Moracin M

1: Ko W, Liu Z, Kim KW, Dong L, Lee H, Kim NY, Lee DS, Woo ER. Kuwanon T and Sanggenon a Isolated from Morus alba Exert Anti-Inflammatory Effects by Regulating NF-κB and HO-1/Nrf2 Signaling Pathways in BV2 and RAW264.7 Cells. Molecules. 2021 Dec 16;26(24):7642. doi: 10.3390/molecules26247642. PMID: 34946724; PMCID: PMC8708433. 2: Rao Rao Shimoga Janakirama A, Mathad Shivayogi S, Kolkar Satyanarayana J, Chapeyil Kumaran R. Characterization of isolated compounds from Morus spp. and their biological activity as anticancer molecules. Bioimpacts. 2021;11(3):187-197. doi: 10.34172/bi.2021.09. Epub 2020 Dec 7. PMID: 34336607; PMCID: PMC8314033. 3: Zhang Y, Zhao Z, Chen H, Fu Y, Wang W, Li Q, Li X, Wang X, Fan G, Zhang Y. The Underlying Molecular Mechanisms Involved in Traditional Chinese Medicine Smilax china L. for the Treatment of Pelvic Inflammatory Disease. Evid Based Complement Alternat Med. 2021 Apr 8;2021:5552532. doi: 10.1155/2021/5552532. PMID: 33927774; PMCID: PMC8052137. 4: Vo QV, Hoa NT. The radical scavenging activity of moracins: theoretical insights. RSC Adv. 2020 Oct 6;10(60):36843-36848. doi: 10.1039/d0ra06555b. PMID: 35517966; PMCID: PMC9057055. 5: Wu K, Wu LL, Zhou CY, Che CM. Transition-Metal-Free C(sp2 )-C(sp2 ) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters. Angew Chem Int Ed Engl. 2020 Sep 7;59(37):16202-16208. doi: 10.1002/anie.202006542. Epub 2020 Jul 14. PMID: 32558142. 6: Lee J, Mandava S, Ahn SH, Bae MA, So KS, Kwon KS, Kim HP. Potential Moracin M Prodrugs Strongly Attenuate Airway Inflammation In Vivo. Biomol Ther (Seoul). 2020 Jul 1;28(4):344-353. doi: 10.4062/biomolther.2019.212. PMID: 32388942; PMCID: PMC7327141. 7: Jeon YH, Choi SW. Isolation, Identification, and Quantification of Tyrosinase and α-Glucosidase Inhibitors from UVC-Irradiated Mulberry (Morus alba L.) Leaves. Prev Nutr Food Sci. 2019 Mar;24(1):84-94. doi: 10.3746/pnf.2019.24.1.84. Epub 2018 Nov 15. PMID: 31008101; PMCID: PMC6456241. 8: Guo F, Zou Y, Zheng Y. Moracin M inhibits lipopolysaccharide-induced inflammatory responses in nucleus pulposus cells via regulating PI3K/Akt/mTOR phosphorylation. Int Immunopharmacol. 2018 May;58:80-86. doi: 10.1016/j.intimp.2018.03.015. Epub 2018 Mar 17. PMID: 29558663. 9: Rao MLN, Murty VN, Nand S. Functional group manoeuvring for tuning stability and reactivity: synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products. Org Biomol Chem. 2017 Nov 15;15(44):9415-9423. doi: 10.1039/c7ob02459b. PMID: 29095465. 10: Li M, Wu X, Wang X, Shen T, Ren D. Two novel compounds from the root bark of Morus alba L. Nat Prod Res. 2018 Jan;32(1):36-42. doi: 10.1080/14786419.2017.1327862. Epub 2017 May 19. PMID: 28521570. 11: Chaita E, Lambrinidis G, Cheimonidi C, Agalou A, Beis D, Trougakos I, Mikros E, Skaltsounis AL, Aligiannis N. Anti-Melanogenic Properties of Greek Plants. A Novel Depigmenting Agent from Morus alba Wood. Molecules. 2017 Mar 23;22(4):514. doi: 10.3390/molecules22040514. PMID: 28333105; PMCID: PMC6154579. 