ProtoaescigeninCAS# 20853-07-0 |
- Gymnemagenin
Catalog No.:BCN7841
CAS No.:22467-07-8
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 20853-07-0 | SDF | Download SDF |
| PubChem ID | 131636595 | Appearance | White powder |
| Formula | C30H50O6 | M.Wt | 506.7 |
| Type of Compound | Isoprenoids | Storage | Desiccate at -20°C |
| Synonyms | Protoaescigenin | ||
| Solubility | Soluble in DMSO; slightly soluble in water | ||
| Chemical Name | (3R,4R,4aR,5R,6aR,6aS,6bR,9S,10S,12aR,14bR)-4a,9-bis(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,4,5,10-tetrol | ||
| SMILES | CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CC(C2(C(C1O)O)CO)O)C)C)(C)CO)O)C)C | ||
| Standard InChIKey | VKJLHZZPVLQJKG-JWCXVLEDSA-N | ||
| Standard InChI | InChI=1S/C30H50O6/c1-25(2)13-18-17-7-8-20-26(3)11-10-21(33)27(4,15-31)19(26)9-12-28(20,5)29(17,6)14-22(34)30(18,16-32)24(36)23(25)35/h7,18-24,31-36H,8-16H2,1-6H3/t18-,19?,20-,21+,22-,23+,24+,26+,27-,28-,29-,30+/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. |
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| 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. |
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| 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. | ||
Protoaescigenin Dilution Calculator
Protoaescigenin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9736 mL | 9.8678 mL | 19.7355 mL | 39.4711 mL | 49.3389 mL |
| 5 mM | 0.3947 mL | 1.9736 mL | 3.9471 mL | 7.8942 mL | 9.8678 mL |
| 10 mM | 0.1974 mL | 0.9868 mL | 1.9736 mL | 3.9471 mL | 4.9339 mL |
| 50 mM | 0.0395 mL | 0.1974 mL | 0.3947 mL | 0.7894 mL | 0.9868 mL |
| 100 mM | 0.0197 mL | 0.0987 mL | 0.1974 mL | 0.3947 mL | 0.4934 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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[Application of high performance liquid-ion trap mass spectrometry in analyzing saponins in sodium aescinate].[Pubmed:28905567]
Zhongguo Zhong Yao Za Zhi. 2016 Jul;41(13):2449-2454.
Sodium aescinate, which is produced from saponins of Chinese Buckeye Seed, is a prescription drug for treatment of brain edema and all kinds of swellings caused by surgery. In this article, high-performance liquid chromatography/ion trap (HPLC-IT) mass spectrometry was applied to study the characteristic ions of ten reference substances, namely escin a, escin b, isoescin a, isoescin b, aesculiside A, aesculiside B, aesculuside A, escin c, escina and escin , which were isolated from aescinate. Furthermore, 19 saponin compounds were predicted in sodium aescinate, besides the above mentioned reference substances. The study showed that sapogenins in sodium aescinate had two structural types, namely Protoaescigenin and barringenol C, and the substituent acetyl, tigloyl or angeloyl was usually located at C-21, C-22 or C-28 position. Among these predicted saponins, their sugar chains were all located at C-3 position consisting of glucose and glucuronide. This study provides experimental data for chemical constituents in sodium aescinate and scientific basis for quality and safety evaluation.
Paviosides A-H, eight new oleane type saponins from Aesculus pavia with cytotoxic activity.[Pubmed:22507208]
Bioorg Med Chem. 2012 May 15;20(10):3280-6.
A phytochemical analysis of Aesculus pavia has led to the isolation of eight novel triterpenoid saponins, based on oleane type skeleton and named paviosides A-H (1a, 1b-4a, 4b). On the basis of chemical, and 2D NMR and mass spectrometry data, the structures of the new compounds were elucidated as 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-d-glucopyranosyl (1 --> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (1a), 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-D-glucopyranosyl (1 --> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (1b), 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-D-galactopyranosyl (1 --> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (2a), 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-D-galactopyranosyl (1 --> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (2b), 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-D-xylopyranosyl (1 --> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (3a), 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-D-xylopyranosyl (1 --> 4)]-beta-d-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (3b), 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-D-xylopyranosyl (1 --> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl Protoaescigenin (4a), and 3-O-[beta-D-xylopyranosyl (1 --> 2)] [-beta-D-xylopyranosyl (1 --> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl Protoaescigenin (4b). The compounds showed cytotoxic activity on J-774, murine monocyte/macrophage, and WEHI-164, murine fibrosarcoma, cell lines. Among them, paviosides E-H (3a, 3b and 4a, 4b) showed higher activity with values ranging from 2.1 to 3.6 mug/mL. Structure-activity relationship studies indicated the positive effect on the activity of xylose unit in the place of glucose, while a little detrimental effect is observed when glucose is substituted by galactose. The aglycone structure and the presence of a tigloyl or an angeloyl group at C-21 do not affect significantly the inhibitory activity on both tested cell lines.
