Pharmacological Study on Citrus Fruits. II. Anti-allergic Effect of Fruit of Citrus unshiu MARKOVICH (2). On Flavonoid Components

Matsuda, Hideaki; Yano, Maki; Kubo, Michinori; Iinuma, Munekazu; Oyama, Masayoshi; Mizuno, Mizuo

doi:10.1248/yakushi1947.111.3_193

Cited by 42 publications

(23 citation statements)

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“…C. paradisi (grapefruit) showed strong CYP inhibition, consistent with previous reports on C. paradisi and grapefruit juice. [39][40][41][42][43][44][45] Grapefruit juice enhances the bioavailability or systemic exposure of numerous CYP3A4 substrates by inhibiting intestinal first-pass metabolism. For the other citrus extracts examined, further studies should investigate the inhibitory effects on substrate metabolism, as shown by the CYP inhibition patterns of each citrus extract.…”

Section: Discussionmentioning

confidence: 99%

Comparative Evaluation of 12 Immature Citrus Fruit Extracts for the Inhibition of Cytochrome P450 Isoform Activities

Fujita

Kawase

Niwa

et al. 2008

Biological & Pharmaceutical Bulletin

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In a previous study we found that 50% ethanol extracts of immature fruits of Citrus unshiu (satsuma mandarin) have anti-allergic effects against the Type I, II and IV allergic reactions. However, many adverse interactions between citrus fruit, especially grapefruit juice, and drugs have been reported due to the inhibition of cytochrome P450 (CYP) activities. The purpose of this study was to examine the competitive inhibitory effects of extracts from immature citrus fruit on CYP activity. Extracts were prepared from 12 citrus species or cultivars, and were tested against three kinds of major CYPs, CYP2C9, CYP2D6 and CYP3A4, in human liver microsomes. We also estimated the amounts of flavonoids (narirutin, hesperidin, naringin and neohesperidin) and furanocoumarins (bergapten, 6,7-dihydroxybergamottin and bergamottin) in each extract using HPLC. Citrus paradisi (grapefruit) showed the greatest inhibition of CYP activities, while Citrus unshiu which has an antiallergic effect, showed relatively weak inhibitory effects. Extracts having relatively strong inhibitory effects for CYP3A4 tended to contain higher amounts of naringin, bergamottin and 6,7-dihydroxybergamottin. These results, providing comparative information on the inhibitory effects of citrus extracts on CYP isoforms, suggest that citrus extracts containing high levels of narirutin and hesperidin and lower levels of furanocoumarins such as C. unshiu are favorable as antiallergic functional ingredients.

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Section: Discussionmentioning

confidence: 99%

Comparative Evaluation of 12 Immature Citrus Fruit Extracts for the Inhibition of Cytochrome P450 Isoform Activities

Fujita

Kawase

Niwa

et al. 2008

Biological & Pharmaceutical Bulletin

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“…So, it is figuratively said that allergic diseases are the current national disease in Japan. Under such condition, the functional foods to alleviate allergic symptoms, such as Citrus unshiu unripe fruit, were focused [1,2] .…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory effects of flavonoids in Citrus jabara fruit peels

Azuma

Murakami²,

Azuma³

et al. 2018

Trends Immunother

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Currently, about half of people in Japan suffer from allergic diseases. Thus, Citrus jabara fruits have been paid attention as one of quite effective anti-allergic functional foods. C. jabara is an endemic species originally grown only in Kitayama village, Wakayama prefecture in Japan. Although genetic characterization and diversity of various Citrus fruits including C. jabara were researched, but there is room for the study on flavonoids characteristics in C. jabara fruit. For the alleviation of allergic symptom, anti-inflammatory effects are also important. In this study, characteristics of flavonoids in C. jabara fruit peels, and the anti-inflammatory effects of these purified flavonoids were investigated. Our results revealed that C. jabara is a unique Citrus that almost all of flavonoids in fruit peels was narirutin. There was no Citrus species with a flavanone glycosides content ratio like C. jabara. Although anti-inflammatory effects of narirutin was weak, but its aglycone naringenin exhibited following inhibitory effects: nitric oxide synthesis (IC 50 = 105 μM), nitric oxide synthase induction, Interleukin-6 synthesis (IC 50 = 65 μM), and inducible soluble epoxide hydrolase activity (IC 50 = 267 μM). Since narirutin is deglycosylated to naringenin that is then absorbed by colonocytes, it is considered that narirutin exists like a prodrug and its aglycone naringenin works as an active form of anti-inflammatory effect in a living body at oral ingestion of C. jabara fruit peels. Keywords: Citrus jabara; anti-inflammatory effects; flavonoids; narirutin; naringenin ARTICLE INFO

