Diarylheptanoids with Free Radical Scavenging and Hepatoprotective Activity in vitro from Curcuma longa

Song, Eun-Kyoung; Cho, Hyun; Kim, Jeong-Sik; Kim, Nayoung; An, Nyeon-Hyeong; Kim, Jeong Ah; Lee, Seungho; Kim, Youn‐Chul

doi:10.1055/s-2001-18860

Cited by 103 publications

(66 citation statements)

References 7 publications

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“…The number (n) of Dmc and Bdmc was 2.0 and 1.4, respectively. In agreement with other studies 17,18,24,28,29) curcumin was more effective than Dmc and Bdmc at scavenging DPPH radicals, and inhibiting free radical induced lipid peroxidation, red cell hemolysis, and protein oxidation.…”

Section: Discussionsupporting

confidence: 80%

Comparative Antioxidant Activities of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Somparn¹,

Phisalaphong²,

Nakornchai³

et al. 2007

Biological & Pharmaceutical Bulletin

313

187

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Oxidative stress plays a major role in the pathogenesis of various diseases including neurodegenerative diseases, myocardial ischemia-reperfusion injury and cancer. Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5,-dione], the principal yellow pigment isolated from turmeric (Curcuma longa Linn), is known as a potent antioxidant comparable to a-tocopherol. Its antioxidant activities have been studied in several in vitro models. 1) Despite its poor bioavailability, 2-4) the therapeutic benefits of curcumin in animals have been demonstrated in several oxidative stress models such as Alzheimer's disease, 5) ethanol induced oxidative injury in brain, liver, heart and kidney, 6,7) and myocardial ischemic damage.8) It is possible that the metabolites of curcumin could mediate major antioxidant activities in vivo.In mouse, curcumin is first biotransformed to dihydrocurcumin (DHC) and tetrahydrocurcumin (THC) and these compounds are subsequently converted to monoglucuronide conjugates including curcumin-glucuronide, dihydrocurcuminglucuronide and tetrahydrocurcumin-glucuronide. 9) In human and rat hepatocytes, curcumin is metabolized into curcumin glucuronide, curcumin sulfate, THC, hexahydrocurcumin (HHC) and octahydrocurcumin (OHC). 10,11) Antioxidant activities of THC have already been studied both in vitro and in vivo. Venkatesan et al. 12) reported that THC had higher activity than curcumin in protecting the nitrite induced oxidation of haemoglobin and lysis of erythrocytes. THC has also been demonstrated to be more potent than curcumin in protection against ferric nitrilotriacetate (Fe-NTA) induced oxidative renal damage in mice. 13) THC produces this protective effect to cells against oxidative stress by scavenging of free radicals, 14) inhibition of lipid peroxidation and formation of hydroperoxides. 15) To the best of our knowledge, the antioxidant activities of HHC and OHC have not been reported.We are also interested in the antioxidant activities of natural demethoxyl derivatives of curcumin, demethoxycurcumin (Dmc) and bisdemethoxycurcumin (Bdmc), which are always found together with curcumin in tumeric extracts and in commercial preparation of curcumin. Antioxidant activities of Dmc and Bdmc have been reported in the model systems of hydroxyl radical induced DNA damage, 16) DPPH radical scavenging activity 17) and recently in lipid peroxidation. 18)However, to date, there has been no comparative study on the antioxidant activities of curcumin with its natural demethoxy derivatives and metabolite hydrogenated derivatives. In particular, the ability to provide protection against lipid and cell membrane damage of all of those derivatives has not yet been reported. The aim of this study is to compare the antioxidant activities of curcumin, its demethoxy derivatives (Dmc and Bdmc), and hydrogenated derivatives (THC, HHC and OHC) using three in vitro models: radical scavenging activity by DPPH (2,2-diphenyl-1-picrylhydrazyl) assay, AAPH [2,2Ј-azobis(2-amidinopropane)dihydrochloride] induced linole...

