Dihydrowogonin

Dihydrowogonin
Names
	IUPAC name 5,7-dihydroxy-8-methoxy-2-phenylchroman-4-one
	Other names 5,7-dihydroxy-8-methoxy-2-phenylchroman-4-one
Identifiers
CAS Number	4431-41-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:174734;
ChemSpider	9666238;
PubChem CID	11491431;
	InChI 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;
	SMILES COC1=C(C=C(C2=C1OC(CC2=O)C3=CC=CC=C3)O)O;
Properties
Chemical formula	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). Infobox references

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.

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]

References

^ ^a ^b 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.
^ 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.
^ "Dihydrowogonin". Cymit Química. Retrieved 27 April 2025.

[PMC7148530-1] 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.

[Nature-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.

[Cymit-3] "Dihydrowogonin". Cymit Química. Retrieved 27 April 2025.

[1]

[2]

[3]

Chemical characteristics

Biological activity and applications

See also

References