Loliolide
(Synonyms: 地芰普内酯) 目录号 : GC49177
A monoterpene lactone with diverse biological activities
Cas No.:5989-02-6
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
Loliolide is a monoterpene lactone that has been found in P. urinaria and has diverse biological activities.1,2,3,4 It scavenges DPPH and peroxide radicals in cell-free assays when used at concentrations ranging from 62.5 to 250 µM and reduces peroxide-induced apoptosis in Vero cells.1 Loliolide (10 µg/ml) inhibits LPS-induced proliferation of isolated mouse T and B cells.2 It reduces hepatitis C virus (HCV) infectivity in Huh7.5 cells (EC50 = 2.48 µM) and inhibits HCV binding to Huh7.5 cells when used at concentrations of 10 and 50 µM.3 Loliolide also increases A. cephalotes preference for control flakes when applied to test flakes at a concentration of 6.8 mg/g of rye, indicating insect repellent activity.4
1.Yang, X., Kang, M.-C., Lee, K.-W., et al.Antioxidant activity and cell protective effect of loliolide isolated from Sargassum ringgoldianum subsp. coreanumAlgae26(2)201-208(2011) 2.Okada, N., Shirata, K., Niwano, M., et al.Immunosuppressive activity of a monoterpene from Eucommia ulmoidesPhytochemistry37(1)281-282(1994) 3.Chung, C.-Y., Liu, C.-H., Burnouf, T., et al.Activity-based and fraction-guided analysis of Phyllanthus urinaria identifies loliolide as a potent inhibitor of hepatitis C virus entryAntiviral Res.13058-68(2016) 4.Okunade, A.L., and Wiemer, D.F.(-)-Loliolide, an ant-repellent compound from Xanthoxyllum setulosumJ. Nat. Prod.48(3)472-473(1985)
| Cas No. | 5989-02-6 | SDF | |
| 别名 | 地芰普内酯 | ||
| Canonical SMILES | C[C@]12C(C(C)(C[C@@H](C1)O)C)=CC(O2)=O | ||
| 分子式 | C11H16O3 | 分子量 | 196.2 |
| 溶解度 | Methanol : 58.87 mg/mL (299.99 mM; Need ultrasonic and warming) | 储存条件 | Store at -20°C,protect from light and air |
| 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 | 5.0968 mL | 25.4842 mL | 50.9684 mL |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL |
| 10 mM | 0.5097 mL | 2.5484 mL | 5.0968 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。
Loliolide Presents Antiapoptosis and Antiscratching Effects in Human Keratinocytes
Int J Mol Sci 2019 Feb 2;20(3):651.PMID:30717391DOI:10.3390/ijms20030651.
Loliolide is a monoterpenoid hydroxylactone present in freshwater algae that has anti-inflammatory and antiaging activity; however, its effects on ultraviolet-damaged skin have yet to be elucidated. This study investigated the antiapoptosis and wound-healing effects of Loliolide using HaCaT cells (a human keratinocyte cell line). Loliolide inhibited the expression of reactive oxygen species (ROS) induced by ultraviolet radiation as well as wrinkle formation-related matrix metalloproteinase genes and increased the expression of the damage repair-related gene SIRT1. The apoptosis signaling pathway was confirmed by Western blot analysis, which showed that Loliolide was able to reduce the expression of caspases 3, 8, and 9, which are related to ROS-induced apoptosis. In addition, Western blotting, reverse-transcription polymerase chain reaction (PCR), and real-time PCR analyses showed that Loliolide enhanced the expression of the epidermal growth factor receptor signaling pathway (PI3K, AKT) and migration factors, such as K6, K16, and K17; keratinocyte growth factor; and inflammatory cytokines, such as interleukin (IL)-1, IL-17, and IL-22 expressed during the cellular scratching process, suggesting a putative wound-healing ability. Because of the antiapoptosis and antiscratching effects on skin of both Loliolide and loliolide-rich Prasiola japonica ethanol extract, we consider the former to be an important compound used in the cosmeceutical industry.
Loliolide, a Carotenoid Metabolite, Is a Potential Endogenous Inducer of Herbivore Resistance
Plant Physiol 2019 Apr;179(4):1822-1833.PMID:30700538DOI:10.1104/pp.18.00837.
