Ligustroside
(Synonyms: 女贞甙,Ligstroside) 目录号 : GC63973
Ligustroside (Ligstroside) 是一种 secoiridoid 衍生物，在早期阿尔茨海默病 (AD) 和脑老化模型中的线粒体生物能量学方面表现出色，其机制可能不会干扰 Aβ 的产生。Ligustroside 显着抑制脂多糖激活的 RAW264.7 巨噬细胞中一氧化氮的产生。
Cas No.:35897-92-8
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
Ligustroside (Ligstroside), a secoiridoid derivative, has outstanding performance on mitochondrial bioenergetics in models of early Alzheimer’s disease (AD) and brain ageing by mechanisms that may not interfere with Aβ production. Ligustroside significantly inhibits nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages[1][2].
Ligstroside increases mRNA expression of SIRT1, CREB1, complex I, and GPx1 in SH-SY5Y-APP695 cells[1].
Ligstroside (50 mg/kg; a supplemented diet for 6 months) protects against mitochondrial dysfunction in models of early Alzheimer’s disease and brain ageing[1].
[1]. Grewal R, et al. Purified oleocanthal and ligstroside protect against mitochondrial dysfunction in models of early Alzheimer’s disease and brain ageing. Exp Neurol. 2020;328:113248. [2]. Liu J, et al. Chemical structures of constituents from the flowers of Osmanthus fragrans var. aurantiacus. J Nat Med. 2015;69(1):135-141.
| Cas No. | 35897-92-8 | SDF | Download SDF |
| 别名 | 女贞甙,Ligstroside | ||
| 分子式 | C25H32O12 | 分子量 | 524.51 |
| 溶解度 | 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 | 1.9065 mL | 9.5327 mL | 19.0654 mL |
| 5 mM | 0.3813 mL | 1.9065 mL | 3.8131 mL |
| 10 mM | 0.1907 mL | 0.9533 mL | 1.9065 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。
Salidroside, 8( E)-Nuezhenide, and Ligustroside from Ligustrum japonicum Fructus Inhibit Expressions of MMP-2 and -9 in HT 1080 Fibrosarcoma
Int J Mol Sci 2022 Feb 28;23(5):2660.PMID:35269801DOI:10.3390/ijms23052660.
A phenyl ethanoid, salidroside (SAL), and two secoiridoids, 8(E)-nuezhenide (NZD) and Ligustroside (LIG), were isolated from fruits of Ligustrumjaponicum, used as traditional folk medicine, and their chemical structures were elucidated by the comparison of spectral data with published literature. Matrix metalloproteinases (MMPs) are major enzymes that play crucial roles in the metastasis and invasive behavior of tumors. In particular, MMP-2 and MMP-9, regulated by the MAPK signaling pathways, including p38, ERK and JNK, are known to play a key role in the degradation of the basement membrane. In the present study, the effects of SAL, NZD and LIG on the expression of MMP-2 and -9 were examined in phorbol 12-myristate 13-acetate (PMA)-induced HT 1080 cells. All the compounds significantly lowered the amount of MMP-2 and MMP-9 released, as determined by gelatin zymography and ELISA. In addition, the mRNA and protein expression levels of MMP-2 and MMP-9 were significantly suppressed, as measured by RT-PCR and Western blotting. According to the Western blotting assay, SAL and LIG effectively reduced the expression of MMP-2 in a dose-dependent manner. NZD lowered the expression of MMP-9 in a similar way. The phosphorylation of p38, ERK and JNK was also significantly suppressed by these compounds. These findings suggest that all the compounds regulate the release and expression of MMP-2 and MMP-9 via MAPK signaling pathways.
Cytotoxic and EGFR tyrosine kinase inhibitory activities of aglycone derivatives obtained by enzymatic hydrolysis of oleoside-type secoiridoid glucosides, oleuropein and Ligustroside
J Nat Med 2011 Jan;65(1):237-40.PMID:21042869DOI:10.1007/s11418-010-0476-8.
Hydrolysis of oleoside-type secoiridoid glucosides, oleuropein (1) and Ligustroside (2), in the presence of β-glucosidase provided their aglycones, named (5S,8R,9S)-7-3,4-dihydroxyphenethyl elenolate (3) and (5S,8R,9S)-7-4-hydroxyphenethyl elenolate (4), respectively. The structures of 3 and 4 were identified by spectroscopic means and optical rotation measurements. Evaluation of the cytotoxic and epidermal growth factor receptor (EGFR) tyrosine kinase inhibitory activities of compounds 1-4 showed that compounds 3 and 4 exhibited moderate cytotoxicity against a disease-oriented panel of 39 human cancer cell lines in vitro, whereas compound 3 inhibited the enzyme.
Molecular modeling of non-covalent binding of Ligustrum lucidum secoiridoid glucosides to AP-1/matrix metalloproteinase pathway components
J Bioenerg Biomembr 2018 Aug;50(4):315-327.PMID:29687366DOI:10.1007/s10863-018-9756-x.
