacol. 2010 Oct 28;132(1):233-9.

Vessel endothelium injury caused by reactive oxygen species (ROS) including H(2)O(2) plays a critical role in the pathogenesis of cardiovascular disorders. Therefore, agents or antioxidants that can inhibit production of ROS has highly clinical values in cardiovascular therapy. Curculigoside is the major bioactive compounds present in Curculigo orchioides, and possess potent antioxidant properties against oxidative stress insults through undefined mechanism(s). The present study was designed to test the hypothesis that Curculigoside can inhibit H(2)O(2)-induced injury in human umbilical vein endothelial cells.
METHODS AND RESULTS:
Human umbilical vein endothelial cells (HUVECs) were treated with Curculigoside in the presence/absence of hydrogen peroxide (H(2)O(2)). The protective effects of Curculigoside OP-D against H(2)O(2) were evaluated. HUVECs incubated with 400 μM H(2)O(2) had significantly decreased the viability of endothelial cells, which was accompanied with apparent cells apoptosis, the activation of caspase-3 and the upregulation of p53 mRNA expression. In addition, H(2)O(2) treatment induced a marked increase of MDA, LDH content and in intracellular ROS, decreased the content of nitric oxide (NO) and GSH-Px activities in endothelial cells. However, pretreatment with 0.5.5,10 μM Curculigoside resulted in a significant recovery from H(2)O(2)-induced cell apoptosis. Also, it decreased other H(2)O(2)-induced damages in a concentration-dependent manner. Furthermore, pretreatment with Curculigoside decreased the activity of caspase-3 and p53 mRNA expression, which was known to play a key role in H(2)O(2)-induced cell apoptosis.
CONCLUSIONS:
The present study shows that Curculigoside can protect endothelial cells against oxidative injury induced by H(2)O(2), suggesting that this compound may constitute a promising intervention against cardiovascular disorders.

The effect of curculigoside on the expression of matrix metalloproteinase-1 in cultured human skin fibroblasts.[Pubmed: 19898807 ]

Arch Pharm Res. 2009 Oct;32(10):1433-9.

The dried rhizomes of Curculigo orchioides G. yielded two phenolic glycosides, Curculigoside (1), orcinol-beta-D-glucoside (4), and two cycloartane saponins, curculigosaponin G (2), curculigosaponin I (3). The structures were determined using spectroscopic methods.
METHODS AND RESULTS:
Among these isolates, compound 1 exhibited potent inhibitory activity against matrix metalloproteinase-1 in cultured human skin fibroblasts. In addition, it increased the level of Bcl-2 protein expression and decreased the level of Bax protein expression. Compound 4 was isolated from this plant for the first time.

In vivo

Curculigoside promotes osteogenic differentiation of bone marrow stromal cells from ovariectomized rats.[Pubmed: 23738728 ]

J Pharm Pharmacol. 2013 Jul;65(7):1005-13.

Curculigoside, a natural compound isolated from the medicinal plant Curculigo orchioides has been reported to prevent bone loss in ovariectomized rats. However, the underlying molecular mechanisms are largely unknown. This study investigated the effects of Curculigoside on proliferation and osteogenic differentiation of bone marrow stromal cells (BMSCs).
METHODS AND RESULTS:
The toxicity, proliferation and osteogenic differentiation of BMSCs cultured with various concentrations (0 as control, 10, 100 and 500 μm) of Curculigoside were measured by viability assay, MTT analysis, alkaline phosphatase (ALP) activity assay, alizarin red staining and mineralization assay, real-time PCR analysis on osteogenic genes including ALP, type I collagen (Col I), osteocalcin (OCN) and osteoprotegerin (OPG), runt-related transcription factor 2 (Runx2), as well as OPG enzyme-linked immunosorbent assay. No significant cytotoxicity was observed for BMSCs after supplementation with Curculigoside. The proliferation of BMSCs was enhanced after administration of Curculigoside, especially 100 μm Curculigoside. Moreover, the osteogenic gene expression was significantly enhanced with 100 μm Curculigoside treatment. Importantly, Curculigoside significantly increased OPG secretion.
CONCLUSIONS:
The data indicate that Curculigoside could promote BMSC proliferation and induce osteogenic differentiation of BMSCs. The most profound response was observed with 100 μm Curculigoside. These findings may be valuable for understanding the mechanism of the effect of Curculigoside on bone, especially in relation to osteoporosis.

