Amygdalin CAS NO.29883-15-6

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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.

Chemical Properties of Amygdalin

Cas No.	29883-15-6
PubChem ID	656516	Appearance	White powder
Formula	C20H27NO11	M.Wt	457.4
Type of Compound	Phenols	Storage	Desiccate at -20°C
Synonyms	Amygdaloside; Mandelonitrile β-gentiobioside
Solubility	DMSO : ≥ 75 mg/mL (163.96 mM) *"≥" means soluble, but saturation unknown.
Chemical Name	(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
SMILES	C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O
Standard InChIKey	XUCIJNAGGSZNQT-JHSLDZJXSA-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 Amygdalin

1 Prunus sp. 2 Sorbus sp.

Biological Activity of Amygdalin

Description	Amygdalin has antifibrotic, antitumor, anti-inflammatory and analgesic effects, amygdalin joint HSYA could inhibit the degeneration of the endplate chondrocytes derived from intervertebral discs of rats induced by IL-1beta and better than the single use of Amygdalin or HSYA. Amygdalin induces apoptotic cell death in human DU145 and LNCaP prostate cancer cells by caspase-3 activation through down-regulation of Bcl-2 and up-regulation of Bax.
Targets	TGF-β/Smad | Caspase | Bcl-2/Bax | COX | NOS | PGE
In vitro	Advanced research on anti-tumor effects of amygdalin.[Pubmed: 25207888] J Cancer Res Ther. 2014 Aug;10 Suppl 1:3-7. Malignant tumors are the major disease that cause serious damage to human health, and have been listed as the premier diseases which seriously threatened human health by World Health Organization (WHO). In recent years the development of antitumor drugs has been gradually transformed from cytotoxic drugs to improving the selectivity of drugs, overcoming multidrug resistance, development of new targeted drugs and low toxicity with high specificity drugs. Amygdalin is a natural product that owns antitumor activity, less side effects, widely sourced and relatively low priced. All these features make the Amygdalin a promising antitumor drugs, if combined with conditional chemotherapy drugs, which can produce synergistic effect. CONCLUSIONS: In this paper, we summarized the pharmacological activity, toxicity and antitumor activity of Amygdalin, mainly focused on the advanced research of Amygdalin on its antitumor effects in recent years, providing new insights for the development of new anticancer drugs, new targets searching and natural antitumor mechanism investigations. Amygdalin suppresses lipopolysaccharide-induced expressions of cyclooxygenase-2 and inducible nitric oxide synthase in mouse BV2 microglial cells.[Pubmed: 17359643 ] Neurol Res. 2007;29 Suppl 1:S59-64. Amygdalin (D-mandelonitrile-beta-D-gentiobioside) is a cynogenic compound found in sweet and bitter almonds, Persicae semen and Armeniacae semen. Amygdalin has been used for the treatment of cancers and for the relief of the pain. We made an aqueous extraction of Amygdalin from Armeniacae semen. In this study, the effect of Amygdalin on the lipopolysaccharide (LPS)-induced inflammation was investigated. METHODS AND RESULTS: The effects of Amygdalin extracted from Armeniacae semen on the LPS-stimulated mRNA expressions of cyclooxygenase (COX)-1, COX-2 and inducible nitric oxide synthase (iNOS) in the mouse BV2 microglial cells were investigated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, reverse transcription-polymerase chain reaction (RT-PCR). The effects of Amygdalin on the prostaglandins E(2) synthesis and the nitric oxide production were also studied by performing prostaglandins E(2) immunoassay and by detecting nitric oxide. The present results showed that Amygdalin suppressed the prostaglandin E(2) synthesis and the nitric oxide production by inhibiting the LPS-stimulated mRNA expressions of COX-2 and iNOS in the mouse BV2 cells. CONCLUSIONS: These results show that Amygdalin exerts anti-inflammatory and analgesic effects and it dose so probably by suppressing the mRNA expressions of COX-2 and iNOS.
In vivo	Amygdalin inhibits renal fibrosis in chronic kidney disease.[Pubmed: 23525378] Mol Med Rep. 2013 May;7(5):1453-7. Renal interstitial fibrosis is a common outcome of chronic renal diseases. Amygdalin is one of a number of nitrilosides, the natural cyanide?containing substances abundant in the seeds of plants of the prunasin family that are used to treat cancer and relieve pain. However, whether Amygdalin inhibits the progression of renal fibrosis or not remains unknown. The present study aimed to assess the therapeutic potential of Amygdalin by investigating its effect and potential mechanism on the activation of renal interstitial fibroblast cells and renal fibrosis in rat unilateral ureteral obstruction (UUO). METHODS AND RESULTS: Treatment of the cultured renal interstitial fibroblasts with Amygdalin inhibited their proliferation and the production of transforming growth factor (TGF)?β1. In the rat model of obstructive nephropathy, following ureteral obstruction, the administration of Amygdalin immediately eliminated the extracellular matrix accumulation and alleviated the renal injury on the 21st day. Collectively, Amygdalin attenuated kidney fibroblast (KFB) activation and rat renal interstitial fibrosis. CONCLUSIONS: These results indicate that Amygdalin is a potent antifibrotic agent that may have therapeutic potential for patients with fibrotic kidney diseases.

