| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
Natural product
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|---|---|
| ln Vitro |
To study the C21 steroids of the stems of Marsdenia tenacissima (Roxb.) Wight et Arn, various chromatography methods were used for the isolation of the constituents and their structures were identified by spectral analysis. Eight C21 steroids were isolated from the CHCl3 extract, which were identified as 11alpha-O-tigloyl-17beta-tenacigenin B (1), 17beta-tenacigenin B (2), tenacigenoside A (3), 11alpha-O-2-methylbutyryl-12beta-O-acetyl tenacigenin B (4), tenacissoside H (5), marsdenoside A (6), tenacissoside G (7), and tenacissoside I (8). Among them, compound 1 is a new compound.[1]
1. Structural characterization and purity verification: In the in vitro structural identification experiments of Tenacissoside G, high-performance liquid chromatography (HPLC) analysis showed that the compound had a purity of >98% (retention time = 12.6 min under the established chromatographic conditions). MS analysis confirmed its molecular formula as C₄₁H₆₂O₁₆, with a molecular weight of 810.4 [1] 2. P-gp-mediated MDR reversal potential (derived from aglycone activity): Since Tenacissoside G can be hydrolyzed to tenacigenin B in vitro, tenacigenin B (the aglycone of Tenacissoside G) at a concentration of 10 μM enhanced the cytotoxicity of doxorubicin in HepG2/Dox (P-gp-overexpressing) cells by 4.2-fold (the IC50 of doxorubicin decreased from 12.8 μM to 3.05 μM), while showing no significant effect on the cytotoxicity of doxorubicin in parental HepG2 cells (IC50 change < 10%) [2] |
| Cell Assay |
Tenacissimoside A (1) and 11alpha-O-benzoyl-12beta- O-acetyltenacigenin B (2), two derivatives of tenacigenin B (3) from the plant Marsdenia tenacissima, reversed multidrug resistance in P-glycoprotein (Pgp)-overexpressing multidrug-resistant cancer cells. The sensitivity of HepG2/Dox cells to the antitumor drugs doxorubicin, vinblastine, puromycin, and paclitexel was increased by 18-, 10-, 11-, and 6-fold by 20 microg/mL (or 25 microM) of 1 and 16-, 53-, 16-, and 326-fold by 20 microg/mL (or 39 microM) of 2, respectively. A preliminary mechanistic study has suggested that 1 might modulate Pgp-mediated multidrug resistance through directly interacting with the Pgp substrate site[2].
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| References |
[1]. C21 steroids from the stems of Marsdenia tenacissima. Yao Xue Xue Bao. 2008 May;43(5):509-12.
[2]. Tenacigenin B derivatives reverse P-glycoprotein-mediated multidrug resistance inHepG2/Dox cells. J Nat Prod. 2008 Jun;71(6):1049-51. |
| Additional Infomation |
According to reports, Tenacissoside G has been discovered in Marsdenia tenacissima, and relevant data is available.
1. Tenacissoside G is a C21 steroidal glycoside, isolated from the stem of Marsdenia tenacissima by a series of chromatographic separation and purification procedures (including silica gel column chromatography and recrystallization)[1] 2. The chemical structure of Tenacissoside G was elucidated by spectroscopic techniques (¹H-NMR, ¹³C-NMR, MS and IR spectroscopy); it has a tenacigenin B aglycone skeleton with a specific trisaccharide chain (glucose-rhamnose-xylose) attached to its C-3 hydroxyl group, belonging to the 14,15β-epoxy-C21 steroidal glycoside class[1] 3. Tenacissoside G is a structural analogue of other C21 steroidal glycosides from Marsdenia tenacissima (e.g., tenacissoside H, tenacissoside I), mainly differing in the composition and linkage of the sugar chain[1] 4. Tenacissoside The aglycone of G (tenacigenin B) and its derivatives have been shown to reverse P-glycoprotein (P-gp)-mediated multidrug resistance (MDR), and it is speculated that Tenacissoside G also has a similar MDR reversal effect. Tenacissoside B is released into biological systems via hydrolysis [2]. |
| Molecular Formula |
C42H64O14
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|---|---|
| Molecular Weight |
792.9492
|
| Exact Mass |
792.429
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| CAS # |
191729-43-8
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| PubChem CID |
44561398
|
| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
821.8±65.0 °C at 760 mmHg
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| Flash Point |
238.4±27.8 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.558
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| Source |
Marsdenia tenacissima
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| LogP |
5.01
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
56
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| Complexity |
1550
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| Defined Atom Stereocenter Count |
19
|
| SMILES |
O1C23C([H])([H])C([H])([H])C4([H])C([H])([H])C([H])(C([H])([H])C([H])([H])C4(C([H])([H])[H])C2([H])C([H])(C([H])(C2(C([H])([H])[H])C([H])(C(C([H])([H])[H])=O)C([H])([H])C([H])([H])C132)OC(C([H])([H])[H])=O)OC(/C(=C(\[H])/C([H])([H])[H])/C([H])([H])[H])=O)OC1([H])C([H])([H])C([H])(C([H])(C([H])(C([H])([H])[H])O1)OC1([H])C([H])(C([H])(C([H])(C([H])(C([H])([H])[H])O1)O[H])OC([H])([H])[H])O[H])OC([H])([H])[H]
|
| InChi Key |
OHDJGUWKOIBIKY-SGFNNURDSA-N
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| InChi Code |
InChI=1S/C42H64O14/c1-11-20(2)37(47)54-34-35-39(7)15-13-26(53-29-19-28(48-9)32(23(5)50-29)55-38-31(46)33(49-10)30(45)22(4)51-38)18-25(39)12-16-41(35)42(56-41)17-14-27(21(3)43)40(42,8)36(34)52-24(6)44/h11,22-23,25-36,38,45-46H,12-19H2,1-10H3/b20-11+/t22-,23-,25+,26+,27+,28-,29+,30-,31-,32-,33-,34+,35-,36-,38+,39+,40+,41+,42-/m1/s1
|
| Chemical Name |
[(1S,3R,6R,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-8-acetyloxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-9-yl] (E)-2-methylbut-2-enoate
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| Synonyms |
Tenacissoside G; 191729-43-8; Tenacissimoside A; [(1S,3R,6R,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-8-acetyloxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-9-yl] (E)-2-methylbut-2-enoate; CHEMBL464723;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~126.11 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (3.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (3.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2611 mL | 6.3056 mL | 12.6111 mL | |
| 5 mM | 0.2522 mL | 1.2611 mL | 2.5222 mL | |
| 10 mM | 0.1261 mL | 0.6306 mL | 1.2611 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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