Antioxidant activity of chlorophylls and their derivatives

Lanfer-Marquez, Ursula Maria; Barros, Rosa Maria Cerdeira; Sinnecker, Patrícia

doi:10.1016/j.foodres.2005.02.012

Cited by 381 publications

(263 citation statements)

References 25 publications

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“…Pheopytin a has been reported to have various activities. 26,[31][32][33] Nevertheless, this study is the first report on LOX inhibition of pheophytin a.…”

Section: Introductionmentioning

confidence: 73%

“…Pheopytin a has been reported to have various activities. 26,[31][32][33] Nevertheless, this study is the first report on LOX inhibition of pheophytin a.In conclusion, we isolated soybean LOX inhibitors as alkapolyenes 1 and 2 from the brown alga S. thunbergii and pheophytin a (3) from the red alga O. corymbifera. They inhibited the enzyme more strongly than the well-known inhibitor NDGA.…”

mentioning

confidence: 72%

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Lipoxygenase inhibitors derived from marine macroalgae

Kurihara

Kagawa

Konno

et al. 2014

Bioorganic & Medicinal Chemistry Letters

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The solvent extracts from the algae Sargassum thunbergii (Sargassaceae) and Odonthalia corymbifera (Rhodomelaceae) were subjected to soybean lipoxygenase inhibitory screening. Two hydrophobic inhibitors were obtained from the extracts of S. thunbergii through inhibitory assay-guided fractionation. The inhibitors were identified as known exo-methylenic alkapolyenes (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene (1) and (6Z,9Z,12Z,15Z,18Z)- 1,6,9,12,15,18-henicosahexaene (2). The alkapolyenes 1 and 2 showed higher inhibitory activity than the known inhibitor nordihydroguaiaretic acid (NDGA). Pheophytin a (3) was obtained from the extract of O.corymbifera. The inhibitor 3 also showed higher inhibitory activity than NDGA. This is the first report on lipoxygenase inhibition of exo-methylenic alkapolyenes and a chlorophyll a-related substance. Many studies have been carried out on highly unsaturated fatty acids, leukotrienes, and LOX activity originated from macroalgae, 6-9 whereas a few studies were performed on LOX inhibitors. 10,11 During our screening of enzyme inhibitors derived from algal extracts, we disclosed potent LOX inhibitory activity of the extracts from the brown alga Sargassum thunbergii and the red alga Odonthalia corymbifera. In the present study, we isolated two exo-methylenic alkapolyenes from S. thunbergii and a chlorophyll a-related substance from O. corymbifera.S. thunbergii (2.85 kg, air-dried) was collected at the coast of Otobe, south-western Hokkaido, Japan. Fresh alga washed with tap water was extracted with MeOH-water (9:1, v/v) for a week. LOX inhibitory activity was assayed by a modified absorptiometry method 12-14 for the extract and at a series of separation steps. An ethyl acetate-soluble fraction (8.46 g) partitioned from the extract (69.5 g) was chromatographed on silica gel column with hexane-EtOAc (3:1, v/v) as eluent. Further chromatography was employed on silica gel column with n-hexane-EtOAc (19:1, v/v). The active fraction was twice separated on preparative thin-layer chromatography with n-hexane-EtOAc (3:1, v/v) and 100% hexane as developing solvent to afford inhibitors 1 (7.9 mg, 2.8 ppm yield) and 2 (2.8 mg, 1.1 ppm yield). Inhibitors 1 and 2were identified as (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene 15 (HEP, Figure 1) and (6Z,9Z,12Z,15Z,18Z)--1,6,9,12,15,18-henicosahexaene 14 (HEH, Figure 1), respectively, by their spectral data, 16 compared with the literature data. [17][18][19][20] Stereostructures of double bonds of 1 and 2 were deduced to be all Z configurations from the 13 C NMR data (δ 25.63-25.64 for 1; δ 25.52-25.64 for 2) for the allylic positions in 1,4-pentadiene moieties of them. Pfeffer et al. 21 reported that the 13 C NMR data of δ 25.7, 30.5, and 35.7 for the allylic positions in 1,4-pentadiene moieties of polyunsaturated fatty acid residues were assigned as Z,Z-, Z,E-, and E,E-isomers, respectively. HEP (1) and HEH (2) inhibited soybean LOX in concentration-dependent manners (Figure 2). The IC 50 values of 1 and 2 were calculated 40 µM and 5...

