Myricanol

Myricanol

Identifiers
IUPAC name (9R)-16,17-dimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,15-triol
CAS Number	33606-81-4
PubChem CID	161779
ChemSpider	142086
ChEMBL	ChEMBL2152654
CompTox Dashboard (EPA)	DTXSID10955239
Chemical and physical data
Formula	C21H26O5
Molar mass	358.434 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C2C=C(CCCC[C@H](CCC3=CC2=C(C=C3)O)O)C(=C1OC)O
InChI InChI=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 Key: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, ^[4] reno-protective ^[7] neuroprotective ^[8] and anti-cancer properties ^[9] in experimental models, and lowers levels of microtubule-associated protein tau. ^{[10] [11]}

References

1. Lyu P, Li S, Han Y, Shen S, Feng Z, Hao P, et al. (April 2023). "Affinity-based protein profiling-driven discovery of myricanol as a Nampt activator". Bioorganic Chemistry. 133 106435. doi:10.1016/j.bioorg.2023.106435. PMID   36841049.
2. Shen S, Liao Q, Liu J, Pan R, Lee SM, Lin L (April 2019). "Myricanol rescues dexamethasone-induced muscle dysfunction via a sirtuin 1-dependent mechanism". Journal of Cachexia, Sarcopenia and Muscle. 10 (2): 429–444. doi:10.1002/jcsm.12393. PMC   6463464 . PMID   30793539.
3. Li T, Hu X, Fan L, Yang Y, He K (May 2024). "Myricanol improves metabolic profiles in dexamethasone induced lipid and protein metabolism disorders in mice". Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie. 174 116557. doi:10.1016/j.biopha.2024.116557. PMID   38583337.
4. Ohta S, Sakurai N, Kamogawa A, Yaguchi Y, Inoue T, Shinoda M (April 1992). "[Protective effects of the bark of Myrica rubra Sieb. et Zucc. on experimental liver injuries]". Yakugaku Zasshi. 112 (4): 244–252. doi:10.1248/yakushi1947.112.4_244. PMID   1403657.
5. Matsuda H, Morikawa T, Tao J, Ueda K, Yoshikawa M (February 2002). "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. doi:10.1248/cpb.50.208. PMID   11848211.
6. Bochicchio A, Schiavo L, Chiummiento L, Lupattelli P, Funicello M, Hanquet G, et al. (November 2018). "Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid". Organic & Biomolecular Chemistry. 16 (45): 8859–8869. doi:10.1039/c8ob02052c. PMID   30411771.
7. Zheng M, Jiang Q, You J, Gao B, Cui W, Yao W, et al. (December 2024). "Myricanol represses renal fibrosis by activating TFAM and ZNRF1 to inhibit tubular epithelial cells ferroptosis". European Journal of Pharmacology. 984 176999. doi:10.1016/j.ejphar.2024.176999. PMID   39349116.
8. Shen S, Zhao M, Li C, Chang Q, Liu X, Liao Y, et al. (August 2019). "Study on the Material Basis of Neuroprotection of Myrica rubra Bark". Molecules. 24 (16): 2993. doi: 10.3390/molecules24162993 . PMC   6720352 . PMID   31426594.
9. Dai G, Tong Y, Chen X, Ren Z, Ying X, Yang F, et al. (January 2015). "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. doi: 10.3390/ijms16022717 . PMC   4346861 . PMID   25629230.
10. Jones JR, Lebar MD, Jinwal UK, Abisambra JF, Koren J, Blair L, et al. (January 2011). "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. Bibcode:2011JNAtP..74...38J. doi:10.1021/np100572z. PMC   3070757 . PMID   21141876.
11. Martin MD, Calcul L, Smith C, Jinwal UK, Fontaine SN, Darling A, et al. (April 2015). "Synthesis, stereochemical analysis, and derivatization of myricanol provide new probes that promote autophagic tau clearance". ACS Chemical Biology. 10 (4): 1099–1109. doi:10.1021/cb501013w. PMC   4971885 . PMID   25588114.

Further reading

• Shen S, Liao Q, Zhang T, Pan R, Lin L (October 2019). "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. doi:10.1111/bph.14802. PMC   6811775 . PMID   31339170.
• Wu Y, Yang X, Zhang D, Lu C (2020). "Myricanol Inhibits the Type III Secretion System of Salmonella enterica Serovar Typhimurium by Interfering With the DNA-Binding Activity of HilD". Frontiers in Microbiology. 11 571217. doi: 10.3389/fmicb.2020.571217 . PMC   7546796 . PMID   33101243.
• Fan S, Wang C, Huang K, Liang M (2021). "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. 12 790345. doi: 10.3389/fphys.2021.790345 . PMC   8850918 . PMID   35185599.
• Shen S, Liao Q, Lyu P, Wang J, Lin L (June 2024). "Myricanol prevents aging-related sarcopenia by rescuing mitochondrial dysfunction via targeting peroxiredoxin 5". MedComm. 5 (6) e566. doi:10.1002/mco2.566. PMC   11167181 . PMID   38868327.