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Phyllanthin

(Synonyms: 1,1'-[(2S,3S)-2,3-双(甲氧基甲基)-1,4-丁二基]双[3,4-二甲氧基苯]) 目录号 : GC44638

A hepatoprotective plant lignan

Phyllanthin Chemical Structure

Cas No.:10351-88-9

规格 价格 库存 购买数量
500μg
¥364.00
现货
1mg
¥582.00
现货
5mg
¥2,549.00
现货
10mg
¥4,370.00
现货

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产品描述

Phyllanthin is a major bioactive lignan component of P. amarus with antioxidative and hepatoprotective properties. It scavenges DPPH radicals with an IC50 value of 7.4 µM and, at 30 µM, has been shown to alleviate carbon tetrachloride-induced lipid peroxidation and cytotoxicity in a human hepatoma HepG2 cell line.

Chemical Properties

Cas No. 10351-88-9 SDF
别名 1,1'-[(2S,3S)-2,3-双(甲氧基甲基)-1,4-丁二基]双[3,4-二甲氧基苯]
Canonical SMILES COC1=C(OC)C=C(C[C@]([C@@](CC2=CC=C(OC)C(OC)=C2)([H])COC)([H])COC)C=C1
分子式 C24H34O6 分子量 418.5
溶解度 DMF: 15 mg/ml,DMSO: 10 mg/ml,Ethanol: 5 mg/ml 储存条件 Store at -20°C
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10 mM 0.2389 mL 1.1947 mL 2.3895 mL
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Research Update

Phyllanthin inhibits MOLT-4 leukemic cancer cell growth and induces apoptosis through the inhibition of AKT and JNK signaling pathway

J Biochem Mol Toxicol 2021 Jun;35(6):1-10.PMID:33724660DOI:10.1002/jbt.22758.

Among cancers, leukemia is a multistep progression that involves genetic modifications of normal hematopoietic progenitor cells to cancerous cells. In recent times, leukemia cases and their mortality rate have increased rapidly. Therefore, the immense need for a therapeutic approach is crucial that can control this type of cancer. Phyllanthin is a lignan compound constituent from the Phyllanthus species and has numerous beneficial effects as a dietary component. The present study aims to determine the impact of Phyllanthin on the MOLT-4 cytotoxic effect. MOLT-4 cells and MS-5 cells were cultured at different concentrations of Phyllanthin (5, 10, 25, 50, 75, and 100 μM/ml), and the viability was assessed by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide method. The level of reactive oxygen species, the membrane potential of mitochondria, apoptosis by 2',7'-dichlorofluorescin-diacetate (DCF-DA), rhodamine, acridine orange (AO)/ethidium bromide (EB), 4',6-diamidino-2-phenylindole (DAPI)/propidium iodide (PI) staining, gene expression of signaling molecules, and protein levels were assessed by reverse-transcription polymerase chain reaction and western blot analysis. Phyllanthin did not show toxicity toward MS-5 cells and significantly decreased the cell viability of MOLT-4 cells with an IC50 value of 25 µM/ml. Also, Phyllanthin induced the production of reactive oxygen species and led to the loss of mitochondrial membrane potential. AO/EB and DAPI/PI staining fluorescent image confirmed the induction of apoptosis by Phyllanthin treatment. The messenger RNA (mRNA) expression of cell cycle regulator cyclin D1, antiapoptotic gene Bcl-2, NF-κB, and TNF-α decreased, but the proapoptotic Bax mRNA expression was increased. The phosphorylated protein levels of p-PI3K1/2, p-ERK1/2, and p-AKT were decreased, whereas the levels of p-p38 and p-JNKT1/2 increased. Our results confirmed that Phyllanthin inhibits the MOLT-4 cells, increases apoptosis, and inhibits MOLT-4 migration and cell invasion. Therefore, Phyllanthin can be used as a potential target for leukemia treatment.

Phyllanthin prevents diethylnitrosamine (DEN) induced liver carcinogenesis in rats and induces apoptotic cell death in HepG2 cells

Biomed Pharmacother 2021 May;137:111335.PMID:33581648DOI:10.1016/j.biopha.2021.111335.

