Lupenone
(Synonyms: 羽扇烯酮) 目录号 : GC36494
A triterpenoid with diverse biological activities
Cas No.:1617-70-5
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
Lupenone is a triterpenoid that has been found in L. eriocalyx and has diverse biological activities.1,2,3,4 It inhibits HIV-1 reverse transcriptase (IC50 = 2.1 μM).1 Lupenone is active against the W2 and D6 strains of P. falciparum (IC50s = 208.1 and 394.7 ng/ml, respectively).2 It induces melanogenesis in (EC50 = 0.35 ?M), and inhibits the growth of, B16 2F2 melanoma cells in vitro (IC50 = 25.4 ?M).3 Topical application of lupenone (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate in mice.4 It also inhibits acetic acid-induced writhing in mice when administered at a dose of 100 mg/kg.2
1.Akihisa, T., Ogihara, J., Kato, J., et al.Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptaseLipids36(5)507-512(2001) 2.Manguro, L.O.A., Owuor, P.O., and Ochung, A.A.Isolation, characterization and biological activities of phytoconstituents from Lonchocarpus eriocalyx harms leavesTrends Phytochem. Res.2(3)135-146(2018) 3.Hata, K., Hori, K., and Takahashi, S.Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell lineJ. Nat. Prod.65(5)645-648(2002) 4.Yasukawa, K., Yu, S., Yamanouchi, S., et al.Some lupane-type triterpenes inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skinPhytomedicine1(4)309-313(1995)
| Cas No. | 1617-70-5 | SDF | |
| 别名 | 羽扇烯酮 | ||
| Canonical SMILES | C[C@]12[C@@](CC[C@@]3([H])[C@]2(CC[C@](C4(C)C)([H])[C@@]3(CCC4=O)C)C)([H])[C@]5([H])[C@](C)(CC[C@H]5C(C)=C)CC1 | ||
| 分子式 | C30H48O | 分子量 | 424.7 |
| 溶解度 | Ethanol: 3.33 mg/mL (7.84 mM) | 储存条件 | 4°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 | 2.3546 mL | 11.773 mL | 23.546 mL |
| 5 mM | 0.4709 mL | 2.3546 mL | 4.7092 mL |
| 10 mM | 0.2355 mL | 1.1773 mL | 2.3546 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。
Beneficial health effects of Lupenone triterpene: A review
Biomed Pharmacother 2018 Jul;103:198-203.PMID:29653365DOI:10.1016/j.biopha.2018.04.019.
There are a large number of new structure compounds with good pharmacological activity in the natural plants, can be applied to the treatment of human diseases. Finding active ingredients from the plants is one of the important ways to develop new drugs. Triterpenes are widespread in plants, and Lupenone belongs to lupane type triterpenoids. Lupenone is very common natural ingredient distributed in multi-family plants including Asteraceae, Balanophoraceae, Cactaceae, Iridaceae, Musaceae, Urticaceae, Leguminosae, Bombacaceae, etc., but its distribution has no regular. The consumption of Lupenone in vegetarian diet is high in human life. Pharmacological screening of Lupenone revealed various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity. Based on these important pharmacological activities, this review provides detailed account of pre-clinical studies conducted to determine the utility of Lupenone as a therapeutic and chemopreventive agent for the treatment of various diseases.
Lupenone is a good anti-inflammatory compound based on the network pharmacology
Mol Divers 2020 Feb;24(1):21-30.PMID:30796639DOI:10.1007/s11030-019-09928-5.
The dried rhizome of Musa basjoo Sieb. et Zucc. is Rhizoma Musae. It has been used to treat diabetes in Miao medicine in China. Lupenone was isolated from Rhizoma Musae and has good anti-diabetic activity. Its mechanism of action is unclear. Diabetes is a chronic low-level systemic inflammatory disease, and Lupenone has anti-inflammatory activity, but the underlying mechanism is not fully elucidated. In this study, we aimed to construct the drug-target biologic network and predict the anti-inflammatory mechanism of Lupenone. The network-based pharmacologic analysis platform was used to identify the target proteins related to inflammation. Furthermore, the effects of Lupenone on acute, subacute and diabetic pancreatic inflammation were evaluated. The "component-target-disease" network was constructed using Cytoscape. Lupenone could regulate transcription factor p65, NF-kappa-B inhibitor alpha, transcription factor AP-1, NF-kappa-B essential modulator, nuclear factor NF-kappa-B p105 subunit, epidermal growth factor receptor, hypoxia-inducible factor 1-alpha and other proteins related to the PI3K-Akt, Toll-like receptor and NF-kappa B signaling pathways. In addition, Lupenone significantly decreased acute and subacute inflammation in mice as well as the IL-1β and IFN-γ levels in the pancreas of diabetic rats. The above results provide strong support for studying the molecular mechanism of Lupenone in the treatment of diabetes from the perspective of anti-inflammation.