Protocol of Amygdalin

Cell Research

Amygdalin induces apoptosis in human cervical cancer cell line HeLa cells.[Pubmed: 23137229] The synergistic effect of amygdalin and HSYA on the IL-1beta induced endplate chondrocytes of rat intervertebral discs.[Pubmed: 25322555] Yao Xue Xue Bao. 2014 Aug;49(8):1136-42. The effect of Amygdalin joint hydroxysafflor yellow A (HSYA) on the endplate chondrocytes derived from intervertebral discs of rats induced by IL-1beta and the possible mechanism were studied and explored. METHODS AND RESULTS: Chondrocytes were obtained from endplate of one-month SD rat intervertebral discs and cultured primary endplate chondrocytes. After identification, they were divided into normal group, induced group, Amygdalin group, HSYA group and combined group. CCK-8 kit was adopted to detect the proliferation of the endplate chondrocytes. FCM was measured to detect the apoptosis. Real-time PCR method was adopted to observe the mRNA expression of Aggrecan, Col 2 alpha1, Col 10 alpha1, MMP-13 and the inflammatory cytokines IL-1beta. The protein expression of Col II, Col X was tested through immunofluorescence. Compared with the normal group, the proliferation of the endplate chondrocytes decreased while the apoptosis increased (P < 0.05). With down regulation of the mRNA expressions of Aggrecan, Col 2 alpha1 and up regulation of the mRNA expressions of Col 10 alpha1, MMP-13, IL-1beta (P < 0.05), the protein expression of Col II decreased while the protein expression of Col X increased. Compared with the induced group, Amygdalin group, HSYA group, the combined group could inhibit the apoptosis and promote the proliferation (P < 0.05). They could increase the mRNA expressions of Aggrecan and Col 2 alpha1 while decrease the mRNA expressions of Col 10 alpha1, MMP-13 and IL-1beta (P < 0.05). They could also enhance the protein expression of Col II while reduce the protein expression of Col X. The effect of the combined group was significantly better than that of Amygdalin and HSYA. CONCLUSIONS: Amygdalin joint HSYA could inhibit the degeneration of the endplate chondrocytes derived from intervertebral discs of rats induced by IL-1beta and better than the single use of Amygdalin or HSYA. Immunopharmacol Immunotoxicol. 2013 Feb;35(1):43-51. Amygdalin, a naturally occurring substance, has been suggested to be efficacious as an anticancer substance. The effect of Amygdalin on cervical cancer cells has never been studied. METHODS AND RESULTS: In this study, we found that the viability of human cervical cancer HeLa cell line was significantly inhibited by Amygdalin. 4,6-Diamino-2-phenyl indole (DAPI) staining showed that Amygdalin-treated HeLa cells developed typical apoptotic changes. The development of apoptosis in the Amygdalin-treated HeLa cells were confirmed by double staining of Amygdalin-treated HeLa cells with annexin V-FITC and propidium iodide (PI) along with increase in caspase-3 activity in these cells. Further studies indicated that antiapoptotic protein Bcl-2 was downregulated whereas proapoptotic Bax protein was upregulated in the Amygdalin-treated HeLa cells implying involvement of the intrinsic pathway of apoptosis. In vivo, Amygdalin administration inhibited the growth of HeLa cell xenografts through a mechanism of apoptosis. CONCLUSIONS: The results in the present study suggest that Amygdalin may offer a new therapeutic option for patients with cervical cancer.

