Myricanol Explained
| Drug Name: | Myricanol |
| Image Class: | skin-invert-image |
| Cas Number: | 33606-81-4 |
| Pubchem: | 161779 |
| Chemspiderid: | 142086 |
| Chembl: | 2152654 |
| Iupac Name: | (9R)-16,17-dimethoxytricyclo[12.3.1.1<sup>2,6</sup>]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,15-triol |
| C: | 21 |
| H: | 26 |
| O: | 5 |
| Smiles: | COC1=C2C=C(CCCC[C@H](CCC3=CC2=C(C=C3)O)O)C(=C1OC)O |
| Stdinchi: | 1S/C21H26O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,15,22-24H,3-7,9H2,1-2H3/t15-/m1/s1 |
| Stdinchikey: | SBGBAZQAEOWGFT-OAHLLOKOSA-N |
Myricanol, is a natural product which acts as an activator of the enzymes nicotinamide phosphoribosyltransferase (NAMPT)[1] and SIRT1,[2] [3] along with various other activities. It is derived from the ayurvedic medicinal plant Myrica nagi and other related species along with other similar compounds such as myricetin.[4] [5] [6]
It has hepatoprotective, reno-protective[7] neuroprotective[8] and anti-cancer properties[9] in experimental models, and lowers levels of microtubule-associated protein tau.[10] [11]
Further reading
- Shen S, Liao Q, Zhang T, Pan R, Lin L . Myricanol modulates skeletal muscle-adipose tissue crosstalk to alleviate high-fat diet-induced obesity and insulin resistance . British Journal of Pharmacology . 176 . 20 . 3983–4001 . October 2019 . 31339170 . 10.1111/bph.14802 . 6811775 .
- Wu Y, Yang X, Zhang D, Lu C . Myricanol Inhibits the Type III Secretion System of Salmonella enterica Serovar Typhimurium by Interfering With the DNA-Binding Activity of HilD . Frontiers in Microbiology . 2020 . 11 . 571217 . 33101243 . 10.3389/fmicb.2020.571217 . 7546796 . free .
- Fan S, Wang C, Huang K, Liang M . Myricanol Inhibits Platelet Derived Growth Factor-BB-Induced Vascular Smooth Muscle Cells Proliferation and Migration in vitro and Intimal Hyperplasia in vivo by Targeting the Platelet-Derived Growth Factor Receptor-β and NF-κB Signaling . Frontiers in Physiology . 2021 . 12 . 790345 . 35185599 . 10.3389/fphys.2021.790345 . 8850918 . free .
- Shen S, Liao Q, Lyu P, Wang J, Lin L . Myricanol prevents aging-related sarcopenia by rescuing mitochondrial dysfunction via targeting peroxiredoxin 5 . MedComm . 5 . 6 . e566 . June 2024 . 38868327 . 10.1002/mco2.566 . 11167181 .
Notes and References
- Lyu P, Li S, Han Y, Shen S, Feng Z, Hao P, Li Z, Lin L . Affinity-based protein profiling-driven discovery of myricanol as a Nampt activator . Bioorganic Chemistry . 133 . 106435 . April 2023 . 36841049 . 10.1016/j.bioorg.2023.106435 .
- Shen S, Liao Q, Liu J, Pan R, Lee SM, Lin L . Myricanol rescues dexamethasone-induced muscle dysfunction via a sirtuin 1-dependent mechanism . Journal of Cachexia, Sarcopenia and Muscle . 10 . 2 . 429–444 . April 2019 . 30793539 . 10.1002/jcsm.12393 . 6463464 .
- Li T, Hu X, Fan L, Yang Y, He K . Myricanol improves metabolic profiles in dexamethasone induced lipid and protein metabolism disorders in mice . Biomedicine & Pharmacotherapy . 174 . 116557 . May 2024 . 38583337 . 10.1016/j.biopha.2024.116557 . free .
- Ohta S, Sakurai N, Kamogawa A, Yaguchi Y, Inoue T, Shinoda M . [Protective effects of the bark of Myrica rubra Sieb. et Zucc. on experimental liver injuries] . Yakugaku Zasshi . 112 . 4 . 244–252 . April 1992 . 1403657 . 10.1248/yakushi1947.112.4_244 .
- Matsuda H, Morikawa T, Tao J, Ueda K, Yoshikawa M . Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra . Chemical & Pharmaceutical Bulletin . 50 . 2 . 208–215 . February 2002 . 11848211 . 10.1248/cpb.50.208 .
- Bochicchio A, Schiavo L, Chiummiento L, Lupattelli P, Funicello M, Hanquet G, Choppin S, Colobert F . Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid . Organic & Biomolecular Chemistry . 16 . 45 . 8859–8869 . November 2018 . 30411771 . 10.1039/c8ob02052c .
- Zheng M, Jiang Q, You J, Gao B, Cui W, Yao W, Su F, Sun X, La L . Myricanol represses renal fibrosis by activating TFAM and ZNRF1 to inhibit tubular epithelial cells ferroptosis . European Journal of Pharmacology . 984 . 176999 . December 2024 . 39349116 . 10.1016/j.ejphar.2024.176999 .
- Shen S, Zhao M, Li C, Chang Q, Liu X, Liao Y, Pan R . Study on the Material Basis of Neuroprotection of Myrica rubra Bark . Molecules . 24 . 16 . August 2019 . 2993 . 31426594 . 10.3390/molecules24162993 . 6720352 . free .
- Dai G, Tong Y, Chen X, Ren Z, Ying X, Yang F, Chai K . Myricanol induces apoptotic cell death and anti-tumor activity in non-small cell lung carcinoma in vivo . International Journal of Molecular Sciences . 16 . 2 . 2717–2731 . January 2015 . 25629230 . 10.3390/ijms16022717 . 4346861 . free .
- Jones JR, Lebar MD, Jinwal UK, Abisambra JF, Koren J, Blair L, O'Leary JC, Davey Z, Trotter J, Johnson AG, Weeber E, Eckman CB, Baker BJ, Dickey CA . The diarylheptanoid (+)-aR,11S-myricanol and two flavones from bayberry (Myrica cerifera) destabilize the microtubule-associated protein tau . Journal of Natural Products . 74 . 1 . 38–44 . January 2011 . 21141876 . 10.1021/np100572z . 3070757 . 2011JNAtP..74...38J .
- Martin MD, Calcul L, Smith C, Jinwal UK, Fontaine SN, Darling A, Seeley K, Wojtas L, Narayan M, Gestwicki JE, Smith GR, Reitz AB, Baker BJ, Dickey CA . Synthesis, stereochemical analysis, and derivatization of myricanol provide new probes that promote autophagic tau clearance . ACS Chemical Biology . 10 . 4 . 1099–1109 . April 2015 . 25588114 . 10.1021/cb501013w . 4971885 .
