Chemotaxonomic studies on the genus Citrus. I. Distribution of flavones in the subgroup microcarpa.

Mizuno, Mizuo; Iinuma, Munekazu; Tanaka, Toŝhiyuki; Matoba, Yoshinobu; Fujii, Yoshiko; Murata, Jin; Murata, Hiroko; Iwamasa, Masao

doi:10.1248/cpb.35.3025

Cited by 13 publications

(12 citation statements)

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“…HPLC analysis has been performed in several citrus species and to several parts of them (Kanes et al, 1993;Nogata et al, 1994;Del Rio et al, 1994;Castillo et al, 1994;Mizuno et al, 1987;Mouly et al, 1993;Del Rio et al, 1997Machida and Osawa, 1989;Castillo et al, 1993;Ortuno et al, 1997;Krause and Galensa, 1991;Ross et al, 2000) because the contained flavonoids are extremely interesting for their physiological effects on animal and man, their protection to the plant itself against UV radiation and microorganisms , their relation to taste and bitterness (Matthews et al, 1990) and also for their chemotaxonomic properties (Mouly et al, 1994).…”

Section: Introductionmentioning

confidence: 99%

Analysis of antioxidant compounds in sweet orange peel by HPLC–diode array detection–electrospray ionization mass spectrometry

Anagnostopoulou¹,

Kefalas

Kokkalou³

et al. 2004

Biomedical Chromatography

137

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HPLC-diode array detection-electrospray ionization mass spectrometry was used to determine qualitatively and quantitatively the flavonoid content of several fractions and residues of extracts of Greek navel sweet orange peel (Citrus sinensis) from the region of southern Greece (Leonidi-Tripoli). The main groups of flavonoids found according to HPLC retention times, spectral data and literature references were polymethoxylated flavones, C-glycosylated flavones, O-glycosylated flavones, O-glycosylated flavanones, flavonols and phenolic acids and their derivatives. The ethyl acetate fraction which has been shown in previous work to possess the best radical scavenging activity among the others was found to contain C-glycosylated flavones, polymethoxylated flavones, O-glycosylated flavones, O-glycosylated flavanones, two phenolic acid derivatives and two unknown compounds, all in low concentrations. The group of C-glycosylated flavones was reported for the first time in the peel of Navel sweet orange. The C-glycosylated flavones found according to their spectral characteristics and literature were 6-C-beta-glucosyldiosmin, 6,8-di-C-glucopyranosylapigenin, 6,8-di-C-beta-glucosyldiosmin and two unknown. The results suggest that the ethyl acetate fraction of navel Citrus sinensis peel consists of significant antioxidant compounds and can be used as a food additive of natural origin or a pharmaceutical supplement using as a source of peel the byproducts of the orange juice industry.

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Section: Introductionmentioning

confidence: 99%

Analysis of antioxidant compounds in sweet orange peel by HPLC–diode array detection–electrospray ionization mass spectrometry

Anagnostopoulou¹,

Kefalas

Kokkalou³

et al. 2004

Biomedical Chromatography

137

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“…They include nobiletin (5,6,7,8,3Ј,4Ј-hexamethoxyflavone), tangeretin (5,6,7,8,4Ј-pentamethoxyflavone), sinensetin (5,6,7,3Ј,4Ј-pentamethoxyflavone) and natsudaidain (3-hydroxy-5,6,7,8,3Ј,4Ј-hexamethoxyflavone). [1][2][3][4][5] Studies have demonstrated that nobiletin possesses various biological properties such as anti-proliferative, 6,7) anti-carcinogenic, [8][9][10] and anti-inflammatoric [11][12][13] along with potent cell differencing activity. [14][15][16] For example, nobiletin suppresses inflammation through the inhibition of cyclooxygenase (COX)-2, a causal enzyme for skin inflammation and decreases tumor invasion through the suppression of matrix metalloproteinase 9, a collagenase that hydrolyzes components of the cell matrix such as collagen and gelatin.…”

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confidence: 99%

Comparative Study on Nobiletin Metabolism with Liver Microsomes from Rats, Guinea Pigs and Hamsters and Rat Cytochrome P450

