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MedKoo Cat#: 471140 | Name: Trifolirhizin
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Description:

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

Trifolirhizin is a flavonoid isolated from Sophora flavescens that has anticancer and vasorelaxant activities

Chemical Structure

Trifolirhizin
Trifolirhizin
CAS#6807-83-6

Theoretical Analysis

MedKoo Cat#: 471140

Name: Trifolirhizin

CAS#: 6807-83-6

Chemical Formula: C22H22O10

Exact Mass: 446.1210

Molecular Weight: 446.41

Elemental Analysis: C, 59.19; H, 4.97; O, 35.84

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 600.00 2 Weeks
25mg USD 1,000.00 2 Weeks
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Related CAS #
No Data
Synonym
(−)-Maackiain 3-O-glucoside; Trifolirhizin; Sophojaponicin B1
IUPAC/Chemical Name
(2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-dihydro-6H-[1,3]dioxolo[4',5':5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
InChi Key
VGSYCWGXBYZLLE-QEEQPWONSA-N
InChi Code
InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1
SMILES Code
[H][C@]12C3=CC4=C(C=C3O[C@]1(C5=CC=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C=C5OC2)[H])OCO4
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 446.41 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
1: Wang Y, Fang Y. Trifolirhizin targets PTK6 to induce autophagy and exerts antitumor effects in nasopharyngeal carcinoma. Drug Dev Res. 2024 Nov;85(7):e70000. doi: 10.1002/ddr.70000. PMID: 39392221. 2: Lin Z, Zhou Z, Ye J, Wei J, Chen S, Zhou W, Bi Y, Zhou Z, Xie G, Yuan G, Yao G. Trifolirhizin protects ovariectomy-induced bone loss in mice by inhibiting osteoclast differentiation and bone resorption. Heliyon. 2024 Jul 6;10(14):e34250. doi: 10.1016/j.heliyon.2024.e34250. PMID: 39130482; PMCID: PMC11315080. 3: Huang J, Song D, Xu M, Gan K, Wang C, Chen L, Huang Q, Chen J, Su Y, Xu J, Zhao J, Liu Q. Trifolirhizin reduces osteoclast formation and prevents inflammatory osteolysis by inhibiting RANKL-induced activation of NF-κB and MAPK signaling pathways and ROS. Phytother Res. 2024 Sep;38(9):4650-4666. doi: 10.1002/ptr.8299. Epub 2024 Aug 4. PMID: 39098645. 4: Wang J, Lin F, Zhou Y, Cong Y, Yang S, Wang S, Guan X. Chemopreventive effect of modified zeng-sheng-ping on oral squamous cell carcinoma by regulating tumor associated macrophages through targeting tnf alpha induced protein 6. BMC Complement Med Ther. 2024 Jul 27;24(1):287. doi: 10.1186/s12906-024-04593-0. PMID: 39068492; PMCID: PMC11283705. 5: Swargiary A, Daimari M, Swargiary A, Biswas A, Brahma D, Singha H. Identification of phytocompounds as potent inhibitors of sodium/glucose cotransporter-2 leading to diabetes treatment. J Biomol Struct Dyn. 2024 Feb 20:1-14. doi: 10.1080/07391102.2024.2319674. Epub ahead of print. PMID: 38379332. 6: Yun HM, Cho MH, Jeong H, Kim SH, Jeong YH, Park KR. Osteogenic Activities of Trifolirhizin as a Bioactive Compound for the Differentiation of Osteogenic Cells. Int J Mol Sci. 2023 Dec 4;24(23):17103. doi: 10.3390/ijms242317103. PMID: 38069425; PMCID: PMC10706948. 7: Alotaibi BS. Targeting Filamenting temperature-sensitive mutant Z (FtsZ) with bioactive phytoconstituents: An emerging strategy for antibacterial therapy. PLoS One. 2023 Aug 30;18(8):e0290852. doi: 10.1371/journal.pone.0290852. PMID: 37647309; PMCID: PMC10468062. 8: Jiang X, Yin H, Su W, Quan H, Yuan X, Feng X, Li P, He Y, Xiao J, Li R. Trifolirhizin inhibits proliferation, migration and invasion in nasopharyngeal carcinoma cells via PI3K/Akt signaling pathway suppression. Biochem Biophys Res Commun. 