Protodioscin

CAS# 55056-80-9

Protodioscin

2D Structure

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Protodioscin

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Chemical Properties of Protodioscin

Cas No. 55056-80-9 SDF Download SDF
PubChem ID 441891 Appearance White powder
Formula C51H84O22 M.Wt 1049.21
Type of Compound Steroids Storage Desiccate at -20°C
Solubility H2O : 50 mg/mL (47.66 mM; Need ultrasonic)
DMSO : 50 mg/mL (47.66 mM; Need ultrasonic)
SMILES CC1C2C(CC3C2(CCC4C3CC=C5C4(CCC(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)C)O)O)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)OC1(CCC(C)COC9C(C(C(C(O9)CO)O)O)O)O
Standard InChIKey LVTJOONKWUXEFR-UEZXSUPNSA-N
Standard InChI InChI=1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/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 Protodioscin

1 Smilax sp. 2 Tribulus sp.

Biological Activity of Protodioscin

DescriptionProtodioscin has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties. It appears to possess aphrodisiac activity probably due to its androgen increasing property, it will be useful in developing health food supplement(s) and/or drug(s) against hyperlipidemia.
TargetsAndrogen Receptor

Protodioscin Dilution Calculator

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Protodioscin Molarity Calculator

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Preparing Stock Solutions of Protodioscin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.9531 mL 4.7655 mL 9.531 mL 19.062 mL 23.8275 mL
5 mM 0.1906 mL 0.9531 mL 1.9062 mL 3.8124 mL 4.7655 mL
10 mM 0.0953 mL 0.4765 mL 0.9531 mL 1.9062 mL 2.3827 mL
50 mM 0.0191 mL 0.0953 mL 0.1906 mL 0.3812 mL 0.4765 mL
100 mM 0.0095 mL 0.0477 mL 0.0953 mL 0.1906 mL 0.2383 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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Background on Protodioscin

Protodioscin, a major steroidal saponin in dioscoreae rhizome, has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties.

In Vivo:Protodioscin (5 and 10 mg/kg) significantly improves glucose intolerance and reduced the levels of serum UA, BUN, Cr, TC and TG. Protodioscin significantly reduces renal concentrations of IL-1β, IL-6 and TNF-α by inhibiting the activation of nuclear factor-κB, c-Jun N-terminal kinase, p38 mitogen-activated protein kinase and extracellular signal-regulated kinase[1]. Protodioscin ameliorates the death rate, inhibits the increase in neurological deficit scores and infarct volume, and reduces the apoptotic nerve cells induced by MCAO in rats. Protodioscin attenuates the change of relevant apoptins, suppresses the release of pro-inflammatory cytokines in serum and reverses the protein expression of NF-κB (in nucleus and cytoplasm) and IκBα (in cytoplasm) induced by MCAO in rats[2]. Protodioscin (0.5 mg/kg, i.p.) increases the coagulation time by appr 50 % as compared to that of high-fat diet control rats. Protodioscin possesses a promising effect in lowering the blood levels of both lipoproteins, especially LDL, thus resulting in a high ratio of HDL/LDL[3].

References:
[1]. Shen J, et al. Protodioscin ameliorates fructose-induced renal injury via inhibition of the mitogen activated protein kinase pathway. Phytomedicine. 2016 Nov 15;23(12):1504-1510. [2]. Zhang X, et al. Potential neuroprotection of protodioscin against cerebral ischemia-reperfusion injury in rats through intervening inflammation and apoptosis. Steroids. 2016 Sep;113:52-63. [3]. Wang T, et al. Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica. Planta Med. 2010 Oct;76(15):1642-6.

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References on Protodioscin

Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panel.[Pubmed:11988850]

Planta Med. 2002 Apr;68(4):297-301.

Protodioscin (NSC-698 796) is a furostanol saponin isolated from the rhizome of Dioscorea collettii var. hypoglauca (Dioscoreaceae), a Chinese herbal remedy for the treatment of cervical carcinoma, carcinoma of urinary bladder and renal tumor for centuries. To systematically evaluate its potential anticancer activity, Protodioscin was tested for cytotoxicity in vitro against 60 human cancer cell lines in the NCI's (National Cancer Institute, USA) anticancer drug screen. As a result, Protodioscin was cytotoxic against most cell lines from leukemia and solid tumors in the NCI's human cancer panel, especially selectively against one leukemia line (MOLT-4), one NSCLC line (A549/ATCC), two colon cancer lines (HCT-116 and SW-620), one CNS cancer line (SNB-75), one melanoma line (LOX IMVI), and one renal cancer line (786 - 0) with GI50 < or = 2.0 microM. In the general view of mean graphs, leukemia, colon cancer and prostate cancer are the most sensitive subpanels, while ovarian cancer is the least sensitive subpanel. Based on an analysis of COMPARE computer program with Protodioscin as a seed compound, no compounds in the NCI's anticancer drug screen database have cytotoxicity patterns (mean graphs) similar to those of Protodioscin, indicating that a potential novel mechanism of anticancer action is involved.

