Dihydrowogonin

Last updated
Dihydrowogonin
Dihydrowogonin.svg
Names
IUPAC name
5,7-dihydroxy-8-methoxy-2-phenylchroman-4-one
Other names
5,7-dihydroxy-8-methoxy-2-phenylchroman-4-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C16H14O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-7,13,17,19H,8H2,1H3
    Key: FKAOWOSRYSMEBS-UHFFFAOYSA-N
  • COC1=C(C=C(C2=C1OC(CC2=O)C3=CC=CC=C3)O)O
Properties
C16H14O5
Molar mass 286.283 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dihydrowogonin is a naturally occurring flavonoid belonging to the flavanone subclass. It is characterized by a flavan backbone with hydroxyl and methoxy functional groups, contributing to its biological activity. The compound has attracted interest due to its potential antioxidant, anti-inflammatory, and neuroprotective properties.

Contents

Chemical characteristics

Dihydrowogonin has been identified as a major constituent in the methanol extract of Prunus avium (wild cherry) bark. [1] It has also been detected in other parts of the plant, such as leaves and stems.[ citation needed ]

Biological activity and applications

Studies have demonstrated that dihydrowogonin exhibits significant antimicrobial and antibiofilm activities, particularly against Gram-positive bacteria like Staphylococcus aureus . [1] Fractions enriched in dihydrowogonin showed a strong decrease in both planktonic growth and biofilm formation.[ citation needed ]

Additionally, dihydrowogonin has been shown to interact with glutathione transferases in white-rot fungi, suggesting a role in the detoxification processes during wood degradation. [2]

Given its bioactive properties, dihydrowogonin is being explored for potential applications in pharmacology, particularly as an antimicrobial agent and in neuroprotective therapies. Its presence in plant extracts also indicates potential uses in natural product chemistry and medicinal applications. [3]

See also

References

  1. 1 2 Gomes, Aline; Teixeira, Adilson L.; Rodrigues, João H. S.; Silva, Gabriela (2020). "The impact of Prunus avium extracts on microbial growth and biofilm formation". Plants. 9 (4): 466. doi: 10.3390/plants9040466 . PMC   7148530 . PMID   32272704.
  2. ↑ Kersten, Philippe; Kühnel, Sarah; Alfaro, María E.; Lundell, Taina (2018). "Conserved flavonoid-based signaling in wood-decaying fungi". Scientific Reports. 8 (20): 562–563. doi:10.1038/s41598-018-26601-3. PMC   5981210 . PMID   29777071.
  3. ↑ "Dihydrowogonin". Cymit Química. Retrieved 27 April 2025.
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