Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein

Kretzschmar, Georg; Zierau, Oliver; Wober, Jannette; Tischer, Sandra; Metz, Peter; Vollmer, Günter

doi:10.1016/j.jsbmb.2009.08.005

Cited by 76 publications

(51 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In conclusion, prenylation of plant secondary metabolites has a considerable impact on biological activity of these compounds in mammalian cell culture systems [17,31]. Starting from genistein, prenylation at various positions is capable of modifying estrogen receptor selectivity, activity and potency of this plant secondary metabolite.…”

Section: Discussionmentioning

confidence: 98%

“…The raising interest in the role of the isoprenyl group as a determinant of ER-binding affinity and activity is supported by the example of naringenins. While the flavanone naringenin exhibits weak estrogenic activity if any, its isoprenylated derivative, 8-prenylnaringenin, ranks among the most estrogenic natural product discovered to this date [15][16][17]29].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Estrogenic properties of naturally occurring prenylated isoflavones in U2OS human osteosarcoma cells: Structure–activity relationships

Djiogue

Njamen

Halabalaki

et al. 2010

The Journal of Steroid Biochemistry and Molecular Biology

Self Cite

View full text Add to dashboard Cite

Section: Discussionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Estrogenic properties of naturally occurring prenylated isoflavones in U2OS human osteosarcoma cells: Structure–activity relationships

Djiogue

Njamen

Halabalaki

et al. 2010

The Journal of Steroid Biochemistry and Molecular Biology

Self Cite

View full text Add to dashboard Cite

“…Another study on structure-estrogenicity relationships in three functionally different estrogen receptor assays, including yeast-based assay, MVLN breast cancer cells and Ishikawa endometrial cancer cells, showed strong estrogenic activities of 8-PN in all assays used, while the parent compound naringenin displayed only very weak estrogenicity (Kretzschmar et al, 2010).…”

Section: Osteogenic Activitymentioning

confidence: 97%

A systematic review on biological activities of prenylated flavonoids

Chen

Mukwaya

Wong

et al. 2013

Pharmaceutical Biology

198

136

View full text Add to dashboard Cite

Context: Prenylated flavonoids are a unique class of naturally occurring flavonoids that exist especially for the plant's self-defensive strategy. This special class of flavonoids increases the bioactivities of their backbone flavonoids with non-prenylation; therefore, prenylated flavonoids have more potential to be developed and utilized. Objective: The number, position and type of the prenyl group on the flavonoids backbone structure may have close relationships with the bioactivities of flavonoids. Methods: PubMed and WEB OF KNOWLEDGEÕ were used to search articles published in English between 1 January 2002 and 31 December 2012, which discuss the structure-activity relationship between prenylated flavonoids and their bioactivities. Results: It is proposed that the prenyl-moiety makes the backbone compound more lipophilic, which leads to its high affinity with cell membranes. The prenylation brings the flavonoids with enhancement of antibacterial, anti-inflammatory, antioxidant, cytotoxicity, larvicidal as well as estrogenic activities. However, it is reported that the prenyl-moiety decreases the bioavailability and plasma absorption of prenylated flavonoids. Conclusion: The prenyl group affects the bioactivities of flavonoids in certain ways, while the action mechanisms and the structure-activity relationship as well as more in vivo studies even clinical validation trials need to be further investigated.

show abstract

“…orders of magnitude higher than that observed for the parent compound naringenin [15][16][17] or its regioisomer 6-prenylnaringenin ( Figure 1). [18] It has been reasoned that the increased bioactivity might originate from an increased lipophilicity and facilitated permeation through cell membranes.…”

Section: Introductionmentioning

confidence: 59%

Tandem Claisen Rearrangement/6‐endo Cyclization Approach to Allylated and Prenylated Chromones

2015

View full text Add to dashboard Cite

Allyl, dimethylallyl and prenyl ethers derived from o‐acylphenols reacted upon microwave irradiation to form C‐allylated or ‐prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6‐endo‐trig or 6‐endo‐dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6‐prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.

show abstract

Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein

Cited by 76 publications

References 25 publications

Estrogenic properties of naturally occurring prenylated isoflavones in U2OS human osteosarcoma cells: Structure–activity relationships

Estrogenic properties of naturally occurring prenylated isoflavones in U2OS human osteosarcoma cells: Structure–activity relationships

A systematic review on biological activities of prenylated flavonoids

Tandem Claisen Rearrangement/6‐endo Cyclization Approach to Allylated and Prenylated Chromones

Contact Info

Product

Resources

About

Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein

Cited by 76 publications

References 25 publications

Estrogenic properties of naturally occurring prenylated isoflavones in U2OS human osteosarcoma cells: Structure–activity relationships

Estrogenic properties of naturally occurring prenylated isoflavones in U2OS human osteosarcoma cells: Structure–activity relationships

A systematic review on biological activities of prenylated flavonoids

Tandem Claisen Rearrangement/6‐endo Cyclization Approach to Allylated and Pren­ylated Chromones

Contact Info

Product

Resources

About

Tandem Claisen Rearrangement/6‐endo Cyclization Approach to Allylated and Prenylated Chromones