Prenylated Flavonoids: Pharmacology and Biotechnology

Botta, Bruno; Vitali, Alberto; Menéndez, Pilar; Misiti, D.; Monache, Giuliano Delle

doi:10.2174/0929867053202241

Cited by 279 publications

(195 citation statements)

References 2 publications

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“…Here, for the first time, we identified BVC, a natural prenylated isoflavanone, as a potent pan-PPAR agonist. The prenylated group of flavones can produce an increased affinity for biological membranes and an improved interaction with proteins [36].…”

Section: Discussionmentioning

confidence: 99%

Bavachinin, as a novel natural pan-PPAR agonist, exhibits unique synergistic effects with synthetic PPAR-γ and PPAR-α agonists on carbohydrate and lipid metabolism in db/db and diet-induced obese mice

Luo

et al. 2016

Diabetologia

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Section: Discussionmentioning

confidence: 99%

Bavachinin, as a novel natural pan-PPAR agonist, exhibits unique synergistic effects with synthetic PPAR-γ and PPAR-α agonists on carbohydrate and lipid metabolism in db/db and diet-induced obese mice

Luo

et al. 2016

Diabetologia

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“…were observed in the genomic Southern blot using fulllength SfN8DT-1 as a probe (data not shown). Controlled expression of SfN8DT-1 in plants will provide new resources to supply prenylated flavonoids, which have beneficial effects for human health, such as prevention of cancer and nonantibiotic antibacterial agents that have become more important to suppress multiple drug resistant microorganisms in the medical field (Stevens and Page, 2004;Botta et al, 2005). Similar metabolic engineering will be also applicable for the agricultural field to confer disease resistance in crop plants, for instance, against soil-borne pathogens like Fusarium spp.…”

Section: Table II Production Of Prenylated Flavonoids In Transgenicmentioning

confidence: 99%

Cloning and Characterization of Naringenin 8-Prenyltransferase, a Flavonoid-Specific Prenyltransferase of Sophora flavescens

et al. 2008

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Prenylated flavonoids are natural compounds that often represent the active components in various medicinal plants and exhibit beneficial effects on human health. Prenylated flavonoids are hybrid products composed of a flavonoid core mainly attached to either 5-carbon (dimethylallyl) or 10-carbon (geranyl) prenyl groups derived from isoprenoid (terpenoid) metabolism, and the prenyl groups are crucial for their biological activity. Prenylation reactions in vivo are crucial coupling processes of two major metabolic pathways, the shikimate-acetate and isoprenoid pathways, in which these reactions are also known as a rate-limiting step. However, none of the genes responsible for the prenylation of flavonoids has been identified despite more than 30 years of research in this field. We have isolated a prenyltransferase gene from Sophora flavescens, SfN8DT-1, responsible for the prenylation of the flavonoid naringenin at the 8-position, which is specific for flavanones and dimethylallyl diphosphate as substrates. Phylogenetic analysis shows that SfN8DT-1 has the same evolutionary origin as prenyltransferases for vitamin E and plastoquinone. The gene expression of SfN8DT-1 is strictly limited to the root bark where prenylated flavonoids are solely accumulated in planta. The ectopic expression of SfN8DT-1 in Arabidopsis thaliana resulted in the formation of prenylated apigenin, quercetin, and kaempferol, as well as 8-prenylnaringenin. SfN8DT-1 represents the first flavonoid-specific prenyltransferase identified in plants and paves the way for the identification and characterization of further genes responsible for the production of this large and important class of secondary metabolites.The prenylation of aromatic compounds is a major contributor to the diversity of plant secondary metabolites due to differences in prenylation position on the aromatic ring, various lengths of prenyl chain, and further modifications of the prenyl moiety, e.g. cyclization and hydroxylation, resulting in the occurrence of more than 1,000 prenylated compounds in plants (Tahara and Ibrahim, 1995;Barron and Ibrahim, 1996). In particular, prenylated flavonoids in higher plants protect them by exhibiting strong antibacterial and antifungal activities (Sohn et al., 2004). Many prenylated flavonoids have been identified as active components in medicinal plants with biological activities, such as anticancer, anti-androgen, anti-leishmania, and anti-nitric oxide production (De Naeyer et al., 2004;Ahmed-Belkacem et al., 2005;Han et al., 2006). Due to the beneficial effects for human health, prenylated flavonoids are of particular interest as lead compounds for producing new drugs and functional foods. The prenylation of the flavonoid core increases the lipophilicity and the membrane permeability, which is one of the proposed reasons for the enhanced biological activities of prenylated flavonoids (Wang et al., 1997;Maitrejean et al., 2000;Murakami et al., 2000). However, none of the genes responsible for the prenylation reactions has been identified d...

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“…Most of the prenylated isoflavonoids are considered to be the products of inducible metabolites (Ibrahim, 2005;Wang et al, 2001) and comes from the Leguminosae subfamily Papilionoideae (Botta et al, 2005;Yazaki et al, 2009). Recently the research on prenylated flavanones becomes a hot pot due to their promising and diverse bioactivities on multitarget tissues.…”

Section: Introductionmentioning

confidence: 99%

A systematic review on biological activities of prenylated flavonoids

Chen

Mukwaya

Wong

et al. 2013

Pharmaceutical Biology

190

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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.

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Prenylated Flavonoids: Pharmacology and Biotechnology

Cited by 279 publications

References 2 publications

Bavachinin, as a novel natural pan-PPAR agonist, exhibits unique synergistic effects with synthetic PPAR-γ and PPAR-α agonists on carbohydrate and lipid metabolism in db/db and diet-induced obese mice

Bavachinin, as a novel natural pan-PPAR agonist, exhibits unique synergistic effects with synthetic PPAR-γ and PPAR-α agonists on carbohydrate and lipid metabolism in db/db and diet-induced obese mice

Cloning and Characterization of Naringenin 8-Prenyltransferase, a Flavonoid-Specific Prenyltransferase of Sophora flavescens

A systematic review on biological activities of prenylated flavonoids

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