Apiin
(Synonyms: 芹菜甙) 目录号 : GC35372
A flavonoid glycoside with diverse biological activities
Cas No.:26544-34-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Apiin is a polyketide synthase-derived flavonoid glycoside that has been found in A. graveolens and has diverse biological activities.1,2,3,4 It inhibits Aurora B kinase in a cell-free assay using the human enzyme (IC50 = 12.14 ?M).2 Apiin (10 and 50 ?g/ml) inhibits LPS-induced increases in nitric oxide (NO) release and inducible nitric oxide synthase (iNOS) levels in J774.A1 macrophages.3 It scavenges DPPH , superoxide, and hydroxyl radicals (IC50s = 68, 390, and 48 ?g/ml, respectively), as well as increases the levels of superoxide dismutase (SOD) and catalase in mouse serum, brain, heart, liver, and kidney when administered at a dose of 50 mg/kg.4
1.Cheung, V.W.N., Xue, B., Hernandez-Valladares, M., et al.Identification of polyketide inhibitors targeting 3-dehydroquinate dehydratase in the shikimate pathway of Enterococcus faecalisPLoS One9(7)e103598(2014) 2.Jung, Y., Shin, S.Y., Yong, Y., et al.Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationshipsChem. Biol. Drug Des.85(5)574-585(2015) 3.Mencherini, T., Cau, A., Bianco, G., et al.An extract of Apium graveolens var. dulce leaves: Structure of the major constituent, apiin, and its anti-inflammatory propertiesJ. Pharm. Pharmacol.59(6)891-897(2007) 4.Li, P., Jia, J., Zhang, D., et al.In vitro and in vivo antioxidant activities of a flavonoid isolated from celery (Apium graveolens L. var. dulce)Food Funct.5(1)50-56(2014)
| Cas No. | 26544-34-3 | SDF | |
| 别名 | 芹菜甙 | ||
| Canonical SMILES | O=C(C=C(C1=CC=C(O)C=C1)OC2=CC(O[C@H](O[C@H](CO)[C@@H](O)[C@@H]3O)[C@@H]3O[C@@](OC[C@]4(O)CO)([H])[C@@H]4O)=C5)C2=C5O | ||
| 分子式 | C26H28O14 | 分子量 | 564.49 |
| 溶解度 | DMSO : 100 mg/mL (177.15 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 | 1.7715 mL | 8.8576 mL | 17.7151 mL |
| 5 mM | 0.3543 mL | 1.7715 mL | 3.543 mL |
| 10 mM | 0.1772 mL | 0.8858 mL | 1.7715 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。
Parsley: a review of ethnopharmacology, phytochemistry and biological activities
J Tradit Chin Med 2013 Dec;33(6):815-26.PMID:24660617DOI:10.1016/s0254-6272(14)60018-2.
Objective: To summarize comprehensive information concerning ethnomedicinal uses, phytochemistry, and pharmacological activities of parsley. Methods: Databases including PubMed, Scopus, Google Scholar, and Web of Science were searched for studies focusing on the ethnomedicinal use, phytochemical compounds and biological and pharmacological activities of parsley. Data were collected from 1966 to 2013. The search terms were: "Parsley" or "Petroselinum crispum" or "Petroselinum hortence". Results: Parsley has been used as carminative, gastro tonic, diuretic, antiseptic of urinary tract, anti-urolithiasis, anti-dote and anti-inflammatory and for the treatment of amenorrhea, dysmenorrhea, gastrointestinal disorder, hypertension, cardiac disease, urinary disease, otitis, sniffle, diabetes and also various dermal disease in traditional and folklore medicines. Phenolic compounds and flavonoids particularly apigenin, Apiin and 6"-Acetylapiin; essential oil mainly myristicin and apiol; and also coumarins are the active compounds identified in Petroselinum crispum. Wide range of pharmacological activity including antioxidant, hepatoprotective, brain protective, anti-diabetic, analgesic, spasmolytic, immunosuppressant, anti-platelet, gastroprotective, cytoprotective, laxative, estrogenic, diuretic, hypotensive, antibacterial and antifungal activities have been exhibited for this plant in modern medicine. Conclusion: It is expectant that this study resulted in improvement the tendencies toward Petroselinum crispum as a useful and important medicinal plant with wide range of proven medicinal activity.
The Healing Power of Clean Rivers: In Silico Evaluation of the Antipsoriatic Potential of Apiin and Hyperoside Plant Metabolites Contained in River Waters
Int J Environ Res Public Health 2022 Feb 22;19(5):2502.PMID:35270196DOI:10.3390/ijerph19052502.
Humanity may benefit greatly from intact riverine ecosystems not only because they supply water to be used in the most common human activities, but also for the effects that clean rivers can have on human health. Herein, we used a computational approach to show that some phytochemicals produced by riparian plants as secondary metabolites, which are naturally released into river waters, can have therapeutic properties. These include antipsoriatic activities which we demonstrated in silico by modelling the interaction of Apiin, guanosine and hyperoside, a few main river plant metabolites, with NF-kB, IL-17 and IL-36, which are recognized targets involved in psoriasis disease. In particular, we found that Apiin and hyperoside are endowed with docking energies and binding affinities which are more favorable than the known reference inhibitors of the three protein targets whilst, in silico, guanosine shows comparable activity with respect to the inhibitors of IL-36 and NF-kB. The low skin permeation (logKp < −8) we predicted for Apiin and hyperoside led us to hypothesize their possible utilization as topic antipsoriatic therapeutics, and in particular after PAINS (pan-assay interference compounds) score evaluation, we reached the conclusion that Apiin, with no predicted tendency to react nonspecifically with the numerous targets involved in the biological cellular pathways, is particularly interesting for the desired therapeutic application.