A comparative tissue-specific metabolite analysis and determination of protodioscin content in Asparagus species used in traditional Chinese medicine and Ayurveda by use of laser microdissection, UHPLC-QTOF/MS and LC-MS/MS.[Pubmed:24737553]

Phytochem Anal. 2014 Nov-Dec;25(6):514-28.

INTRODUCTION: Asparagus is esteemed in Traditional Chinese Medicine and Ayurveda, and it is commercially one of the most important drugs in the global herbal market. Comparative metabolite profiling of different species would help in determining the similarities and ascertain their validity for being used as substitutes for each other. Laser microdissection (LMD) facilitates identification of metabolites in specific tissues, and thus it can aid in exploration of metabolic pathways in target tissues. OBJECTIVE: To compare tissue-specific metabolites and Protodioscin content of Asparagus cochinchinensis (Lour.) Merr. and Asparagus racemosus Willd. used in China and India. METHODS: Metabolite analysis of laser-dissected tissues was carried out using UHPLC-QTOF/MS and LC-MS/MS. The Protodioscin contents were determined and the method was validated as per the International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use guidelines. RESULTS: Metabolite analysis reveals that the velamen tissue, among other tissues such as cortex, vascular bundles and pith, contained maximum components, specifically those belonging to the steroidal saponin class. Although the metabolite profiles were similar, the content of Protodioscin was found to be higher in Chinese than Indian species. CONCLUSION: The study provided a suitable methodology for metabolite profiling and Protodioscin content determination of Asparagus by use of LMD, UHPLC-QTOF/MS and LC-MS/MS. The similarities in metabolite profiles indicate that Asparagus species from India and China can serve as substitute for each other in various therapeutic and pharmaceutical applications.

Quantification of protodioscin and rutin in asparagus shoots by LC/MS and HPLC methods.[Pubmed:14518934]

J Agric Food Chem. 2003 Oct 8;51(21):6132-6.

A liquid chromatography/mass spectrometry (LC/MS) method with selected ion monitoring was developed and validated to analyze the contents of Protodioscin and rutin in asparagus. The distribution of rutin and Protodioscin within the shoots was found to vary by location, with the tissue closest to the rhizome found to be a rich source of Protodioscin, at an average level of 0.025% tissue fresh weight in the three tested lines, while the upper youngest shoot tissue contained the highest amount of rutin at levels of 0.03-0.06% tissue fresh weight. The lower portions of the asparagus shoots that are discarded during grading and processing should instead be considered a promising source of a new value-added nutraceutical product.

Antihyperlipidemic effect of protodioscin, an active ingredient isolated from the rhizomes of Dioscorea nipponica.[Pubmed:20509104]

Planta Med. 2010 Oct;76(15):1642-6.

Developing drugs against metabolic-related disorders, including obesity and hyperlipidemia, is of importance for human health. Here, a bioactive phytochemical, Protodioscin, isolated from the rhizomes of Dioscorea nipponica (Rhizoma Dioscoreae Nipponicae), was identified for its anti-hyperlipidemic effect. In hyperlipidemic rats, the post-administration of Protodioscin significantly reduced the time of blood coagulation. In addition, the blood levels of triglyceride, cholesterol, low-density and high-density lipoproteins were also changed accordingly. Taken together, this was the first report of an antihyperlipidemic effect of Protodioscin. Its great availability in various vegetables and medicinal plants will be useful in developing health food supplement(s) and/or drug(s) against hyperlipidemia.

Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats.[Pubmed:12127159]

Life Sci. 2002 Aug 9;71(12):1385-96.

Tribulus terrestris (TT) has long been used in the traditional Chinese and Indian systems of medicine for the treatment of various ailments and is popularly claimed to improve sexual functions in man. Sexual behaviour and intracavernous pressure (ICP) were studied in both normal and castrated rats to further understand the role of TT containing Protodioscin (PTN) as an aphrodisiac. Adult Sprague-Dawley rats were divided into five groups of 8 each that included distilled water treated (normal and castrated), testosterone treated (normal and castrated, 10 mg/kg body weight, subcutaneously, bi-weekly) and TT treated (castrated, 5 mg/kg body weight, orally once daily). Decreases in body weight, prostate weight and ICP were observed among the castrated groups of rats compared to the intact group. There was an overall reduction in the sexual behaviour parameters in the castrated groups of rats as reflected by decrease in mount and intromission frequencies (MF and IF) and increase in mount, intromission, ejaculation latencies (ML, IL, EL) as well as post-ejaculatory interval (PEI). Compared to the castrated control, treatment of castrated rats (with either testosterone or TT extract) showed increase in prostate weight and ICP that were statistically significant. There was also a mild to moderate improvement of the sexual behaviour parameters as evidenced by increase in MF and IF; decrease in ML, IL and PEI. These results were statistically significant. It is concluded that TT extract appears to possess aphrodisiac activity probably due to androgen increasing property of TT (observed in our earlier study on primates).

Description

Protodioscin, a major steroidal saponin in dioscoreae rhizome, has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties.

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