159278-74-7
Chemical Structure
Rhinacanthin C
- CAS No.: 159278-74-7
- Formula:C25H30O5
- Molecular Weight:410.50
InChIKey: HBWJZSWEQJLURT-QIGLBIQCSA-N
SMILES: O=C1C2=CC=CC=C2C(C(O)=C1CC(C)(C)COC(/C(C)=C/CC/C(C)=C/C)=O)=O
Biological Activity: Rhinacanthin C is an orally active naphthoquinone ester and P-gp inhibitor (IC50 = 5.20 μM). Rhinacanthin C exerts effects in ameliorating hepatic steatosis, insulin resistance, and inflammation by inhibiting P-gp, BCRP, OATP1B1/1B3, and multiple CYP enzymes, downregulating lipid synthesis-related factors such as ACC and FAS, and upregulating AMPKα phosphorylation and SIRT1. Rhinacanthin C can be used in research on non-alcoholic fatty liver disease, diabetes, abnormal osteolysis, Alzheimer's disease, and inflammation[1][2][3][4][5][6][7][8][9][10][11][12].
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Rhinacanthin C | Rhinacanthin C is an orally active naphthoquinone ester and P-gp inhibitor (IC50 = 5.20 μM). Rhinacanthin C exerts effects in ameliorating hepatic steatosis, insulin resistance, and inflammation by inhibiting P-gp, BCRP, OATP1B1/1B3, and multiple CYP enzymes, downregulating lipid synthesis-related factors such as ACC and FAS, and upregulating AMPKα phosphorylation and SIRT1. Rhinacanthin C can be used in research on non-alcoholic fatty liver disease, diabetes, abnormal osteolysis, Alzheimer's disease, and inflammation. | |||||||||||||||||||||
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References
- [1]. Gong Z, et al. Rhinacanthin C Ameliorates Insulin Resistance and Lipid Accumulation in NAFLD Mice via the AMPK/SIRT1 and SREBP-1c/FAS/ACC Signaling Pathways. Evid Based Complement Alternat Med. 2023 Jan 10;2023:6603522.
- [2]. Adam SH, et al. Rhinacanthin C ameliorates hyperglycaemia, hyperlipidemia and pancreatic destruction in streptozotocin-nicotinamide induced adult male diabetic rats. European journal of pharmacology. 2016 Jan 15;771:173-90.
- [3]. Tomomura M, et al. Rhinacanthin C Inhibits Osteoclast Differentiation and Bone Resorption: Roles of TRAF6/TAK1/MAPKs/NF-κB/NFATc1 Signaling. PLoS One. 2015 Jun 17;10(6):e0130174.
- [4]. Chuang KA, et al. Rhinacanthin C Alleviates Amyloid- Fibrils' Toxicity on Neurons and Attenuates Neuroinflammation Triggered by LPS, Amyloid-, and Interferon- in Glial Cells. Oxidative medicine and cellular longevity. 2017;2017:5414297.
- [5]. Dunkoksung W, et al. Rhinacanthin-C Mediated Herb-Drug Interactions with Drug Transporters and Phase I Drug-Metabolizing Enzymes. Drug metabolism and disposition: the biological fate of chemicals. 2019 Oct;47(10):1040-1049.
- [6]. Chaisit T, et al. Rhinacanthin-C enhances doxorubicin cytotoxicity via inhibiting the functions of P-glycoprotein and MRP2 in breast cancer cells. European journal of pharmacology. 2017 Jan 15;795:50-57.
- [7]. Tewtrakul S, et al. Effects of rhinacanthins from Rhinacanthus nasutus on nitric oxide, prostaglandin E2 and tumor necrosis factor-alpha releases using RAW264.7 macrophage cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2009 Jun;16(6-7):581-5.
- [8]. Wongwanakul R, et al. Effects of rhinacanthin-C on function and expression of drug efflux transporters in Caco-2 cells. Fitoterapia. 2013 Sep;89:80-5.
- [9]. Gotoh A, et al. Antiproliferative activity of Rhinacanthus nasutus (L.) Kurz extracts and the active moiety, Rhinacanthin C. Biological & pharmaceutical bulletin. 2004 Jul;27(7):1070-4.
- [10]. Tewtrakul S, et al. Anti-allergic principles of Rhinacanthus nasutus leaves. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2009 Oct;16(10):929-34.
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[11]. Muhammad Ajmal Shah, et al.
α-Glucosidase inhibitory effect of rhinacanthins-rich extract from Rhinacanthus nasutus leaf and synergistic effect in combination with acarbose, Journal of Functional Foods, Volume 36, 2017, Pages 325-331, ISSN 1756-4646. - [12]. Zhao LL, et al. Rhinacanthins-rich extract and rhinacanthin C ameliorate oxidative stress and inflammation in streptozotocin-nicotinamide-induced diabetic nephropathy. Journal of food biochemistry. 2019 Apr;43(4):e12812.
