Peroxynitrite scavenging of flavonoids: structure activity relationship

Heijnen, Chantal G.M; Haenen, Guido R.M.M.; Vekemans, Jef A. J. M.; Bast, Aalt

doi:10.1016/s1382-6689(01)00083-7

Cited by 165 publications

(119 citation statements)

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“…The results provided by the flavonoids in this study, as well as the structure-activity relationships, are in agreement with other previous works. [39][40][41][42] The results from the assays performed in the presence of 25 mM NaHCO 3 show a decrease in the effect of the catecholic B-ring-like compounds, either 2-styrylchromones or flavonoids. The same behavior was previously observed for quercetin and luteolin by other authors.…”

Section: Discussionmentioning

confidence: 99%

2-Styrylchromones: Novel strong scavengers of reactive oxygen and nitrogen species

Gomes

Fernandes

Silva

et al. 2007

Bioorganic & Medicinal Chemistry

129

173

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Abstract-2-Styrylchromones are a small group of naturally occurring chromones, vinylogues of flavones (2-phenylchromones). Natural and synthetic 2-styrylchromones have been tested in different biological systems, showing activities with potential therapeutic applications. In particular, the potential and hitherto understudied antioxidant behavior of these compounds has been raised as a matter of interest. Thus the present work consisted in the study of the in vitro scavenging activities for reactive oxygen species (ROS) and reactive nitrogen species (RNS) of various 2-styrylchromone derivatives and structurally similar flavonoids. Some of the studied 2-styrylchromones proved to be extremely efficient scavengers of the different ROS and RNS, showing, in some cases, IC 50 s under 1 lM. The hydroxylation pattern of 2-styrylchromones, especially in the B-ring but also in the A ring, modulates the activity of these compounds, the catecholic derivatives being the most effective scavengers. The styryl pattern also contributes to their observed outstanding antioxidant activity. In conclusion, the scavenging activities for ROS/RNS of 2-styrylchromone derivatives, here shown for the first time, provide novel and most promising compounds to be applied as antioxidants.

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Section: Discussionmentioning

confidence: 99%

2-Styrylchromones: Novel strong scavengers of reactive oxygen and nitrogen species

Gomes

Fernandes

Silva

et al. 2007

Bioorganic & Medicinal Chemistry

129

173

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“…For example, hydroquinone, catechol and resorcinol expressed higher ONOO -scavenging activity than phenol (Fig. 4) (Heijnen et al 2001). Correspondingly, it was reported that increasing the number of OH groups increased the antioxidant activity (Cao et al 1997).…”

Section: Antioxidant Activity Of Bioactive Compounds From Mangosteen mentioning

confidence: 92%

“…3a, f) can decrease the antioxidant activities due to the steric hindrance of the molecule structure (Suvarnakuta et al 2011). Furthermore, Heijnen et al (2001) reported that the most negative Hammett Sigma constant as electron donating effect was observed when the OH is at the o-or p-positions of conjugated ring. In contrast, positive Hammett Sigma constant as electron withdrawing effect was observed when the OH is at the meta (m-) position (Fig.…”

Section: Antioxidant Activity Of Bioactive Compounds From Mangosteen mentioning

confidence: 99%

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In vitro antioxidant properties of mangosteen peel extract

2012

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The growing interest in the replacement of synthetic food antioxidants by natural ones has fostered research on the screening of plant-derived raw materials for identifying new antioxidants. The special attention of research today is focused on inexpensive or residual sources from agricultural industries. Fruit peels as sources of powerful natural antioxidants are often the waste parts of various fruits from consumption and food industry. Among the fruit peels, mangosteen peel is an important source of natural phenolic antioxidants. The mangosteen peel contains various bioactive substances, i.e., phenolic acids and flavonoids, which possess biological and medicinal properties, especially antioxidant properties. The aim of this review, after presenting analytical techniques for determining in vitro antioxidant activity of mangosteen peel extract, is to summarize available data on the factors affecting antioxidant activity of mangosteen peel extract. In addition, the potential antioxidant activity of mangosteen peel extract, the bioactive compounds identified from mangosteen peel extract and their antioxidant activity are presented. Potential applications of the mangosteen peel extract in food, pharmaceutical and cosmetic products are also discussed.

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“…Differently, in the m-position, the OH group acts as an electron withdrawing group, providing a destabilizing effect [41,42]. As can be deduced from the structure-activity relationship, position of the groups on the molecule affects the electron donating effect and the scavenging potency of the molecules [43]. When the electron donating groups were replaced by an electron withdrawing group like chloro or fluoro group of phenyl ring resulted in lower the activity.…”

Section: Structure-activity Relationshipmentioning

confidence: 99%