Protocol of Curculigoside

Cell Research

Neuroprotective effects of curculigoside against NMDA-induced neuronal excitoxicity in vitro.[Pubmed: 22902827 ]

Food Chem Toxicol. 2012 Nov;50(11):4010-5.

Glutamate is an important excitatory neurotransmitter in the central nervous system. Excessive accumulation of glutamate can cause excitotoxicity, which plays a key role in spinal cord injury, traumatic brain injury, stroke, and neurodegenerative diseases. Curculigoside (CCGS) is a major bioactive compound isolated from the rhizome of Curculigo orchioides Gaertn. CCGS has an extensive biological effect and has been used in Traditional Chinese Medicine. However, little is known about the neuroprotective effects of CCGS on glutamate-induced excitotoxicity. This study aims to evaluate the neuroprotective effects of CCGS in cultured cortical neurons.
METHODS AND RESULTS:
The results indicated that treatment with 1 and 10 μM CCGS evidently prevented N-methyl-d-aspartate (NMDA)-induced neuronal cell loss and reduced the number of apoptotic and necrotic cells in a time- and concentration-dependent manner. The neuroprotective effects of CCGS are related to down regulating the apoptotic protein levels and reducing the production of intracellular reactive oxygen species in cultured cortical neurons.
CONCLUSIONS:
These findings give a new insight into the development of natural anti-excitotoxicity agents.

Animal Research

Effects of Curculigoside on Memory Impairment and Bone Loss via Anti-Oxidative Character in APP/PS1 Mutated Transgenic Mice.[Pubmed: 26186010]

Ameliorative effects of curculigoside from Curculigo orchioides Gaertn on learning and memory in aged rats.[Pubmed: 22922281]

Molecules. 2012 Aug 24;17(9):10108-18.

This study was designed to evaluate the ameliorating effects of Curculigoside from Curculigo orchioides Gaertn on learning and memory in aged rats. In the present study, the ameliorating effects of Curculigoside were determined through animal behaviour studies (including step-down test and Y-maze test), and the possible mechanisms were explored by evaluation of the activity of acetylcholinesterase (AchE) and determination of the expression of BACE1.
METHODS AND RESULTS:
Oral adminstration of the Curculigoside (20, 40 mg/kg/day) for 14 days can significantly improve the latency and number of errors in aged rats based on the behaviour study results. In addition, the activity of AchE can be decreased by treatment of the Curculigoside (10, 20, 40 mg/kg/day). Moreover, the expression of BACE1 can be down-regulated in the hippocampus of aged rats treated with Curculigoside. The results of our present work have indicated that Curculigoside can improve cognitive function in aged animals, possibly by decreasing the activity of AchE in the cerebra and inhibiting the expression of BACE1 in the hippocampus.
CONCLUSIONS:
In conclusion, our results suggested that Curculigoside can be possible developed as a new drug for the treatment of Alzheimer's disease in the future.

PLoS One. 2015 Jul 17;10(7):e0133289.

