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MedKoo Cat#: 563476 | Name: Plantamajoside
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Plantamajoside is an antioxidant that act by decreasing the ROS generation and lipid peroxidation. Plantamajoside (PMS), a phenylethanoid glycoside component extracted from Plantago asiatica. CXCR4 inhibition promotes the inhibitory effect of plantamajoside on the proliferation and metastasis of cells, leading to apoptosis.

Chemical Structure

Plantamajoside
Plantamajoside
CAS#104777-68-6

Theoretical Analysis

MedKoo Cat#: 563476

Name: Plantamajoside

CAS#: 104777-68-6

Chemical Formula: C29H36O16

Exact Mass: 640.2003

Molecular Weight: 640.59

Elemental Analysis: C, 54.37; H, 5.66; O, 39.96

Price and Availability

Size Price Availability Quantity
1mg USD 480.00
5mg USD 890.00
10mg USD 1,150.00
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Related CAS #
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Synonym
Plantamajoside; Purpureasid-A; Purpureasid A;
IUPAC/Chemical Name
(2R,3R,4R,5R,6R)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate
InChi Key
KFEFLPDKISUVNR-QJEHNBJNSA-N
InChi Code
InChI=1S/C29H36O16/c30-11-19-22(37)23(38)24(39)29(42-19)45-27-25(40)28(41-8-7-14-2-5-16(33)18(35)10-14)43-20(12-31)26(27)44-21(36)6-3-13-1-4-15(32)17(34)9-13/h1-6,9-10,19-20,22-35,37-40H,7-8,11-12H2/b6-3+/t19-,20-,22-,23+,24-,25-,26-,27-,28-,29+/m1/s1
SMILES Code
O=C(O[C@@H]1[C@@H](CO)O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)/C=C/C4=CC=C(O)C(O)=C4
Appearance
A crystalline solid
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Plantamajoside is an antioxidant that act by decreasing the ROS generation and lipid peroxidation.
In vitro activity:
The results demonstrated that PMS (plantamajoside) significantly inhibited hypoxia-caused increases in cell migration and invasion of cervical cancer cells. The hypoxia-induced epithelial-mesenchymal transition (EMT) process was prevented by PMS with increased E-cadherin expression, and decreased expression levels of N-cadherin and vimentin in cervical cancer cells. Besides, the expression levels of transcription factors slug and snail were suppressed by PMS in hypoxia-induced cervical cancer cells. The increased mRNA and protein levels of hypoxia-inducible factor 1alpha (HIF-1α) in hypoxia-induced cervical cancer cells were prevented by PMS. Furthermore, PMS blocked the hypoxia-induced activation of NF-κB and PI3K/Akt pathway in cervical cancer cells. Reference: J Recept Signal Transduct Res. 2021 Aug;41(4):339-348. https://pubmed.ncbi.nlm.nih.gov/32865085/
In vivo activity:
This study found that PMS (plantamajoside) improved LPS-induced behavioral dysfunction in PD mice. PMS attenuated LPS-induced SN injury in PD mice. PMS could suppress LPS-induced microglial overactivation in PD mice. In addition, MS inhibited LPS-induced activation of the HDAC2/MAPK pathway in PD mice and BV-2 cells. It further revealed that PMS alleviated microglia polarization by inhibiting HDAC2. Reference: ACS Chem Neurosci. 2023 Mar 15;14(6):1119-1125. https://pubmed.ncbi.nlm.nih.gov/36859770/
