Gypsogenic Acid
(Synonyms: Astrantiagenin J) 目录号 : GC49837
A triterpene acid with antibacterial and trypanocidal activities
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Gypsogenic acid is a triterpene acid that has been found in M. stenostachya and has antibacterial and trypanocidal activities.1,2 It is active against the oral bacterial pathogens E. faecalis, S. salivarius, S. sanguinis, S. mitis, S. mutans, and S. sobrinus (MICs = 50-200 µg/ml).1 Gypsogenic acid induces lysis of T. cruzi in isolated mouse blood (IC50 = 56.6 µM).2
1.Cunha, L.C.S., e Silva, M.L.A., Furtado, N.A.J.C., et al.Antibacterial activity of triterpene acids and semi-synthetic derivatives against oral pathogensZ. Naturforsch. C. J. Biosci.62(9-10)668-672(2007) 2.Cunha, W.R., Martins, C.H., da Silva, F., D., et al.In vitro trypanocidal activity of triterpenes from Miconia speciesPlanta Med.69(5)470-472(2003)
| Cas No. | 5/5/5143 | SDF | Download SDF |
| 别名 | Astrantiagenin J | ||
| Canonical SMILES | C[C@@]12C([C@@]3([H])[C@@](CC2)(CCC(C)(C3)C)C(O)=O)=CC[C@@]4([H])[C@]1(CC[C@]5([H])[C@@]4(CC[C@@H]([C@@]5(C)C(O)=O)O)C)C | ||
| 分子式 | C30H46O5 | 分子量 | 486.7 |
| 溶解度 | DMSO: slightly soluble,Methanol: slightly soluble | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.0547 mL | 10.2733 mL | 20.5465 mL |
| 5 mM | 0.4109 mL | 2.0547 mL | 4.1093 mL |
| 10 mM | 0.2055 mL | 1.0273 mL | 2.0547 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Cytotoxicity of Gypsogenic Acid isolated from Gypsophila trichotoma
Pharmacogn Mag 2014 Apr;10(Suppl 2):S430-3.PMID:24991123DOI:10.4103/0973-1296.133299.
Background: Gypsophila trichotoma Wend. (Caryophyllaceae) is a medicinal plant which is protected in Bulgaria by the Biodiversity Law. Previous studies have showed the presence of triterpene saponins, sterols, flavonoids, triterpens, etc. Objective: Gypsogenic Acid, isolated from Gypsophila trichotoma roots, was evaluated for cytotoxic activity. Materials and methods: The structure of the compound was elucidated by spectral methods. The cell survival fraction was determined by the MTT dye reduction assay, performed with some modifications. Results: Gypsogenic Acid was tested in a panel of human tumor cell lines and was found to inhibit the proliferation of malignant cells. It was active against leukemic cells with lymphoid (SKW-3 and BV-173) or myeloid phenotype (HL-60, K-562, and LAMA-84), as well as against the EJ bladder carcinoma cell line. Bcr-Abl expressing myeloid cells (LAMA-84 and especially K-562) displayed lower sensitivity. HL-60/Dox cells were less sensitive to Gypsogenic Acid than the parent cell line, which shows that Gypsogenic Acid is probably a substrate of MRP-1.
Two new triterpenoids from Gypsophila oldhamiana
Nat Prod Res 2016;30(9):1068-74.PMID:26539898DOI:10.1080/14786419.2015.1107060.
Two new triterpenoids (1-2) were isolated and elucidated from the roots of Gypsophila oldhamiana, together with four known triterpenoids (3-6). Their structures were identified to be 3β-hydroxyolean-13(18)-ene-23, 28-dioic acid (1), 3β, 12α-dihydroxy-23-carboxyolean-28, 13β-olide (2), 3β, 16α-dihydroxy-23-oxoolean-13(18)-en-28-oic acid (3), gypsogenin (4), quillaic acid (5) and Gypsogenic Acid (6) by spectral methods. All compounds were tested for their cytotoxicities against human tumour cell lines (lung cancer H460 and gastric cancer SGC-7901) and for their antiangiogenic effects using a zebra fish model. All compounds showed interesting antiangiogenic activities and the significant cytotoxicities against H460.