Alzheimer's disease (AD) and osteoporosis are two closely related multifactorial progressively degenerative diseases that predominantly affect aged people. These two diseases share many common risk factors, including old age, being female, smoking, excessive drinking, low estrogen, and vitamin D3 levels. Additionally, oxidative damage and the dysfunction of the antioxidant system play important roles in the pathogenesis of osteoporosis and AD. Aβ not only leads to impaired memory but also plays a crucial role in the demineralization process of bone tissues of older people and women with menopause. Curculigoside can promote calcium deposition and increase the levels of ALP and Runx2 in osteoblasts under oxidative stress via anti-oxidative character.
METHODS AND RESULTS:
Therefore, we investigated the effects of CUR on the spatial learning and memory by the Morris water maze and brain immunohistochemistry, and bone microstructure and material properties of femurs by micro-computed tomography and mechanical testing in APP/PS1 mutated transgenic mice. Oral administration of CUR can significantly enhance learning performance and ameliorate bone loss in APP/PS1 mutated transgenic mice, and the mechanism may be related to its antioxidant effect.
CONCLUSIONS:
Based on these results, CUR has real potential as a new natural resource for developing medicines or dietary supplements for the prevention and treatment of the two closely linked multifactorial progressive degenerative disorders, AD and osteoporosis.

Curculigoside Dilution Calculator

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Preparing Stock Solutions of Curculigoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1441 mL 10.7204 mL 21.4408 mL 42.8816 mL 53.6021 mL
5 mM 0.4288 mL 2.1441 mL 4.2882 mL 8.5763 mL 10.7204 mL
10 mM 0.2144 mL 1.072 mL 2.1441 mL 4.2882 mL 5.3602 mL
50 mM 0.0429 mL 0.2144 mL 0.4288 mL 0.8576 mL 1.072 mL
100 mM 0.0214 mL 0.1072 mL 0.2144 mL 0.4288 mL 0.536 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 Curculigoside

Neuroprotective effects of curculigoside against NMDA-induced neuronal excitoxicity in vitro.[Pubmed:22902827]

Food Chem Toxicol. 2012 Nov;50(11):4010-5.

Glutamate is an important excitatory neurotransmitter in the central nervous system. Excessive accumulation of glutamate can cause excitotoxicity, which plays a key role in spinal cord injury, traumatic brain injury, stroke, and neurodegenerative diseases. Curculigoside (CCGS) is a major bioactive compound isolated from the rhizome of Curculigo orchioides Gaertn. CCGS has an extensive biological effect and has been used in Traditional Chinese Medicine. However, little is known about the neuroprotective effects of CCGS on glutamate-induced excitotoxicity. This study aims to evaluate the neuroprotective effects of CCGS in cultured cortical neurons. The results indicated that treatment with 1 and 10 muM CCGS evidently prevented N-methyl-d-aspartate (NMDA)-induced neuronal cell loss and reduced the number of apoptotic and necrotic cells in a time- and concentration-dependent manner. The neuroprotective effects of CCGS are related to down regulating the apoptotic protein levels and reducing the production of intracellular reactive oxygen species in cultured cortical neurons. These findings give a new insight into the development of natural anti-excitotoxicity agents.

Curculigoside attenuates human umbilical vein endothelial cell injury induced by H2O2.[Pubmed:20713149]

J Ethnopharmacol. 2010 Oct 28;132(1):233-9.

AIM OF THE STUDY: Vessel endothelium injury caused by reactive oxygen species (ROS) including H(2)O(2) plays a critical role in the pathogenesis of cardiovascular disorders. Therefore, agents or antioxidants that can inhibit production of ROS has highly clinical values in cardiovascular therapy. Curculigoside is the major bioactive compounds present in Curculigo orchioides, and possess potent antioxidant properties against oxidative stress insults through undefined mechanism(s). The present study was designed to test the hypothesis that Curculigoside can inhibit H(2)O(2)-induced injury in human umbilical vein endothelial cells. MATERIALS AND METHODS: Human umbilical vein endothelial cells (HUVECs) were treated with Curculigoside in the presence/absence of hydrogen peroxide (H(2)O(2)). The protective effects of Curculigoside OP-D against H(2)O(2) were evaluated. RESULTS: HUVECs incubated with 400 muM H(2)O(2) had significantly decreased the viability of endothelial cells, which was accompanied with apparent cells apoptosis, the activation of caspase-3 and the upregulation of p53 mRNA expression. In addition, H(2)O(2) treatment induced a marked increase of MDA, LDH content and in intracellular ROS, decreased the content of nitric oxide (NO) and GSH-Px activities in endothelial cells. However, pretreatment with 0.5.5,10 muM Curculigoside resulted in a significant recovery from H(2)O(2)-induced cell apoptosis. Also, it decreased other H(2)O(2)-induced damages in a concentration-dependent manner. Furthermore, pretreatment with Curculigoside decreased the activity of caspase-3 and p53 mRNA expression, which was known to play a key role in H(2)O(2)-induced cell apoptosis. CONCLUSION: The present study shows that Curculigoside can protect endothelial cells against oxidative injury induced by H(2)O(2), suggesting that this compound may constitute a promising intervention against cardiovascular disorders.

