Isovitexin (Saponaretin)
(Synonyms: 异牡荆黄素; Saponaretin; Homovitexin) 目录号 : GC33844
A C-glycosylated flavone with diverse biological activities
Cas No.:38953-85-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cell experiment: | Cell viability is determined by an MTT assay. RAW 264.7 cells are plated in 96-well plates (1 × 104 cells/well) and incubated with various concentrations of Isovitexin (final concentration: 0-200 μg/mL) and LPS (2 μg/mL) for 24 h. In addition, the cells are pretreated with IV (25 or 50 μg/mL) for 1 h, followed by the addition of H2O2 (300 μM). After 24 h, MTT (5 mg/mL) is added to the cells, which are then incubated for another 4 h[1]. |
Animal experiment: | Mice[1]To create an ALI model, mice are randomLy divided into six groups: control (saline), Isovitexin only (100 mg/kg, dissolved in 0.5% DMSO), LPS only (0.5 mg/kg, dissolved in saline), LPS (0.5 mg/kg) + Isovitexin (50 or 100 mg/kg), and LPS (0.5 mg/kg) + dexamethasone (Dex, 5 mg/kg dissolved in saline). Isovitexin or Dex (5 mg/kg) are administered Isovitexin. After exposure to Isovitexin or Dex for 1 h, the mice are anesthetized with diethyl ether, and LPS is administered intranasally (i.n.) to induce lung injury. After LPS administration for 12 h, the animals are euthanized. Accordingly, bronchoalveolar lavage fluid (BALF) and lung tissue samples are harvested to measure cytokine levels; ROS generation; SOD, GSH, MDA and MPO activity; and COX-2, iNOS, HO-1, and Nrf2 protein expression[1]. |
References: [1]. Lv H, et al. Isovitexin Exerts Anti-Inflammatory and Anti-Oxidant Activities on Lipopolysaccharide-Induced Acute Lung Injury by Inhibiting MAPK and NF-κB and Activating HO-1/Nrf2 Pathways. Int J Biol Sci. 2016 Jan 1;12(1):72-86. | |
Isovitexin is a C-glycosylated flavone that has been found in Patrinia villosa and has diverse biological activities.1,2,3,4,5 It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in a cell-free assay (IC50 = 370 ?g/ml).2 Isovitexin (50 and 100 ?g/ml) is cytotoxic to HepG2 hepatic, MCF-7 breast, and HCT116 colorectal cancer cells.3 It inhibits LPS-induced production of TNF-α and IL-6 and decreases inducible nitric oxide synthase (iNOS) and COX-2 levels in RAW 264.7 cells when used at a concentration of 50 ?g/ml.4 Isovitexin (200 ?g/ml) reduces cytotoxicity induced by amyloid-β (25-35) (Aβ (25-35)) in PC12 cells.5
1.He, M., Min, J.-W., Kong, W.-L., et al.A review on the pharmacological effects of vitexin and isovitexinFitoterapia11574-85(2016) 2.Zhang, J., Yuan, K., Zhou, W.-L., et al.Studies on the active components and antioxidant activities of the extracts of Mimosa pudica Linn. from southern ChinaPharmacogn. Mag.7(25)35-39(2011) 3.Mohammed, R.S., Zeid, A.H.A., Hawary, S.S.E., et al.Flavonoid constituents, cytotoxic and antioxidant activities of Gleditsia triacanthos L. leavesSaudi J. Biol. Sci.21(6)547-553(2014) 4.Lv, H., Yu, Z., Zheng, Y., et al.Isovitexin exerts anti-inflammatory and anti-oxidant activities on lipopolysaccharide-induced acute lung injury by inhibiting MAPK and NF-κB and activating HO-1/Nrf2 pathways.Int. J. Biol. Sci.12(1)72-86(2016) 5.Guimar?es, C.C.O., D.D., Valdevite, M., Fachin Saltoratto, A.L., et al.The glycosylated flavonoids vitexin, isovitexin, and quercetrin isolated from Serjania erecta Radlk (Sapindaceae) leaves protect PC12 cells against amyloid-β25-35 peptide-induced toxicityFood Chem. Toxicol.8688-94(2015)
| Cas No. | 38953-85-4 | SDF | |
| 别名 | 异牡荆黄素; Saponaretin; Homovitexin | ||
| Canonical SMILES | OC1=C(C2=O)C(OC(C3=CC=C(O)C=C3)=C2)=CC(O)=C1[C@@H]([C@@H]([C@@H](O)[C@@H]4O)O)O[C@@H]4CO | ||
| 分子式 | C21H20O10 | 分子量 | 432.38 |
| 溶解度 | DMSO : ≥ 86.6 mg/mL (200.29 mM) | 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 | 2.3128 mL | 11.5639 mL | 23.1278 mL |
| 5 mM | 0.4626 mL | 2.3128 mL | 4.6256 mL |
| 10 mM | 0.2313 mL | 1.1564 mL | 2.3128 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。
Changes in isovitexin-O-glycosylation during the development of young barley plants
Phytochemistry 2018 Apr;148:11-20.PMID:29421507DOI:10.1016/j.phytochem.2018.01.001.
