1,3,5,8-Tetrahydroxyxanthone
(Synonyms: 去甲基雏菊叶龙胆酮,Demethylbellidifolin) 目录号 : GC39046
1,3,5,8-Tetrahydroxyxanthone是一种天然产物，存在于黑鸢尾和野油菜中。它具有作为代谢物、EC 3.1.1.7（乙酰胆碱酯酶）抑制剂、诱变剂、抗氧化剂和自由基清除剂的作用。它是氧杂蒽酮和四醇的成员。它在功能上与氧杂蒽酮相关。
Cas No.:2980-32-7
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
1,3,5,8-Tetrahydroxyxanthone (Desmethylbellidifolin) is a natural xanthone extracted from Gentianella acuta. 1,3,5,8-Tetrahydroxyxanthone has antispasmodic effect and anti-inflammatory activity[1].
[1]. Ni Y, et al. Desmethylbellidifolin From Gentianella acuta Ameliorate TNBS-Induced Ulcerative Colitis Through Antispasmodic Effect and Anti-Inflammation. Front Pharmacol. 2019 Sep 20;10:1104.
| Cas No. | 2980-32-7 | SDF | |
| 别名 | 去甲基雏菊叶龙胆酮,Demethylbellidifolin | ||
| Canonical SMILES | O=C1C2=C(OC3=C1C(O)=CC=C3O)C=C(O)C=C2O | ||
| 分子式 | C13H8O6 | 分子量 | 260.2 |
| 溶解度 | DMSO : 100 mg/mL (384.32 mM; Need ultrasonic) | 储存条件 | Store at -20°C,protect from light |
| 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 | 3.8432 mL | 19.216 mL | 38.432 mL |
| 5 mM | 0.7686 mL | 3.8432 mL | 7.6864 mL |
| 10 mM | 0.3843 mL | 1.9216 mL | 3.8432 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。
1,3,5,8-Tetrahydroxyxanthone suppressed adipogenesis via activating Hedgehog signaling in 3T3-L1 adipocytes
Food Sci Biotechnol 2022 Jul 16;31(11):1473-1480.PMID:PMC9433504DOI:10.1007/s10068-022-01130-y.
In this study, we investigated the effect of 1,3,5,8-Tetrahydroxyxanthone (THX) on the adipogenesis of 3T3-L1 adipocytes. THX, a xanthone isolated from Gentianella acuta, inhibited lipid accumulation in 3T3-L1 adipocytes and reduced the protein levels of the key adipogenic transcriptional factors, peroxisome proliferator-activated receptor gamma (PPARγ) and CCAAT/enhancer-binding protein α (C/EBPα), in a dose-dependent manner. In addition, THX enhanced the transcriptional activity of Gli1 known as the key indicator of Hedgehog (Hh) signaling activity and increased the expression of Gli1 and its upstream regulator Smo. The Smo activator SAG exerted the similar effect with THX on regulating Gli1, Smo, PPARγ and C/EBPα expression, which led to the suppression of fat formation in 3T3-L1 adipocytes. Furthermore, we found that the inhibitory effect of THX on adipogenesis was derived from regulation of the early stage of adipogenesis. These results suggest that THX suppresses the differentiation of adipocyte through Hh signaling and may be considered as a potent agent for the prevention of obesity.
1,3,5,8-Tetrahydroxyxanthone regulates ANGPTL3-LPL pathway to lessen the ketosis in mice
Eur J Pharm Sci 2012 May 12;46(1-2):26-31.PMID:22342712DOI:10.1016/j.ejps.2012.02.001.
Ketosis is a metabolic disorder closely associated with both lipid and carbohydrate metabolism. Recent studies show that angiopoietin-like protein 3 (ANGPTL3) contributes to the development of metabolic disorder. The objective of this study was to explore the inhibitory effect of 1,3,5,8-Tetrahydroxyxanthone (Xan), a naturally occurring flavonoid compound, on ketosis and the mechanisms involved in this regulation. After 4weeks, Xan (10 or 30mg/kg, intragastrically) treatment decreased plasma total ketone bodies, malondialdehyde, 8-isoprostane, triglyceride, total cholesterol levels, and hepatic ANGPTL3 expression concomitantly with increased plasma glucose concentration and adipose lipoprotein lipase (LPL) expression in ketosis murine. The present results suggest that Xan regulates ANGPTL3-LPL pathway to lessen the ketosis in mice.