Curculigoside improves osteogenesis of human amniotic fluid-derived stem cells.[Pubmed:24007307]

Stem Cells Dev. 2014 Jan 15;23(2):146-54.

Curculigoside, a phenolic glycoside, is the main active compound of Curculigo orchioides (Amaryllidaceae, rhizome). C. orchioides is a traditional Chinese herbal medicine and has been commonly used to treat orthopedic disorders and bone healing in Asia. This study evaluated the effect of Curculigoside on osteogenic differentiation of human amniotic fluid-derived stem cells (hAFSCs). The results showed that Curculigoside stimulated alkaline phosphatase activity and calcium deposition of hAFSCs during osteogenic differentiation in a dose-dependent manner (1-100 mug/mL), while the effects were reduced at the higher concentration of 200 mug/mL. From reverse transcriptase-polymerase chain reaction analysis, the osteogenic genes osteopontin (OPN) and Collagen I were upregulated with Curculigoside treatment (1-100 mug/mL). Concurrently, the ratio of osteoprotegerin (OPG) to receptor activator of nuclear factor kappa-B ligand (RANKL) was increased, indicating the inhibition of osteoclastogenesis by Curculigoside. Moreover, the role of Wnt/beta-catenin signaling during Curculigoside treatment was revealed by the upregulation of beta-catenin and Cyclin D1. In summary, Curculigoside improved osteogenesis and inhibited osteoclastogenesis of hAFSCs, suggesting its potential use to regulate hAFSC osteogenic differentiation for treating bone disorders.

Curculigoside promotes osteogenic differentiation of bone marrow stromal cells from ovariectomized rats.[Pubmed:23738728]

J Pharm Pharmacol. 2013 Jul;65(7):1005-13.

OBJECTIVES: Curculigoside, a natural compound isolated from the medicinal plant Curculigo orchioides has been reported to prevent bone loss in ovariectomized rats. However, the underlying molecular mechanisms are largely unknown. This study investigated the effects of Curculigoside on proliferation and osteogenic differentiation of bone marrow stromal cells (BMSCs). METHODS: The toxicity, proliferation and osteogenic differentiation of BMSCs cultured with various concentrations (0 as control, 10, 100 and 500 microm) of Curculigoside were measured by viability assay, MTT analysis, alkaline phosphatase (ALP) activity assay, alizarin red staining and mineralization assay, real-time PCR analysis on osteogenic genes including ALP, type I collagen (Col I), osteocalcin (OCN) and osteoprotegerin (OPG), runt-related transcription factor 2 (Runx2), as well as OPG enzyme-linked immunosorbent assay. KEY FINDINGS: No significant cytotoxicity was observed for BMSCs after supplementation with Curculigoside. The proliferation of BMSCs was enhanced after administration of Curculigoside, especially 100 microm Curculigoside. Moreover, the osteogenic gene expression was significantly enhanced with 100 microm Curculigoside treatment. Importantly, Curculigoside significantly increased OPG secretion. CONCLUSIONS: The data indicate that Curculigoside could promote BMSC proliferation and induce osteogenic differentiation of BMSCs. The most profound response was observed with 100 microm Curculigoside. These findings may be valuable for understanding the mechanism of the effect of Curculigoside on bone, especially in relation to osteoporosis.