Biological synthesis of silver and gold nanoparticles using Apiin as reducing agent
Colloids Surf B Biointerfaces 2009 Jan 1;68(1):55-60.PMID:18977643DOI:10.1016/j.colsurfb.2008.09.021.
We report a novel strategy for the biological synthesis of anisotropic gold and quasi-spherical silver nanoparticles by using Apiin as the reducing and stabilizing agent. The size and shape of the nanoparticles can be controlled by varying the ratio of metal salts to Apiin compound in the reaction medium. The resultant nanoparticles were characterized by UV-vis-NIR, transmission electron microscopy (TEM), FT-IR spectroscopy, X-ray diffraction (XRD) and thermogravimetric analysis (TGA). The interaction between nanoparticles with carbonyl group of Apiin compound was confirmed by using FT-IR analysis. TEM photograph confirming the average size of the gold and silver nanoparticles were found to be at 21 and 39 nm. The NIR absorption of the gold nanotriangles is expected to be of application in hyperthermia of cancer cells and in IR-absorbing optical coatings.
Extraction optimization, structural characterization and potential alleviation of hyperuricemia by flavone glycosides from celery seeds
Food Funct 2022 Oct 3;13(19):9832-9846.PMID:36047466DOI:10.1039/d2fo01715f.
Celery seeds are commonly used as condiments and in herbal teas with high medicinal value. In the present study, we investigated the contents of extracts derived under different extraction conditions and determined the optimal conditions for only extracting flavone glycosides from celery seeds. The compositional analysis identified three primary flavone glycosides in the ethanolic extract, and Apiin, graveobioside A, and graveobioside B were isolated. Apigenin, luteolin, and chrsyeriol were obtained by the acid hydrolysis of flavone glycosides under high-temperature conditions. Here we investigated the inhibitory activity of apigenin and Apiin on xanthine oxidase by reducing the rate of oxidative cytochrome C and found that both apigenin and Apiin reduced cytochrome C production, except for low concentrations of Apiin. In vivo analysis with hyperuricemia mice and rats showed that Apiin had excellent uric acid-lowering effects and high dose-dependence, while apigenin was relatively slightly uric acid-lowering. In addition, the flavone glycoside extracts from celery seeds exhibited similar effects of reducing uric acid with Apiin. Surprisingly, in hyperuricemia rats, the uric acid-lowering effects of high-dose Apiin and flavone glycoside extracts were almost comparable to that of allopurinol. Besides, our experimental results showed that apigenin could improve uric acid clearance by increasing the glomerular filtration capacity, which was reflected in reducing the renal function parameters SUN and SCr; also, Apiin showed better results. This study also showed that celery seeds have a unique medicinal value in treating hyperuricemia and that the flavone glycoside extracts from celery seeds can be developed as medicine for hyperuricemia.
An extract of Apium graveolens var. dulce leaves: structure of the major constituent, Apiin, and its anti-inflammatory properties
J Pharm Pharmacol 2007 Jun;59(6):891-7.PMID:17637182DOI:10.1211/jpp.59.6.0016.
Flavonoids, natural compounds widely distributed in the plant kingdom, are reported to affect the inflammatory process and to possess anti-inflammatory as well as immunomodulatory activity in-vitro and in-vivo. Since nitric oxide (NO) produced by inducible nitric oxide synthase (iNOS) is one of the inflammatory mediators, the effects of the ethanol/water (1:1) extract of the leaves of Apium graveolens var. dulce (celery) on iNOS expression and NO production in the J774.A1 macrophage cell line stimulated for 24 h with Escherichia coli lipopolysaccharide (LPS) were evaluated. The extract of A. graveolens var. dulce contained Apiin as the major constituent (1.12%, w/w, of the extract). The extract and Apiin showed significant inhibitory activity on nitrite (NO) production in-vitro (IC50 0.073 and 0.08 mg mL(-1) for the extract and Apiin, respectively) and iNOS expression (IC50 0.095 and 0.049 mg mL(-1) for the extract and Apiin, respectively) in LPS-activated J774.A1 cells. The croton-oil ear test on mice showed that the extract exerted anti-inflammatory activity in-vivo (ID50 730 microg cm(-2)), with a potency seven-times lower than that of indometacin (ID50 93 microg cm(-2)), the non-steroidal anti-inflammatory drug used as reference. Our results clearly indicated the inhibitory activity of the extract and Apiin in-vitro on iNOS expression and nitrite production when added before LPS stimulation in the medium of J774.A1 cells. The anti-inflammatory properties of the extract demonstrated in-vivo might have been due to reduction of iNOS enzyme expression.