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“…Pheopytin a has been reported to have various activities. 26,[31][32][33] Nevertheless, this study is the first report on LOX inhibition of pheophytin a.…”

Section: Introductionmentioning

confidence: 73%

mentioning

confidence: 72%

Lipoxygenase inhibitors derived from marine macroalgae

Kurihara

Kagawa

Konno

et al. 2014

Bioorganic & Medicinal Chemistry Letters

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“…Activity was governed by form or derivatives of chlorophylls (Ferruzzi et al 2002). Also, chelated metal in porphyrin ring was a prime factor determining antioxidative activity (Lanfer-Marquez et al 2005). Thus, it was postulated that the phenolic compounds with higher antioxidative activity were more concentrated after chlorophyll removal.…”

Section: Antioxidative Activitiesmentioning

confidence: 99%

Antioxidant activities of lead (Leucaena leucocephala) seed as affected by extraction solvent, prior dechlorophyllisation and drying methods

et al. 2012

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Extracts of brown lead (Leucaena leucocephala) seed prepared using different extraction solvents were determined for antioxidative activities using different assays. The highest yield (3.4-4.0%) was obtained when water was used as an extraction solvent, compared with all ethanolic extracts used (1.2-2.0 %) (P<0.05). Much lower chlorophyll content was found in the water extract. When hot water was used, the resulting extract contained lower total phenolic and mimosine contents (P<0.05). In general, 60-80 % ethanolic extracts had higher 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging activities, ferric reducing antioxidant power (FRAP) and metal chelating activity than water extracts (P<0.05). When brown lead seed was dechlorophyllised prior to extraction, the water extract had slightly increased yield with lower chlorophyll content. Nevertheless, prior chlorophyll removal resulted in the increase in antioxidative activities but lower total phenolic and mimosine contents (P<0.05). Generally, phenolic compounds and mimosine were more released when water was used as the extraction solvent, while the lower amount of chlorophyll was extracted. Oven-drying exhibited the negative effect on antioxidative activities and mimosine content. The higher antioxidative activities with concomitant higher total phenolic and mimosine contents were found in water extract dried by freeze drying. Thus, extraction solvent, dechlorophyllisation and drying methods directly influenced the yield and antioxidative activity of lead seed extract.

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“…In general, a green colored extract might be an obstacle for further application. Moreover, Lanfer-Marquez, Barros, and Sinnecker (2005) noted that chlorophyll could act as a photooxidizer. Chlorophylls as well as oxidized products in the extract might severe as pro-oxidant, in which singlet oxygen derived from photooxidation could be formed (Andersen, Skibsted, & Risbo, 2010).…”

Section: Total Chlorophyll Content (Tcc) and Colormentioning

confidence: 99%

Untitled

Yarnpakdee¹,

Benjakul²,

Senphan³

2019

Turk. J. Fish. Aquat. Sci.

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Characteristic and antioxidant activity of the extracts from freshwater macroalgae (C. glomerata) as influenced by extraction media, i.e., water or ethanol (20-100%, v/v) were studied. The highest yield (28.0%) was obtained when water was used. Ethanolic extracts had significantly lower yields (2.98-15.5%) (P<0.05). However, total phenolic and chlorophyll contents were lower in water extract. Among all extracts, the 60% ethanolic extract (E60) had the highest antioxidant activities, including DPPH and ABTS radical scavenging activities, ferric reducing antioxidant power and metal chelating activity. Based on LC/MS of E60, quercetin, isoquercetin and hydroquinin were the major phenolic compounds. When E60 at different levels (100, 200 and 400 mg/kg) were added to eastern little tuna (Euthynnus affinis) slices, the reduction in lipid oxidation was dose-dependent (P<0.05) as shown by smaller increases in peroxide and thiobarbituric acid-reactive substances (TBARS) values, compared to the control. Therefore, C. glomerata could be a source of alternative natural antioxidant in lipid based muscle food.

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Antioxidant activity of chlorophylls and their derivatives

Cited by 381 publications

References 25 publications

Lipoxygenase inhibitors derived from marine macroalgae

Lipoxygenase inhibitors derived from marine macroalgae

Antioxidant activities of lead (Leucaena leucocephala) seed as affected by extraction solvent, prior dechlorophyllisation and drying methods

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