2023 Jul 30;667:111-119. doi: 10.1016/j.bbrc.2023.05.030. Epub 2023 May 10. PMID: 37216826. 9: Yang H, Duan Y, Wei Z, Wu Y, Zhang C, Wu W, Lyu L, Li W. Integrated Physiological and Metabolomic Analyses Reveal the Differences in the Fruit Quality of the Blueberry Cultivated in Three Soilless Substrates. Foods. 2022 Dec 7;11(24):3965. doi: 10.3390/foods11243965. PMID: 36553707; PMCID: PMC9777891. 10: Zhu XF, Sun ZL, Ma J, Hu B, Yu MC, Liu XJ, Yang P, Xu Y, Ju D, Mu Q. Synergistic anticancer effect of flavonoids from Sophora alopecuroides with Sorafenib against hepatocellular carcinoma. Phytother Res. 2023 Feb;37(2):592-610. doi: 10.1002/ptr.7637. Epub 2022 Sep 30. PMID: 36180975. 11: Zhang Q, Wang S, Ji S. Trifolirhizin regulates the balance of Th17/Treg cells and inflammation in the ulcerative colitis mice through inhibiting the TXNIP-mediated activation of NLRP3 inflammasome. Clin Exp Pharmacol Physiol. 2022 Aug;49(8):787-796. doi: 10.1111/1440-1681.13654. Epub 2022 Jun 20. PMID: 35575951. 12: Chen J, Liu Y, Gai X, Ye Q, Zhou S, Tian C, Zhang T. Studies on Quality Markers of Kaihoujian Spray for Anti-Inflammation Based on Gray Correlation Analysis Strategy. Evid Based Complement Alternat Med. 2022 Apr 20;2022:1273066. doi: 10.1155/2022/1273066. PMID: 35497922; PMCID: PMC9045996. 13: Sun J, Li M, Lin T, Wang D, Chen J, Zhang Y, Mu Q, Su H, Wu N, Liu A, Yu Y, Liu Y, Wang S, Yu X, Guo J, Yu W. Cell cycle arrest is an important mechanism of action of compound Kushen injection in the prevention of colorectal cancer. Sci Rep. 2022 Mar 14;12(1):4384. doi: 10.1038/s41598-022-08336-4. PMID: 35288618; PMCID: PMC8921286. 14: Yuan WL, Huang ZR, Xiao SJ, Ye J, Zhang WD, Shen YH. [Metabolites and metabolic pathways of maackiain in rats based on UPLC-Q-TOF-MS]. Zhongguo Zhong Yao Za Zhi. 2021 Dec;46(23):6278-6288. Chinese. doi: 10.19540/j.cnki.cjcmm.20210902.201. PMID: 34951255. 15: Li P, Chai WC, Wang ZY, Tang KJ, Chen JY, Venter H, Semple SJ, Xiang L. Bioactivity-guided isolation of compounds from Sophora flavescens with antibacterial activity against Acinetobacter baumannii. Nat Prod Res. 2022 Sep;36(17):4340-4348. doi: 10.1080/14786419.2021.1983570. Epub 2021 Oct 1. PMID: 34592853. 16: Zhang K, Liu W, Qu Z, Liu Q, Chen J, Tao R, Deng Y, Zhang Y. In vitro and in vivo human gastric cancer inhibition by Trifolirhizin is facilitated via autophagy, mitochondrial mediated programmed cell death, G2/M phase cell cycle arrest and inhibition of m-TOR/PI3K/AKT signalling pathway. J BUON. 2021 Mar- Apr;26(2):639. PMID: 34077023. 17: Manal Ahmad A, Yasser Ibrahim K, Manal Mohammad A. Efficacy of extract from Ononis spinosa L. on ethanol-induced gastric ulcer in rats. J Tradit Chin Med. 2021 Apr;41(2):270-275. PMID: 33825407. 18: Wei G, Chen Y, Guo X, Wei J, Dong L, Chen S. Biosyntheses characterization of alkaloids and flavonoids in Sophora flavescens by combining metabolome and transcriptome. Sci Rep. 2021 Apr 1;11(1):7388. doi: 10.1038/s41598-021-86970-0. PMID: 33795823; PMCID: PMC8016917. 19: Sun D, Tao W, Zhang F, Shen W, Tan J, Li L, Meng Q, Chen Y, Yang Y, Cheng H. Trifolirhizin induces autophagy-dependent apoptosis in colon cancer via AMPK/mTOR signaling. Signal Transduct Target Ther. 2020 Aug 27;5(1):174. doi: 10.1038/s41392-020-00281-w. PMID: 32855395; PMCID: PMC7452898. 20: Kim S, Jeong YJ, Park SH, Park SC, Lee SB, Lee J, Kim SW, Ha BK, Kim HS, Kim H, Ryu YB, Jeong JC, Kim CY. The Synergistic Effect of Co-Treatment of Methyl Jasmonate and Cyclodextrins on Pterocarpan Production in Sophora flavescens Cell Cultures. Int J Mol Sci. 2020 May 30;21(11):3944. doi: 10.3390/ijms21113944. PMID: 32486319; PMCID: PMC7313034.