Phillyrin | CAS#487-41-2 | anti-diabetic

MedKoo Cat#: 585050 | Name: Phillyrin

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Description:

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

Phillyrin is a natural lignan that has the potential to ameliorate the inflammatory changes and insulin resistance in obese adipose tissue. Phillyrin is a potential antiosteoarthritic agent.

Chemical Structure

Phillyrin

CAS#487-41-2

Theoretical Analysis

MedKoo Cat#: 585050

Name: Phillyrin

CAS#: 487-41-2

Chemical Formula: C27H34O11

Exact Mass: 534.2101

Molecular Weight: 534.56

Elemental Analysis: C, 60.67; H, 6.41; O, 32.92

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Synonym

Phillyrin

IUPAC/Chemical Name

beta-D-Glucopyranoside, 4-(4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-2-methoxyphenyl, (1S-(1alpha,3aalpha,4beta,6aalpha))-

InChi Key

KFFCKOBAHMGTMW-KBTYFEGOSA-N

InChi Code

InChI=1S/C27H34O11/c1-32-17-6-4-13(8-19(17)33-2)25-15-11-36-26(16(15)12-35-25)14-5-7-18(20(9-14)34-3)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,15-16,21-31H,10-12H2,1-3H3/t15-,16-,21+,22-,23-,24+,25?,26?,27-/m0/s1

SMILES Code

O[C@H]([C@H]([C@H]([C@@H](CO)O1)O)O)[C@H]1OC2=CC=C(C3OC[C@@]4([H])[C@]3([H])COC4C5=CC=C(OC)C(OC)=C5)C=C2OC

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

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Phillyrin has potential inductive effects on rat CYP1A2 and CYP2D1 activities, without affecting CYP2C11 and CYP3A1/2 activities.

In vitro activity:

This study found that phillyrin suppressed high glucose-induced lipid accumulation in HepG2 cells. Phillyrin strongly inhibited high glucose-induced fatty acid synthase (FAS) expression by modulating sterol regulatory element-binding protein-1c (SREBP-1c) activation. Moreover, use of the pharmacological AMP-activated protein kinase (AMPK) inhibitor compound C revealed that AMPK is essential for suppressing SREBP-1c expression in phillyrin-treated cells. Finally, this study found that liver kinase B1 (LKB1) phosphorylation is required for the phillyrin-enhanced activation of AMPK in HepG2 hepatocytes. Reference: Food Chem. 2013 Jan 15;136(2):415-25. https://pubmed.ncbi.nlm.nih.gov/23122079/

In vivo activity:

Thirdly, a mouse model of IL-6 injection into visceral adipose tissue is explored to confirm the anti-basal lipolytic effect of Phillyrin against IL-6 in vivo. The results show that Phillyrin treatment reduces circulating level of glycerol, decreases hepatic steatosis and improves insulin sensitivity in obese mice. Meanwhile, Phillyrin attenuates obesity-related inflammation and IL-6 production in adipose tissue in obese mice. Furthermore, Phillyrin treatment results in resistance to IL-6-induced basal lipolysis in adipose tissue through suppressing expression of adipose triglyceride lipase (ATGL) both in vivo and in vitro. Reference: Front Nutr. 2022 Oct 5;9:956218. https://pubmed.ncbi.nlm.nih.gov/36276810/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	56.12
	DMSO	126.7	236.96
	DMSO:PBS (pH 7.2) (1:9)	0.1	0.19

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 534.56 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.

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. Qu XY, Li QJ, Zhang HM, Zhang XJ, Shi PH, Zhang XJ, Yang J, Zhou Z, Wang SQ. Protective effects of phillyrin against influenza A virus in vivo. Arch Pharm Res. 2016 Jul;39(7):998-1005. doi: 10.1007/s12272-016-0775-z. Epub 2016 Jun 21. PMID: 27323762. 2. Do MT, Kim HG, Choi JH, Khanal T, Park BH, Tran TP, Hwang YP, Na M, Jeong HG. Phillyrin attenuates high glucose-induced lipid accumulation in human HepG2 hepatocytes through the activation of LKB1/AMP-activated protein kinase-dependent signalling. Food Chem. 2013 Jan 15;136(2):415-25. doi: 10.1016/j.foodchem.2012.09.012. Epub 2012 Sep 17. PMID: 23122079. 3. Fang Z, Wei L, Lv Y, Wang T, Hamezah HS, Han R, Tong X. Phillyrin restores metabolic disorders in mice fed with high-fat diet through inhibition of interleukin-6-mediated basal lipolysis. Front Nutr. 2022 Oct 5;9:956218. doi: 10.3389/fnut.2022.956218. PMID: 36276810; PMCID: PMC9581271. 4. Zhang G, Zhang Y, Wang C, Zhou C, Yan S. Phillyrin Prevents Ovariectomy-Induced Osteolysis by Inhibiting Osteoclast Differentiation. Evid Based Complement Alternat Med. 2022 Jun 10;2022:6065494. doi: 10.1155/2022/6065494. PMID: 35722159; PMCID: PMC9205725.