Lupenone Protects Neuroblastoma SH-SY5y Cells Against Methamphetamine-Induced Apoptotic Cell Death via PI3K/Akt/mTOR Signaling Pathway
Int J Mol Sci 2020 Feb 27;21(5):1617.PMID:32120831DOI:10.3390/ijms21051617.
Methamphetamine (METH) is an addictive psychostimulant showing neurotoxicity through neuronal apoptosis and the neuro-inflammatory pathway. Lupenone, a lupane triterpenoid, is an isolated compound exhibiting anti-oxidative, anti-inflammation, and anti-diabetic activities. However, whether Lupenone plays a protective role against apoptosis induced by METH in SH-SY5y neuroblastoma cells remains unknown. In the present study, we elucidated that Lupenone had no toxicity to SH-SY5y cells at different concentrations. On the other hand, we found that the treatment of SH-SY5y cells with an optimal concentration of Lupenone could lead to protection against cell death induced by METH. AnnexinV/PI apoptosis analysis revealed a dramatically reduced level of the apoptotic cell population in lupenon and METH treated SH-SY5y cells. Moreover, diminished expression of anti-apoptotic proteins, including Bcl-2, Caspase3, Caspase7, and Caspase8 in METH-exposed SH-SY5y cells, was significantly recovered by treatment with Lupenone. This protection in the expression of anti-apoptotic proteins was due to an increased phosphorylation level of PI3K/Akt in METH-treated SH-SY5y cells pre-incubated with Lupenone. These findings suggest that Lupenone can protect SH-SY5y cells against METH-induced neuronal apoptosis through the PI3K/Akt pathway.
Dynamics of natural product Lupenone as a potential fusion inhibitor against the spike complex of novel Semliki Forest Virus
PLoS One 2022 Feb 25;17(2):e0263853.PMID:35213606DOI:10.1371/journal.pone.0263853.
The Semliki Forest Virus (SFV) is an RNA virus with a positive-strand that belongs to the Togaviridae family's Alphavirus genus. An epidemic was observed among French troops stationed in the Central African Republic, most likely caused by the SFV virus. The two transmembrane proteins El and E2 and the peripheral protein E3 make up the viral spike protein. The virus binds to the host cell and is internalized via endocytosis; endosome acidification causes the E1/E2 heterodimer to dissociate and the E1 subunits to trimerize. Lupenone was evaluated against the E1 spike protein of SFV in this study based on state-of-the-art cheminformatics approaches, including molecular docking, molecular dynamics simulation, and binding free energy calculation. The molecular docking study envisaged major interactions of Lupenone with binding cavity residues involved non-bonded van der Waal's and Pi-alkyl interactions. Molecular dynamic simulation of a time scale 200 ns corroborated interaction pattern with molecular docking studies between Lupenone and E1 spike protein. Nevertheless, Lupenone intearcation with the E1 spike protein conforming into a stable complex substantiated by free energy landscape (FEL), PCA analysis. Free energy decomposition of the binding cavity resdiues of E1 spike protein also ensured the efficient non-bonded van der Waal's interaction contributing most energy to interact with the Lupenone. Therefore, Lupenone interacted strongly at the active site conforming into higher structural stability throughout the dynamic evolution of the complex. Thus, this study perhaps comprehend the efficiency of Lupenone as lead molecule against SFV E1 spike protein for future therapeutic purpose.
Lupenone isolated from Adenophora triphylla var. japonica extract inhibits adipogenic differentiation through the downregulation of PPARγ in 3T3-L1 cells
Phytother Res 2013 May;27(5):761-6.PMID:22848028DOI:10.1002/ptr.4779.
Adenophora triphylla var. japonica (Campanulaceae) is known to have anti-inflammatory and anti-tussive effects. Dysfunction of adipocytes and adipose tissue in obesity is related to various inflammatory cytokines or adipokines. In this study, we investigated whether Lupenone isolated from A. triphylla var. japonica extract inhibits adipocyte differentiation and expression of adipogenic marker genes in 3T3-L1 preadipocytes. We demonstrated that Lupenone resulted in a significant reduction in lipid accumulation and expression of adipogenic marker genes in a dose-dependent manner. In addition, Lupenone decreased the transcriptional activity of peroxisome proliferator-activated receptor γ (PPARγ) induced by troglitazone, and we also demonstrated that Lupenone suppressed the PPARγ and CCAAT-enhancer-binding protein α (C/EBPα) protein levels. These findings demonstrated that Lupenone isolated from A. triphylla var. japonica extract effectively inhibited adipocyte differentiation through downregulation of related transcription factor, particularly the PPARγ gene.