Amarogentin
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MedKoo CAT#: 592764

CAS#: 21018-84-8

Description: Amarogentin displays immunomodulatory effects in human Mast Cells and Keratinocytes. Amarogentin isolated from G. rigescens, which is a TCM, showed a significant antiaging effect on yeasts and neuroprotective and neuritogenic activities in PC12 cells, a mammalian cell line. Amarogentin prolonged the replicative lifespan and neuroprotective activities by antioxidative stress activity.

Chemical Structure

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Amarogentin
CAS# 21018-84-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 592764
Name: Amarogentin
CAS#: 21018-84-8
Chemical Formula: C29H30O14
Exact Mass: 602.16
Molecular Weight: 602.545
Elemental Analysis: C, 57.81; H, 5.02; O, 37.17

Price and Availability

Size Price Availability Quantity
10mg USD 285 2 Weeks
25mg USD 485 2 Weeks
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Synonym: Amarogentin

IUPAC/Chemical Name: (4aS,5S,6R)-1-oxo-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-3,4,5,6-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4a-yl 3,3',5-trihydroxy-[1,1'-biphenyl]-2-carboxylate

InChi Key: JDMGEYUDOKCUKA-PCNNGFATSA-N

InChi Code: InChI=1S/C29H30O14/c1-2-17-27(42-28-24(36)23(35)22(34)20(11-30)41-28)40-12-18-25(37)39-7-6-29(17,18)43-26(38)21-16(9-15(32)10-19(21)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,17,20,22-24,27-28,30-36H,1,6-7,11H2/t17-,20-,22-,23+,24-,27-,28+,29+/m1/s1

SMILES Code: O=C1C2=CO[C@H](O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@@H](C=C)[C@@]2(OC(C4=C(O)C=C(O)C=C4C5=CC=CC(O)=C5)=O)CCO1

Appearance: Solid powder

Purity: >98% (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:
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Biological target: Amarogentin promotes apoptosis, arrests G2/M cell cycle and downregulates of PI3K/Akt/mTOR signalling pathways.
In vitro activity: The effects of amarogentin on the growth of yeast under oxidative stress induced by 10 mM H2O2 are shown in Figure 2(a). The growth of yeast on the agar plate with H2O2 in the amarogentin-treated groups was better than negative control and RES-treated groups. To quantify the change induced by amarogentin on oxidative stress, we used another analytical method. The survival rate of yeast under oxidative stress induced by 5.5 mM H2O2 in the amarogentin-treated group was significantly increased compared with that in the control group (Figure 2(b)). The effect of amarogentin on antioxidative stress at a concentration of 3 μM is similar to that of RES at a concentration of 10 μM. These results indicate that amarogentin showed antiaging effect by inhibiting oxidative stress. Reference: Oxid Med Cell Longev. 2020; 2020: 3184019. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7421772/
In vivo activity: The tumor weights and volumes of the iRFA model mice were significantly decreased by amarogentin (Figure 3(a) and Supplementary Figure 2). Consistently, the expression levels of CD133, VEGFA, Dll4, and Notch1 in iRFA tumor tissues were decreased by amarogentin, and phosphorylated p53 levels were increased (Figures 3(b) and 3(c)). Thus, these data implied that amarogentin suppresses liver cancer growth by inhibiting angiogenesis in xenograft mice. Reference: Biomed Res Int. 2020; 2020: 5391058. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7596460/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 67.3 111.74
DMF 1.0 1.66
Ethanol 50.0 82.98
PBS (pH 7.2) 0.1 0.17