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“…1,[3][4][5] Recently, the tyrosinase inhibitory activities of the peel of Citrus fruit (Citrus unshiu Markovich) and its flavonoids, such as nobiletin, have been reported. 6,7) As a part of our continuous studies on the biological activities of Citrus species, [8][9][10][11][12] we found that a 50% ethanolic extract (CH-ext) obtained from the unripe fruit of Citrus hassaku HORT ex T. TANAKA, which was collected by thinning out in July, exhibited potent mushroom tyrosinase inhibitory activity. Thinning out the unripe fruit of C. hassaku in July is important for a rich harvest of ripe fruit in December.…”

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Inhibitory Effects of Citrus hassaku Extract and Its Flavanone Glycosides on Melanogenesis

Itoh

Hirata

Masuda

et al. 2009

Biological & Pharmaceutical Bulletin

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Melanogenesis stimulated by UV irradiation occurs in plants, microorganisms, and mammalian cells by an enzymatic oxidation process starting with L-tyrosine. Various ingredients for skin-whitening cosmetics are developing to reduce melanogenesis. Tyrosinase catalyzes the oxidation of L-tyrosine to 3,4-dihydroxyphenyl-L-alanine (L-DOPA), followed by the oxidation of L-DOPA to dopaquinone, and oxidative polymerization of several dopaquinone derivatives produces melanin. Thus the tyrosinase inhibitor is one of the candidates for reduction of melanogenesis.1) On the other hand, it has been reported that superoxide dismutase (SOD) is one of the key factors that reduce melanin production caused by UV irradiation.2) Therefore tyrosinase inhibitors with SOD-like activity and/or antioxidant activity may be useful ingredients in the field of skin-whitening cosmetics. During our screening program to find a potential tyrosinase inhibitor from natural resources, we reported several crude drugs, such as Glebnia littoralis F. SCHMIDT, Prunus zippeliana M., Myrica rubra S. et ZUCC., and Arctostaphylos uva-ursi L. SPRENGEL, some of which have been applied to cosmetic beauty preparations. 1,[3][4][5] Recently, the tyrosinase inhibitory activities of the peel of Citrus fruit (Citrus unshiu Markovich) and its flavonoids, such as nobiletin, have been reported. 6,7) As a part of our continuous studies on the biological activities of Citrus species, [8][9][10][11][12] we found that a 50% ethanolic extract (CH-ext) obtained from the unripe fruit of Citrus hassaku HORT ex T. TANAKA, which was collected by thinning out in July, exhibited potent mushroom tyrosinase inhibitory activity. Thinning out the unripe fruit of C. hassaku in July is important for a rich harvest of ripe fruit in December. Thus this study was undertaken to examine whether the unripe fruit of C. hassaku collected in July by thinning can be utilized as a plant resource for skin-whitening cosmetic agents, because, to the best of our knowledge, there is no report on the tyrosinase inhibitory activity of C. hassaku. First, to identify the active component, we carried out activity-guided fractionation of the CH-ext using tyrosinase inhibitory assay. For antioxidant activity, SOD-like and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities of the CH-ext and its flavanone glycosides were also studied. Second, according to the method of Imokawa, 13) we examined the effects of the CH-ext on melanogenesis using cultured murine B16 melanoma cells after exposure to glucosamine. Third, we examined the in vivo preventive effects of the CH-ext against UVB-induced pigmentation of dorsal skin in brownish guinea pigs. 14) MATERIALS AND METHODSReagents Hesperidin, naringin, and neohesperidin were purchased from Sigma-Aldrich Japan (Tokyo, Japan). Narirutin was isolated from fruit of C. unshiu.10) Other chemical and biochemical reagents were of reagent grade and were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan) and/or Nacalai Tesque, Inc. (Kyoto, Japan)...

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Pharmacological Study on Citrus Fruits. II. Anti-allergic Effect of Fruit of Citrus unshiu MARKOVICH (2). On Flavonoid Components

Cited by 42 publications

References 0 publications

Comparative Evaluation of 12 Immature Citrus Fruit Extracts for the Inhibition of Cytochrome P450 Isoform Activities

Comparative Evaluation of 12 Immature Citrus Fruit Extracts for the Inhibition of Cytochrome P450 Isoform Activities

Anti-inflammatory effects of flavonoids in Citrus jabara fruit peels

Inhibitory Effects of Citrus hassaku Extract and Its Flavanone Glycosides on Melanogenesis

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