Effects of Curculigoside on Memory Impairment and Bone Loss via Anti-Oxidative Character in APP/PS1 Mutated Transgenic Mice.[Pubmed:26186010]

PLoS One. 2015 Jul 17;10(7):e0133289.

Alzheimer's disease (AD) and osteoporosis are two closely related multifactorial progressively degenerative diseases that predominantly affect aged people. These two diseases share many common risk factors, including old age, being female, smoking, excessive drinking, low estrogen, and vitamin D3 levels. Additionally, oxidative damage and the dysfunction of the antioxidant system play important roles in the pathogenesis of osteoporosis and AD. Abeta not only leads to impaired memory but also plays a crucial role in the demineralization process of bone tissues of older people and women with menopause. Curculigoside can promote calcium deposition and increase the levels of ALP and Runx2 in osteoblasts under oxidative stress via anti-oxidative character. Therefore, we investigated the effects of CUR on the spatial learning and memory by the Morris water maze and brain immunohistochemistry, and bone microstructure and material properties of femurs by micro-computed tomography and mechanical testing in APP/PS1 mutated transgenic mice. Oral administration of CUR can significantly enhance learning performance and ameliorate bone loss in APP/PS1 mutated transgenic mice, and the mechanism may be related to its antioxidant effect. Based on these results, CUR has real potential as a new natural resource for developing medicines or dietary supplements for the prevention and treatment of the two closely linked multifactorial progressive degenerative disorders, AD and osteoporosis.

Ameliorative effects of curculigoside from Curculigo orchioides Gaertn on learning and memory in aged rats.[Pubmed:22922281]

Molecules. 2012 Aug 24;17(9):10108-18.

This study was designed to evaluate the ameliorating effects of Curculigoside from Curculigo orchioides Gaertn on learning and memory in aged rats. In the present study, the ameliorating effects of Curculigoside were determined through animal behaviour studies (including step-down test and Y-maze test), and the possible mechanisms were explored by evaluation of the activity of acetylcholinesterase (AchE) and determination of the expression of BACE1. Oral adminstration of the Curculigoside (20, 40 mg/kg/day) for 14 days can significantly improve the latency and number of errors in aged rats based on the behaviour study results. In addition, the activity of AchE can be decreased by treatment of the Curculigoside (10, 20, 40 mg/kg/day). Moreover, the expression of BACE1 can be down-regulated in the hippocampus of aged rats treated with Curculigoside. The results of our present work have indicated that Curculigoside can improve cognitive function in aged animals, possibly by decreasing the activity of AchE in the cerebra and inhibiting the expression of BACE1 in the hippocampus. In conclusion, our results suggested that Curculigoside can be possible developed as a new drug for the treatment of Alzheimer's disease in the future.

The effect of curculigoside on the expression of matrix metalloproteinase-1 in cultured human skin fibroblasts.[Pubmed:19898807]

Arch Pharm Res. 2009 Oct;32(10):1433-9.

The dried rhizomes of Curculigo orchioides G. yielded two phenolic glycosides, Curculigoside (1), orcinol-beta-D-glucoside (4), and two cycloartane saponins, curculigosaponin G (2), curculigosaponin I (3). The structures were determined using spectroscopic methods. Among these isolates, compound 1 exhibited potent inhibitory activity against matrix metalloproteinase-1 in cultured human skin fibroblasts. In addition, it increased the level of Bcl-2 protein expression and decreased the level of Bax protein expression. Compound 4 was isolated from this plant for the first time.

Description

Curculigoside is the main saponin in C. orchioide, exerts significant antioxidant, anti-osteoporosis, antidepressant and neuroprotection effects. Curculigoside possesses significant anti-arthritic effects in vivo and in vitro via regulation of the JAK/STAT/NF-κB signaling pathway.

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