Fargesin
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MedKoo CAT#: 330106

CAS#: 31008-19-2

Description: Fargesin is a lignan from Magnolia fargesii, an oriental medicine used in the treatment of nasal congestion and sinusitis. Fargesin exhibits anti-inflammation effects on THP-1 cells via suppression of PKC pathway including downstream JNK, nuclear factors AP-1 and NF-ĸB. Fargesin as a potential β₁ adrenergic receptor antagonist protects the hearts against ischemia/reperfusion injury in rats via attenuating oxidative stress and apoptosis.

Chemical Structure

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Fargesin
CAS# 31008-19-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 330106
Name: Fargesin
CAS#: 31008-19-2
Chemical Formula: C21H22O6
Exact Mass: 370.14
Molecular Weight: 370.401
Elemental Analysis: C, 68.10; H, 5.99; O, 25.92

Price and Availability

Size Price Availability Quantity
10mg USD 425 2 weeks
50mg USD 1050 2 weeks
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Synonym: Fargesin

IUPAC/Chemical Name: 1H,3H-Furo(3,4-C)furan, 1alpha-(3,4-dimethoxyphenyl)-3abeta,4,6,6abeta-tetrahydro-4beta-((3,4-methylenedioxy)phenyl)-

InChi Key: AWOGQCSIVCQXBT-USWJAIAZSA-N

InChi Code: InChI=1S/C21H22O6/c1-22-16-5-3-12(7-18(16)23-2)20-14-9-25-21(15(14)10-24-20)13-4-6-17-19(8-13)27-11-26-17/h3-8,14-15,20-21H,9-11H2,1-2H3/t14?,15?,20-,21+/m0/s1

SMILES Code: COC1=CC=C([C@@H]2OCC3C2CO[C@@H]3C4=CC(OCO5)=C5C=C4)C=C1OC

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: Fargesin is a bioactive neolignan isolated from magnolia plants, with antihypertensive and anti-inflammatory effects.
In vitro activity: Fargesin suppressed cell proliferation of JB6 Cl41 and HaCaT cells in a dose-dependent manner (Figure 1a). Both JB6 Cl41 and HaCaT cells showed a 50% inhibitory effect of cell proliferation at approximately 22–23 μM fargesin concentration (Figure 1a). Reference: Int J Mol Sci. 2021 Feb; 22(4): 2073. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7922630/
In vivo activity: Although fargesin treatment demonstrated a slight decrease in synovial hyperplasia, no significant differences in the knee synovitis score were present between fargesin and control mice 3 weeks after intra-articular injection (Fig. 1d, i). However, the synovitis score was significantly reduced in fargesin-treated mice 6 weeks after intra-articular injection (Fig. 1e, j). These findings demonstrated that fargesin prevented OA progression to cartilage damage and synovial inflammation. Reference: Arthritis Res Ther. 2021; 23: 142. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8120707/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 80.5 217.33

Preparing Stock Solutions

The following data is based on the product molecular weight 370.40 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. Hong PTL, Kim HJ, Kim WK, Nam JH. Flos magnoliae constituent fargesin has an anti-allergic effect via ORAI1 channel inhibition. Korean J Physiol Pharmacol. 2021 May 1;25(3):251-258. doi: 10.4196/kjpp.2021.25.3.251. PMID: 33859065; PMCID: PMC8050608. 2. Lee GE, Lee CJ, An HJ, Kang HC, Lee HS, Lee JY, Oh SR, Cho SJ, Kim DJ, Cho YY. Fargesin Inhibits EGF-Induced Cell Transformation and Colon Cancer Cell Growth by Suppression of CDK2/Cyclin E Signaling Pathway. Int J Mol Sci. 2021 Feb 19;22(4):2073. doi: 10.3390/ijms22042073. PMID: 33669811; PMCID: PMC7922630. 3. Lu J, Zhang H, Pan J, Hu Z, Liu L, Liu Y, Yu X, Bai X, Cai D, Zhang H. Fargesin ameliorates osteoarthritis via macrophage reprogramming by downregulating MAPK and NF-κB pathways. Arthritis Res Ther. 2021 May 14;23(1):142. doi: 10.1186/s13075-021-02512-z. PMID: 33990219; PMCID: PMC8120707. 4. Wang G, Gao JH, He LH, Yu XH, Zhao ZW, Zou J, Wen FJ, Zhou L, Wan XJ, Tang CK. Fargesin alleviates atherosclerosis by promoting reverse cholesterol transport and reducing inflammatory response. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 May;1865(5):158633. doi: 10.1016/j.bbalip.2020.158633. Epub 2020 Jan 25. PMID: 31988050.
In vitro protocol: 1. Hong PTL, Kim HJ, Kim WK, Nam JH. Flos magnoliae constituent fargesin has an anti-allergic effect via ORAI1 channel inhibition. Korean J Physiol Pharmacol. 2021 May 1;25(3):251-258. doi: 10.4196/kjpp.2021.25.3.251. PMID: 33859065; PMCID: PMC8050608. 2. Lee GE, Lee CJ, An HJ, Kang HC, Lee HS, Lee JY, Oh SR, Cho SJ, Kim DJ, Cho YY. Fargesin Inhibits EGF-Induced Cell Transformation and Colon Cancer Cell Growth by Suppression of CDK2/Cyclin E Signaling Pathway. Int J Mol Sci. 2021 Feb 19;22(4):2073. doi: 10.3390/ijms22042073. PMID: 33669811; PMCID: PMC7922630.
In vivo protocol: 1. Lu J, Zhang H, Pan J, Hu Z, Liu L, Liu Y, Yu X, Bai X, Cai D, Zhang H. Fargesin ameliorates osteoarthritis via macrophage reprogramming by downregulating MAPK and NF-κB pathways. Arthritis Res Ther. 2021 May 14;23(1):142. doi: 10.1186/s13075-021-02512-z. PMID: 33990219; PMCID: PMC8120707. 2. Wang G, Gao JH, He LH, Yu XH, Zhao ZW, Zou J, Wen FJ, Zhou L, Wan XJ, Tang CK. Fargesin alleviates atherosclerosis by promoting reverse cholesterol transport and reducing inflammatory response. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 May;1865(5):158633. doi: 10.1016/j.bbalip.2020.158633. Epub 2020 Jan 25. PMID: 31988050.