12: Ma F, Shen W, Zhang X, Li M, Wang Y, Zou Y, Li Y, Wang H. Anti-HSV Activity of Kuwanon X from Mulberry Leaves with Genes Expression Inhibitory and HSV-1 Induced NF-κB Deactivated Properties. Biol Pharm Bull. 2016;39(10):1667-1674. doi: 10.1248/bpb.b16-00401. PMID: 27725444. 13: Zhang L, Tao G, Chen J, Zheng ZP. Characterization of a New Flavone and Tyrosinase Inhibition Constituents from the Twigs of Morus alba L. Molecules. 2016 Sep 2;21(9):1130. doi: 10.3390/molecules21091130. PMID: 27598113; PMCID: PMC6274457. 14: Lang L, Dong N, Wu D, Yao X, Lu W, Zhang C, Ouyang P, Zhu J, Tang Y, Wang W, Li J, Huang J. 2-Arylbenzo[b]furan derivatives as potent human lipoxygenase inhibitors. J Enzyme Inhib Med Chem. 2016;31(sup4):98-105. doi: 10.1080/14756366.2016.1220376. Epub 2016 Sep 2. PMID: 27590167. 15: Lee JH, Ko HJ, Woo ER, Lee SK, Moon BS, Lee CW, Mandava S, Samala M, Lee J, Kim HP. Moracin M inhibits airway inflammation by interrupting the JNK/c-Jun and NF-κB pathways in vitro and in vivo. Eur J Pharmacol. 2016 Jul 15;783:64-72. doi: 10.1016/j.ejphar.2016.04.055. Epub 2016 Apr 29. PMID: 27138708. 16: Gross N. The COPD Pipeline XXXI. Chronic Obstr Pulm Dis. 2016 Apr 18;3(2):589-593. doi: 10.15326/jcopdf.3.2.2016.0140. PMID: 28848883; PMCID: PMC5559161. 17: Wang Z, Wang Y, Wang B, Li W, Huang L, Li X. Design, Synthesis, and Evaluation of Orally Available Clioquinol-Moracin M Hybrids as Multitarget- Directed Ligands for Cognitive Improvement in a Rat Model of Neurodegeneration in Alzheimer's Disease. J Med Chem. 2015 Nov 12;58(21):8616-37. doi: 10.1021/acs.jmedchem.5b01222. Epub 2015 Oct 27. PMID: 26473791. 18: Xu T, Zhang E, Wang D, Wang Y, Zou Y. Cu-Catalyzed Consecutive Hydroxylation and Aerobic Oxidative Cycloetherification under Microwave Conditions: Entry to 2-Arylbenzofuran-3-carboxylic Acids. J Org Chem. 2015 May 1;80(9):4313-24. doi: 10.1021/jo502802k. Epub 2015 Apr 16. PMID: 25836742. 19: Park JH, Jung YJ, Jung JW, Shrestha S, Han D, Lim DW, Baek NI. Two new isoarylbenzofuran diglucosides from the root bark of Morus alba. J Asian Nat Prod Res. 2015;17(4):357-63. doi: 10.1080/10286020.2014.971775. Epub 2014 Nov 17. PMID: 25401999. 20: Sun J, He XM, Zhao MM, Li L, Li CB, Dong Y. Antioxidant and nitrite- scavenging capacities of phenolic compounds from sugarcane (Saccharum officinarum L.) tops. Molecules. 2014 Aug 26;19(9):13147-60. doi: 10.3390/molecules190913147. PMID: 25162956; PMCID: PMC6270697.

C14H10O4

242.23

242.06

C, 69.42; H, 4.16; O, 26.42

56317-21-6

OC1=CC(C(O2)=CC3=C2C=C(O)C=C3)=CC(O)=C1

LHPRYOJTASOZGJ-UHFFFAOYSA-N

InChI=1S/C14H10O4/c15-10-2-1-8-5-13(18-14(8)7-10)9-3-11(16)6-12(17)4-9/h1-7,15-17H

5-(6-Hydroxy-1-benzofuran-2-yl)benzene-1,3-diol

Moracin M;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~16.67 mg/mL (~68.82 mM)

Solubility in Formulation 1: ≥ 1.67 mg/mL (6.89 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 1.67 mg/mL (6.89 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 1.67 mg/mL (6.89 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)