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MedKoo Cat#: 540156 | Name: Gentiopicrin
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Description:

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

Gentiopicrin is found in gentiana and cephalaria. It displays many biological properties, including suppressing expression of NMDA receptors in the anterior cingulate cortex, inhibiting morphine conditioned place preference, and preventing arachidonic acid and PMA-induced superoxide generation.

Chemical Structure

Gentiopicrin
Gentiopicrin
CAS#20831-76-9

Theoretical Analysis

MedKoo Cat#: 540156

Name: Gentiopicrin

CAS#: 20831-76-9

Chemical Formula: C16H20O9

Exact Mass: 356.1107

Molecular Weight: 356.33

Elemental Analysis: C, 53.93; H, 5.66; O, 40.41

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
100mg USD 650.00 2 Weeks
250mg USD 950.00 2 Weeks
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Synonym
Gentiopicrin; Gentiopicroside; NSC 606402; NSC606402; NSC-606402;
IUPAC/Chemical Name
(5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one
InChi Key
DUAGQYUORDTXOR-GPQRQXLASA-N
InChi Code
InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
SMILES Code
O[C@@H]([C@H](O)[C@@H](CO)O1)[C@@H](O)[C@@H]1O[C@H]2[C@H](C=C)C(C3=CO2)=CCOC3=O
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
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Gentiopicroside inhibits P450 activity, with an IC50 and a Ki of 61 µM and 22.8 µM for CYP2A6.
In vitro activity:
GPS reduced expressions of FN, vimentin, and α-SMA and promoted the E-cad expression in HG-induced NRK-52E cells (Figures 5A–C). Moreover, the migration ability was decreased after GPS treatment (Figure 5D, Supplementary Figure S1E). The aforementioned results indicated that GPS inhibited the HG-induced EMT process in NRK-52E cells. Reference: J Nat Med. 2022 Jan;76(1):178-187. https://pubmed.ncbi.nlm.nih.gov/35814242/
In vivo activity:
Figure 2a, b showed that GPS (gentiopicrin) and colchicine relieve paw swelling induced by MSU (monosodium urate). Compared with MSU + Veh group, 100 mg/kg and 200 mg/kg GPS groups showed significant inhibition on instep swelling index (Fig. 2c). Next, this study evaluated the effects of GPS on MSU-induced pain. The results showed that the severity of pain induced by MSU achieved its peak at 8 h after stimulus. And 100 mg/kg, 200 mg/kg GPS had analgesic effect on mechanical hyperalgesia, while the 50 mg/kg GPS did not show (Fig. 2d, e). Furthermore, MSU-induced a severe thermal hyperplasia, which was inhibited by the treatment of GPS with 100 mg/kg and 200 mg/kg (Fig. 2f, g). Reference: J Nat Med. 2022 Jan;76(1):178-187. https://pubmed.ncbi.nlm.nih.gov/34586567/
Solvent mg/mL mM
Solubility
DMF 50.0 140.32
DMSO 73.7 206.74
Ethanol 2.0 5.61
PBS (pH 7.2) 10.0 28.06
Water 100.0 280.64
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 356.33 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. Xu Z, Zhang M, Wang Y, Chen R, Xu S, Sun X, Yang Y, Lin Z, Wang S, Huang H. Gentiopicroside Ameliorates Diabetic Renal Tubulointerstitial Fibrosis via Inhibiting the AT1R/CK2/NF-κB Pathway. Front Pharmacol. 2022 Jun 23;13:848915. doi: 10.3389/fphar.2022.848915. PMID: 35814242; PMCID: PMC9260113. 2. Xiao H, Sun X, Lin Z, Yang Y, Zhang M, Xu Z, Liu P, Liu Z, Huang H. Gentiopicroside targets PAQR3 to activate the PI3K/AKT signaling pathway and ameliorate disordered glucose and lipid metabolism. Acta Pharm Sin B. 2022 Jun;12(6):2887-2904. doi: 10.1016/j.apsb.2021.12.023. Epub 2022 Jan 6. PMID: 35755276; PMCID: PMC9214054. 