Gallotannin
(Synonyms: 单宁酸) 目录号 : GC43726A polyphenol with diverse biological activities
Cas No.:1401-55-4
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
Gallotannin is a polyphenol of gallic acid that has been found in various plants and has antioxidant, anti-inflammatory, antiviral, and antiproliferative biological activities. Gallotannin (1 μM) inhibits the intracellular production of reactive oxygen species (ROS) and DNA damage induced by phorbol 12-myristate 13-acetate in human polymorphonuclear neutrophils (PMNs). It also decreases TPA-induced nitric oxide release by 90% from primary rat hepatocytes when used at a concentration of 0.5 mM. Gallotannin inhibits hepatitis C virus (HCV) entry into Huh7.5 human hepatoma cells (IC50 = 5.8 μM) and inhibits the proliferation of MDA-MB-231 and MCF-7 human breast cancer cells (IC50s = 2.5 and 4 μM, respectively). In a rat model of middle cerebral artery occlusion (MCAO), it increases superoxide dismutase (SOD1) protein levels and decreases the amount of proteins modified by malondialdehyde (MDA) in ischemic brain tissue when administered at a dose of 10 mg/kg.
| Cas No. | 1401-55-4 | SDF | |
| 别名 | 单宁酸 | ||
| Canonical SMILES | OC1=C(O)C(O)=CC(C(OC2=CC(C(OC[C@@H]3[C@@H](OC(C4=CC(O)=C(O)C(OC(C5=CC(O)=C(O)C(O)=C5)=O)=C4)=O)[C@H](OC(C6=CC(O)=C(O)C(OC(C7=CC(O)=C(O)C(O)=C7)=O)=C6)=O)[C@@H](OC(C8=CC(O)=C(O)C(OC(C9=CC(O)=C(O)C(O)=C9)=O)=C8)=O)[C@H](OC(C%10=CC(O)=C(O)C(OC(C%11=CC(O | ||
| 分子式 | C76H52O46 | 分子量 | 1701.2 |
| 溶解度 | DMF: 10 mg/ml,DMSO: 10 mg/ml,PBS (pH 7.2): 0.3 mg/ml | 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 | 0.5878 mL | 2.9391 mL | 5.8782 mL |
| 5 mM | 0.1176 mL | 0.5878 mL | 1.1756 mL |
| 10 mM | 0.0588 mL | 0.2939 mL | 0.5878 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。
Recent Advances in Tannic Acid (Gallotannin) Anticancer Activities and Drug Delivery Systems for Efficacy Improvement; A Comprehensive Review
Molecules 2021 Mar 9;26(5):1486.PMID:33803294DOI:10.3390/molecules26051486.
Tannic acid is a chief gallo-tannin belonging to the hydrolysable tannins extracted from gall nuts and other plant sources. A myriad of pharmaceutical and biological applications in the medical field has been well recognized to tannic acid. Among these effects, potential anticancer activities against several solid malignancies such as liver, breast, lung, pancreatic, colorectal and ovarian cancers have been reported. Tannic acid was found to play a maestro-role in tuning several oncological signaling pathways including JAK/STAT, RAS/RAF/mTOR, TGF-β1/TGF-β1R axis, VEGF/VEGFR and CXCL12/CXCR4 axes. The combinational beneficial effects of tannic acid with other conventional chemotherapeutic drugs have been clearly demonstrated in literature such as a synergistic anticancer effect and enhancement of the chemo-sensitivity in several resistant cases. Yet, clinical applications of tannic acid have been limited owing to its poor lipid solubility, low bioavailability, off-taste, and short half-life. To overcome such obstacles, novel drug delivery systems have been employed to deliver tannic acid with the aim of improving its applications and/or efficacy against cancer cells. Among these drug delivery systems are several types of organic and metallic nanoparticles. In this review, the authors focus on the molecular mechanisms of tannic acid in tuning several neoplastic diseases as well as novel drug delivery systems that can be used for its clinical applications with an attempt to provide a systemic reference to promote the development of tannic acid as a cheap drug and/or drug delivery system in cancer management.
Enzymology of Gallotannin and ellagitannin biosynthesis
Phytochemistry 2005 Sep;66(17):2001-11.PMID:16153405DOI:10.1016/j.phytochem.2005.01.009.