Solvent mg/mL mM
Solubility
DMF 50.0 78.05
DMSO 47.7 74.41
Ethanol 10.0 15.61
PBS (pH 7.2) 10.0 15.61
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 640.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Du Y, Li J, Cai C, Gong F, Zhou G, Liu F, Wu Q, Liu F. Plantamajoside alleviates hypoxia-reoxygenation injury through integrin-linked kinase/c-Src/Akt and the mitochondrial apoptosis signaling pathways in H9c2 myocardial cells. BMC Complement Med Ther. 2023 Feb 24;23(1):64. doi: 10.1186/s12906-023-03880-6. PMID: 36829192; PMCID: PMC9951442. 2. Zuo X, Li L, Sun L. Plantamajoside inhibits hypoxia-induced migration and invasion of human cervical cancer cells through the NF-κB and PI3K/akt pathways. J Recept Signal Transduct Res. 2021 Aug;41(4):339-348. doi: 10.1080/10799893.2020.1808679. Epub 2020 Aug 30. PMID: 32865085. 3. Guo X, Chen L, Li J. Plantamajoside Alleviates Substantia Nigra Damage in Parkinson's Disease Mice by Inhibiting HDAC2/MAPK Signaling and Reducing Microglia Polarization. ACS Chem Neurosci. 2023 Mar 15;14(6):1119-1125. doi: 10.1021/acschemneuro.2c00668. Epub 2023 Mar 1. PMID: 36859770. 4. Wu H, Zhao G, Jiang K, Chen X, Zhu Z, Qiu C, Li C, Deng G. Plantamajoside ameliorates lipopolysaccharide-induced acute lung injury via suppressing NF-κB and MAPK activation. Int Immunopharmacol. 2016 Jun;35:315-322. doi: 10.1016/j.intimp.2016.04.013. Epub 2016 Apr 16. PMID: 27089391.
In vitro protocol:
1. Du Y, Li J, Cai C, Gong F, Zhou G, Liu F, Wu Q, Liu F. Plantamajoside alleviates hypoxia-reoxygenation injury through integrin-linked kinase/c-Src/Akt and the mitochondrial apoptosis signaling pathways in H9c2 myocardial cells. BMC Complement Med Ther. 2023 Feb 24;23(1):64. doi: 10.1186/s12906-023-03880-6. PMID: 36829192; PMCID: PMC9951442. 2. Zuo X, Li L, Sun L. Plantamajoside inhibits hypoxia-induced migration and invasion of human cervical cancer cells through the NF-κB and PI3K/akt pathways. J Recept Signal Transduct Res. 2021 Aug;41(4):339-348. doi: 10.1080/10799893.2020.1808679. Epub 2020 Aug 30. PMID: 32865085.
In vivo protocol:
1. Guo X, Chen L, Li J. Plantamajoside Alleviates Substantia Nigra Damage in Parkinson's Disease Mice by Inhibiting HDAC2/MAPK Signaling and Reducing Microglia Polarization. ACS Chem Neurosci. 2023 Mar 15;14(6):1119-1125. doi: 10.1021/acschemneuro.2c00668. Epub 2023 Mar 1. PMID: 36859770. 2. Wu H, Zhao G, Jiang K, Chen X, Zhu Z, Qiu C, Li C, Deng G. Plantamajoside ameliorates lipopolysaccharide-induced acute lung injury via suppressing NF-κB and MAPK activation. Int Immunopharmacol. 2016 Jun;35:315-322. doi: 10.1016/j.intimp.2016.04.013. Epub 2016 Apr 16. PMID: 27089391.
