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Segetalin A

CAS# 161875-97-4

Segetalin A

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Quality Control of Segetalin A

Number of papers citing our products

Chemical structure

Segetalin A

3D structure

Chemical Properties of Segetalin A

Cas No. 161875-97-4 SDF Download SDF
PubChem ID 10483858 Appearance Powder
Formula C31H43N7O6 M.Wt 609.7
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,9S,12S,15S,18S)-12-(1H-indol-3-ylmethyl)-9-methyl-3,15-di(propan-2-yl)-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosane-2,5,8,11,14,17-hexone
SMILES CC1C(=O)NCC(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)N1)CC3=CNC4=CC=CC=C43)C(C)C)C(C)C
Standard InChIKey YVUZOKYOUUCVBV-WJTDBPPMSA-N
Standard InChI InChI=1S/C31H43N7O6/c1-16(2)25-30(43)35-22(13-19-14-32-21-10-7-6-9-20(19)21)28(41)34-18(5)27(40)33-15-24(39)36-26(17(3)4)31(44)38-12-8-11-23(38)29(42)37-25/h6-7,9-10,14,16-18,22-23,25-26,32H,8,11-13,15H2,1-5H3,(H,33,40)(H,34,41)(H,35,43)(H,36,39)(H,37,42)/t18-,22-,23-,25-,26-/m0/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 Segetalin A

The herbs of Vaccaria segetalis

Biological Activity of Segetalin A

Description1. Segetalin A has estrogen-like activity.
TargetsEstrogen receptor | Progestogen receptor

Segetalin A Dilution Calculator

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Segetalin A Molarity Calculator

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Preparing Stock Solutions of Segetalin A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6402 mL 8.2008 mL 16.4015 mL 32.803 mL 41.0038 mL
5 mM 0.328 mL 1.6402 mL 3.2803 mL 6.5606 mL 8.2008 mL
10 mM 0.164 mL 0.8201 mL 1.6402 mL 3.2803 mL 4.1004 mL
50 mM 0.0328 mL 0.164 mL 0.328 mL 0.6561 mL 0.8201 mL
100 mM 0.0164 mL 0.082 mL 0.164 mL 0.328 mL 0.41 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 Segetalin A

A sensitive and selective LC-MS/MS method for the quantitative determination of segetalin A from the plasma of rats.[Pubmed:26295277]

Biomed Chromatogr. 2016 Apr;30(4):606-11.

A sensitive and selective LC-MS/MS method was developed and validated for the determination and pharmacokinetic investigation of Segetalin A in rat plasma. Sample preparation was accomplished through a simple SPE procedure for the removal and preconcentration of the analyte and IS. Plasma samples were separated by HPLC on a Symmetry C18 column using a mobile phase consisting of methanol and 0.1% formic acid in water (70:30, v/v) with isocratic elution. The quantification was performed using multiple reaction monitoring with the transitions m/z 610.3 --> 511.2 for Segetalin A and m/z 779.4 --> 751.4 for IS, respectively. The calibration curve was linear over the range of 8.0-4000 ng/mL with a limit of quantitation (LOQ) of 8.0 ng/mL. This method was applied in a pharmacokinetic study of Segetalin A in rats. For intravenous (i.v.) administration, the plasma concentrations of Segetalin A decreased quickly (t1/2z, 1.31 +/- 0.341 h). For oral administration, the plasma concentrations of Segetalin A increased to a peak value at 1.50 +/- 0.577 h, followed by a gradual decrease to the LOQ in 12 h. The mean AUC values after i.v. and oral administration were 553 +/- 105 and 1482 +/- 110 ng h/mL, respectively.

Antiproliferative activity of Saponaria vaccaria constituents and related compounds.[Pubmed:22056663]

Fitoterapia. 2012 Jan;83(1):170-81.

