Limonoid Glucosides in Juices of Satsuma Mandarin<i>(Citrus unshiu</i>Marc.)

Ozaki, Yoshihiko; Ayano, Shigeru; Miyazaki, Masaki; Maeda, Hideo; Ifuku, Yasushi; Hasegawa, Shin

doi:10.1271/bbb.56.836

Cited by 6 publications

(5 citation statements)

References 3 publications

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“…Most of the published literature on citrus bioactive compounds concerns the quantification of limonoids using TLC and HPLC Herman et al, 1990;Ozaki et al, 1992;Schoch et al, 2002;Ishii et al, 2003). However, this published data suggests that certain citrus limonoids are present in low concentrations and may vary markedly among the different citrus varieties and byproducts.…”

Section: Introductionmentioning

confidence: 99%

Red Mexican Grapefruit: A Novel Source for Bioactive Limonoids and their Antioxidant Activity

Mandadi

Jayaprakasha

Bhat³

et al. 2007

Zeitschrift Für Naturforschung C

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Citrus limonoids have shown to inhibit the growth of cancer in colon, lung, mouth, stomach and breast in animal and cell culture studies. For the first time in the present study, an attempt has been made to isolate antioxidant fractions and five limonoids from red Mexican grapefruit seeds. Defatted seed powder was successively extracted with hexane, ethyl acetate (EtOAc), acetone, methanol (MeOH) and MeOH/water and the extracts were concentrated under vacuum. Radical scavenging activity of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and total phenolic content were also measured for comparison with the antioxidant capacity in the phosphomolybdenum method for the above extracts. Acetone and MeOH extracts, respectively, showed the highest (85.7%) and lowest (53.3%) radical scavenging activity, at 500 ppm. The total phenolic contents were found to be highest in the acetone extract (15.94%) followed by the MeOH extract (5.92%), ethyl acetate extract (5.54%) and water extract (5.26%). Antioxidant capacity of the extracts as equivalents to ascorbic acid (μmol/g of the extract) was in the order, EtOAc extract Ͼ acetone extract Ͼ water extract Ͼ methanol extract. Furthermore, the EtOAC and acetone extracts were loaded onto silica gel columns to obtain four limonoid aglycons. MeOH fraction was loaded onto a dowex-50 and sepabeads resin column to obtain a limonoid glucoside. The purity of the isolated five compounds was analyzed by HPLC using a C 18 column and UV detection at 210 nm. Finally, the structures of the compounds were identified as obacunone, nomilin, limonin, deacetylnomilin (DAN) and limonin-17--d-glucopyranoside (LG) using 1 H and 13 C NMR studies.

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Section: Introductionmentioning

confidence: 99%

Red Mexican Grapefruit: A Novel Source for Bioactive Limonoids and their Antioxidant Activity

Mandadi

Jayaprakasha

Bhat³

et al. 2007

Zeitschrift Für Naturforschung C

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“…Limonin is known as a primary source of undesirable bitterness in the juice of citrus fruits and 6 ppm is the objectionable level for humans. ( 6 ) Taking into consideration that limonin glucoside is involved in commercially available citrus juice at almost 180 ppm, ( 23 ) and is involved in Satsuma mandarin juice at around 130 ppm, ( 24 ) the amount of 500 ppm will be achieved by taking limonin as a supplement.…”

Section: Discussionmentioning

confidence: 99%

Suppression of intestinal carcinogenesis in <i>Apc</i>-mutant mice by limonin

Shimizu

Miyamoto

Fujii

et al. 2015

J. Clin. Biochem. Nutr.

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Limonoids in citrus fruits are known to possess multiple biological functions, such as anti-proliferative functions in human cancer cell lines. Therefore, we aimed to investigate the suppressive effect of limonin on intestinal polyp development in Apc-mutant Min mice. Five-week-old female Min mice were fed a basal diet or a diet containing 250 or 500 ppm limonin for 8 weeks. The total number of polyps in mice treated with 500 ppm limonin decreased to 74% of the untreated control value. Neoplastic cell proliferation in the polyp parts was assessed by counting PCNA positive cells, and a tendency of reduction was obtained by limonin treatment. Moreover, expression levels of c-Myc and MCP-1 mRNA in the polyp part were reduced by administration of limonin. We finally confirmed the effects of limonin on β-catenin signaling, and found limonin significantly inhibited T-cell factor/lymphocyte enhancer factor-dependent transcriptional activity in a dose-dependent manner in the Caco-2 human colon cancer cell line. Our results suggest that limonin might be a candidate chemopreventive agent against intestinal carcinogenesis.

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“…Commercial orange juices, for example, contain glucosides and aglycones at a ratio of 150 to 1 . Limonin is the predominant limonoid aglycone (Maier et at., 1977) and limonin glucoside is the predominant limonoid glucoside present in fruit tissues Ozaki et at., 1992.…”

Section: Accumulation and Degradationmentioning

confidence: 99%

“…Limonin glucoside is the predominant limonoid glucoside in fruit tissues, comprising over 50% of totallimonoid glucosides (Fong et al, 1992;Herman et aI., 1990;Ozaki et al, 1992Ozaki et al, , 1995. On the other hand, nomilin glucoside is the major glucoside in citrus seeds (Ozaki et al, 1991).…”

Section: Occurrences Of Limonoidsmentioning

confidence: 99%