In vitro protocol:

In vivo protocol:

1. Fang Z, Wei L, Lv Y, Wang T, Hamezah HS, Han R, Tong X. Phillyrin restores metabolic disorders in mice fed with high-fat diet through inhibition of interleukin-6-mediated basal lipolysis. Front Nutr. 2022 Oct 5;9:956218. doi: 10.3389/fnut.2022.956218. PMID: 36276810; PMCID: PMC9581271. 2. Zhang G, Zhang Y, Wang C, Zhou C, Yan S. Phillyrin Prevents Ovariectomy-Induced Osteolysis by Inhibiting Osteoclast Differentiation. Evid Based Complement Alternat Med. 2022 Jun 10;2022:6065494. doi: 10.1155/2022/6065494. PMID: 35722159; PMCID: PMC9205725.

1: Ma J, Wang Z, Sun Y, Zheng R, Tan H, Zhang H, Jin Z, Wu Y, Sun Z. Phillyrin: A potential therapeutic agent for osteoarthritis via modulation of NF-κB and Nrf2 signaling pathways. Int Immunopharmacol. 2024 Aug 18;141:112960. doi: 10.1016/j.intimp.2024.112960. Epub ahead of print. PMID: 39159565. 2: Liu Y, Wang C, Chen Z, Yuan H, Lei R, Li X, Ma S, Liu C. Distribution of active ingredients and quality control of Forsythia suspensa with AP-MALDI mass spectrometry imaging. J Mass Spectrom. 2024 Aug;59(8):e5073. doi: 10.1002/jms.5073. PMID: 38989767. 3: Du H, Zhang L, Sun H, Zheng S, Zhang H, Yuan S, Zhou J, Fang Z, Song J, Mei M, Deng C. Exploring the Underlying Mechanisms of Qingxing Granules Treating H1N1 Influenza Based on Network Pharmacology and Experimental Validation. Pharmaceuticals (Basel). 2024 Jun 5;17(6):731. doi: 10.3390/ph17060731. PMID: 38931398; PMCID: PMC11206762. 4: Xiao X, Zhang Y, Sun K, Liu S, Li Q, Zhang Y, Godspower BO, Xu T, Zhang Z, Li Y, Liu Y. Enzymatic and ultrasound assisted β-cyclodextrin extraction of active ingredients from Forsythia suspensa and their antioxidant and anti-inflammatory activities. Ultrason Sonochem. 2024 Aug;108:106944. doi: 10.1016/j.ultsonch.2024.106944. Epub 2024 Jun 6. PMID: 38878712; PMCID: PMC11227030. 5: Li J, Wang Y, Li J, Xu S, Wang S, Liu W, Fu L, Jiang M, Bai G. Phillyrin and its metabolites treat pulmonary embolism by targeting PLCβ3 to inhibit platelet activation. J Ethnopharmacol. 2024 Oct 28;333:118457. doi: 10.1016/j.jep.2024.118457. Epub 2024 Jun 10. PMID: 38866117. 6: Chen E, Li M, Liao Z, Yao D, Li Y, Huang L. Phillyrin reduces ROS production to alleviate the progression of intervertebral disc degeneration by inhibiting NF-κB pathway. J Orthop Surg Res. 2024 May 22;19(1):308. doi: 10.1186/s13018-024-04695-y. PMID: 38773639; PMCID: PMC11110443. 7: Li JJ, Chen ZH, Liu CJ, Kang YS, Tu XP, Liang H, Shi W, Zhang FX. The phytochemistry, pharmacology, pharmacokinetics, quality control, and toxicity of Forsythiae Fructus: An updated systematic review. Phytochemistry. 2024 Jun;222:114096. doi: 10.1016/j.phytochem.2024.114096. Epub 2024 Apr 17. PMID: 38641141. 8: Yang C, Bao L, Shi Z, Xv X, Jiang D, You L. Phillyrin alleviates high glucose-induced oxidative stress and inflammation in HBZY-1 cells through inhibition of the PI3K/Akt signaling pathway. J Pharm Pharmacol. 2024 Jul 5;76(7):776-787. doi: 10.1093/jpp/rgae028. PMID: 38507775. 9: Luo Q, Liu Q, Tang K, Zhong B, Yang S, Li X. Phillyrin improves myocardial remodeling in salt-sensitive hypertensive mice by reducing endothelin1 signaling. J Pharm Pharmacol. 2024 Jun 6;76(6):672-680. doi: 10.1093/jpp/rgae018. PMID: 38447186. 