Terminolic acid
(Synonyms: 积雪草苷B苷元) 目录号 : GC61321
Terminolicacid是一种从Combretumracemosum中分离出的五环三萜糖苷。Terminolicacid可以通过结合IL-1β和IL-6的受体活性位点来抑制促炎细胞因子，并且可以通过结合IL4受体的结合位点来增强抗炎细胞因子。Terminolicacid还表现出中等的抗菌活性。
Cas No.:564-13-6
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
Terminolic acid is a pentacyclic triterpenoid glucoside isolated from Combretum racemosum. Terminolic acid can inhibit the pro-inflammatory cytokines by binding to receptor active site of IL-1β and IL-6, and enhance anti-inflammatory cytokines by binding to IL-4 receptor binding sites. Terminolic acid also exhibits moderate antibacterial activity[1][1].
[1]. Gossan DPA, et, al. Antibacterial and cytotoxic triterpenoids from the roots of Combretum racemosum. Fitoterapia. 2016 Apr;110:89-95. [2]. Legiawati L, et, al. In silico study of Centella asiatica active compounds as anti-inflammatory agent by decreasing Il-1 and Il-6 activity, promoting Il-4 activity. /J. Pharm. Sci. & Res. Vol. 10(9), 2018, 2142-2147.
| Cas No. | 564-13-6 | SDF | |
| 别名 | 积雪草苷B苷元 | ||
| Canonical SMILES | C[C@@]1(C[C@H]2O)[C@@](CC=C([C@]3([H])CC4(C)C)[C@]1(CC[C@]3(CC4)C(O)=O)C)([H])[C@]([C@]2([H])[C@@](C)([C@H]5O)CO)(C[C@H]5O)C | ||
| 分子式 | C30H48O6 | 分子量 | 504.7 |
| 溶解度 | DMSO : 100 mg/mL (198.14 mM; ultrasonic and warming and heat to 60°C) | 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 | 1.9814 mL | 9.9069 mL | 19.8138 mL |
| 5 mM | 0.3963 mL | 1.9814 mL | 3.9628 mL |
| 10 mM | 0.1981 mL | 0.9907 mL | 1.9814 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。
Antibacterial and cytotoxic triterpenoids from the roots of Combretum racemosum
Fitoterapia 2016 Apr;110:89-95.PMID:26946378DOI:10.1016/j.fitote.2016.03.002.
A new pentacyclic triterpenoid glucoside, together with fourteen known compounds, was isolated from the roots of Combretum racemosum. Combretaceae). The structure of the new compound was established as 28-O-β-d-glucopyranosyl-2α,3β,21β,23-tetrahydroxyolean-18-en-28-oate (1) on the basis of detailed spectroscopic data including MS, 1D, and 2D NMR. The inhibitory activity of compounds 1-15 against promyelocytic leukemia HL-60 and human erythromyeloblastoid leukemia K562 cell lines was evaluated. Compounds 11 (3-O-β-acetyl-ursolic acid), 14 (betulinic acid), and 15 (quadranoside II) exhibited significant cytotoxicity, with IC50 values of 13 to 50 μM. Among the isolated triterpenes, compounds 1, 3 (arjungenin), 5 (Terminolic acid), and 11 exhibited moderate antibacterial activity against Staphylococcus aureus, Escherichia coli and Enterococcus faecalis (MICs within a range of 64 and 256 μg/mL).
Antibacterial triterpenes from Syzygium guineense (Myrtaceae)
J Ethnopharmacol 2005 Oct 3;101(1-3):283-6.PMID:15967609DOI:10.1016/j.jep.2005.05.008.
Antibacterial bioassay-guided fractionation of Syzygium guineense leaf extracts afforded 10 triterpenes, namely betulinic acid 1, oleanolic acid 2, a mixture of 2-hydroxyoleanolic acid 3a, 2-hydroxyursolic acid 3b, arjunolic acid 4a, asiatic acid 4b, a mixture of Terminolic acid 5a, 6-hydroxyasiatic acid 5b, and a mixture of arjunolic acid 28-beta-glucopyranosyl ester 6a and the asiatic acid 28-beta-glucopyranosyl ester 6b. Isolated compounds were submitted to an antibacterial assay system against gram-positive and -negative bacteria and human pathogen bacteria. Compounds 4a and 4b showed the most significant antibacterial activity against Escherichia coli, Bacillus subtilis and Shigella sonnei. The fraction 5a-5b was the least active, whereas compounds 1, 2 and the mixtures of 3a-3b and 6a-6b were inactive in the assays.