Preparing Stock Solutions

The following data is based on the product molecular weight 602.55 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. Disasa D, Cheng L, Manzoor M, Liu Q, Wang Y, Xiang L, Qi J. Amarogentin from Gentiana rigescens Franch Exhibits Antiaging and Neuroprotective Effects through Antioxidative Stress. Oxid Med Cell Longev. 2020 Aug 1;2020:3184019. doi: 10.1155/2020/3184019. PMID: 32831994; PMCID: PMC7421772. 2. Huang C, Li R, Zhang Y, Gong J. Amarogentin Induces Apoptosis of Liver Cancer Cells via Upregulation of p53 and Downregulation of Human Telomerase Reverse Transcriptase in Mice. Technol Cancer Res Treat. 2017 Oct;16(5):546-558. doi: 10.1177/1533034616657976. Epub 2016 Jul 11. PMID: 27402632; PMCID: PMC5665146. 3. Zhang Y, Zhang Y, Wang J, Gu H. Amarogentin Inhibits Liver Cancer Cell Angiogenesis after Insufficient Radiofrequency Ablation via Affecting Stemness and the p53-Dependent VEGFA/Dll4/Notch1 Pathway. Biomed Res Int. 2020 Oct 20;2020:5391058. doi: 10.1155/2020/5391058. PMID: 33145353; PMCID: PMC7596460. 4. Potunuru UR, Priya KV, Varsha MKNS, Mehta N, Chandel S, Manoj N, Raman T, Ramar M, Gromiha MM, Dixit M. Amarogentin, a secoiridoid glycoside, activates AMP- activated protein kinase (AMPK) to exert beneficial vasculo-metabolic effects. Biochim Biophys Acta Gen Subj. 2019 Aug;1863(8):1270-1282. doi: 10.1016/j.bbagen.2019.05.008. Epub 2019 May 22. PMID: 31125678.
In vitro protocol: 1. Disasa D, Cheng L, Manzoor M, Liu Q, Wang Y, Xiang L, Qi J. Amarogentin from Gentiana rigescens Franch Exhibits Antiaging and Neuroprotective Effects through Antioxidative Stress. Oxid Med Cell Longev. 2020 Aug 1;2020:3184019. doi: 10.1155/2020/3184019. PMID: 32831994; PMCID: PMC7421772. 2. Huang C, Li R, Zhang Y, Gong J. Amarogentin Induces Apoptosis of Liver Cancer Cells via Upregulation of p53 and Downregulation of Human Telomerase Reverse Transcriptase in Mice. Technol Cancer Res Treat. 2017 Oct;16(5):546-558. doi: 10.1177/1533034616657976. Epub 2016 Jul 11. PMID: 27402632; PMCID: PMC5665146.
In vivo protocol: 1. Zhang Y, Zhang Y, Wang J, Gu H. Amarogentin Inhibits Liver Cancer Cell Angiogenesis after Insufficient Radiofrequency Ablation via Affecting Stemness and the p53-Dependent VEGFA/Dll4/Notch1 Pathway. Biomed Res Int. 2020 Oct 20;2020:5391058. doi: 10.1155/2020/5391058. PMID: 33145353; PMCID: PMC7596460. 2. Potunuru UR, Priya KV, Varsha MKNS, Mehta N, Chandel S, Manoj N, Raman T, Ramar M, Gromiha MM, Dixit M. Amarogentin, a secoiridoid glycoside, activates AMP- activated protein kinase (AMPK) to exert beneficial vasculo-metabolic effects. Biochim Biophys Acta Gen Subj. 2019 Aug;1863(8):1270-1282. doi: 10.1016/j.bbagen.2019.05.008. Epub 2019 May 22. PMID: 31125678.

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1: Patel K, Kumar V, Verma A, Rahman M, Patel DK. Amarogentin as Topical Anticancer and Anti-Infective Potential: Scope of Lipid Based Vesicular in its Effective Delivery. Recent Pat Antiinfect Drug Discov. 2019;14(1):7-15. doi: 10.2174/1574891X13666180913154355. PMID: 30210007.


2: Disasa D, Cheng L, Manzoor M, Liu Q, Wang Y, Xiang L, Qi J. Amarogentin from Gentiana rigescens Franch Exhibits Antiaging and Neuroprotective Effects through Antioxidative Stress. Oxid Med Cell Longev. 2020 Aug 1;2020:3184019. doi: 10.1155/2020/3184019. PMID: 32831994; PMCID: PMC7421772.


3: Niu HS, Chao PC, Ku PM, Niu CS, Lee KS, Cheng JT. Amarogentin ameliorates diabetic disorders in animal models. Naunyn Schmiedebergs Arch Pharmacol. 2016 Nov;389(11):1215-1223. doi: 10.1007/s00210-016-1283-x. Epub 2016 Aug 3. PMID: 27485449.


4: Li S, Li X, He F, Jiao R, Zhang S, Li Z. Amarogentin promotes osteoblast differentiation in oestrogen-deficiency-induced osteoporosis rats by modulating the Nrf-2/MAPK/ERK signalling pathway. Arch Med Sci. 2019 Nov 11;19(2):452-457. doi: 10.5114/aoms.2019.89652. PMID: 37034504; PMCID: PMC10074178.


5: Zhang Y, Zhang Y, Wang J, Gu H. Amarogentin Inhibits Liver Cancer Cell Angiogenesis after Insufficient Radiofrequency Ablation via Affecting Stemness and the p53-Dependent VEGFA/Dll4/Notch1 Pathway. Biomed Res Int. 2020 Oct 20;2020:5391058. doi: 10.1155/2020/5391058. PMID: 33145353; PMCID: PMC7596460.


6: Song B, Zhou W. Amarogentin has protective effects against sepsis-induced brain injury via modulating the AMPK/SIRT1/NF-κB pathway. Brain Res Bull. 2022 Oct 15;189:44-56. doi: 10.1016/j.brainresbull.2022.08.018. Epub 2022 Aug 17. PMID: 35985610.


7: Wölfle U, Haarhaus B, Schempp CM. Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. Mediators Inflamm. 2015;2015:630128. doi: 10.1155/2015/630128. Epub 2015 Oct 27. PMID: 26600671; PMCID: PMC4639662.