Two new triterpenoid glycosides isolated from Aesculus assamica GRIFF.[Pubmed:16204989]
Chem Pharm Bull (Tokyo). 2005 Oct;53(10):1310-3.
Phytochemical study of the ethanol extract of the seeds of Aesculus assamica led to the isolation of two new triterpenoid saponins. The structure of the new compounds were elucidated on the basis of spectral data to be 28-O-acetyl-21-O-(4-O-angeloyl)-6-deoxy-beta-glucopyranosyl-3-O-[beta-glucopyrano syl(1-2)-O-[beta-glucopyranosyl(1-4)]-beta-glucuronopyranosyl]Protoaescigenin (1), and 21-O-(4-O-angeloyl)-6-deoxy-beta-glucopyranosyl-3-O-[beta-glucopyranosyl(1-2)-O-[ beta-glucopyranosyl(1-4)]-beta-glucuronopyranosyl]Protoaescigenin (2). Their in vitro bioactivity against plant pathogenic fungus Pyricularia oryzae and cytotoxicity against K562 and HCT-15 cell lines were evaluated.
Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica.[Pubmed:15797609]
Phytochemistry. 2005 Apr;66(7):825-35.
Eight new acylated triterpenoid saponins were isolated from the stem bark of Harpullia austro-caledonica along with the known harpuloside (9). Their structures were established using 1D and 2D NMR and mass spectrometry as 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (1), 3-O-alpha-L-rhamnopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-gluc uronopyranosyl-21 beta, 22 alpha-di-O-angeloyl barringtogenol C (2), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glu curonopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (3), 3-O-alpha-L-arabinofuranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylProtoaescigenin (4), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->2)]-beta-D-gl ucuronopyranosyl-21 beta, 22 alpha-di-O-angeloyl Protoaescigenin (5), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucur onopyranosyl-21 beta, 22 alpha-di-O-angeloylProtoaescigenin (6), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucu ronopyranosyl-21 beta, 22 alpha-di-O-angeloylProtoaescigenin (7), 3-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylProtoaescigenin (8). The EtOH extract of the stem bark showed in vitro cytotoxic activity against KB cells (90% at 10 microg/ml). At a concentration of 5 microg/ml, the saponin mixture showed haemolytic activity and caused 100% haemolysis of a 10% suspension of sheep erythrocytes.
[Studies on the biotransformation of escin Ia by human intestinal bacteria and the anti-tumor activities of desacylescin I].[Pubmed:14970884]
Beijing Da Xue Xue Bao Yi Xue Ban. 2004 Feb;36(1):31-5.
OBJECTIVE: To study Biotransformation of escin Ia by the crude enzymes of human intestinal bacteria and Lactobacillus brevis, determine the structures of biotransformation products and assay the inhibitory effect of desacylescin I on the tumor cell growth. METHODS: The escin Ia was incubated with crude enzymes of human intestinal bacteria and Lactobacillus brevis in vitro, respectively. The biotransformation products were isolated and purified by the chromatographic methods and the structures were determined by the spectroscopic techniques. RESULTS: Escin Ia was converted into isoescin Ia, desacylescin I, 21beta-O-tigloylProtoaescigenin and Protoaescigenin by crude enzymes of human intestinal bacteria and Lactobacillus brevis. Desacylescin I showed potentially inhibitory effects on tumor cell growth of mouse sarcoma-180, hepatic carcinoma H(22) and lung carcinoma in vivo. CONCLUSION: The results suggest that Escin Ia was a prodrug and its structure can be converted by human intestinal bacteria and Lactobacillus brevis. Desacylescin I as a biotransformation product showed potentially inhibitory effects on mouse tumor, and a potential candidate for anti tumor agents.
Triterpenoid saponins and acylated prosapogenins from Harpullia austro-caledonica.[Pubmed:11937161]
Phytochemistry. 2002 Apr;59(8):825-32.
Three new triterpenoid saponins have been isolated from the stem bark of Harpullia austro-caledonica and identified as 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyr anosyl-(1->2)-beta-D-glucopyranosyl]-protoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyr anosyl-(1->2)-beta-D-glucopyranosyl]-16-desoxyprotoaescigenin, 24-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]-28-O-[beta-D-glucopyr anosyl-(1->2)-beta-D-glucopyranosyl]-24-oxo-camelliagenin D. The 21,22-di-O-angeloate esters of Protoaescigenin and barringtogenol C were isolated in the acid hydrolysate of the saponin extract together with a new prosapogenin identified as 21beta,22alpha-di-O-angeloyl camelliagenin D. The structures were established using one- and two- dimensional NMR and mass spectrometry.
[Studies on sapogenins of Aesculus wilsonii Rehd].[Pubmed:9772631]
Zhongguo Zhong Yao Za Zhi. 1996 Oct;21(10):617-8 inside back cover.
Three sapogenins were isolated from the hydrolysate of the saponin mixture extracted from the seeds of Aesculus wilsonii. They were identified as 21-angeloyl-protoaescigenin., aescigenin and Protoaescigenin by physicochemical propertise and spectroscopic analysis.