Liver cancer is a critical clinical condition with augmented malignancy, rapid progression, and poor prognosis. Liver cancer often initiates as fibrosis, develops as cirrhosis, and results in cancer. For centuries, medicinal plants have been incorporated in various liver-associated complications, and recently, research has recognized that many bioactive compounds from medicinal plants may interact with targets related to liver disorders. Phyllanthin from the Phyllanthus species is one such compound extensively used by folklore practitioners for various health benefits. However, most practices continue to be unrecognized scientifically. Hence, in this work, we investigated the protective role of Phyllanthin on diethylnitrosamine (DEN) induced liver carcinoma in Wistar Albino rats and the anti-tumor potential on human hepatocellular carcinoma (HCC) HepG2 cells. The DEN-challenged liver cancer in experimental rats caused increased liver weight, 8-OHD, hepatic tissue injury marker, lipid peroxidation, and tumor markers levels. Remarkably, Phyllanthin counteracted the DEN effect by ameliorating all the liver function enzymes, oxidative DNA damage, and tumor-specific markers by enhanced anti-oxidant capacity and induced caspase-dependent apoptosis through the mTOR/ PI3K signaling pathway. MTT assay demonstrated that Phyllanthin inhibited the HepG2 cell growth in a dose-dependent manner. Fascinatingly, Phyllanthin did not demonstrate any substantial effect on the normal cell line, HL7702. In addition, HepG2 cells were found in the late apoptotic stage upon treatment with Phyllanthin as depicted by acridine orange/ethidium bromide staining. Overall, this work offers scientific justification that Phyllanthin can be claimed to be a safe candidate with potential chemotherapeutic activity against HCC.

Phyllanthin Averts Oxidative Stress and Neuroinflammation in Cerebral Ischemic-Reperfusion Injury through Modulation of the NF-κB and AMPK/Nrf2 Pathways

J Environ Pathol Toxicol Oncol 2021;40(1):85-97.PMID:33639076DOI:10.1615/JEnvironPatholToxicolOncol.2020036307.

Cerebral ischemia-reperfusion (CIR) is a common feature of ischemic stroke and is a major cause of disability and death among stroke patients worldwide. Phyllanthin, a lignin polyphenol, is known for its varied biological properties, although its protective effects against CIR have not been reported. We evaluated the neuroprotective property of Phyllanthin against CIR as well as the involvement of the AMP-activated protein kinase/nuclear factor erythroid 2-related factor 2 (AMPK/Nrf2) and nuclear factor kappa B (NF-κB) signaling pathways. Experimental animals were divided into five groups: controls (sham-operated), CIR-induced by middle cerebral artery occlusion (MCAO), and CIR-induced and administered Phyllanthin at 2.5, 5, and 10 mg/kg, respectively. We investigated neurological functions, various signaling genes, and inflammatory clues. The results of in vitro assays demonstrated that Phyllanthin assertively improved cellular functions through abrogation of the Nrf2 pathway. In vivo, CIR rats demonstrated neurological function deficits, while ischemic severity was evidenced by the activation of neuroinflammatory cytokines and tissue oxidative stress. Moreover, the expression of apoptosis markers such as Bax, B-cell lymphoma (Bcl-2), caspase-3, COX-2, PGE2, and LOX-1 abruptly increased. Phyllanthin prevented brain dysfunction and cerebral edema, and protected brain integrity. Conversely, it improved antioxidative enzyme activity, abrogated inflammatory cytokines, and increased IL-10 in chemokines. Also, Phyllanthin significantly reduced Nrf2 and AMPK levels, with reduced expression of NF-κB indicating that cross-talk between the NF-kB and Nrf2 pathways is activated in CIR. Phyllanthin rescues the ischemic brain by regulating cellular signaling, which supports its use for complications like CIR and associated injury.

Phyllanthin and hypophyllanthin, the isolated compounds of Phyllanthus niruri inhibit protein receptor of corona virus (COVID-19) through in silico approach

J Basic Clin Physiol Pharmacol 2021 Jun 25;32(4):809-815.PMID:34214339DOI:10.1515/jbcpp-2020-0473.