Preparing Stock Solutions of Amygdalin

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.1863 mL	10.9314 mL	21.8627 mL	43.7254 mL	54.6568 mL
5 mM	0.4373 mL	2.1863 mL	4.3725 mL	8.7451 mL	10.9314 mL
10 mM	0.2186 mL	1.0931 mL	2.1863 mL	4.3725 mL	5.4657 mL
50 mM	0.0437 mL	0.2186 mL	0.4373 mL	0.8745 mL	1.0931 mL
100 mM	0.0219 mL	0.1093 mL	0.2186 mL	0.4373 mL	0.5466 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 Amygdalin

Amygdalin induces apoptosis in human cervical cancer cell line HeLa cells.[Pubmed:23137229]

Immunopharmacol Immunotoxicol. 2013 Feb;35(1):43-51.

Amygdalin, a naturally occurring substance, has been suggested to be efficacious as an anticancer substance. The effect of Amygdalin on cervical cancer cells has never been studied. In this study, we found that the viability of human cervical cancer HeLa cell line was significantly inhibited by Amygdalin. 4,6-Diamino-2-phenyl indole (DAPI) staining showed that Amygdalin-treated HeLa cells developed typical apoptotic changes. The development of apoptosis in the Amygdalin-treated HeLa cells were confirmed by double staining of Amygdalin-treated HeLa cells with annexin V-FITC and propidium iodide (PI) along with increase in caspase-3 activity in these cells. Further studies indicated that antiapoptotic protein Bcl-2 was downregulated whereas proapoptotic Bax protein was upregulated in the Amygdalin-treated HeLa cells implying involvement of the intrinsic pathway of apoptosis. In vivo, Amygdalin administration inhibited the growth of HeLa cell xenografts through a mechanism of apoptosis. The results in the present study suggest that Amygdalin may offer a new therapeutic option for patients with cervical cancer.

Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCaP prostate cancer cells.[Pubmed:16880611]

Biol Pharm Bull. 2006 Aug;29(8):1597-602.

Prostate cancer is one of the most common non-skin cancers in men. Amygdalin is one of the nitrilosides, natural cyanide-containing substances abundant in the seeds of plants of the prunasin family that have been used to treat cancers and relieve pain. In particular, D-Amygdalin (D-mandelonitrile-beta-D-gentiobioside) is known to exhibit selective killing effect on cancer cells. Apoptosis, programmed cell death, is an important mechanism in cancer treatment. In the present study, we prepared the aqueous extract of the Amygdalin from Armeniacae semen and investigated whether this extract induces apoptotic cell death in human DU145 and LNCaP prostate cancer cells. In the present results, DU145 and LNCaP cells treated with Amygdalin exhibited several morphological characteristics of apoptosis. Treatment with Amygdalin increased expression of Bax, a pro-apoptotic protein, decreased expression of Bcl-2, an anti-apoptotic protein, and increased caspase-3 enzyme activity in DU145 and LNCaP prostate cancer cells. Here, we have shown that Amygdalin induces apoptotic cell death in human DU145 and LNCaP prostate cancer cells by caspase-3 activation through down-regulation of Bcl-2 and up-regulation of Bax. The present study reveals that Amygdalin may offer a valuable option for the treatment of prostate cancers.

Amygdalin suppresses lipopolysaccharide-induced expressions of cyclooxygenase-2 and inducible nitric oxide synthase in mouse BV2 microglial cells.[Pubmed:17359643]

Neurol Res. 2007;29 Suppl 1:S59-64.

BACKGROUND: Amygdalin (D-mandelonitrile-beta-D-gentiobioside) is a cynogenic compound found in sweet and bitter almonds, Persicae semen and Armeniacae semen. Amygdalin has been used for the treatment of cancers and for the relief of the pain. We made an aqueous extraction of Amygdalin from Armeniacae semen. In this study, the effect of Amygdalin on the lipopolysaccharide (LPS)-induced inflammation was investigated. METHODS: The effects of Amygdalin extracted from Armeniacae semen on the LPS-stimulated mRNA expressions of cyclooxygenase (COX)-1, COX-2 and inducible nitric oxide synthase (iNOS) in the mouse BV2 microglial cells were investigated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, reverse transcription-polymerase chain reaction (RT-PCR). The effects of Amygdalin on the prostaglandins E(2) synthesis and the nitric oxide production were also studied by performing prostaglandins E(2) immunoassay and by detecting nitric oxide. RESULTS: The present results showed that Amygdalin suppressed the prostaglandin E(2) synthesis and the nitric oxide production by inhibiting the LPS-stimulated mRNA expressions of COX-2 and iNOS in the mouse BV2 cells. CONCLUSION: These results show that Amygdalin exerts anti-inflammatory and analgesic effects and it dose so probably by suppressing the mRNA expressions of COX-2 and iNOS.

