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MedKoo Cat#: 122934 | Name: Rhyncophylline
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Description:

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

Rhyncophylline is an alkaloid that has been found in U. rhyncophylla and has diverse biological activities

Chemical Structure

Rhyncophylline
Rhyncophylline
CAS#76-66-4

Theoretical Analysis

MedKoo Cat#: 122934

Name: Rhyncophylline

CAS#: 76-66-4

Chemical Formula: C22H28N2O4

Exact Mass: 384.2000

Molecular Weight: 384.48

Elemental Analysis: C, 68.73; H, 7.34; N, 7.29; O, 16.64

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 750.00 2 Weeks
10mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
NSC 21731; Mitrinermine
IUPAC/Chemical Name
(αE,1′R,6′R,7′S,8′aS)-6′-ethyl-1,2,2′,3′,6′,7′,8′,8′a-octahydro-α-(methoxymethylene)-2-oxo-spiro[3H-indole-3,1′(5′H)-indolizine]-7′-acetic acid, methyl ester
InChi Key
DAXYUDFNWXHGBE-KAXDATADSA-N
InChi Code
InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1
SMILES Code
O=C(OC)/C([C@@H](C[C@]12[H])[C@@H](CC)CN1CC[C@@]32C(NC4=C3C=CC=C4)=O)=C/OC
Appearance
To be determined
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 384.48 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 L, Li H, Zhang H, Song X, Jiang H, Wang D, Wang Y. Serum-based metabolomics reveals the mechanism of action of isorhynchophylline in the intervention of atherosclerosis in ApoE-/- mice. Anal Methods. 2024 Feb 15;16(7):1083-1092. doi: 10.1039/d3ay01803b. PMID: 38284158. 2: da Rosa E, Stopiglia CDO, Machado MM, Filho ACD, Soci UPR, Mendez ASL, Fernandes T, de Oliveira EM, Moreira CM. Phytochemistry Profile, Antimicrobial and Antitumor Potential of the Methanolic Extract of Tabernaemontana catharinensis A DC and Eragrostis plana NEES. Evid Based Complement Alternat Med. 2024 Jan 3;2024:5513141. doi: 10.1155/2024/5513141. PMID: 38213844; PMCID: PMC10781527. 3: Wu Y, Bian Y, Fei J, Huang Y. Isorhynchophylline attenuates proliferation and migration of synovial fibroblasts via the FOXC1/β-catenin axis. Autoimmunity. 2023 Dec;56(1):2289868. doi: 10.1080/08916934.2023.2289868. Epub 2023 Dec 6. PMID: 38055770. 4: Mu D, Shao Y, He J, Zhu L, Qiu D, Wilson IW, Zhang Y, Pan L, Zhou Y, Lu Y, Tang Q. Evaluation of Reference Genes for Normalizing RT-qPCR and Analysis of the Expression Patterns of WRKY1 Transcription Factor and Rhynchophylline Biosynthesis-Related Genes in Uncaria rhynchophylla. Int J Mol Sci. 2023 Nov 15;24(22):16330. doi: 10.3390/ijms242216330. PMID: 38003520; PMCID: PMC10671239. 5: Zhu X, Hou Q, Zhang L, Wang D, Tian Z, Liu Y, Wang Y, Li Y, Jiang H. Isorhynchophylline improves lipid metabolism disorder by mediating a circadian rhythm gene Bmal1 in spontaneously hypertensive rat. Phytother Res. 2023 Dec;37(12):5991-6005. doi: 10.1002/ptr.8015. Epub 2023 Sep 26. PMID: 37752617. 6: Jiang MJ, Li J, Luo CH, Zhu C, Chen ZJ, Bai W, Hu TY, Feng CH, Li C, Mo ZX. Rhynchophylline inhibits methamphetamine dependence via modulating the miR-181a-5p/GABRA1 axis. J Ethnopharmacol. 2023 Oct 5;314:116635. doi: 10.1016/j.jep.2023.116635. Epub 2023 May 13. PMID: 37182675. 7: Ballester Roig MN, Leduc T, Dufort-Gervais J, Maghmoul Y, Tastet O, Mongrain V. Probing pathways by which rhynchophylline modifies sleep using spatial transcriptomics. Biol Direct. 2023 May 5;18(1):21. doi: 10.1186/s13062-023-00377-7. PMID: 37143153; PMCID: PMC10161643. 8: Liu K, Liu S, Wu C, Wang Y, Zhang Y, Yu J, Liu S, Li X, Qi X, Su S, Qi X, Zhou L, Li Y. Rhynchophylline relieves nonalcoholic fatty liver disease by activating lipase and increasing energy metabolism. Int Immunopharmacol. 