Occurrences, biosynthesis and properties of aurones as high-end evolutionary products

Boucherle, Benjamin; Peuchmaur, Marine; Boumendjel, Ahcène; Haudecoeur, Romain

doi:10.1016/j.phytochem.2017.06.017

Cited by 98 publications

(80 citation statements)

References 276 publications

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“…There are also flavonoid types that occur sporadically, such as aurones that are found in liverworts and some angiosperms. For aurones this may well represent convergent evolution, as even within angiosperms there are alternative biosynthetic mechanisms (Boucherle et al, 2017). New metabolomic…”

Section: The Evolutionary Significance Of the Occurrence Of Differentmentioning

confidence: 99%

The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective

et al. 2020

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The flavonoid pathway is one of the best characterized specialized metabolite pathways of plants. In angiosperms, the flavonoids have varied roles in assisting with tolerance to abiotic stress and are also key for signaling to pollinators and seed dispersal agents. The pathway is thought to be specific to land plants and to have arisen during the period of land colonization around 550-470 million years ago. In this review we consider current knowledge of the flavonoid pathway in the bryophytes, consisting of the liverworts, hornworts, and mosses. The pathway is less characterized for bryophytes than angiosperms, and the first genetic and molecular studies on bryophytes are finding both commonalities and significant differences in flavonoid biosynthesis and pathway regulation between angiosperms and bryophytes. This includes biosynthetic pathway branches specific to each plant group and the apparent complete absence of flavonoids from the hornworts.

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Section: The Evolutionary Significance Of the Occurrence Of Differentmentioning

confidence: 99%

The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective

et al. 2020

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“…Conversely, aurones (2‐benzylidene‐3(2 H )‐benzofuran‐3‐one) are minor tricyclic flavonoids that consist of a benzofuranone ring and a phenyl moiety linked through a carbon‐carbon double bond (Figure ). Aurones are usually found in vegetables, fruits and flowers, where they contribute to their yellow coloration . Representative naturally occurring aurones are aureusidin, sulfuretin, and maritimetin possessing various hydroxylation patterns .…”

Section: Introductionmentioning

confidence: 99%

“…Aurones are usually found in vegetables, fruits and flowers, where they contribute to their yellow coloration . Representative naturally occurring aurones are aureusidin, sulfuretin, and maritimetin possessing various hydroxylation patterns . Aurones have presented a wide variety of biological activities, including antiparasitic, anticancer, antidiabetes, antihormonal, antimalarial, herbicidal, and soybean lipoxygenase inhibitory activities .…”

Section: Introductionmentioning

confidence: 99%

“…Aurones have presented a wide variety of biological activities, including antiparasitic, anticancer, antidiabetes, antihormonal, antimalarial, herbicidal, and soybean lipoxygenase inhibitory activities . Surprisingly, only few studies on the antioxidant activity of aurones are available, which have proved their potential as antioxidant agents . For example, sulfuretin (3′,4′‐dihydroxy‐6‐ hydroxyaurone) and its dimer isolated from Cotinuscoggygria showed significant antioxidant activity toward DPPH with IC 50 of 16.1 and 9.7 μg/mL, respectively, lower than those for referenced antioxidants, ascorbic acid and BHA .…”

Section: Introductionmentioning

confidence: 99%

“…They have structural similarity and often occur together in plants. Moreover, aurones are biosynthesized from chalcones in the presence of enzyme aureusidin synthase . Recently, a series of substituted chalcones and aurones have been synthesized and tested for their antioxidant activity by Narsinghani et al Their experimental results showed that 2′,5′‐dihydroxy‐4‐dimethylamino chalcone ( CH4 ) and 5‐hydroxy‐4′‐dimethylamino aurone ( AU4 ) has the most promising antioxidant activity.…”

Section: Introductionmentioning

confidence: 99%

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Antioxidant and spectral properties of chalcones and analogous aurones: Theoretical insights

Xue

Liu

Zhang

et al. 2018

Int J of Quantum Chemistry

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Density functional theory (DFT) and time-dependent DFT (TD-DFT) have been employed to elucidate the radical scavenging capacity and the UV-Vis spectral property of several chalcones and analogous aurones. Three main antioxidant mechanisms, hydrogen atom transfer (HAT), electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were investigated. The results indicate that all the studied compounds adopt a fully planar conformation in their neutral, radical, cationic as well as anionic forms. 2 0 -OH plays important role in the stabilization of phenolic radicals due to the formation of intramolecular hydrogen bonds (IHBs). Introduction of electron-donating substituent on B-ring is helpful for improving the activity. For the considered compounds, HAT is proposed as the thermodynamically favored mechanism in gas phase and nonpolar environment, while SPLET is preferred in polar media. The results confirmed the crucial role of hydroxyl group on A-ring, especially on position 5 0 /5, in terms of the radical scavenging ability. The absorption spectra of title compounds were successfully simulated and the lowest energy transitions predominantly correspond to the π-π* transitions from HOMO to LUMO with charge transfer (CT) character. K E Y W O R D Saurones, chalcones, density functional theory, mechanism, radical scavenging activity

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Longevity effects of hispidol in Caenorhabditis elegans

et al. 2020

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In this study, we investigated the longevity effects of hispidol, a 6,4 0-dihydroxyaurone, using the Caenorhabditis elegans model system. Our lifespan assay data revealed that hispidol could prolong the lifespan of wild-type worms under normal culture condition. Moreover, hispidol increased the survival rate of the worms against a heat stress condition through up-regulated expressions of HSP-16.2. Similarly, hispidol protected worms from paraquat-induced oxidative stress. We also found that the hispidol elevated the activities of antioxidant enzymes, thereby attenuating the generation of intracellular reactive oxygen species. These results suggest that the enhancement of lifespan and stress resistance by the hispidol treatment might be attributed to its strong in vivo antioxidant capacity and regulation of stress proteins. Further tests on the aging-related factors revealed that hispidol could regulate the speed of pharyngeal pumping, indicating the association of dietary restriction with the hispidol-mediated longevity. However, there were no significant alterations in the body length of the worms between the groups. We then investigated the effects of hispidol on body movement and lipofuscin accumulation in aged worms. Interestingly, these healthspan parameters were strongly improved by the hispidol treatment. Our genetic studies showed no significant change in the lifespan of the daf-16 null mutants by hispidol supplementation. In addition, enhanced nuclear translocation of DAF-16 was observed in the hispidol-fed DAF-16::GFP fused transgenic mutants, suggesting the requirement of DAF-16/FOXO activation for the longevity effect of hispidol.

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Occurrences, biosynthesis and properties of aurones as high-end evolutionary products

Cited by 98 publications

References 276 publications

The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective

The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective

Antioxidant and spectral properties of chalcones and analogous aurones: Theoretical insights

Longevity effects of hispidol in Caenorhabditis elegans

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