Antioxidative Activity of Tetrahydrocurcuminoids

Osawa, Toshihiko; Sugiyama, Y.; Inayoshi, Muneto; Kawakishi, Shunrô

doi:10.1271/bbb.59.1609

Cited by 244 publications

(168 citation statements)

References 10 publications

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“…This may be related primarily to the differences in the ability to donate hydrogen atoms from a phenolic vs. enolic group due the differences in their chemical structure. [7][8][9]15,16,24,25) The additional hydroxyl group in OHC and the hydrogen atom from the central methylenic group may also contribute to the hydrogen donating ability of these hydrogenated derivatives. 26) In addition, the results confirmed that loss of the orthomethoxyphenolic group in Bdmc caused a greater loss of hydrogen donating activity, whereas the molecule with an ortho-methoxyphenolic group and β-diketone moiety showed the comparable activity to trolox.…”

Section: Resultsmentioning

confidence: 99%

Electron Paramagnetic Resonance Study of the Free Radical Scavenging Capacity of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Morales

Sirijaroonwong

Yamanont

et al. 2015

Biological & Pharmaceutical Bulletin

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The quantitative free radical scavenging capacity of curcumin and its demethoxy derivatives (demethoxycurcumin (Dmc) and bisdemethoxycurcumin (Bdmc)) and hydrogenated derivatives (tetrahydrocurcumin (THC), hexahydrocurcumin (HHC) and octahydrocurcumin (OHC)) towards 1,1-diphenyl-2-picryl hydrazyl (DPPH), nitric oxide radical (NO), hydroxyl radical (HO · ) and superoxide anion radical (O 2 · ) were investigated by electron paramagnetic resonance (EPR) spectroscopy. One mole of the hydrogenated derivatives scavenged about 4 mol of the DPPH radical, while curcumin and Dmc scavenged about 3 mol of the DPPH radical. Curcumin and THC showed moderate scavenging activity towards NO, yielding 200 mmol of NO scavenged per 1 mol of the scavenger. In contrast, curcumin and its derivatives showed very low scavenging activity towards HO · and O 2 · , yielding approximately only 3-12 mmol scavenged per 1 mol of the tested compounds. Our results suggest that curcumin and its derivatives principally act as chain breaking antioxidants rather than as direct free radical scavengers. Furthermore, we showed that the ortho-methoxyphenolic group and the heptadione linkage of these molecules greatly contributed to their DPPH and NO scavenging activity.Key words curcumin; electron paramagnetic resonance; free radical scavenger; spin trapping Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione] is the primary biologically active constituent that is isolated from the spice, turmeric (Curcuma longa LINN). It shows various therapeutically beneficial activities, including anti-oxidant, anti-inflammatory, anti-cancer, and anti-viral activities 1,2) mediated through its interactions with several molecular targets such as enzymes, receptors, and transcription factors.3,4) As a potent anti-oxidant, several mechanisms have been proposed which describe the direct interaction of curcumin with reactive oxygen species (ROS) as well as its involvement in ROS-independent mechanisms (i.e., induction of antioxidant enzymes). 5,6) The structure-antioxidant activity relationship of curcumin and the compound it reduces has been demonstrated in both in vitro and in vivo models, for example, 1,1-diphenyl-2-picrylhydrazyl (DPPH) kinetic analysis, γ-radiolysis of rat liver microsomes, 7) 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH)-induced low density lipoprotein (LDL) oxidation, 8) AAPH-induced linoleic oxidation. 9) Lastly, the protective effects of curcumin on oxidative injury have been demonstrated in vivo in several animal diseases models. [10][11][12] Free radicals are normally formed by the physiological processes of the cell. For example superoxide anion radical (O 2 −· ) is produced during the mitochondrial respiratory chain reaction and the nitric oxide radical (NO) is generated by the activation of nitric oxide synthase. In some circumstances, the overproduction of those radicals, as well as the formation of toxic radicals such as the hydroxyl radical (HO · ) leads to the damage of biological molecules, thus resulting in many ...

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Section: Resultsmentioning

confidence: 99%

Electron Paramagnetic Resonance Study of the Free Radical Scavenging Capacity of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Morales

Sirijaroonwong

Yamanont

et al. 2015

Biological & Pharmaceutical Bulletin

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“…Traditionally, it has been used to treat various diseases/disorders e.g., liver obstruction, jaundice, ulcers, inflammation, dysentery, diabetes, stomach disorders, fresh wounds, insect stings and viral infections including chickenpox and smallpox (Nadkarni, 1976). Plant extracts have been found to have antioxidative (Osawa et al, 1995), antimutgenic (Soni et al, 1997) and imunomodulatory (Antony et al, 1999). A number of pharmacological activities of Curcuma longa have been reported which include nematocidal (Kiuchi et al, 1993), anti-inflamatory (Ammon et al, 1993), internal and external injuries (Lans and Brown, 1998) and food additives on aflatoxininduced mutagenecity and hepatocarcinogenecity (Soni et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

Anticoccidial activity of Curcuma longa L. in broilers

Abbas

Iqbal

Khan

et al. 2010

Braz. arch. biol. technol.

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“…Therefore, utilization of farmyard manure in agriculture is recommended for retaining productivity of problem soils, reducing the usages of chemical fertilizer, improving economy in agriculture and minimizing environmental problems (Sharifuddin and Zaharah, 1991;Neera et al, 1999;Whalen et al, 2003;Xiao et al, 2006). Turmeric is a horticultural root-crop that is important not only as a spice and cosmetic, but also as a medicinal plant worldwide (Hermann and Martin, 1991;Osawa et al, 1995;Sugiyama et al, 1996;Nakamura et al, 1998;Ishimine et al, 2003;Hossain et al, 2005a, b). Considering the medicinal values of turmeric and environmental problems caused by chemicals application, it is important to cultivate turmeric using organic fertilizer (e.g.…”

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confidence: 99%