Phenylalanine-independent biosynthesis of 1,3,5,8-Tetrahydroxyxanthone. A retrobiosynthetic NMR study with root cultures of Swertia chirata
Eur J Biochem 2003 Jul;270(14):2950-8.PMID:12846828DOI:10.1046/j.1432-1033.2003.03669.x.
Root cultures of Swertia chirata (Gentianaceae) were grown with supplements of [1-13C]glucose, [U-13C6]glucose or [carboxy-13C]shikimic acid. 1,3,5,8-Tetrahydroxyxanthone was isolated and analysed by quantitative NMR analysis. The observed isotopomer distribution shows that 1,3,5,8-Tetrahydroxyxanthone is biosynthesized via a polyketide-type pathway. The starter unit, 3-hydroxybenzoyl-CoA, is obtained from an early shikimate pathway intermediate. Phenylalanine, cinnamic acid and benzoic acid were ruled out as intermediates.
2-Phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide Radical (PTIO•) Trapping Activity and Mechanisms of 16 Phenolic Xanthones
Molecules 2018 Jul 11;23(7):1692.PMID:29997352DOI:10.3390/molecules23071692.
This study used the 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•) trapping model to study the antioxidant activities of 16 natural xanthones in aqueous solution, including garcinone C, γ-mangostin, subelliptenone G, mangiferin, 1,6,7-trihydroxy-xanthone, 1,2,5-trihydroxyxanthone, 1,5,6-trihydroxyxanthone, norathyriol, 1,3,5,6-tetrahydroxy-xanthone, isojacareubin, 1,3,5,8-Tetrahydroxyxanthone, isomangiferin, 2-hydroxyxanthone, 7-O-methylmangiferin, neomangiferin, and lancerin. It was observed that most of the 16 xanthones could scavenge the PTIO• radical in a dose-dependent manner at pH 4.5 and 7.4. Among them, 12 xanthones of the para-di-OHs (or ortho-di-OHs) type always exhibited lower half maximal inhibitory concentration (IC50) values than those not of the para-di-OHs (or ortho-di-OHs) type. Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) analysis revealed that most of these xanthones gave xanthone-xanthone dimers after incubation with PTIO•, except for neomangiferin. Based on these data, we concluded that the antioxidant activity of phenolic xanthone may be mediated by electron-transfer (ET) plus H⁺-transfer mechanisms. Through these mechanisms, some xanthones can further dimerize unless they bear huge substituents with steric hindrance. Four substituent types (i.e., para-di-OHs, 5,6-di-OHs, 6,7-di-OHs, and 7,8-di-OHs) dominate the antioxidant activity of phenolic xanthones, while other substituents (including isoprenyl and 3-hydroxy-3-methylbutyl substituents) play a minor role as long as they do not break the above four types.
Xanthones from Swertia mussotii and their α-glycosidase inhibitory activities
Planta Med 2014 Feb;80(2-3):201-8.PMID:24356906DOI:10.1055/s-0033-1360173.
Two new xanthones, 1,8-dihydroxy-3-methoxyxanthone 7-O-[α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranoside] (1) and 1,8- dihydroxy-3-methoxyxanthone 7-O-[α-L-rhamnopyranosyl(1 → 3)-α-L-rhamno-pyranosyl (1 → 2)-β-D-xylopyranoside] (2), together with 26 known xanthones (3-28), were isolated from the aqueous ethanol extract of the traditional Chinese herb Swertia mussotii. Their structures were elucidated via spectroscopic analyses including 2D NMR. The inhibition of α-glucosidase by the isolated xanthones was evaluated by an in vitro high-throughput screening assay. Our results indicated that 1,3,5,8-Tetrahydroxyxanthone is the best inhibitor with an IC50 value of 5.33 ± 0.09 µM, while the O-glycosylated xanthones were poor α-glycosidase inhibitors.