Antiplasmodial activity of triterpenes isolated from the methanolic leaf extract of Combretum racemosum P. Beauv
J Ethnopharmacol 2020 Jan 30;247:112203.PMID:31472271DOI:10.1016/j.jep.2019.112203.
Ethnopharmacological relevance: Combretum racemosum showed activity in previous ethnopharmacological investigations of some Combretum species used in malaria treatment in parts of West Africa. Aim of the study: This study aimed at confirming the antimalarial potential of this plant by an activity-guided isolation of its active principles. Materials and methods: A crude methanolic leaf extract of Combretum racemosum and fractions thereof obtained by partition with chloroform and n-butanol were investigated for antiplasmodial activity against chloroquine-sensitive (D10) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Repeated chromatographic separations were conducted on the chloroform fraction to isolate bioactive compounds for further tests on antiplasmodial activity. The characterization of the isolated substances was performed by applying NMR- and MS-techniques (ESI-MS, HR-ESIMS, 1D and 2D NMR). Results: The chloroform fraction (D10: IC50 = 33.8 ± 1.5 μg/mL and W2: IC50 = 27.8 ± 2.9 μg/mL) exhibited better antiplasmodial activity than the n-butanol fraction (D10: IC50 = 78.1 ± 7.3 μg/mL and W2: IC50 = 78 ± 15 μg/mL) as well as the methanolic raw extract (D10: IC50 = 64.2 ± 2.7 μg/mL and W2: IC50 = 65.8 ± 14.9 μg/mL). Thus, the focus of the phytochemical investigation was laid on the chloroform fraction, which led to the identification of four ursane-type (19α-hydroxyasiatic acid (1), 6β,23-dihydroxytormentic acid (4), madecassic acid (8), nigaichigoside F1 (10)) and four oleanane-type (arjungenin (2), combregenin (5), Terminolic acid (7), arjunglucoside I (11)) triterpenes, as well as abscisic acid (9). Compounds 1 and 2, 4 and 5, 7 and 8 as well as 10 and 11 were isolated as isomeric mixtures in fractions CR-A, CR-C, CR-E and CR-H, respectively. All isolated compounds and mixtures exhibited moderate to low activity, with madecassic acid being most active (D10: IC50 = 28 ± 12 μg/mL and W2: IC50 = 17.2 ± 4.3 μg/mL). Conclusion: This paper reports for the first time antiplasmodial principles from C. racemosum and thereby gives reason to the traditional use of the plant.
[Separation and determination of madecassic acid in triterpenic genins of Centella asiatica by high performance liquid chromatography using beta-cyclodextrin as mobile phase additive]
Se Pu 2007 May;25(3):316-8.PMID:17679419DOI:10.1016/s1872-2059(07)60009-1.
Centella asiatica (L. ) Urban is a tropical medicinal plant with a long history of therapeutic uses. Madecassic acid and Terminolic acid, which are a pair of structural isomers, are two constituents of Centella asiatica. A method using reversed-phase high performance liquid chromatography in which beta-cyclodextrin (beta-CD) was the additive in mobile phase has been developed for separation of the structural isomers and determination of madecassic acid. The two compounds can be isolated with high resolution on a C18 reversed-phase column with the addition of beta-CD in the mobile phase. The separation mechanism of the isomers was discussed. It was assumed that the separation of the isomers might have been resulted from different inclusion forces of complexes with beta-CD. The effects of beta-CD concentration and the pH of mobile phase on resolution were investigated. It was found that the resolution of the isomers increased with the increase of beta-CD concentration when the mobile phase consisted of methanol-water (65 : 35, v/v) at pH 4. The correlation coefficient (r2) of the linear calibration curve between peak area and concentration of madecassic acid was 0.998 9 in the range of 0.1 - 5.0 g/L. This method was successfully used to determine the madecassic acid in triterpenic genins of Centella asiatica.
Chemical constituents from Melastoma dodecandrum and their inhibitory activity on interleukin-8 production in HT-29 cells
Nat Prod Res 2014;28(17):1383-7.PMID:24697659DOI:10.1080/14786419.2014.903480.
In search of anti-inflammatory lead compounds from traditional Chinese medicines, a bioassay-guided phytochemical study on Melastoma dodecandrum was carried out. As a result, 18 compounds have been isolated. Their chemical structures were determined on the basis of their physicochemical properties and spectral data. Among the isolates, three pentacyclic triterpenoids, ursolic acid (1), asiatic acid (3) and Terminolic acid (6), together with one tannin casuarinin (17), were found to significantly decrease interleukin-8 (IL-8) production in human colon cancer cells. The results imply, at least in part, that the anti-inflammatory effect of M. dodecandrum could be due to inhibition of IL-8 production, demonstrated by these naturally occurring compounds described above.