2023 Apr;117:109948. doi: 10.1016/j.intimp.2023.109948. Epub 2023 Mar 11. PMID: 37012893. 9: Zhang C, Xue Z, Zhu L, Zhou J, Zhuo L, Zhang J, Zhang X, Liu W, Han L, Liao W. Rhynchophylline alleviates neuroinflammation and regulates metabolic disorders in a mouse model of Parkinson's disease. Food Funct. 2023 Apr 3;14(7):3208-3219. doi: 10.1039/d2fo02939a. PMID: 36919954. 10: Wang LH, Gu ZW, Li J, Yang WQ, Li YL, Qi DM, Wang DY, Jiang HQ. Isorhynchophylline inhibits inflammatory responses in endothelial cells and macrophages through the NF-κB/NLRP3 signaling pathway. BMC Complement Med Ther. 2023 Mar 11;23(1):80. doi: 10.1186/s12906-023-03902-3. PMID: 36906555; PMCID: PMC10007741. 11: Jiang J, Li J, Xiong C, Zhou X, Liu T. Isorhynchophylline alleviates cartilage degeneration in osteoarthritis by activating autophagy of chondrocytes. J Orthop Surg Res. 2023 Mar 2;18(1):154. doi: 10.1186/s13018-023-03645-4. PMID: 36864518; PMCID: PMC9979446. 12: Liu EY, Yang CL, Tsai JC, Cheng HY, Peng WH. Antidepressive mechanisms of rhynchophylline in mice with chronic unpredictable stress-induced depression. J Ethnopharmacol. 2023 Jun 12;309:116302. doi: 10.1016/j.jep.2023.116302. Epub 2023 Feb 25. PMID: 36842720. 13: Wang J, Wang X, Zhang M, Lang Y, Chen B, Ye Y, Bai Y, Ding S. The activation of spliced X-box binding protein 1 by isorhynchophylline therapy improves diabetic encephalopathy. Cell Biol Toxicol. 2023 Dec;39(6):2587-2613. doi: 10.1007/s10565-022-09789-z. Epub 2023 Jan 25. PMID: 36695953. 14: Wang D, Sun M, Liu Y, Wang L, Li C, Li Y, Jiang H. Isorhynchophylline Regulates the Circadian Rhythm of the Hypothalamus in Spontaneously Hypertensive Rats to Treat Hypertension. Curr Pharm Des. 2023;29(2):139-148. doi: 10.2174/1381612829666221222115134. PMID: 36567301. 15: Yang M, Yao B, Lin R. Profiles of Metabolic Genes in Uncaria rhynchophylla and Characterization of the Critical Enzyme Involved in the Biosynthesis of Bioactive Compounds-(iso)Rhynchophylline. Biomolecules. 2022 Nov 30;12(12):1790. doi: 10.3390/biom12121790. PMID: 36551218; PMCID: PMC9775700. 16: Lin H, Xie L, Lv L, Chen J, Feng F, Liu W, Han L, Liu F. Intranasally administered thermosensitive gel for brain-targeted delivery of rhynchophylline to treat Parkinson's disease. Colloids Surf B Biointerfaces. 2023 Feb;222:113065. doi: 10.1016/j.colsurfb.2022.113065. Epub 2022 Nov 30. PMID: 36473372. 17: Wang L, Wang Y, Chen Y, Liu B, Chou D, Bian X, Li R, Wang M, Zheng C. Rhynchophylline ameliorates cerebral ischemia by improving the synaptic plasticity in a middle cerebral artery occlusion induced stroke model. Eur J Pharmacol. 2023 Feb 5;940:175390. doi: 10.1016/j.ejphar.2022.175390. Epub 2022 Nov 15. PMID: 36400162. 18: Li Z, Shi H, Li Y, Wang W, Li Z, Chen B, Nie D. Isorhynchophylline ameliorates the progression of osteoarthritis by inhibiting the NF-κB pathway. Eur J Pharmacol. 2022 Jun 5;924:174971. doi: 10.1016/j.ejphar.2022.174971. Epub 2022 Apr 22. PMID: 35469836. 19: Li X, Wang XH, Qiang W, Zheng HJ, ShangGuan LY, Zhang MS. Transcriptome revealing the dual regulatory mechanism of ethylene on the rhynchophylline and isorhynchophylline in Uncaria rhynchophylla. J Plant Res. 2022 May;135(3):485-500. doi: 10.1007/s10265-022-01387-8. Epub 2022 Apr 5. PMID: 35380307. 20: Meng Q, Cheng Y, Zhou C. Pharmacokinetic interaction between rhynchopylline and pellodendrine via CYP450 enzymes and P-gp. Pharm Biol. 2021 Dec;59(1):1551-1555. doi: 10.1080/13880209.2021.1999988. PMID: 34757861; PMCID: PMC8583760.