Koga

Matsuo

Ohta

et al. 2007

Biological & Pharmaceutical Bulletin

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Polymethoxy-flavonoids are naturally occurring compounds found abundantly in the juice and peel of citrus fruits such as Citrus nobilis, Citrus aurantium, Citrus hassaku and Citrus depressa HAYATA (Rutaceae). They include nobiletin (5,6,7,8,3Ј,4Ј-hexamethoxyflavone), tangeretin (5,6,7,8,4Ј-pentamethoxyflavone), sinensetin (5,6,7,3Ј,4Ј-pentamethoxyflavone) and natsudaidain (3-hydroxy-5,6,7,8,3Ј,4Ј-hexamethoxyflavone). [1][2][3][4][5] Studies have demonstrated that nobiletin possesses various biological properties such as anti-proliferative, 6,7) anti-carcinogenic, [8][9][10] and anti-inflammatoric [11][12][13] along with potent cell differencing activity. 14-16) For example, nobiletin suppresses inflammation through the inhibition of cyclooxygenase (COX)-2, a causal enzyme for skin inflammation and decreases tumor invasion through the suppression of matrix metalloproteinase 9, a collagenase that hydrolyzes components of the cell matrix such as collagen and gelatin. It has also been reported that nobiletin inhibits the growth of tumor cells more potently than other polyhydroxyflavonoids including quercetin and taxifolin.7) It is thought that nobiletin can enter into cells more easily than polyhydroxy-flavonoids due to its high lipophilicity.Cytochrome P450 (P450) is a key enzyme catalyzing the oxidative metabolism of a large number of exogenous and endogenous compounds 17) and is reported to be involved in the metabolism of flavonoids.18) Nielsen et al. 18,19) used liver microsomes of Aroclor 1254 (a commercial PCB preparation)-pretreated rats to show that the main metabolic pathway of polyhydroxy-flavonoids such as apigenin, naringenin and kaempferol is a hydroxylation in the ring A or B of flavone molecule. They also showed that the main pathways of tangeretin are demethylation in ring A or B and hydroxylation at 3Ј-position of ring B.18,19) Recent studies using recombinant human P450s have demonstrated that genistein, an isoflavone abundant in soy beans, is metabolized predominantly to 3Ј-OH-genistein by CYP1A1, CYP1A2, CYP1B1 and CYP2E1 and to two other metabolites by CYP3A4. 20) As well, the tangeretin metabolism has been shown to be catalyzed by CYP1A2, CYP3A4, CYP2D6 and CYP2C9. 21) On the other hand, there are not many reports on the biotransformation of nobiletin in animals. [22][23][24][25] Yasuda et al. found a few demethylated metabolites in 24 h-urine of rats orally administered nobiletin and determined that a major metabolite is 4Ј-demethylated (4Ј-OH) nobiletin. 24) However, the mechanism which the biological activities mentioned above are exerted by a parent compound or its metabolites remains obscure. For a better understanding of this point, it is very important to compare the metabolic profile of nobiletin in various animals and to elucidate which P450s are involved in the metabolism of nobiletin. Therefore, we investigated the in vitro metabolism of nobiletin using liver microsomes of rats, hamsters and guinea pigs, and ten recombinant rat P450s. We also examined the inductive effects of pro...

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“…By monitoring the bioactivity, each of the EtOAcsoluble fractions was separated by column chromatography on silica gel using EtOAc-hexane to generate several components such as 1 (31 mg), 2 (121 mg), 3 (9 mg), 4 (190 mg), 5 (49 mg), 6 (22 mg), 7 (1.0 mg) from the EtOAc extract (500 mg) of C. kinokuni peels (150 g), and 7 (19 mg), 8 (3 mg), 9 (1.0 mg), 10 (1.0 mg) from the EtOAc extract (1.7 g) of C. canaliculata peels (350 g). The structures of the compounds 1-10 were identified by the spectroscopic analyses with the 1 H-and 13 C-NMR and FABMS and comparison of these data with reported data [4,7,9,16,17,20]. These compounds were further purified by preparative HPLC with an ODS-3 column using 50-70% MeOH in H 2 O, and used for final bioassays ( Table 3).…”

Section: Extraction and Isolationmentioning

confidence: 99%

Identification and physiological evaluation of the components from Citrus fruits as potential drugs for anti-corpulence and anticancer

Hirata

Fujii

Akita

et al. 2009

Bioorganic & Medicinal Chemistry

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On the basis of monitoring the prevention of accumulation of lipid droplets in mouse 3T3-L1 preadipocyte cells and inhibition of the proliferation of human colon cancer HT-29 cells, effective anti-corpulence and anticancer compounds were isolated from the peel of Citrus fruits. These bioactive components were identified as polymethoxyflavones and coumarin derivatives by spectroscopic analyses. 5-Hydroxy-6,7,8,3',4'-pentamethoxyflavone had the greatest anti-corpulence effects and 3,5,6,7,8,3',5'-heptamethoxyflavone had the greatest anticancer effects. Furthermore, distributions of those bioactive components in the peel of 10 species of Citrus fruits were demonstrated by HPLC analyses.

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Chemotaxonomic studies on the genus Citrus. I. Distribution of flavones in the subgroup microcarpa.

Cited by 13 publications

References 0 publications

Analysis of antioxidant compounds in sweet orange peel by HPLC–diode array detection–electrospray ionization mass spectrometry

Analysis of antioxidant compounds in sweet orange peel by HPLC–diode array detection–electrospray ionization mass spectrometry

Comparative Study on Nobiletin Metabolism with Liver Microsomes from Rats, Guinea Pigs and Hamsters and Rat Cytochrome P450

Identification and physiological evaluation of the components from Citrus fruits as potential drugs for anti-corpulence and anticancer

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