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1: Sultana B, Yaqoob S, Zafar Z, Bhatti HN. Escalation of liver malfunctioning: A step toward Herbal Awareness. J Ethnopharmacol. 2018 Jan 6;216:104-119. doi: 10.1016/j.jep.2018.01.002. [Epub ahead of print] Review. PubMed PMID: 29309862.

2: Kim JH, Kwon SS, Jeong HU, Lee HS. Inhibitory Effects of Dimethyllirioresinol, Epimagnolin A, Eudesmin, Fargesin, and Magnolin on Cytochrome P450 Enzyme Activities in Human Liver Microsomes. Int J Mol Sci. 2017 May 1;18(5). pii: E952. doi: 10.3390/ijms18050952. PubMed PMID: 28468305; PubMed Central PMCID: PMC5454865.

3: Pham TH, Kim MS, Le MQ, Song YS, Bak Y, Ryu HW, Oh SR, Yoon DY. Fargesin exerts anti-inflammatory effects in THP-1 monocytes by suppressing PKC-dependent AP-1 and NF-ĸB signaling. Phytomedicine. 2017 Jan 15;24:96-103. doi: 10.1016/j.phymed.2016.11.014. Epub 2016 Nov 21. PubMed PMID: 28160867.

4: Bhatt V, Sharma S, Kumar N, Sharma U, Singh B. Simultaneous quantification and identification of flavonoids, lignans, coumarin and amides in leaves of Zanthoxylum armatum using UPLC-DAD-ESI-QTOF-MS/MS. J Pharm Biomed Anal. 2017 Jan 5;132:46-55. doi: 10.1016/j.jpba.2016.09.035. Epub 2016 Sep 26. PubMed PMID: 27693952.

5: Sha S, Xu D, Wang Y, Zhao W, Li X. Antihypertensive effects of fargesin in vitro and in vivo via attenuating oxidative stress and promoting nitric oxide release. Can J Physiol Pharmacol. 2016 Aug;94(8):900-6. doi: 10.1139/cjpp-2015-0615. Epub 2016 Apr 19. PubMed PMID: 27409158.

6: Zhou X, Chen C, Ye X, Song F, Fan G, Wu F. Analysis of lignans in Magnoliae Flos by turbulent flow chromatography with online solid-phase extraction and high-performance liquid chromatography with tandem mass spectrometry. J Sep Sci. 2016 Apr;39(7):1266-72. doi: 10.1002/jssc.201501167. Epub 2016 Mar 1. PubMed PMID: 26833996.

7: Li DX, Liu M, Zhou XJ. A new dimeric lignan from Zanthoxylum simulans. Zhongguo Zhong Yao Za Zhi. 2015 Jul;40(14):2843-8. PubMed PMID: 26666037.

8: Guo T, Su D, Huang Y, Wang Y, Li YH. Ultrasound-Assisted Aqueous Two-Phase System for Extraction and Enrichment of Zanthoxylum armatum Lignans. Molecules. 2015 Aug 20;20(8):15273-86. doi: 10.3390/molecules200815273. PubMed PMID: 26307958.