8: Sur S, Pal D, Banerjee K, Mandal S, Das A, Roy A, Panda CK. Amarogentin regulates self renewal pathways to restrict liver carcinogenesis in experimental mouse model. Mol Carcinog. 2016 Jul;55(7):1138-49. doi: 10.1002/mc.22356. Epub 2015 Jul 8. PMID: 26154024.


9: Yen TL, Lu WJ, Lien LM, Thomas PA, Lee TY, Chiu HC, Sheu JR, Lin KH. Amarogentin, a secoiridoid glycoside, abrogates platelet activation through PLC γ 2-PKC and MAPK pathways. Biomed Res Int. 2014;2014:728019. doi: 10.1155/2014/728019. Epub 2014 Apr 29. PMID: 24868545; PMCID: PMC4020542.


10: Huang C, Li R, Zhang Y, Gong J. Amarogentin Induces Apoptosis of Liver Cancer Cells via Upregulation of p53 and Downregulation of Human Telomerase Reverse Transcriptase in Mice. Technol Cancer Res Treat. 2017 Oct;16(5):546-558. doi: 10.1177/1533034616657976. Epub 2016 Jul 11. PMID: 27402632; PMCID: PMC5665146.


11: Zhang Y, Zhao H, Li H, Cao W, Wang F, Zhang T, Wang SW. Protective Effects of Amarogentin against Carbon Tetrachloride-Induced Liver Fibrosis in Mice. Molecules. 2017 May 6;22(5):754. doi: 10.3390/molecules22050754. PMID: 28481234; PMCID: PMC6154739.


12: Zhao JG, Zhang L, Xiang XJ, Yu F, Ye WL, Wu DP, Wang JF, Xiong JP. Amarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway. J BUON. 2016 May- Jun;21(3):609-17. Retraction in: JBUON 2021 November-December; 26(6): 2713. Erratum in: J BUON. 2016 Sept-Oct;21(5):1332. PMID: 27569081.


13: Tan Z, Wang W, Peng J, Zhou Z, Pan J, Peng A, Cao H, Fan W. Impact of Amarogentin on Gastric Carcinoma Cell Multiplication, Apoptosis and Migration via circKIF4A/miR-152-3p. J Immunol Res. 2022 Jun 14;2022:2156204. doi: 10.1155/2022/2156204. PMID: 35747689; PMCID: PMC9213178.


14: Zhao JG, Zhang L, Xiang XJ, Yu F, Ye WL, Wu DP, Wang JF, Xiong JP. Amarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through the mediation of G2/M cell cycle arrest and PI3K/Akt signalling pathway. J BUON. 2021 Jan-Feb;26(1):296. PMID: 33721481.


15: Zhang Q, Wang H, Ran C, Lyu Y, Li F, Yao Y, Xing S, Wang L, Chen S. Anti- inflammatory effects of amarogentin on 2,4-dinitrochlorobenzene-induced atopic dermatitis-like mice and in HaCat cells. Animal Model Exp Med. 2022 Sep 21. doi: 10.1002/ame2.12260. Epub ahead of print. PMID: 36131559.


16: Kar P, Kumar V, Vellingiri B, Sen A, Jaishee N, Anandraj A, Malhotra H, Bhattacharyya S, Mukhopadhyay S, Kinoshita M, Govindasamy V, Roy A, Naidoo D, Subramaniam MD. Anisotine and amarogentin as promising inhibitory candidates against SARS-CoV-2 proteins: a computational investigation. J Biomol Struct Dyn. 2022 Jul;40(10):4532-4542. doi: 10.1080/07391102.2020.1860133. Epub 2020 Dec 11. PMID: 33305988; PMCID: PMC7808002.


17: Fiorito S, Epifano F, Marchetti L, Palumbo L, Mascioli F, Bastianini M, Cardellini F, Spogli R, Genovese S. An improved method for the isolation of amarogentin, the bitter principle of yellow gentian roots. Food Chem. 2021 Dec 1;364:130383. doi: 10.1016/j.foodchem.2021.130383. Epub 2021 Jun 16. PMID: 34153596.


18: Gupta R, Sood H. Optimizing nutrient media conditions for continuous production of shoot biomass enriched in major medicinal constituents, amarogentin and mangiferin of endangered medicinal herb, Swertia chirayita. Vegetos. 2022 Aug 29:1-9. doi: 10.1007/s42535-022-00464-6. Epub ahead of print. PMID: 36061345; PMCID: PMC9423889.


19: Pal D, Sur S, Roy R, Mandal S, Panda CK. Hypomethylation of LIMD1 and P16 by downregulation of DNMT1 results in restriction of liver carcinogenesis by amarogentin treatment. J Biosci. 2021;46:53. PMID: 34148876.


20: Jia F, Ji R, Qiao G, Sun Z, Chen X, Zhang Z. Amarogentin inhibits vascular smooth muscle cell proliferation and migration and attenuates neointimal hyperplasia via AMPK activation. Biochim Biophys Acta Mol Basis Dis. 2023 Jun;1869(5):166667. doi: 10.1016/j.bbadis.2023.166667. Epub 2023 Mar 9. PMID: 36906074.