Medicagenic acid
(Synonyms: 苜蓿酸,Castanogenin) 目录号 : GC38211
Medicagenic acid (Castanogenin), a bioactive triterpenoid pentacyclic glycoside isolated from Herniaria glabra L., has low xanthine oxidase, collagenase, elastase, and tyrosinase inhibitory activity.
Cas No.:599-07-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Medicagenic acid (Castanogenin), a bioactive triterpenoid pentacyclic glycoside isolated from Herniaria glabra L., has low xanthine oxidase, collagenase, elastase, and tyrosinase inhibitory activity.
[1] Solomiia Kozachok, et al. Phytochemistry. 2020 Jan;169:112162.
| Cas No. | 599-07-5 | SDF | |
| 别名 | 苜蓿酸,Castanogenin | ||
| Canonical SMILES | C[C@@]1(C(O)=O)[C@@H](O)[C@@H](O)C[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] | ||
| 分子式 | C30H46O6 | 分子量 | 502.68 |
| 溶解度 | DMSO : 100 mg/mL (198.93 mM; Need ultrasonic) | 储存条件 | Store at -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 | 1.9893 mL | 9.9467 mL | 19.8934 mL |
| 5 mM | 0.3979 mL | 1.9893 mL | 3.9787 mL |
| 10 mM | 0.1989 mL | 0.9947 mL | 1.9893 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。
Effects of Medicagenic acid metabolites, originating from biotransformation of an Herniaria hirsuta extract, on calcium oxalate crystallization in vitro
J Ethnopharmacol 2022 Mar 1;285:114860.PMID:34822955DOI:10.1016/j.jep.2021.114860.
Ethnopharmacological relevance: Herniaria hirsuta is traditionally used in Moroccan folk medicine for treatment of urinary stones and as a diuretic. It is rich in saponins, which are known to be deglycosylated in the colon, whereafter aglycones such as Medicagenic acid are absorbed and further metabolized in the liver. Aim of the study: A sample of hepatic metabolites of Medicagenic acid, with Medicagenic acid glucuronide as the most abundant one, was evaluated for in vitro activity against urinary stones. A crystallization assay and a crystal-cell interaction assay were used to evaluate in vitro activity of hepatic metabolites of Medicagenic acid on CaC2O4 (calciumoxalate) crystals, present in the majority of urinary stones. Materials and methods: In the crystallization assay the effects on nucleation of Ca2+ and C2O42- and aggregation of the CaC2O4 crystals are studied. In the crystal-cell interaction assay crystal retention is investigated by determining the amount of Ca2+ bound to injured monolayers of MDCK I cells. Results: Results of the crystallization assay showed a tentative effect on crystal aggregation. The crystal-cell interaction assay showed a significant inhibition of crystal binding, which may reduce crystal retention in the urinary tract. Conclusions: As both formation of crystals by inhibiting aggregation and retention of crystals is affected, the beneficial effect of H. hirsuta against urinary stones may at least in part be attributed to Medicagenic acid metabolites, indicating that saponins containing Medicagenic acid may act as prodrugs.
Saponins as antimycotic agents: glycosides of Medicagenic acid
Adv Exp Med Biol 1996;404:535-46.PMID:8957322DOI:10.1007/978-1-4899-1367-8_44.
The continuous search for new antimycotic drugs is a consequence of the broad use of immunosuppressive drugs and broad-spectrum antibiotics, high number of AIDS patients, and widespread dermatophyte infections. The concern with increased resistance due to widespread and prolonged antifungal treatment, particularly with azoles, is noteworthy. Our efforts were focused on Medicagenic acid derivatives isolated from alfalfa and on semisynthetic ones. In general, these materials exhibited potent fungistatic effects against several plant pathogens and human dermatophytes. Furthermore, they were fungicidal against medically important yeasts, showing a most impressive activity against Cryptococcus neoformans, the minimal fungicidal concentration (MFC) value of the gluco derivative of Medicagenic acid, compound G2, is 4 micrograms/ml. The mode of action as well as the structure-activity relationships of these compounds were studied. Compound G2, when applied topically, was effective in curing skin lesions of guinea pigs infected with the dermatophyte Trichophyton mentagrophytes and good skin tolerance to the drug was noted. Furthermore, it had a life-prolonging effect on mice infected with C. neoformans and recently, liposomes containing compound G2 were used efficiently as a drug delivery system in treatment of murine cryptococcosis and candidiosis.