1: Laanet PR, Bragina O, Jõul P, Vaher M. Plantago major and Plantago lanceolata Exhibit Antioxidant and Borrelia burgdorferi Inhibiting Activities. Int J Mol Sci. 2024 Jun 28;25(13):7112. doi: 10.3390/ijms25137112. PMID: 39000214; PMCID: PMC11240987. 2: Sun J, Liu W, Fu H, Li Y, Huang J, Wang Y, Zhu L. C-X-C motif chemokine receptor 4 inhibition promotes the effect of plantamajoside in hepatocellular carcinoma. Arab J Gastroenterol. 2024 Feb;25(1):28-36. doi: 10.1016/j.ajg.2023.12.001. Epub 2024 Jan 13. PMID: 38220479. 3: Darwish SF, Elbadry AMM, Elbokhomy AS, Salama GA, Salama RM. The dual face of microglia (M1/M2) as a potential target in the protective effect of nutraceuticals against neurodegenerative diseases. Front Aging. 2023 Sep 6;4:1231706. doi: 10.3389/fragi.2023.1231706. PMID: 37744008; PMCID: PMC10513083. 4: Zhu JX, Guo MX, Zhou L, Yi LT, Huang HL, Wang HL, Cheng HY. Evaluation of the anti-inflammatory material basis of Lagotis brachystachya in HepG2 and THP-1 cells. J Ethnopharmacol. 2024 Jan 10;318(Pt B):117055. doi: 10.1016/j.jep.2023.117055. Epub 2023 Aug 18. PMID: 37597676. 5: Narzary I, Swarnakar A, Kalita M, Middha SK, Usha T, Babu D, Mochahary B, Brahma S, Basumatary J, Goyal AK. Acknowledging the use of botanicals to treat diabetic foot ulcer during the 21st century: A systematic review. World J Clin Cases. 2023 Jun 16;11(17):4035-4059. doi: 10.12998/wjcc.v11.i17.4035. PMID: 37388781; PMCID: PMC10303622. 6: Feng D, Guo R, Liao W, Li J, Cao S. Plantamajoside alleviates acute sepsis- induced organ dysfunction through inhibiting the TRAF6/NF-κB axis. Pharm Biol. 2023 Dec;61(1):897-906. doi: 10.1080/13880209.2023.2215849. PMID: 37288729; PMCID: PMC10251784. 7: Wu JM, Zhaori G, Mei L, Ren XM, Laga AT, Deligen B. Plantamajoside modulates immune dysregulation and hepatic lipid metabolism in rats with nonalcoholic fatty liver disease via AMPK/Nrf2 elevation. Kaohsiung J Med Sci. 2023 Aug;39(8):801-810. doi: 10.1002/kjm2.12712. Epub 2023 Jun 2. PMID: 37265208. 8: Xu H, Yu H, Fu J, Zhang ZW, Hu JC, Lu JY, Yang XY, Bu MM, Jiang JD, Wang Y. Metabolites analysis of plantamajoside based on gut microbiota-drug interaction. Phytomedicine. 2023 Jul 25;116:154841. doi: 10.1016/j.phymed.2023.154841. Epub 2023 Apr 27. PMID: 37196513. 9: Guo X, Chen L, Li J. Plantamajoside Alleviates Substantia Nigra Damage in Parkinson's Disease Mice by Inhibiting HDAC2/MAPK Signaling and Reducing Microglia Polarization. ACS Chem Neurosci. 2023 Mar 15;14(6):1119-1125. doi: 10.1021/acschemneuro.2c00668. Epub 2023 Mar 1. PMID: 36859770. 10: Qayyum S, Sultana A, Heyat MBB, Rahman K, Akhtar F, Haq AU, Alkhamis BA, Alqahtani MA, Gahtani RM. Therapeutic Efficacy of a Formulation Prepared with Linum usitatissimum L., Plantago ovata Forssk., and Honey on Uncomplicated Pelvic Inflammatory Disease Analyzed with Machine Learning Techniques. Pharmaceutics. 2023 Feb 14;15(2):643. doi: 10.3390/pharmaceutics15020643. PMID: 36839965; PMCID: PMC9965963. 11: Budzianowska A, Totoń E, Romaniuk-Drapała A, Kikowska M, Budzianowski J. Cytotoxic Effect of Phenylethanoid Glycosides Isolated from Plantago lanceolata L. Life (Basel). 