Paeonol

Paeonol is a phenolic compound found in peonies[2] such as Paeonia suffruticosa (moutan cortex),[3][4] in Arisaema erubescens,[5] and in Dioscorea japonica.[6] It is a component found in some Traditional Chinese medicine remedies.[7]

Paeonol
Names
IUPAC name
1-(2-Hydroxy-4-methoxyphenyl)ethanone
Other names
  • 2'-Hydroxy-4'-methoxyacetophenone
  • 1-(2-Hydroxy-4-methoxyphenyl)ethan-1-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.194
UNII
Properties
C9H10O3
Molar mass 166.176 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Biological effects

A number of biological effects of paeonol in vitro or in animal models have been observed. Paeonol increases levels of cortical cytochrome oxidase and vascular actin and improves behavior in a rat model of Alzheimer's disease.[8] Paeonol also reduced cerebral infarction involving the superoxide anion and microglia activation in ischemia-reperfusion injured rats.[9]

Paeonol shows antimutagenic activities.[3][6] It also has anti-inflammatory and analgesic effects in carrageenan-evoked thermal hyperalgesia.[10] Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α.[11]

Paeonol has MAO-A and MAO-B inhibiting effects with IC50 values of 54.6 μM and 42.5 μM respectively.[12]

Metal complex

Metal complexes of Paeonol shows tetrahedral and octahedral coordination geometry in the absence and presence of solvent pyridine respectively.[13]

References
  1. "CAS # 552-41-0, Paeonol, 2'-Hydroxy-4'-methoxyacetophenone, 1-(2-hydroxy-4-methoxyphenyl)ethan-1-one".
  2. Zhang, L., Li, D. C., & Liu, L. F. (2019). Paeonol: pharmacological effects and mechanisms of action. International immunopharmacology, 72, 413-421. PMID 31030097 doi:10.1016/j.intimp.2019.04.033
  3. Fukuhara Y, Yoshida D (1987). "Paeonol: a bio-antimutagen isolated from a crude drug, moutan cortex". Agricultural and Biological Chemistry. 51 (5): 1441–1442. doi:10.1271/bbb1961.51.1441. INIST:7609719.
  4. Wu, Xinan; Chen, Hongli; Chen, Xingguo; Hu, Zhide (2003). "Determination of paeonol in rat plasma by high-performance liquid chromatography and its application to pharmacokinetic studies following oral administration of Moutan cortex decoction". Biomedical Chromatography. 17 (8): 504–8. doi:10.1002/bmc.259. PMID 14648606.
  5. Ducki S, Hadfield JA, Lawrence NJ, Zhang X, McGown AT (1995). "Isolation of paeonol from Arisaema erubescens". Planta Medica. 61 (6): 586–587. doi:10.1055/s-2006-959390. PMID 8824957. INIST:2920867.
  6. Miyazawa, Mitsuo; Shimamura, Hideo; Nakamura, Sei-Ichi; Kameoka, Hiromu (1996). "Antimutagenic Activity of (+)-β-Eudesmol and Paeonol fromDioscorea japonica". Journal of Agricultural and Food Chemistry. 44 (7): 1647–1650. doi:10.1021/jf950792u.
  7. Deng, Chunhui; Yao, Ning; Wang, Ben; Zhang, Xiangmin (2006). "Development of microwave-assisted extraction followed by headspace single-drop microextraction for fast determination of paeonol in traditional Chinese medicines". Journal of Chromatography A. 1103 (1): 15–21. doi:10.1016/j.chroma.2005.11.023. PMID 16309693.
  8. Zhou, Jun; Zhou, Li; Hou, Deren; Tang, Jiaochun; Sun, Juanjuan; Bondy, Stephen C. (2011). "Paeonol increases levels of cortical cytochrome oxidase and vascular actin and improves behavior in a rat model of Alzheimer's disease" (PDF). Brain Research. 1388: 141–7. doi:10.1016/j.brainres.2011.02.064. PMID 21377451.
  9. Hsieh, Ching-Liang; Cheng, Chin-Yi; Tsai, Tung-Hu; Lin, I-Hsin; Liu, Chung-Hsiang; Chiang, Su-Yin; Lin, Jaung-Geng; Lao, Chih-Jui; Tang, Nou-Ying (2006). "Paeonol reduced cerebral infarction involving the superoxide anion and microglia activation in ischemia-reperfusion injured rats". Journal of Ethnopharmacology. 106 (2): 208–15. doi:10.1016/j.jep.2005.12.027. PMID 16458462.
  10. Chou, Tz-Chong (2003). "Anti-inflammatory and analgesic effects of paeonol in carrageenan-evoked thermal hyperalgesia". British Journal of Pharmacology. 139 (6): 1146–52. doi:10.1038/sj.bjp.0705360. PMC 1573952. PMID 12871833.
  11. Kim, Sung Hoon; Kim, Seung-Ae; Park, Mi-Kyung; Kim, Seung-Hyung; Park, Young-Doo; Na, Ho-Jeong; Kim, Hyung-Min; Shin, Min-Kyu; Ahn, Kyoo-Seok (2004). "Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α". International Immunopharmacology. 4 (2): 279–87. doi:10.1016/j.intimp.2003.12.013. PMID 14996419.
  12. Kong, L.D.; Cheng, Christopher H.K.; Tan, R.X. (2004). "Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones". Journal of Ethnopharmacology. 91 (2–3): 351–355. doi:10.1016/j.jep.2004.01.013. PMID 15120460.
  13. Patel, Mahesh kumar (2019). "Solvent effect on neutral Co (II) complexes of paeonol derivative equalitative and quantitative studies from energy frame work and Hirshfeld surface analysis". Journal of Molecular Structure. 1196: 119–131. Bibcode:2019JMoSt1196..119P. doi:10.1016/j.molstruc.2019.06.050.
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