Ligustrum lucidum secoiridoid glucosides have been demonstrated to treat various types of diseases such as inflammation, pain, hepatotoxicity and hyperlipidermic as well as tonic for liver and kidney. Matrix metalloproteinases (MMPs) play a key role upon the pathology of photoaging. The present computational study showed that among the six secoiridoid glucosides (Ligustroside, lucidumoside A, lucidumoside C, neonuezhenide, oleoside dimethylester, and oleuropein), Ligustroside and lucidumoside A competitively inhibit all MMP-1, MMP-3, and MMP-9 activities in the docking models. The molecular docking analysis revealed a network of interactions between MMP-1, MMP-3, and MMP-9 and the ligands; Ligustroside and lucidumoside A, and oxygen-containing and hydrophobic functional groups appear to be responsible for these enhanced interactions. The effect of Ligustroside and lucidumoside A on the transcription factor AP-1 action was also investigated using molecular docking and dynamics simulations. The experiments suggested that inhibition of an AP-1-DNA complex formation could be on account of the direct interference of AP-1 binding onto the DNA binding sequence by Ligustroside and lucidumoside A. The results suggest that both compounds have the highest potential for application as an anti-aging agent with the MMP inhibitory and anti-transcriptional activities.
(-)-Oleocanthal induces death preferentially in tumor hematopoietic cells through caspase dependent and independent mechanisms
Food Funct 2022 Oct 31;13(21):11334-11341.PMID:36254591DOI:10.1039/d2fo01222g.
Olive oil is a key component of the highly cardiovascular protective Mediterranean diet. (-)-Oleocanthal (OLC) is one of the most interesting phenolics present in virgin olive oil, and is formed from secoiridoid Ligustroside during the processing of olives to yield the oil. Anti-inflammatory and anti-oxidant properties were identified shortly after OLC isolation, followed by the discovery of anti-tumor activities in a few non-hematopoietic cell lineages. Because of the scarcity of tissues potentially targeted by OLC analyzed so far and the unresolved mechanism(s) for OLC anti-tumor properties, we used a panel of 17 cell lines belonging to 11 tissue lineages to carry out a detailed examination of targets and pathways leading to cell growth inhibition and death. We found that OLC inhibits cell proliferation and induces apoptotic death as revealed by sub-G1 cell cycle analyses and Annexin-V staining in all lineages analyzed except lung carcinoma cell lines. Hematopoietic tumor cell lines, untested until now, were the most sensitive to OLC treatment, whereas non-transformed cells were significantly resistant to cell death. The specificity of OLC-mediated caspase activation was confirmed by blocking experiments and the use of transfectants overexpressing anti apoptotic genes. OLC triggers typical mediators of the intrinsic apoptotic pathway such as production of reactive oxygen species and mitochondrial membrane depolarization (Δψm). Complete blockade of caspases, however, did not result in parallel abrogation of Annexin-V staining, thus suggesting that complex mechanisms are involved in triggering OLC-mediated cell death. Our results demonstrate that OLC preferentially targets hematopoietic tumor cell lines and support that cell death is mediated by caspase-dependent and independent mechanisms.
In vitro anti-inflammatory activity of iridoids and triterpenoid compounds isolated from Phillyrea latifolia L
Biol Pharm Bull 2000 Nov;23(11):1307-13.PMID:11085357DOI:10.1248/bpb.23.1307.
Two iridoids, oleuropeoside and Ligustroside, and two triterpenoid compounds, oleanolic acid and ursolic acid, have been isolated from the leaves of Phillyrea latifolia L. (Oleaceae). These compounds were tested for interactions with the cyclooxygenase (COX) and 5-lipoxygenase (5-LOX) pathways of arachidonate metabolism in calcium ionophore-stimulated mouse peritoneal macrophages and human platelets, and for their effect on cell viability. Structure-activity relationships obtained for in vitro screening results were discussed. These compounds are capable of exerting inhibitory actions on enzymes of the arachidonate cascade. All compounds assayed showed a significant effect on prostaglandin E2 (PGE2)-release, with inhibition percentages similar to the reference drug indomethacin (IC50 = 0.95 microM). The IC50 values of the active compounds are: oleuropeoside 47 microM, Ligustroside 48.53 microM, oleanolic acid 23.51 microM and ursolic acid 60.91 microM. In the leukotriene C4 (LTC4)-assay, only oleanolic acid showed a significant effect (IC50 = 16.79 microM). We also investigated the action of compounds on thromboxane B2 (TXB2)-release induced by calcium ionophore in human platelets. Of all the tested compounds, only Ligustroside (IC50 = 122.63 microM) and ursolic acid (IC50 = 50.21 microM) showed a significant effect, although with less potency than the reference drug ibuprofen (IC50 = 1.27 microM). Thus, our compounds possess an array of potentially beneficial anti-inflammatory properties which may, alongside other constituents, contribute to the claimed therapeutic properties of the plant from which they are derived.