Natural product from Panax notoginseng.

Seven compounds were isolated from the leaves of Panax japonicus var. major by chromatographic methods including silica gel, Sephadex LH-20, ODS and semi-preparative HPLC. Their structures were elucidated by their physical and chemical properties and spectral data analysis as 5, 7-dihydroxy-8-methoxyl flavone (1), ginsenoside Rs2 (2), quinquenoside R1 (3), ginsenoside Rs1 (4), notoginsenoside Fe (5), ginsenoside Rd2 (6) and gypenosiden IX (7). Among them, compound 1 was obtained from the Panax genus for the first time, and compounds 2-7 were isolated from this plant for the first time. [1]

[1]. Development of a method to screen and isolate potential xanthine oxidase inhibitors from Panax japlcus var via ultrafiltration liquid chromatography combined with counter-current chromatography. Talanta. 2015 Mar;134:665-73.

[2]. Chemical constituents of leaves of Panax japonicus var. major. Zhongguo Zhong Yao Za Zhi. 2014 May;39(9):1635-8.

Panax notoginseng saponin Fe is a triterpenoid compound. It has been reported that Panax notoginseng saponin Fe exists in ginseng (Panax japonicus), and related data have been reported. Ginseng (Panax japlcus var.) is a typical traditional Chinese medicine, and its various parts contain a large amount of saponins. Currently used methods for saponin screening and separation are mostly time-consuming and labor-intensive. This study developed a new method based on ultrafiltration-liquid chromatography-mass spectrometry (UF-LC-MS) for the rapid screening and identification of xanthine oxidase ligands in ginseng extracts. Six xanthine oxidase inhibitors were identified from the extract. Subsequently, high-speed countercurrent chromatography (HSCCC) was used to separate the specifically bound ligands, namely 24(R)-maleicin R1, sago saponin IVa, oleanolic acid-28-O-β-D-glucopyranoside, notoginsenoside Fe, ginsenoside Rb2, and ginsenoside Rd (with purities of 95.74%, 96.12%, 93.19%, 94.83%, 95.07%, and 94.62%, respectively). The component ratios of the HSCCC solvent system were calculated and optimized using a multi-exponential function model. Using the partition coefficient (K) value and peak resolution of the target compounds as research indicators, the flow rates of the solvent system and mobile phase in the two-stage separation were optimized using exponential functions and binomial formulas. This study used an optimized two-phase solvent system. The first phase consisted of ethyl acetate, isopropanol, and 0.1% formic acid aqueous solution (volume ratio 1.9:1.0:1.3), and the second phase consisted of dichloromethane, acetonitrile, isopropanol, and 0.1% formic acid aqueous solution (volume ratio 5.6:1.0:2.4:5.2) to separate six compounds from Japanese aster (P. japlcus). The target compounds were separated, collected, and purified by high-speed countercurrent chromatography (HSCCC) and analyzed by ultra-high performance liquid chromatography (UPLC). The chemical structures of all six compounds were identified by ultraviolet spectroscopy (UV), mass spectrometry (MS), and nuclear magnetic resonance (NMR). The results showed that ultrafiltration liquid chromatography-mass spectrometry (UF-LC-MS) combined with high-speed countercurrent chromatography (HSCCC) can not only serve as a powerful tool for screening and separating xanthine oxidase inhibitors in complex samples, but also provide a useful platform for discovering bioactive compounds for the prevention and treatment of gout. [1]

C47H80O17

917.1279

916.539

88105-29-7

90657714

Light yellow to yellow solid powder

1.4±0.1 g/cm3

994.1±65.0 °C at 760 mmHg

555.0±34.3 °C

0.0±0.6 mmHg at 25°C

1.607

5.61

11

17

13

64

1630

24

CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H](O7)CO)O)O)O)O)O)C

MYBAONSAUGZRAX-UBQYYSLZSA-N

InChI=1S/C47H80O17/c1-22(2)10-9-14-47(8,64-42-39(58)36(55)34(53)27(62-42)21-59-40-37(56)33(52)26(20-49)60-40)23-11-16-46(7)31(23)24(50)18-29-44(5)15-13-30(43(3,4)28(44)12-17-45(29,46)6)63-41-38(57)35(54)32(51)25(19-48)61-41/h10,23-42,48-58H,9,11-21H2,1-8H3/t23-,24+,25+,26-,27+,28-,29+,30-,31-,32+,33-,34+,35-,36-,37+,38+,39+,40+,41-,42-,44-,45+,46+,47-/m0/s1

(2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Notoginsenoside Fe; 88105-29-7; DTXSID201316004; RefChem:1092605; DTXCID201745881;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ~50 mg/mL (~54.52 mM)
DMSO :< 1 mg/mL

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)