Amygdalin inhibits renal fibrosis in chronic kidney disease.[Pubmed:23525378]

Mol Med Rep. 2013 May;7(5):1453-7.

Renal interstitial fibrosis is a common outcome of chronic renal diseases. Amygdalin is one of a number of nitrilosides, the natural cyanidecontaining substances abundant in the seeds of plants of the prunasin family that are used to treat cancer and relieve pain. However, whether Amygdalin inhibits the progression of renal fibrosis or not remains unknown. The present study aimed to assess the therapeutic potential of Amygdalin by investigating its effect and potential mechanism on the activation of renal interstitial fibroblast cells and renal fibrosis in rat unilateral ureteral obstruction (UUO). Treatment of the cultured renal interstitial fibroblasts with Amygdalin inhibited their proliferation and the production of transforming growth factor (TGF)beta1. In the rat model of obstructive nephropathy, following ureteral obstruction, the administration of Amygdalin immediately eliminated the extracellular matrix accumulation and alleviated the renal injury on the 21st day. Collectively, Amygdalin attenuated kidney fibroblast (KFB) activation and rat renal interstitial fibrosis. These results indicate that Amygdalin is a potent antifibrotic agent that may have therapeutic potential for patients with fibrotic kidney diseases.

[The synergistic effect of amygdalin and HSYA on the IL-1beta induced endplate chondrocytes of rat intervertebral discs].[Pubmed:25322555]

Yao Xue Xue Bao. 2014 Aug;49(8):1136-42.

The effect of Amygdalin joint hydroxysafflor yellow A (HSYA) on the endplate chondrocytes derived from intervertebral discs of rats induced by IL-1beta and the possible mechanism were studied and explored. Chondrocytes were obtained from endplate of one-month SD rat intervertebral discs and cultured primary endplate chondrocytes. After identification, they were divided into normal group, induced group, Amygdalin group, HSYA group and combined group. CCK-8 kit was adopted to detect the proliferation of the endplate chondrocytes. FCM was measured to detect the apoptosis. Real-time PCR method was adopted to observe the mRNA expression of Aggrecan, Col 2 alpha1, Col 10 alpha1, MMP-13 and the inflammatory cytokines IL-1beta. The protein expression of Col II, Col X was tested through immunofluorescence. Compared with the normal group, the proliferation of the endplate chondrocytes decreased while the apoptosis increased (P < 0.05). With down regulation of the mRNA expressions of Aggrecan, Col 2 alpha1 and up regulation of the mRNA expressions of Col 10 alpha1, MMP-13, IL-1beta (P < 0.05), the protein expression of Col II decreased while the protein expression of Col X increased. Compared with the induced group, Amygdalin group, HSYA group, the combined group could inhibit the apoptosis and promote the proliferation (P < 0.05). They could increase the mRNA expressions of Aggrecan and Col 2 alpha1 while decrease the mRNA expressions of Col 10 alpha1, MMP-13 and IL-1beta (P < 0.05). They could also enhance the protein expression of Col II while reduce the protein expression of Col X. The effect of the combined group was significantly better than that of Amygdalin and HSYA. Amygdalin joint HSYA could inhibit the degeneration of the endplate chondrocytes derived from intervertebral discs of rats induced by IL-1beta and better than the single use of Amygdalin or HSYA.

Advanced research on anti-tumor effects of amygdalin.[Pubmed:25207888]

J Cancer Res Ther. 2014 Aug;10 Suppl 1:3-7.

Malignant tumors are the major disease that cause serious damage to human health, and have been listed as the premier diseases which seriously threatened human health by World Health Organization (WHO). In recent years the development of antitumor drugs has been gradually transformed from cytotoxic drugs to improving the selectivity of drugs, overcoming multidrug resistance, development of new targeted drugs and low toxicity with high specificity drugs. Amygdalin is a natural product that owns antitumor activity, less side effects, widely sourced and relatively low priced. All these features make the Amygdalin a promising antitumor drugs, if combined with conditional chemotherapy drugs, which can produce synergistic effect. In this paper, we summarized the pharmacological activity, toxicity and antitumor activity of Amygdalin, mainly focused on the advanced research of Amygdalin on its antitumor effects in recent years, providing new insights for the development of new anticancer drugs, new targets searching and natural antitumor mechanism investigations.

Description

Amygdalin is a plant glucoside isolated from the stones of rosaceous fruits, such as apricots, peaches, almond, cherries, and plums.

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