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Methyl protogracillin

CAS# 54522-53-1

Methyl protogracillin

Catalog No. BCN8177----Order now to get a substantial discount!

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Quality Control of Methyl protogracillin

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Chemical structure

Methyl protogracillin

3D structure

Chemical Properties of Methyl protogracillin

Cas No. 54522-53-1 SDF Download SDF
PubChem ID 171348 Appearance Powder
Formula C52H86O23 M.Wt 1079.24
Type of Compound Steroids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3R,4R,5R,6S)-2-[(2R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-methoxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
SMILES CC1C2C(CC3C2(CCC4C3CC=C5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)OC7C(C(C(C(O7)CO)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)OC
Standard InChIKey LOSNTJHBTWBJCC-OOVOOHTRSA-N
Standard InChI InChI=1S/C52H86O23/c1-21(20-67-46-41(63)39(61)35(57)30(17-53)70-46)9-14-52(66-6)22(2)33-29(75-52)16-28-26-8-7-24-15-25(10-12-50(24,4)27(26)11-13-51(28,33)5)69-49-45(74-47-42(64)38(60)34(56)23(3)68-47)44(37(59)32(19-55)72-49)73-48-43(65)40(62)36(58)31(18-54)71-48/h7,21-23,25-49,53-65H,8-20H2,1-6H3/t21-,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+,52-/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 Methyl protogracillin

The roots of Dioscorea opposita Thunb.

Biological Activity of Methyl protogracillin

Description1. Methyl protoneogracillin can cause morphological abnormality of Pyricularia oryzae mycelia. 2. Methyl protoneogracillin shows cytotoxic activitiy against the cancer cell line of K562 in vitro as antineoplastic agents.
TargetsAntifection

Methyl protogracillin Dilution Calculator

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Methyl protogracillin Molarity Calculator

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Preparing Stock Solutions of Methyl protogracillin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.9266 mL 4.6329 mL 9.2658 mL 18.5316 mL 23.1644 mL
5 mM 0.1853 mL 0.9266 mL 1.8532 mL 3.7063 mL 4.6329 mL
10 mM 0.0927 mL 0.4633 mL 0.9266 mL 1.8532 mL 2.3164 mL
50 mM 0.0185 mL 0.0927 mL 0.1853 mL 0.3706 mL 0.4633 mL
100 mM 0.0093 mL 0.0463 mL 0.0927 mL 0.1853 mL 0.2316 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 Methyl protogracillin

The cytotoxicity of methyl protoneogracillin (NSC-698793) and gracillin (NSC-698787), two steroidal saponins from the rhizomes of Dioscorea collettii var. hypoglauca, against human cancer cells in vitro.[Pubmed:12820229]

Phytother Res. 2003 Jun;17(6):620-6.

In our continuous studies of anticancer activity of steroidal saponins from the rhizomes of Dioscorea collettii var. hypoglauca (Dioscoreaceae), methyl protoneogracillin (NSC-698793) and gracillin (NSC-698787) were tested for cytotoxicity against human cancer cell lines from leukemia and eight solid tumor diseases. As a result, methyl protoneogracillin was cytotoxic against all the test cell lines with GI(50) < 100 micro M, especially selectively against two leukemia lines (CCRF-CEM and RPMT-8226), one colon cancer line (KM12), two central nervous system (CNS) cancer lines (SF-539 and U251), one melanoma line (M14), one renal cancer line (786-0), one prostate cancer line (DU-145), and one breast cancer line (MDA-MB-435), with GI(50) < or = 2.0 micro M. Leukemia, CNS cancer, and prostate cancer were the most sensitive subpanels, while ovarian cancer was the least sensitive subpanels. The preliminary toxicity studies showed that the maximum tolerant dose was 600 mg/kg for methyl protoneogracillin to mice. Gracillin was cytotoxic against most cell lines with GI(50), TGI and LC(50) at micromolar levels, but no activity against EKVX (non-small cell lung cancer), HT29 (colon cancer), OVCAR-5 (ovarian cancer), and SN12C (renal cancer). Based on structure-activity relationship, C-25 R/S con fi guration was critical for leukemia selectivity between methyl protoneogracillin and Methyl protogracillin. F-ring was critical to selectivity between furostanol (methyl protoneogracillin and Methyl protogracillin) and spirostanol (gracillin) saponins in this study. By an analysis of COMPARE software, no compounds in the NCI's database had similar mean graphs to those of methyl protoneogracillin and gracillin, respectively, indicating potential novel mechanism(s) of action involved. Put all in together, methyl protoneogracillin has been selected as a potential anticancer candidate for hollow fi ber assay to nude mice, but gracillin will not be pursued due to lack of selectivity against human cancer diseases.

Antineoplastic agents. II. Four furostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca.[Pubmed:17252340]

Planta Med. 1997 Apr;63(2):161-5.

During activity-guided fractionations to screen for antineoplastic agents, further studies by means of preparative HPLC led to the isolation of four known furostanol saponins: protoneodioscin, protodioscin, protoneogracillin, protogracillin, along with their corresponding artifacts: methyl protoneodioscin, methyl protodioscin, methyl protoneogracillin, and Methyl protogracillin, from the rhizomes of Dioscorea collettii var. hypoglauca. Among them, protoneodioscin, protodioscin, and protoneogracillin are first reported from the title plant. The structures of the compounds were established on the basis of chemical evidence and spectral analysis (1H-NMR, 13C-IMMR, 1H-1H COSY, HMQC, HMBC, and FAB-MS). These eight compounds all caused morphological abnormality of Pyricularia oryzae mycelia. They also showed cytotoxic activities against the cancer cell line of K562 in vitro as antineoplastic agents.

Description

Methyl protogracillin (NSC-698793), isolated from the roots of Dioscorea opposite Thunb, exhibits strong anti-cancer activity.

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