Objectives: Phyllanthus niruri has been known as an immunomodulator and also reported to possess an antiviral activity against several RNA viruses, such as hepatitis B virus and hepatitis C virus by inhibiting viral entry and replication. Since the current situation of Coronavirus Disease 2019 (COVID-19) which infected among the world and caused severe disease and high morbidity, it urgently needed to find new agents against COVID-19. Therefore, in silico screening against COVID-19 receptors is carried out as an initial stage of drug discovery by evaluating the activity of Phyllanthin and hypophyllanthin, an isolated from Phyllanthus niruri, in inhibiting spike glycoprotein (6LZG) and main protease (5R7Y) which play as target receptors of COVID-19. Methods: Molegro Virtual Docker 6.0 used to determine the best binding energy through the rerank score which shows the total energy bonds calculation. Results: Phyllanthin and hypophyllanthin demonstrated to possess greater binding affinity toward the COVID-19 inhibition sites than their native ligand. The rerank score of Phyllanthin and hypophyllanthin are lower than the native ligands 6LZG and 5R7Y. This result indicated that Phyllanthin and hypophyllanthin have a stronger interaction than the native ligands both in spike glycoprotein (entry inhibitor) and main protease (translation and replication inhibitor). Conclusions: In conclusion, Phyllanthin and hypophyllanthin are predicted to have strong activity against COVID-19 through inhibiting spike glycoprotein and main protease under in silico study. Further research is needed to support the development of P. niruri as inhibitor agents of COVID-19 through bioassay studies.

Phyllanthin from Phyllanthus amarus inhibits cellular and humoral immune responses in Balb/C mice

Phytomedicine 2016 Nov 15;23(12):1441-1450.PMID:27765364DOI:10.1016/j.phymed.2016.08.002.

Background: Phyllanthin found in many Phyllanthus species has various biochemical and pharmacological properties especially on its hepatoprotective effects. However, its effect on the immune system has not been well documented. Purpose: In the present study, Phyllanthin isolated from Phyllanthus amarus was investigated for its immunosuppressive effects on various cellular and humoral immune responses in Balb/C mice. Methods: Male mice were treated daily at 20, 40 and 100mg/kg of Phyllanthin for 14 days by oral gavage. The effects of Phyllanthin on cellular immune responses in treated /non treated mice were determined by measuring CD 11b/CD 18 integrin expression, phagocytosis, nitric oxide (NO) production, myeloperoxidase activity (MPO), T and B cells proliferation, lymphocyte phenotyping, serum cytokines production by activated T-cells and delayed type hypersensitivity (DTH). Its effects on humoral immune responses were evaluated by determining the serum levels of lysozyme and ceruloplasmin, and immunoglobulins (IgG and IgM). Results: Phyllanthin dose-dependently inhibited CD11b/CD18 adhesion, the engulfment of E. coli by peritoneal macrophages molecules, NO and MPO release in treated mice. Phyllanthin caused significant and dose-dependent inhibition of T and B lymphocytes proliferation and down-regulation of the Th1 (IL-2 and IFN-γ) and Th2 (IL-4) cytokines. Phyllanthin at 100mg/kg caused a significant reduction in the percentage expression of CD4+ and CD8+ in splenocytes and the inhibition was comparable to that of cyclosporin A at 50mg/kg. At 100mg/kg, Phyllanthin also dose-dependently exhibited strong inhibition on the sheep red blood cell (sRBC)-induced swelling rate of mice paw in DTH. Significant inhibition of serum levels of ceruloplasmin and lysozyme were observed in mice fed with higher doses (40 and 100mg/kg) of Phyllanthin. Anti-sRBC immunoglobulins (IgM and IgG) antibody titer was down-regulated in immunized and phyllanthin-treated mice in a dose-dependent manner with maximum inhibition being observed at 100mg/kg. Conclusion: The strong inhibitory effects of Phyllanthin on the cellular and humoral immune responses suggest that Phyllanthin may be a good candidate for development into an effective immunosuppressive agent.