3. He M, Hu C, Chen M, Gao Q, Li L, Tian W. Effects of Gentiopicroside on activation of NLRP3 inflammasome in acute gouty arthritis mice induced by MSU. J Nat Med. 2022 Jan;76(1):178-187. doi: 10.1007/s11418-021-01571-5. Epub 2021 Sep 29. PMID: 34586567; PMCID: PMC8732881. 4. Jiang H, Zhong J, Li W, Dong J, Xian CJ, Shen YK, Yao L, Wu Q, Wang L. Gentiopicroside promotes the osteogenesis of bone mesenchymal stem cells by modulation of β-catenin-BMP2 signalling pathway. J Cell Mol Med. 2021 Dec;25(23):10825-10836. doi: 10.1111/jcmm.16410. Epub 2021 Nov 15. PMID: 34783166; PMCID: PMC8642693.
In vitro protocol:
1. Xu Z, Zhang M, Wang Y, Chen R, Xu S, Sun X, Yang Y, Lin Z, Wang S, Huang H. Gentiopicroside Ameliorates Diabetic Renal Tubulointerstitial Fibrosis via Inhibiting the AT1R/CK2/NF-κB Pathway. Front Pharmacol. 2022 Jun 23;13:848915. doi: 10.3389/fphar.2022.848915. PMID: 35814242; PMCID: PMC9260113. 2. Xiao H, Sun X, Lin Z, Yang Y, Zhang M, Xu Z, Liu P, Liu Z, Huang H. Gentiopicroside targets PAQR3 to activate the PI3K/AKT signaling pathway and ameliorate disordered glucose and lipid metabolism. Acta Pharm Sin B. 2022 Jun;12(6):2887-2904. doi: 10.1016/j.apsb.2021.12.023. Epub 2022 Jan 6. PMID: 35755276; PMCID: PMC9214054.
In vivo protocol:
1. He M, Hu C, Chen M, Gao Q, Li L, Tian W. Effects of Gentiopicroside on activation of NLRP3 inflammasome in acute gouty arthritis mice induced by MSU. J Nat Med. 2022 Jan;76(1):178-187. doi: 10.1007/s11418-021-01571-5. Epub 2021 Sep 29. PMID: 34586567; PMCID: PMC8732881. 2. Jiang H, Zhong J, Li W, Dong J, Xian CJ, Shen YK, Yao L, Wu Q, Wang L. Gentiopicroside promotes the osteogenesis of bone mesenchymal stem cells by modulation of β-catenin-BMP2 signalling pathway. J Cell Mol Med. 2021 Dec;25(23):10825-10836. doi: 10.1111/jcmm.16410. Epub 2021 Nov 15. PMID: 34783166; PMCID: PMC8642693.
1: Zhang K, Lv S, Li X, Feng Y, Li X, Liu L, Li S, Li Y. Preparation, characterization, and in vivo pharmacokinetics of nanostructured lipid carriers loaded with oleanolic acid and gentiopicrin. Int J Nanomedicine. 2013;8:3227-39. doi: 10.2147/IJN.S45031. Epub 2013 Aug 22. PubMed PMID: 24009420; PubMed Central PMCID: PMC3758216. 2: el-Sedawy AI, Hattori M, Kobashi K, Namba T. Metabolism of gentiopicroside (gentiopicrin) by human intestinal bacteria. Chem Pharm Bull (Tokyo). 1989 Sep;37(9):2435-7. PubMed PMID: 2605687. 3: van der Sluis WG, van der Nat JM, Spek AL, Ikeshiro Y, Labadie RP. Gentiogenal, a conversion product of gentiopicrin (gentiopicroside)*. Planta Med. 1983 Dec;49(12):211-5. PubMed PMID: 17405055. 4: Xu YW, Qi Y, Han X, Xu LN, Xu QW, Peng JY. [Preparative separation of gentiopicrin from Radix Gentianae by high-speed counter-current chromatography with macroporous resin]. Zhongguo Zhong Yao Za Zhi. 2007 Dec;32(24):2595-7. Chinese. PubMed PMID: 18338594. 5: Lv J, Gu WL, Chen CX. Effect of gentiopicroside on experimental acute pancreatitis induced by retrograde injection of sodium taurocholate into the biliopancreatic duct in rats. Fitoterapia. 2015 Apr;102:127-33. doi: 10.1016/j.fitote.2015.03.002. Epub 2015 Mar 7. PubMed PMID: 25759121. 6: Yin H, Zhao Q, Sun FM, An T. Gentiopicrin-producing endophytic fungus isolated from Gentiana macrophylla. Phytomedicine. 