Phenylpropanoids are a class of plant natural products that have many biological functions, including stress defence. In barley, phenylpropanoids have been described as having protective properties against excess UV-B radiation and have been linked to resistance to pathogens. Although the phenylpropanoid composition of barley has recently been addressed in more detail, the biosynthesis and regulation of this pathway have not been fully established. Barley introgression lines, such as the S42IL-population offer a set of genetically diverse plants that enable the correlation of metabolic data to distinct genetic regions on the barley genome and, subsequently, identification of relevant genes. The phenylpropanoid profiles of the first and third leaf of barley seedlings in Scarlett and four members of the S42IL-population were obtained by LC-MS. Comparison of the leaf profiles revealed a change in the glycosylation pattern of the flavone-6-C-glucoside Isovitexin in the elite cultivar Scarlett. The change was characterized by the stepwise decrease in isovitexin-7-O-glucoside (saponarin) and an increase in isovitexin-2″-O-β-D-glucoside content. The lines S42IL-101-, -177 and -178 were completely devoid of isovitexin-2″-O-β-D-glucoside. Parallel glucosyltransferase assays were consistent with the observed metabolic patterns. The genetic region responsible for this metabolic effect was located on chromosome 1H between 0.21 and 15.08 cM, encompassing 505 gene candidates in the genome of the sequenced cultivar Morex. Only one of these genes displayed sequence similarity with glucosyltransferases of plant secondary metabolism that possessed the characteristic PSPG motif.
Flavonoid biosynthesis in barley primary leaves requires the presence of the vacuole and controls the activity of vacuolar flavonoid transport
Plant Physiol 2007 May;144(1):432-44.PMID:17369433DOI:10.1104/pp.106.094748.
Barley (Hordeum vulgare) primary leaves synthesize saponarin, a 2-fold glucosylated flavone (apigenin 6-C-glucosyl-7-O-glucoside), which is efficiently accumulated in vacuoles via a transport mechanism driven by the proton gradient. Vacuoles isolated from mesophyll protoplasts of the plant line anthocyanin-less310 (ant310), which contains a mutation in the chalcone isomerase (CHI) gene that largely inhibits flavonoid biosynthesis, exhibit strongly reduced transport activity for saponarin and its precursor Isovitexin (apigenin 6-C-glucoside). Incubation of ant310 primary leaf segments or isolated mesophyll protoplasts with naringenin, the product of the CHI reaction, restores saponarin biosynthesis almost completely, up to levels of the wild-type Ca33787. During reconstitution, saponarin accumulates to more than 90% in the vacuole. The capacity to synthesize saponarin from naringenin is strongly reduced in ant310 miniprotoplasts containing no central vacuole. Leaf segments and protoplasts from ant310 treated with naringenin showed strong reactivation of saponarin or Isovitexin uptake by vacuoles, while the activity of the UDP-glucose:Isovitexin 7-O-glucosyltransferase was not changed by this treatment. Our results demonstrate that efficient vacuolar flavonoid transport is linked to intact flavonoid biosynthesis in barley. Intact flavonoid biosynthesis exerts control over the activity of the vacuolar flavonoid/H(+)-antiporter. Thus, the barley ant310 mutant represents a novel model system to study the interplay between flavonoid biosynthesis and the vacuolar storage mechanism.