10: Huang C, Teng J, Liu W, Wang J, Liu A. Modulation of macrophages by a phillyrin-loaded thermosensitive hydrogel promotes skin wound healing in mice. Cytokine. 2024 May;177:156556. doi: 10.1016/j.cyto.2024.156556. Epub 2024 Feb 27. PMID: 38417214. 11: Zhou C, Yan L, Xu J, Hamezah HS, Wang T, Du F, Tong X, Han R. Phillyrin: an adipose triglyceride lipase inhibitor supported by molecular docking, dynamics simulation, and pharmacological validation. J Mol Model. 2024 Feb 13;30(3):68. doi: 10.1007/s00894-024-05875-7. PMID: 38347278. 12: Guo HY, Li X, Sang XT, Quan ZS, Shen QK. Design and synthesis of forsythin derivatives as anti-inflammatory agents for acute lung injury. Eur J Med Chem. 2024 Mar 5;267:116223. doi: 10.1016/j.ejmech.2024.116223. Epub 2024 Feb 7. PMID: 38342013. 13: Orabi MAA, Abdelhamid RA, Elimam H, Elshaier YAMM, Ali AA, Aldabaan N, Alhasaniah AH, Refaey MS. Furofuranoid-Type Lignans and Related Phenolics from Anisacanthus virgularis (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling. Plants (Basel). 2024 Jan 5;13(2):150. doi: 10.3390/plants13020150. PMID: 38256704; PMCID: PMC10820861. 14: Li C, Wu M, Zhang H, Zhu X, Fu L, Wang S, Lu M, Zhong D, Ding Y. Safety, tolerability and pharmacokinetics of forsythin in healthy subjects: a double- blinded, placebo-controlled single-dose and multiple-dose escalation and food effect study. Ann Med. 2023;55(2):2274512. doi: 10.1080/07853890.2023.2274512. Epub 2023 Nov 19. PMID: 37980573; PMCID: PMC10836277. 15: Zhang S, Sun F, Zhu J, Qi J, Wang W, Liu Z, Li W, Liu C, Liu X, Wang N, Song X, Zhang D, Qi D, Wang X. Phillyrin ameliorates influenza a virus-induced pulmonary inflammation by antagonizing CXCR2 and inhibiting NLRP3 inflammasome activation. Virol J. 2023 Nov 13;20(1):262. doi: 10.1186/s12985-023-02219-4. PMID: 37957672; PMCID: PMC10644626. 16: Tang X, Teng J, Lu K. Phillyrin sensitizes lung cancer cells to ferroptosis through inhibiting FTH1/SLC7A11 axis. Int J Clin Pharmacol Ther. 2024 Jan;62(1):8-19. doi: 10.5414/CP204475. PMID: 37942927. 17: Du Y, You L, Ni B, Sai N, Wang W, Sun M, Xu R, Yao Y, Zhang Z, Qu C, Yin X, Ni J. Erratum to "Phillyrin Mitigates Apoptosis and Oxidative Stress in Hydrogen Peroxide-Treated RPE Cells through Activation of the Nrf2 Signaling Pathway". Oxid Med Cell Longev. 2023 Oct 11;2023:9891240. doi: 10.1155/2023/9891240. Erratum for: Oxid Med Cell Longev. 2020 Oct 12;2020:2684672. doi: 10.1155/2020/2684672. PMID: 37868733; PMCID: PMC10586359. 18: Zhang L, Lang F, Feng J, Wang J. Review of the therapeutic potential of Forsythiae Fructus on the central nervous system: Active ingredients and mechanisms of action. J Ethnopharmacol. 2024 Jan 30;319(Pt 2):117275. doi: 10.1016/j.jep.2023.117275. Epub 2023 Oct 4. PMID: 37797873. 19: Yuan H, Tang Y, Zhang S, Yan S, Li A, Yu Y, Sun Y, Zheng F. NLRP3 neuroinflammatory intervention of Mahuang-Lianqiao-Chixiaodou decoction for mental disorders in atopic dermatitis mice. J Ethnopharmacol. 2024 Jan 30;319(Pt 2):117263. doi: 10.1016/j.jep.2023.117263. Epub 2023 Sep 30. PMID: 37783411. 20: Zhu JX, Guo MX, Zhou L, Yi LT, Huang HL, Wang HL, Cheng HY. Evaluation of the anti-inflammatory material basis of Lagotis brachystachya in HepG2 and THP-1 cells. J Ethnopharmacol. 2024 Jan 10;318(Pt B):117055. doi: 10.1016/j.jep.2023.117055. Epub 2023 Aug 18. PMID: 37597676.