Gallotannins and ellagitannins, the two subclasses of hydrolyzable tannins, are derivatives of 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose. Enzyme studies with extracts from oak leaves (Quercus robur, syn. Quercus pedunculata; Quercus rubra) and from staghorn sumac (Rhus typhina) revealed that this pivotal intermediate is synthesized from beta-glucogallin (1-O-galloyl-beta-D-glucopyranose) by a series of strictly position-specific galloylation steps, affording so-called 'simple' gallotannins, i.e., mono- to pentagallyoylglucose esters. Besides its role as starter molecule, beta-glucogallin was also recognized as the principal energy-rich acyl donor required in these transformations. Subsequent pathways to 'complex' gallotannins have recently been elucidated by the isolation of five different enzymes from sumac leaves that were purified to apparent homogeneity. They catalyzed the beta-glucogallin-dependent galloylation of pentagallyoylglucose to a variety of hexa- and heptagalloylglucoses, plus several not yet characterized higher substituted analogous galloylglucoses. With respect to the biosynthesis of ellagitannins, postulates that had been formulated already decades ago were proven by the purification of a new laccase-like phenol oxidase from leaves of fringe cups (Tellima grandiflora) that regio- and stereospecifically oxidized pentagallyoylglucose to the monomeric ellagitannin, tellimagrandin II. This compound was further oxidized by a similar but different laccase-like oxidase to yield a dimeric ellagitannin, cornusiin E.
Synthesis and Evaluation of Gallotannin Derivatives as Antioxidants and α-Glucosidase Inhibitors
Chem Pharm Bull (Tokyo) 2021;69(12):1209-1212.PMID:34853289DOI:10.1248/cpb.c21-00566.
Gallotannins are phenolic natural products containing galloyl moieties connected to polyhydric alcohol cores, e.g., D-glucose. Some gallotannins are reported to have antidiabetic properties, such as α-glucosidase inhibitory activity. In this study, fourteen unnatural Gallotannin derivatives with 1,5-anhydroalditol and inositol as the cyclic polyol cores were synthesized to investigate how their structures affected antioxidative and α-glucosidase inhibitory activities. Tannic acid demonstrated the most potent antioxidative activity (EC50 = 2.84 μM), with potency increasing proportionally to the number of galloyl moieties. Synthetic inositol derivatives outperformed 1,5-anhydroalditol derivatives in rat α-glucosidase inhibitory activity. Pentagalloyl glucose, a natural compound, demonstrated the highest activity (IC50 = 0.336 μM).
Gallotannin 1,2,6-tri-O-galloyl-β-d-glucopyranose: Its availability and changing patterns in tea (Camellia sinensis)
Food Chem 2019 Oct 30;296:40-46.PMID:31202304DOI:10.1016/j.foodchem.2019.05.144.
Gallotannin 1,2,6-tri-O-galloyl-β-d-glucopyranose (1,2,6-TGGP) plays multiple roles against multidrug-resistant bacteria and other diseases. Nevertheless, its availability in tea (Camellia sinensis) has rarely been reported. Herein, the identification and verification of 1,2,6-TGGP from Camellia sinensis using ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry (UPLC-qTOF MS/MS), electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR) were reported. The isolated 1,2,6-TGGP was used for the chemotaxonomy analysis of 17 tea cultivars. The contents of 1,2,6-TGGP ranged from 1.96 to 43.20 mg g-1, with a mean of 13.75 mg g-1. Relatively high 1,2,6-TGGP contents (>30 mg g-1) in two tea cultivars indicate that the beneficial effects of 1,2,6-TGGP can be obtained by consuming these teas. The chemotaxonomy analysis showed a biosynthetic relation between 1,2,6-TGGP and gallic acid. Further analysis showed that the 1,2,6-TGGP contents significantly decreased with the plucking times irrespective of the cultivars. Moreover, a positive and significant correlation was also observed between 1,2,6-TGGP and gallic acid. The identification of tea cultivars that are rich in 1,2,6-TGGP was first reported and the obtained results should boost their potential use in food and medicine.
Gallotannin Improves the Photoaged-Related Proteins by Extracellular Signal-Regulated Kinases/c-Jun N-Terminal Kinases Signaling Pathway in Human Epidermal Keratinocyte Cells
J Med Food 2018 Aug;21(8):785-792.PMID:30004816DOI:10.1089/jmf.2017.4096.
Tannins are a type of polyphenols found in several fruits such as grapes and berries, and nuts such as aronias and acorns. Both hydrolyzable tannins and condensed tannins are referred to as tannins. Among the hydrolyzable tannins, Gallotannin has a strong antioxidative property and is known to protect the skin by inhibiting the precursors of elastolytic enzymes. However, its mechanism of protection against ultraviolet B (UVB) damage in human fibroblasts and keratinocytes has not yet been elucidated. In this study, we investigate the antioxidant and antiaging effect of Gallotannin on UVB-irradiated human cells by studying its effect on extracellular signal-regulated kinases/c-Jun N-terminal kinases (EKRs/JNKs) signaling related to cell growth and differentiation/stress apoptosis. The results showed that Gallotannin improved collagen synthesis, reduced metalloproteinase-1 (MMP-1) expression in a dose-dependent manner, and downregulated MMP-1 levels through the ERK/JNK signaling pathway in UVB-irradiated human cells. Gallotannin also increased glutathione but did not increase transforming growth factor beta 1, which induces fibrosis. We propose that Gallotannin is a novel agent for protection against UVB, and acts as an antiaging agent that can be used in food, pharmaceuticals, and cosmetics.