Acylated flavone C-glycosides from Cucumis sativus
Phytochemistry 2001 Sep;58(1):167-72.PMID:11524127DOI:10.1016/s0031-9422(01)00156-x.
Leaves of Cucumis sativus plants treated with silicon and infected with Sphaerotheca fuliginea yielded five new acylated flavone C-glycosides identified as Isovitexin 2"-O-(6"'-(E)-p-coumaroyl)glucoside (6), Isovitexin 2"-O-(6"'-(E)-p-coumaroyl)glucoside-4'-O-glucoside (7), Isovitexin 2"-O-(6"'-(E)-feruloyl)glucoside-4'-O-glucoside (11), isoscoparin 2"-O-(6"'-(E)-p-coumaroyl)glucoside (9), and isoscoparin 2"-O-(6"'-(E)-feruloyl)glucoside-4'-O-glucoside (12). The known flavone-glycosides Isovitexin (1), saponarin (2), saponarin 4'-O-glucoside (3), vicenin-2 (4), apigenin 7-O-(6"-O-p-coumaroylglucoside) (5), Isovitexin 2"-O-(6"'-(E)-feruloyl)glucoside (8) and isoscoparin 2"-O-(6"'-(E)-feruloyl)glucoside (10), were also identified in this plant material.
Uridinediphosphate-glucose: Isovitexin 7-O-glucosyltransferase from barley protoplasts: Subcellular localization
Planta 1979 Jan;146(2):199-202.PMID:24318059DOI:10.1007/BF00388232.
Protoplasts isolated from 6-d-old primary leaves of barley (Hordeum vulgare L.) contain an enzyme which transfers the glucosyl moiety of uridine-diphosphateglucose to Isovitexin, resulting in the formation of saponarin, the major flavonoid of barley. Purified chloroplasts isolated from protoplasts contained less than 2% of the total glucosyltransferase activity. These chloroplasts were 97% intact, based on ribulose-bisphosphate-carboxylase activity. Similarly low levels of glucosyltransferase activity were found in mitochondria and microbody or microsomal preparations from protoplasts. The soluble fraction (cytosol) contained at least 93% of the Isovitexin 7-O-glucosyltransferase activity.
Induction of Biosynthesis Antioxidant Molecules in Young Barley Plants by Trioxygen
Molecules 2022 Oct 24;27(21):7195.PMID:36364021DOI:10.3390/molecules27217195.
Young barley plants are a good source of bioactive compounds. This paper presents the effects of gaseous O3 (trioxygen or ozone) on the biosynthesis of compounds, determining the antioxidant potential of young barley plants. The total content of polyphenols was determined along with their profile, as well as total antioxidant potential and vitamin C content. The highest contents of these compounds were identified in young barley plants exposed to gaseous O3. The main bioactive compound, representing polyphenols, determined in the examined raw materials was saponarin (Isovitexin 7-O-glucoside). The induction of increased biosynthesis of these molecules was directly linked to the modification of the activity of selected enzymes. The increased polyphenol content resulted from the modified activities of polyphenol oxidase (PPO) and phenylalanine ammonia lyase (PAL). On the other hand, the oxidative effect of ozone on barley plants was reduced, owing to the modified activities of catalases (CAT), glutathione peroxidases (SOD) and guaiacol peroxidase (GPOX). Analysis of the results showed that by applying gaseous O3 at a dose of 50 ppm for 10 min, the contents of bioactive compounds can be maximised in a residue-free way by activating oxidative stress defence mechanisms.