Three new triterpenoid saponins from Dianthus superbus
Chem Pharm Bull (Tokyo) 2011;59(4):518-21.PMID:21467688DOI:10.1248/cpb.59.518.
Three new triterpenoid saponins (1-3) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were established as 3-O-β-D-glucopyranosyl Gypsogenic Acid 28-O-[β-D-6-O-((3S)-3-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl Gypsogenic Acid 28-O-[β-D-glucopyranosyl(1→3)][β-D-6-O-((3S)-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (2), 3-O-α-L-arabinopyranosyl-3β,16α-dihydroxyolean-12-en-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (3), on the basis of various spectroscopic analyses and chemical degradations.
Highlighting Aglycone-dependent Glycosylation Aspects in Caryophyllaceae Saponins by a Simplex Simulation Approach
Curr Top Med Chem 2021;21(7):612-627.PMID:33459236DOI:10.2174/1568026621666210114153216.
Background: Saponin metabolism shows high structural variability due to the diversity of aglycones and glycosylations (Gly). Although they represent a potential source of drug design, their metabolism remains misunderstood yet due to insufficient investments in analytical methods. Aims: Bibliographic structural data offer a wide field for extensive statistical analysis, highlighting mechanistic orders governing metabolic diversity. This work presents an original simulation method based on simplex rule for highlighting regulatory mechanisms of metabolism from categorical structural data. Methods: Simulation was applied on a set of 231 saponins of the Caryophyllaceae plant family initially affiliated to four aglycone types: gypsogenin (Gyp), quillaic acid (QA), Gypsogenic Acid (GA), and 16-OH-gypsogenic acid (16-OH-GA). Molecules were initially characterized by relative glycosylation levels of different carbons. Simplex approach was applied by combining saponins of the four aglycone groups using a complete set of N gradual weightings between structural groups. In silico combinations were applied by randomly sampling representative saponins from the four groups conforming to their weights given by mixture design. Gly profiles of sampled saponins were averaged to calculate a barycentric molecular profile for each mixture. With N mixtures, N barycentric molecules were iteratively calculated by bootstrap, leading to smoothed data from which Gly trends between carbons were highlighted. Results: Sequential, competing and cooperative Gly trends were highlighted according to the types of aglycones, attached saccharides and positions of substituted carbons. Such various conditional Gly trends seemed to be linked to multiple factors, including steric effects, regio-selectivity, enzymatic specificity and enzymatic promiscuity. These simulated results could be helpfully useful in chemical synthesis and drug design. Conclusion: These simulated results could usefully help for chemical syntheses and drug design.
Antibacterial oleanane-type triterpenoids from pericarps of Akebia trifoliata
Food Chem 2015 Feb 1;168:623-9.PMID:25172756DOI:10.1016/j.foodchem.2014.07.105.
Three new oleanane triterpenoids, 2α,3β,29-trihydroxyolean-12-en-28-oic acid (1), 2α,3β-dihydroxy-23-oxo-olean-12-en-28-oic acid (2) and 2α,3β,21β,22α-tetrahydroxyolean-12-en-28,29-dioic acid (3), and ten known ones, maslinic acid (4), arjunolic acid (5), oleanolic acid (6), 3-epi-oleanolic acid (7), stachlic acid A (8), serratagenic acid (9), Gypsogenic Acid (10), 2α,3β-dihydroxyol-ean-13(18)-en-28-oic acid (11), mesembryanthemoidigenic acid (12) and 12α-hydroxy-δ-lactone (13), were isolated from the pericarps of Akebia trifoliata, a new valued fruit crop in China. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compounds 8, 10, 11 and 13 were isolated for the first time from the genus Akebia. All the compounds were tested for their antimicrobial activity against five bacterial strains. Compounds 4, 6 and 11 showed significant antibacterial activity toward all the assayed microorganisms with MIC values ranging from 0.9 to 15.6μg/mL, which were close or even more potent than the reference compound Kanamycin (MIC values ranging from 1.9 to 3.9μg/mL).