Medicagenic acid saponins from Aster batangensis
Phytochemistry 1995 Jul;39(4):875-81.PMID:7626267DOI:10.1016/0031-9422(95)00016-z.
Two new Medicagenic acid saponins, named asterbatanoside J and K, were isolated from the roots of Aster batangensis. On the basis of chemical and spectral studies especially 2D NMR including COSY, HETCOR, HMQC, HOHAHA, TOCSY, ROESY and HMBC techniques, their structures were established as 3-O-beta-D-glucopyranosyl-(1--> 6)-beta-D-glucopyranosyl-2 beta, 3 beta-dihydroxy-olean-12-en-23 alpha, 28-dioic acid- 28-O-alpha-L-arabinopyranosyl-(1-->3)-alpha-L- rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside and 3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl- medicagenic acid-28-O-beta-D-xylopyranosyl-(-->4)-[alpha-L- arabinopyranosyl-(1 -->3)-alpha-L-rhamnopyranosyl-(1-->2) -beta-D-fucopyranside, respectively.
A comparative study on the in vitro biotransformation of Medicagenic acid using human liver microsomes and S9 fractions
Chem Biol Interact 2020 Sep 1;328:109192.PMID:32712081DOI:10.1016/j.cbi.2020.109192.
Many natural products are prodrugs which are biotransformed and activated after oral administration. The investigation of gastrointestinal and hepatic biotransformation can be facilitated by in vitro screening methods. This study compares two widely used in vitro models for hepatic biotransformation: 1) human S9 fractions and 2) human liver microsomes and cytosolic fractions in a two-step sequence, with the purpose of identifying differences in the biotransformation of Medicagenic acid, the putative precursor of active metabolites, responsible for the medicinal effects of the herb Herniaria hirsuta. The combination of liquid chromatography coupled to high-resolution mass spectrometry with subsequent suspect and non-target data analysis allowed the identification of thirteen biotransformation products, four of which are reported here for the first time. Eight biotransformation products resulting from oxidative Phase I reactions were identified. Phase II conjugation reactions resulted in the formation of three glucuronidated and two sulfated biotransformation products. No major differences could be observed between incubations with human liver S9 or when utilizing human microsomal and cytosolic fractions. Apart from two metabolites, both methods rendered the same qualitative metabolic profile, with minor quantitative differences. As a result, both protocols applied in this study can be used to study in vitro human liver biotransformation reactions.
Synthesis and antifungal activity of Medicagenic acid saponins on plant pathogens: modification of the saccharide moiety and the 23 alpha substitution
Carbohydr Res 1993 May 21;244(1):161-9.PMID:8339299DOI:10.1016/0008-6215(93)80012-4.
The study of structure-antifungal activity relationships of Medicagenic acid saponins was widened to include synthetic glycosides of mannose, galactose, cellobiose, and lactose as well as a 23 alpha-hydroxymethyl analog of Medicagenic acid, namely, methyl 2 beta,3 beta-dihydroxy-23 alpha-hydroxymethyl-delta (12)-oleanene-28 beta-carboxylate, against Sclerotium rolfsii, Rhizoctonia solani, Trichoderma viride, Aspergillus niger, and Fusarium oxysporum. The native glucose-containing saponin was a more effective antifungal agent than the aforementioned saponins, except in the case of the cellobiose-containing derivative and F. oxysporum. A carboxyl substituent at the 23 alpha position of the sapogenin brought about higher fungistatic activity than a methyl carboxylate which, in turn, was more effective than an hydroxymethyl group at the same position.