9: Wang X, Cheng Y, Xue H, Yue Y, Zhang W, Li X. Fargesin as a potential β₁ adrenergic receptor antagonist protects the hearts against ischemia/reperfusion injury in rats via attenuating oxidative stress and apoptosis. Fitoterapia. 2015 Sep;105:16-25. doi: 10.1016/j.fitote.2015.05.016. Epub 2015 May 27. PubMed PMID: 26025856.

10: Bhatt V, Kumar V, Singh B, Kumar N. A new geranylbenzofuranone from Zanthoxylum armatum. Nat Prod Commun. 2015 Feb;10(2):313-4. PubMed PMID: 25920270.

11: Samad A, Badshah S, Khan D, Ali F, Amanullah M, Hanrahan J. New prenylated carbazole alkaloids from Zanthoxylum armatum. J Asian Nat Prod Res. 2014 Dec;16(12):1126-31. doi: 10.1080/10286020.2014.967228. Epub 2014 Oct 30. PubMed PMID: 25355272.

12: Liu YQ, Yang SH, Liu Q, Pei G, Pan WW, Liu M, Peng CY. [Study on chemical constituents of Zanthoxyli cortex's ethyl acetate extract]. Zhong Yao Cai. 2013 Nov;36(11):1792-5. Chinese. PubMed PMID: 24956821.

13: Kumar V, Kumar S, Singh B, Kumar N. Quantitative and structural analysis of amides and lignans in Zanthoxylum armatum by UPLC-DAD-ESI-QTOF-MS/MS. J Pharm Biomed Anal. 2014 Jun;94:23-9. doi: 10.1016/j.jpba.2014.01.028. Epub 2014 Jan 30. PubMed PMID: 24534301.

14: Jun AY, Kim HJ, Park KK, Son KH, Lee DH, Woo MH, Chung WY. Tetrahydrofurofuran-type lignans inhibit breast cancer-mediated bone destruction by blocking the vicious cycle between cancer cells, osteoblasts and osteoclasts. Invest New Drugs. 2014 Feb;32(1):1-13. doi: 10.1007/s10637-013-9969-0. Epub 2013 May 15. PubMed PMID: 23673814.

15: Shan D, Gao Y, Jia Y. Intramolecular Larock indole synthesis: preparation of 3,4-fused tricyclic indoles and total synthesis of fargesine. Angew Chem Int Ed Engl. 2013 Apr 26;52(18):4902-5. doi: 10.1002/anie.201300571. Epub 2013 Mar 20. PubMed PMID: 23520020.

16: Choi SS, Cha BY, Choi BK, Lee YS, Yonezawa T, Teruya T, Nagai K, Woo JT. Fargesin, a component of Flos Magnoliae, stimulates glucose uptake in L6 myotubes. J Nat Med. 2013 Apr;67(2):320-6. doi: 10.1007/s11418-012-0685-4. Epub 2012 Jul 12. PubMed PMID: 22791412.

17: Lee YS, Cha BY, Choi SS, Harada Y, Choi BK, Yonezawa T, Teruya T, Nagai K, Woo JT. Fargesin improves lipid and glucose metabolism in 3T3-L1 adipocytes and high-fat diet-induced obese mice. Biofactors. 2012 Jul-Aug;38(4):300-8. doi: 10.1002/biof.1022. Epub 2012 Jun 2. PubMed PMID: 22674784.

18: Jiménez-Arellanes A, León-Díaz R, Meckes M, Tapia A, Molina-Salinas GM, Luna-Herrera J, Yépez-Mulia L. Antiprotozoal and Antimycobacterial Activities of Pure Compounds from Aristolochia elegans Rhizomes. Evid Based Complement Alternat Med. 2012;2012:593403. doi: 10.1155/2012/593403. Epub 2012 Feb 16. PubMed PMID: 22454670; PubMed Central PMCID: PMC3292206.

19: Guo T, Deng YX, Xie H, Yao CY, Cai CC, Pan SL, Wang YL. Antinociceptive and anti-inflammatory activities of ethyl acetate fraction from Zanthoxylum armatum in mice. Fitoterapia. 2011 Apr;82(3):347-51. doi: 10.1016/j.fitote.2010.11.004. Epub 2010 Nov 6. PubMed PMID: 21059381.

20: Jeong JH, Kim DK, Ji HY, Oh SR, Lee HK, Lee HS. Liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry for the simultaneous determination of dimethoxyaschantin, dimethylliroresinol, dimethylpinoresinol, epimagnolin A, fargesin and magnolin in rat plasma. Biomed Chromatogr. 2011 Aug;25(8):879-89. doi: 10.1002/bmc.1538. Epub 2010 Nov 5. PubMed PMID: 21058411.