2023 Feb 16;13(2):556. doi: 10.3390/life13020556. PMID: 36836912; PMCID: PMC9967538. 12: Du Y, Li J, Cai C, Gong F, Zhou G, Liu F, Wu Q, Liu F. Plantamajoside alleviates hypoxia-reoxygenation injury through integrin-linked kinase/c-Src/Akt and the mitochondrial apoptosis signaling pathways in H9c2 myocardial cells. BMC Complement Med Ther. 2023 Feb 24;23(1):64. doi: 10.1186/s12906-023-03880-6. PMID: 36829192; PMCID: PMC9951442. 13: Lin S, Lu J, Chen Q, Jiang H, Lou C, Lin C, Wang W, Lin J, Pan X, Xue X. Plantamajoside suppresses the activation of NF-κB and MAPK and ameliorates the development of osteoarthritis. Int Immunopharmacol. 2023 Feb;115:109582. doi: 10.1016/j.intimp.2022.109582. Epub 2022 Dec 28. PMID: 36584575. 14: Zhang L, Guo YN, Liu J, Wang LH, Wu HQ, Wang T, Deng B, Wang JY, Lu L, Chen ZX, He JQ, Liang BR, Li H, Huang YS, Yang ZQ, Xian SX, Wang LJ, Ye XH. Plantamajoside attenuates cardiac fibrosis via inhibiting AGEs activated- RAGE/autophagy/EndMT pathway. Phytother Res. 2023 Mar;37(3):834-847. doi: 10.1002/ptr.7663. Epub 2022 Nov 8. PMID: 36349468. 15: Wang X, Zhang C, Liu L, Zhong Y, Wang Y, Liu F, Zhu J, Mu Z, Zhang S, Wang X, Zhong G, Liang J, Zeng J. Effective materials and mechanisms study of Tibetan herbal medicine Lagotis integra W. W. Smith treating DSS-induced ulcerative colitis based on network pharmacology, molecular docking and experimental validation. J Ethnopharmacol. 2023 Jan 30;301:115800. doi: 10.1016/j.jep.2022.115800. Epub 2022 Oct 11. PMID: 36228890. 16: Lim L, Ki YJ, Kim H, Chu B, Choi IY, Choi DH, Song H. Plantamajoside Attenuates Neointima Formation via Upregulation of Tissue Inhibitor of Metalloproteinases in Balloon-Injured Rats. J Med Food. 2022 May;25(5):503-512. doi: 10.1089/jmf.2021.K.0162. Epub 2022 Apr 28. PMID: 35483086. 17: Wang Z, Zuo J, Zhang L, Zhang Z, Wei Y. Plantamajoside promotes metformin- induced apoptosis, autophagy and proliferation arrest of liver cancer cells via suppressing Akt/GSK3β signaling. Hum Exp Toxicol. 2022 Jan- Dec;41:9603271221078868. doi: 10.1177/09603271221078868. PMID: 35350904. 18: Yu N, Li Y, Wang Y, Xu H, Ye F, Fu Q. Healing effect of carboxymethyl chitosan-plantamajoside hydrogel on burn wound skin. Burns. 2022 Jun;48(4):902-914. doi: 10.1016/j.burns.2022.01.019. Epub 2022 Jan 29. PMID: 35153110. 19: Dossou SSK, Xu F, Cui X, Sheng C, Zhou R, You J, Tozo K, Wang L. Comparative metabolomics analysis of different sesame (Sesamum indicum L.) tissues reveals a tissue-specific accumulation of metabolites. BMC Plant Biol. 2021 Jul 24;21(1):352. doi: 10.1186/s12870-021-03132-0. PMID: 34303354; PMCID: PMC8305604. 20: Guo H, Feng C, Hu L, Zhao X, Tang X, Huang Y, Luo J, Xu M, Xie W. Exploration of a ternary deep eutectic solvent for the efficient extraction of plantamajoside, acteoside, quercetin and kaempferol from Plantago asiatica L. Phytochem Anal. 2022 Jan;33(1):94-104. doi: 10.1002/pca.3071. Epub 2021 Jun 16. PMID: 34137102.