Jasmonic acid (JA) plays an important role in the induction of herbivore resistance in many plants. However, JA-independent herbivore resistance has been suggested. An herbivore-resistance-inducing substance was isolated from Tobacco mosaic virus-infected tobacco (Nicotiana tabacum) leaves in which a hypersensitive response (HR) was induced and identified as Loliolide, which has been identified as a β-carotene metabolite. When applied to tomato (Solanum lycopersicum) leaves, Loliolide decreased the survival rate of the two-spotted spider mite, Tetranychus urticae, egg deposition by the same pest, and the survival rate of larvae of the common cutworm Spodoptera litura without exhibiting toxicity against these herbivores. Endogenous Loliolide levels increased not only with an infestation by S litura larvae, but also with the exogenous application of their oral secretions in tomato. A microarray analysis identified cell-wall-associated defense genes as loliolide-responsive tomato genes, and exogenous JA application did not induce the expression of these genes. Suppressor of zeaxanthin-less (szl), an Arabidopsis (Arabidopsis thaliana) mutant with a point mutation in a key gene of the β-carotene metabolic pathway, exhibited the decreased accumulation of endogenous Loliolide and increased susceptibility to infestation by the western flower thrip (Frankliniella occidentalis). A pretreatment with Loliolide decreased susceptibility to thrips in the JA-insensitive Arabidopsis mutant coronatine-insensitive1 Exogenous Loliolide did not restore reduced electrolyte leakage in szl in response to a HR-inducing bacterial strain. These results suggest that Loliolide functions as an endogenous signal that mediates defense responses to herbivores, possibly independently of JA, at least in tomato and Arabidopsis plants.
Loliolide, a New Therapeutic Option for Neurological Diseases? In Vitro Neuroprotective and Anti-Inflammatory Activities of a Monoterpenoid Lactone Isolated from Codium tomentosum
Int J Mol Sci 2021 Feb 14;22(4):1888.PMID:33672866DOI:10.3390/ijms22041888.
Parkinsons Disease (PD) is the second most common neurodegenerative disease worldwide, and is characterized by a progressive degeneration of dopaminergic neurons. Without an effective treatment, it is crucial to find new therapeutic options to fight the neurodegenerative process, which may arise from marine resources. Accordingly, the goal of the present work was to evaluate the ability of the monoterpenoid lactone Loliolide, isolated from the green seaweed Codium tomentosum, to prevent neurological cell death mediated by the neurotoxin 6-hydroxydopamine (6-OHDA) on SH-SY5Y cells and their anti-inflammatory effects in RAW 264.7 macrophages. Loliolide was obtained from the diethyl ether extract, purified through column chromatography and identified by NMR spectroscopy. The neuroprotective effects were evaluated by the MTT method. Cells' exposure to 6-OHDA in the presence of Loliolide led to an increase of cells' viability in 40%, and this effect was mediated by mitochondrial protection, reduction of oxidative stress condition and apoptosis, and inhibition of the NF-kB pathway. Additionally, Loliolide also suppressed nitric oxide production and inhibited the production of TNF-α and IL-6 pro-inflammatory cytokines. The results suggest that Loliolide can inspire the development of new neuroprotective therapeutic agents and thus, more detailed studies should be considered to validate its pharmacological potential.
Loliolide in marine algae
Nat Prod Res 2009;23(5):460-5.PMID:19296390DOI:10.1080/14786410802076069.
Loliolide content was determined in 13 marine algae including red, brown and green algae collected from the Black Sea, the Dardanelles and the Aegean Sea. Identification and quantification were performed by gas chromatography-mass spectrometry. The Loliolide content in green alga is 1.76 microg g(-1), ranges from 0.14 to 4.35 microg g(-1) in red and from 0.18 to 4.83 microg g(-1) in brown algae. The results obtained are in the same range as previously reported for algae, as well as terrestrial plants. This article represents the first report of Loliolide occurrence in green algae.
Monoterpenoid Loliolide Regulates Hair Follicle Inductivity of Human Dermal Papilla Cells by Activating the Akt/β-Catenin Signaling Pathway
J Microbiol Biotechnol 2019 Nov 28;29(11):1830-1840.PMID:31601058DOI:10.4014/jmb.1908.08018.
Loliolide is one of the most ubiquitous monoterpenoid compounds found in algae, and its potential therapeutic effect on various dermatological conditions via agent-induced biological functions, including anti-oxidative and anti-apoptotic properties, was demonstrated. Here, we investigated the effects of Loliolide on hair growth in dermal papilla (DP) cells, the main components regulating hair growth and loss conditions. For this purpose, we used a threedimensional (3D) DP spheroid model that mimics the in vivo hair follicle system. Biochemical assays showed that low doses of Loliolide increased the viability and size of 3D DP spheroids in a dose-dependent manner. This result correlated with increases in expression levels of hair growth-related autocrine factors including VEGF, IGF-1, and KGF. Immunoblotting and luciferase-reporter assays further revealed that Loliolide induced AKT phosphorylation, and this effect led to stabilization of β-catenin, which plays a crucial role in the hair-inductive properties of DP cells. Further experiments showed that Loliolide increased the expression levels of the DP signature genes, ALP, BMP2, VCAN, and HEY1. Furthermore, conditioned media from loliolide-treated DP spheroids significantly enhanced proliferation and the expression of hair growth regulatory genes in keratinocytes. These results suggested that Loliolide could function in the hair growth inductivity of DP cells via the AKT/ β-catenin signaling pathways.