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Section: Discussionsupporting

confidence: 80%

Comparative Antioxidant Activities of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Somparn¹,

Phisalaphong²,

Nakornchai³

et al. 2007

Biological & Pharmaceutical Bulletin

313

187

View full text Add to dashboard Cite

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“…A portion (10 g) of the bioactive CHCl3 soluble extract was subjected to silica gel column chromatography eluting with CHCl3-CH3OH (80:1-16:1, step gradient) to yield compound 1 (2.21 g), compound 2 (0.34 g) and compound 3 (1.30 g). The compounds were identified as curcumin, demethoxycurcumin (DMC) and bis-demethoxycurcumin (BDMC), respectively, by comparison of mass spectroscopy, 1 H-NMR, and 13 C-NMR data with those in the literature (Song et al, 2001).…”

Section: Isolation and Purification Of Curcumin And Its Two Derivativesmentioning

confidence: 99%

Comparative effects of curcuminoids on endothelial heme oxygenase-1 expression: ortho-methoxy groups are essential to enhance heme oxygenase activity and protection

Jeong

Oh²,

Pae³

et al. 2006

Exp Mol Med

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Recently, it has been reported that curcumin, which is known as a potent antioxidant, acts as a nonstressful and non-cytotoxic inducer of the cytoprotective heme oxygenase (HO)-1. In this study, naturally occurring curcuminoids, such as pure curcumin, demethoxycurcumin (DMC) and bis-demethoxycurcumin (BDMC), were compared for their potential ability to modulate HO-1 expression and cytoprotective activity in human endothelial cells. All three curcuminoids could induce HO-1 expression and HO activity with differential levels. The rank order of HO activity was curcumin, DMC and BDMC. In comparison with endothelial protection against H2O2-induced cellular injury, cytoprotective capacity was found to be highest with curcumin, followed by DMC and BDMC. Interestingly, cytoprotective effects afforded by curcuminoids were considerably associated with their abilities to enhance HO activity. Considering that the main difference among the three curcuminoids is the number of methoxy groups (none for BDMC, one for DMC, and two for curcumin), the presence of methoxy groups in the ortho position on the aromatic ring was suggested to be essential to enhance HO-1 expression and cytoprotection in human endothelial cells. Our results may be useful in designing more efficacious HO-1 inducers which could be considered as promising pharmacological agents in the development of therapeutic approaches for the prevention or treatment of endothelial diseases caused by oxidative damages.

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“…[7] H. pylori which is a Gram-negative spiral bacterium found in gastric epithelium is found to have inhibited by C. longa.…”

Section: [31]mentioning

confidence: 99%

“…Various studies have shown that extract of C. longa possesses anti-ulcer actions [5] in addition to its anti H. pylori, [6] antioxidant, [7] and anti-inflammatory [2] actions. There are some conflicting reports showing its ulcerogenic potential also.…”

Section: [3]mentioning

confidence: 99%

Anti-ulcer effect of extract of rhizome of Curcuma longa. L against aspirin-induced peptic ulcer in rats

Savaringal¹,

Sanalkumar²

2018

Natl J Physiol Pharm Pharmacol

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Background: Rhizome of Curcuma longa has many therapeutic implications in traditional Indian medicine. It is used in traditional medicine for flatulence, dyspepsia, and other gastric problems. There is conflicting reports regarding its antiulcer and ulcerogenic potential. Aims and Objectives: The study is with the aim of determining the gastoprotective effect of C. longa extract on aspirin-induced gastric ulcer in rats. Materials and Methods: C. longa rhizomes were collected locally. Preparation of extract was done with 50% ethanol using Soxhlet extraction. Albino rats of Wistar strain were used for the study. Aspirin was purchased from Sigma Labs, Mumbai. Anti-ulcer effect of the extract was studied in rats after inducing mucosal damage by aspirin. Results: It was found that extract of C. longa exhibited significant protection against aspirin-induced ulcer at dose levels of 250-mg/kg, 500-mg/kg, and 1000 mg/kg body weight. There is a dose-dependent increase in the ulcer protective action of the extract. Conclusion: The present study with extract of C. longa revealed its anti-ulcer activity.

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Diarylheptanoids with Free Radical Scavenging and Hepatoprotective Activity in vitro from Curcuma longa

Cited by 103 publications

References 7 publications

Comparative Antioxidant Activities of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Comparative Antioxidant Activities of Curcumin and Its Demethoxy and Hydrogenated Derivatives

Comparative effects of curcuminoids on endothelial heme oxygenase-1 expression: ortho-methoxy groups are essential to enhance heme oxygenase activity and protection

Anti-ulcer effect of extract of rhizome of Curcuma longa. L against aspirin-induced peptic ulcer in rats

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