Amentoflavone

Amentoflavone is a naturally occurring biflavonoid molecule found in various plant species, particularly in the cypress family (Cupressaceae) and the ginkgo family (Ginkgoaceae). It is a secondary plant metabolite that has become a focus of research due to its potential health effects. Amentoflavone is studied primarily for its potentially anti-inflammatory, antioxidant, and antitumor properties.

What health benefits can Amentoflavone have?

  • Antioxidant effect: Amentoflavone shows a strong antioxidant effect that can neutralize free radicals. These reactive molecules play a key role in aging and in the development of numerous diseases such as cancer and neurodegenerative disorders (1,2,3,4).
  • Anti-inflammatory properties: Studies have shown that Amentoflavone has anti-inflammatory effects by inhibiting the production of pro-inflammatory enzymes and molecules, such as cytokines. This could make it useful in the treatment of chronic inflammatory diseases such as arthritis or inflammatory bowel diseases (4,5).
  • Antitumor and cancer-inhibiting effect: Amentoflavone has also been investigated in laboratory studies for potential antitumor properties (4,6,7). Among other findings, an Amentoflavone-enhanced anti-OSCC efficacy of cisplatin was observed there (6). However, there are still no clinical studies confirming these results in humans.
  • Neuroprotective effects: Amentoflavone also shows potential neuroprotective effects by slowing the degeneration of nerve cells in models of neurodegenerative diseases such as Alzheimer's. These effects are likely attributable to its antioxidant and anti-inflammatory properties (1,4).
  • Vasodilatory effects: In investigations, Amentoflavone showed a potentially vasodilatory effect by relaxing the blood vessels to allow stronger blood flow (7)
  • Antiviral and antibacterial effects: Some studies suggest that Amentoflavone could also be effective against certain viruses and bacteria. For example, an inhibitory effect against the influenza virus and possibly even an effect on the dengue virus have been observed (4,8,9,10). These antiviral properties could make it a useful component in fighting infections.

Chemical structure

Amentoflavone belongs to the class of flavonoids and consists of two interconnected flavone units. This biflavonoid structure gives it its biological properties. Flavonoids are known for their ability to act as antioxidants by neutralizing free radicals and thus protecting cells from oxidative stress.

Chemical interactions and mechanisms

Amentoflavone works by influencing several biochemical signaling pathways. It has been linked to an inhibitory effect on the activity of enzymes such as cyclooxygenase (COX-2) and lipoxygenase (11). It also inhibited signaling pathways such as the NF-κB pathway, which is involved in the regulation of inflammation and cell survival (12). This inhibitory effect on signaling pathways is of central importance for its potentially anti-inflammatory and cancer-inhibiting effects.

Safety and side effects

To date, there are no extensive clinical studies examining the side effect profile of Amentoflavone. However, no serious toxic effects have been found in animal models. Since Amentoflavone occurs naturally in plants traditionally used in medicine, such as ginkgo, it is generally considered safe. Nevertheless, people who supplement flavonoids or take herbal preparations should discuss this with their doctor, especially if they are already taking medications, as interactions are possible.

Conclusion

Amentoflavone is a promising natural molecule with antioxidant, anti-inflammatory, cancer-inhibiting, and neuroprotective properties. It could potentially be used in the treatment of inflammation, cancer, and neurodegenerative diseases. Although the laboratory results to date are promising, further clinical studies are necessary to confirm the effects in humans and possible side effects.

Sources:

  1. Frota, L. S., Alves, D. R., Marinho, M. M., da Silva, L. P., Almeida Neto, F. W. Q., Marinho, E. S., & de Morais, S. M. (2023). Antioxidant and anticholinesterase activities of amentoflavone isolated from Ouratea fieldingiana (Gardner) Engl. through in vitro and chemical-quantum studies. Journal of biomolecular structure & dynamics, 41(4), 1206–1216. https://doi.org/10.1080/07391102.2021.2017353
  2. Rusu ME, Fizeșan I, Vlase L, Popa DS. Antioxidants in Age-Related Diseases and Anti-Aging Strategies. Antioxidants (Basel). 2022 Sep 21;11(10):1868. doi: 10.3390/antiox11101868. PMID: 36290589; PMCID: PMC9598595.
  3. Varela-López, A., Romero-Márquez, J. M., Navarro-Hortal, M. D., Ramirez-Tortosa, C. L., Battino, M., Forbes-Hernández, T. Y., & Quiles, J. L. (2023). Dietary antioxidants and lifespan: Relevance of environmental conditions, diet, and genotype of experimental models. Experimental gerontology, 178, 112221. https://doi.org/10.1016/j.exger.2023.112221
  4. Xiong X, Tang N, Lai X, Zhang J, Wen W, Li X, Li A, Wu Y, Liu Z. Insights Into Amentoflavone: A Natural Multifunctional Biflavonoid. Front Pharmacol. 2021 Dec 22;12:768708. doi: 10.3389/fphar.2021.768708. PMID: 35002708; PMCID: PMC8727548.
  5. Kim, H. K., Son, K. H., Chang, H. W., Kang, S. S., & Kim, H. P. (1998). Amentoflavone, a plant biflavone: a new potential anti-inflammatory agent. Archives of pharmacal research, 21(4), 406–410. https://doi.org/10.1007/BF02974634
  6. Chen, C. H., Huang, Y. C., Lee, Y. H., Tan, Z. L., Tsai, C. J., Chuang, Y. C., Tu, H. F., Liu, T. C., & Hsu, F. T. (2020). Anticancer Efficacy and Mechanism of Amentoflavone for Sensitizing Oral Squamous Cell Carcinoma to Cisplatin. Anticancer research, 40(12), 6723–6732. https://doi.org/10.21873/anticanres.14695
  7. Kang, D. G., Yin, M. H., Oh, H., Lee, D. H., & Lee, H. S. (2004). Vasorelaxation by amentoflavone isolated from Selaginella tamariscina. Planta medica, 70(8), 718–722. https://doi.org/10.1055/s-2004-827201
  8. Birt DF, Widrlechner MP, Hammer KD, Hillwig ML, Wei J, Kraus GA, Murphy PA, McCoy J, Wurtele ES, Neighbors JD, Wiemer DF, Maury WJ, Price JP. Hypericum in infection: Identification of anti-viral and anti-inflammatory constituents. Pharm Biol. 2009;47(8):774-782. doi: 10.1080/13880200902988645. PMID: 19907671; PMCID: PMC2774925.
  9. Cho WK, Choi HJ, Ma JY. Selaginella tamariscina Ethanol Extract Attenuates Influenza A Virus Infection by Inhibiting Hemagglutinin and Neuraminidase. Nutrients. 2024 Jul 22;16(14):2377. doi: 10.3390/nu16142377. PMID: 39064820; PMCID: PMC11280371.
  10. Ferrari, Ivan Vito. (2024). Molecular Docking Study Reveals Amentoflavone as a Potential Inhibitor of Dengue Virus Envelope Protein. 10.20944/preprints202409.0083.v1.
  11. Banerjee, T., Van der Vliet, A., & Ziboh, V. A. (2002). Downregulation of COX-2 and iNOS by amentoflavone and quercetin in A549 human lung adenocarcinoma cell line. Prostaglandins, leukotrienes, and essential fatty acids, 66(5-6), 485–492. https://doi.org/10.1054/plef.2002.0387
  12. Chen, J. H., Chen, W. L., & Liu, Y. C. (2015). Amentoflavone Induces Anti-angiogenic and Anti-metastatic Effects Through Suppression of NF-κB Activation in MCF-7 cells. Anticancer research, 35(12), 6685–6693.