Total methanolic extracts of Saponaria vaccaria seed derived from several varieties, as well as various purified components obtained through successive chromatographic separations of total extracts were evaluated for their growth inhibitory activity in WiDr (colon), MDA-MB-231 (breast), NCI-417 (lung) and PC-3 (prostate) human cancer cells as well as the non-tumorigenic fibroblast BJ (CRL-2522) cell line using MTT colorimetric assay. Purified bisdesmosidic saponins segetoside H and I were further examined using microscopy and apoptosis assays. Bisdesmosidic saponins exhibited dose-dependent growth inhibitory and selective apoptosis-inducing activity. Growth inhibitory effects were particularly strong in a breast (MDA-MB-231) and a prostate (PC-3) cancer cell line. Total extracts exhibited a different preference being most active against a colon cancer cell line (WiDr). In a comparison of varieties, all of the total seed extracts exhibited similar dose-dependent activities, but with some variation in potency. Monodesmosidic saponins vaccarosides A and B, phenolic vaccarin, and cyclopeptide Segetalin A, co-occurring seed substituents, did not exhibit activity. The non-tumorigenic fibroblast cell line BJ (CRL 2522) was growth inhibited but did not undergo apoptosis when treated with bisdesmosidic saponins at low micromolar concentrations. Saponin-rich extracts from Kochia scoparia seed and Chenopodium quinoa were also evaluated alongside Saponaria saponins but did not exhibit activity. Closely related Quillaja saponins exhibited activity but were less potent.

The biosynthesis of Caryophyllaceae-like cyclic peptides in Saponaria vaccaria L. from DNA-encoded precursors.[Pubmed:21554452]

Plant J. 2011 Aug;67(4):682-90.

Cyclic peptides (CPs) are produced in a very wide range of taxa. Their biosynthesis generally involves either non-ribosomal peptide synthases or ribosome-dependent production of precursor peptides. Plants within the Caryophyllaceae and certain other families produce CPs which generally consist of 5-9 proteinogenic amino acids. The biological roles for these CPs in the plant are not very clear, but many of them have activity in mammalian systems. There is currently very little known about the biosynthesis of CPs in the Caryophyllaceae. A collection of expressed sequence tags from developing seeds of Saponaria vaccaria was investigated for information about CP biosynthesis. This revealed genes that appeared to encode CP precursors which are subsequently cyclized to mature CPs. This was tested and confirmed by the expression of a cDNA encoding a putative precursor of the CP Segetalin A in transformed S. vaccaria roots. Similarly, extracts of developing S. vaccaria seeds were shown to catalyze the production of Segetalin A from the same putative (synthetic) precursor. Moreover, the presence in S. vaccaria seeds of two segetalins, J [cyclo(FGTHGLPAP)] and K [cyclo(GRVKA)], which was predicted by sequence analysis, was confirmed by liquid chromatography/mass spectrometry. Sequence analysis also predicts the presence of similar CP precursor genes in Dianthus caryophyllus and Citrus spp. The data support the ribosome-dependent biosynthesis of Caryophyllaceae-like CPs in the Caryophyllaceae and Rutaceae.

Application of high-speed counter-current chromatography for preparative separation of cyclic peptides from Vaccaria segetalis.[Pubmed:21396894]

J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Apr 1;879(11-12):811-4.

Following an initial clean-up step on silica gel, high-speed counter-current chromatography (HSCCC) was used to separate cyclic peptides from an extract of the seeds of Vaccaria segetalis. The two-phase solvent system used for HSCCC separation was composed of petroleum ether-ethyl acetate-methanol-water at an optimized volume ratio of 0.5:3.5:1:5. From 190 mg of crude extract, 38.0 mg of segetalin B and 28.5 mg of Segetalin A were obtained with purities of 98.1% and 95.6% as determined by HPLC, respectively. The chemical structures of the target compounds were confirmed by high resolution electrospray ionization time of flight MS (HRESI-TOF-MS) and (1)H NMR analyses.

Thionation of segetalins A and B, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis.[Pubmed:9113340]

Bioorg Med Chem. 1997 Mar;5(3):631-6.

Thionation of estrogen-like active cyclic peptides, segetalins A (1) and B (2), with Lawesson's reagent provided each two thiosegetalins; thioSegetalin A1 [Gly-1-psi(CS-NH)-Val-2; Trp-5-psi (CS-NH)-Ala-6]Segetalin A, thioSegetalin A2 [Gly-1-psi(CS-NH)-Val-2; Ala-6-psi(CS-NH)-Gly-1]Segetalin A, thiosegetalin B1 [Gly-1-psi (CS-NH)-Val-2; Ala-3-psi(CS-NH)-Trp-4]segetalin B, and thiosegetalin B2 [Gly-1-psi(CS-NH)-Val-2; Trp-4-psi(CS-NH)-Ala-1]segetalin B. ThioSegetalin A2 only showed estrogen-like activity against ovariectomized rats. On the basis of their conformations analysed by NMR experiments, the backbone conformation was considered to play an important role in estrogen-like activity for segetalins.

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