2009 Aug;16(8):793-7. doi: 10.1016/j.phymed.2008.12.009. Epub 2009 Feb 5. PubMed PMID: 19200701. 7: Wang YY, Wang YP, Liu JY, Yan S, Sun CH, Xu SQ. [Preparative separation of gentiopicrin from Gentiana scabra bunge by high speed counter current chromatography]. Zhong Yao Cai. 2007 Jul;30(7):789-91. Chinese. PubMed PMID: 17944185. 8: Huang Z, Lin S. [Determination gentiopicrin in biyanqingdu granulae by SPE-HPLC]. Zhong Yao Cai. 2005 Jun;28(6):507-8. Chinese. PubMed PMID: 16209272. 9: Mihailović V, Katanić J, Mišić D, Stanković V, Mihailović M, Uskoković A, Arambašić J, Solujić S, Mladenović M, Stanković N. Hepatoprotective effects of secoiridoid-rich extracts from Gentiana cruciata L. against carbon tetrachloride induced liver damage in rats. Food Funct. 2014 Aug;5(8):1795-803. doi: 10.1039/c4fo00088a. PubMed PMID: 24912992. 10: ALPERT A, RAMSTAD E. A preliminary study of the hydrolytic products of gentiopicrin by paper chromatography. J Am Pharm Assoc Am Pharm Assoc. 1955 Jun;44(6):340-2. PubMed PMID: 14381299. 11: van der Sluis WG, Labadie RP. Secoiridoids and Xanthones in the genus Centaurium. Planta Med. 1981 Mar;41(3):221-31. PubMed PMID: 17401846. 12: Niu YT, Zhao YP, Jiao YF, Zheng J, Yang WL, Zhou R, Niu Y, Sun T, Li YX, Yu JQ. Protective effect of gentiopicroside against dextran sodium sulfate induced colitis in mice. Int Immunopharmacol. 2016 Oct;39:16-22. doi: 10.1016/j.intimp.2016.07.003. Epub 2016 Jul 7. PubMed PMID: 27394986. 13: van der Sluis WG, Labadie RP. Fungitoxic activity of the secoiridoid glucoside gentiopicrin (gentiopicroside). Planta Med. 1981 Jun;42(6):139-40. PubMed PMID: 17401945. 14: Wang Z, Tang S, Jin Y, Zhang Y, Hattori M, Zhang H, Zhang N. Two main metabolites of gentiopicroside detected in rat plasma by LC-TOF-MS following 2,4-dinitrophenylhydrazine derivatization. J Pharm Biomed Anal. 2015 Mar 25;107:1-6. doi: 10.1016/j.jpba.2014.12.003. Epub 2014 Dec 12. PubMed PMID: 25556816. 15: van der Nat J, van der Sluis WG, Labadie RP. Gentiogenal, a new antimicrobial iridoid derived from gentiopicrin (gentiopicroside). Planta Med. 1982 Jul;45(3):161-2. PubMed PMID: 17396888. 16: Ruan M, Yu B, Xu L, Zhang L, Long J, Shen X. Attenuation of stress-induced gastrointestinal motility disorder by gentiopicroside, from Gentiana macrophylla Pall. Fitoterapia. 2015 Jun;103:265-76. doi: 10.1016/j.fitote.2015.04.015. Epub 2015 May 1. PubMed PMID: 25936770. 17: Fan G, Luo WZ, Luo SH, Li Y, Meng XL, Zhou XD, Zhang Y. Metabolic discrimination of Swertia mussotii and Swertia chirayita known as "Zangyinchen" in traditional Tibetan medicine by (1)H NMR-based metabolomics. J Pharm Biomed Anal. 2014 Sep;98:364-70. doi: 10.1016/j.jpba.2014.06.014. Epub 2014 Jun 16. PubMed PMID: 24992216. 18: Amakura Y, Yoshimura M, Morimoto S, Yoshida T, Tada A, Ito Y, Yamazaki T, Sugimoto N, Akiyama H. Chromatographic Evaluation and Characterization of Components of Gentian Root Extract Used as Food Additives. Chem Pharm Bull (Tokyo). 2016;64(1):78-82. doi: 10.1248/cpb.c15-00776. PubMed PMID: 26726749. 19: Zhang X, Allan AC, Li C, Wang Y, Yao Q. De Novo Assembly and Characterization of the Transcriptome of the Chinese Medicinal Herb, Gentiana rigescens. Int J Mol Sci. 2015 May 20;16(5):11550-73. doi: 10.3390/ijms160511550. PubMed PMID: 26006235; PubMed Central PMCID: PMC4463717. 20: PESONEN S, RAMSTAD E. Studies on gentiopicrin. J Am Pharm Assoc Am Pharm Assoc. 1956 Aug;45(8):522-5. PubMed PMID: 13357340.