Inhibitory Effects of Flavonoid Glycosides Isolated from the Peel of Japanese Persimmon (Diospyros kaki 'Fuyu') on Melanin Biosynthesis

Ohguchi, Ken-ichi; Nakajima, Chizuru; Oyama, Masayoshi; Iinuma, Munekazu; Itoh, Tomohiro; Akao, Yukihiro; Nozawa, Yoshinori; Ito, Masafumi

doi:10.1248/bpb.33.122

Cited by 39 publications

(27 citation statements)

References 12 publications

(7 reference statements)

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“…Recent reports have demonstrated that the extracts prepared from leaves, peels and flesh of persimmon have anti-tumour (Khanal, Oh, Thuong, Cho, & Choi, 2010), anti-hyperlipidemia (Lee, Cho, & Yokozawa, 2008a), anti-diabetes (Lee, Kim, Cho, & Yokozawa, 2007), anti-oxidant (Chen, Fan, Yue, Wu, & Li, 2008;Lee, Cho, & Yokozawa, 2008b), and neuroprotective activities (Bei et al, 2009). In our previous study, we isolated two distinct flavonoid glycosides from the peel of persimmon, which were shown to inhibit melanogenesis in B16 mouse melanoma cells (Ohguchi et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Inhibitory effects of flavonoid glycosides isolated from the peel of Japanese persimmon (Diospyros kaki Fuyu) on antigen-stimulated degranulation in rat basophilic leukaemia RBL-2H3 cells

Itoh¹,

Ohguchi²,

Nakajima

et al. 2011

Food Chemistry

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Section: Introductionmentioning

confidence: 99%

Inhibitory effects of flavonoid glycosides isolated from the peel of Japanese persimmon (Diospyros kaki Fuyu) on antigen-stimulated degranulation in rat basophilic leukaemia RBL-2H3 cells

Itoh¹,

Ohguchi²,

Nakajima

et al. 2011

Food Chemistry

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“…3,[8][9][10] The peels of fresh astringent persimmons are usually removed and dried, which yields sweet dried persimmon peels. The peel was found to contain more polyphenols 11) and carotenoids 12) than the fruit body.…”

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confidence: 99%

“…[2][3][4][5][6][7] With regard to its pharmacological activities, many studies have reported pharmacological effects including antioxidant activity and tyrosinase inhibitory activity. 3,[8][9][10] The peels of fresh astringent persimmons are usually removed and dried, which yields sweet dried persimmon peels. The peel was found to contain more polyphenols 11) and carotenoids 12) than the fruit body.…”

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Characterization of Carotenoid Fatty Acid Esters from the Peels of the Persimmon <i>Diospyros kaki</i>

et al. 2013

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Separation and structural determination of the chloroform-soluble components obtained from the peels of the persimmon (Diospyros kaki Thunb.) were performed. β-Carotene, lycopene, β-cryptoxanthin monomyristic acid ester, zeaxanthin di-myristic acid ester, the latter two of which were accompanied by a small amount of palmitoleic acid in the fatty acid moiety, and oleanolic acid were identified. Among these components, the mono-fatty acid ester of β-cryptoxanthin and the di-fatty acid ester of zeaxanthin were characterized for the first time.Key words persimmon peel; carotenoid; β-cryptoxanthin mono-fatty acid ester; zeaxanthin di-fatty acid ester; myristic acid; palmitoleic acidThe persimmon Diospyros kaki Thunb. is a fruit that is indigenous to Japan, and China, Korea, and Japan produce most of the fruits used for commercial consumption. Persimmons (Kaki) are also used traditionally for medicinal purposes, because of their preventive action against infection, diabetes, and arteriosclerosis, and because of their diuretic effect.1) The persimmon contains many compounds such as different sugars, starch, organic acids, ascorbic acid, tannins, flavonoids, carotenoids, triterpenoids, and fatty acids.2-7) With regard to its pharmacological activities, many studies have reported pharmacological effects including antioxidant activity and tyrosinase inhibitory activity. 3,[8][9][10] The peels of fresh astringent persimmons are usually removed and dried, which yields sweet dried persimmon peels. The peel was found to contain more polyphenols 11) and carotenoids 12) than the fruit body. The persimmon flesh contained large amounts of carotenoids, which are responsible for the color of the fruits.4,5) Unlike vitamin C and vitamin E, β-carotene and other carotenoids can scavenge singlet oxygen.13) Also, carotenoids are known to exist as free compounds or as fatty acid esters in plants. Because the peels of persimmons are usually discarded, we believe that it might be possible to recover the peels for industrial utilization or for use as a food supplement.Breithaupt and Bamedi 14) suggested, on the basis of HPLC results, the occurrence of carotenoid esters as β-cryptoxanthin ester and zeaxanthin ester in persimmons. Weller and Breithaupt 15) also suggested, on the basis of LC/MS results, the presence of zeaxanthin esters as diesters of dipalmitate and of palmitate and stearate in persimmons. However, they did not isolate these compounds as pure single entities. Differences in the chemical structure of each carotenoid and its ester would lead to different pharmacological effects and physicochemical characteristics. For example, synthetic lutein myristate ester was more stable than free lutein after heat or UV treatment. 16)Sugawara et al. 17) found that Caco-2 cells easily took up more hydrophobic carotenoids than less hydrophobic carotenoids. One can easily envision that different carotenoids with or without ester moieties would have different polar characteristics and that differences in structure would lead to different bioch...

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“…The structures of isolated compounds were identified by a combination of spectroscopic methods (MS, 1 D NMR and 2D NMR) and comparisons with the literature data as a mixture of quercetin 3-β-Ogalactopyranoside or hyperoside (1) and quercetin 3-β-Oglucopyranoside or isoquercitrin (1:1) (2) (Almeida et al, 1998;Costa et al, 2007;Ohguchi et al, 2010), quercetin 3-O-α-rhamnoside or quercitrin (3) (Zhong et al, 1997), luteolin 6-C-β-glucopyranoside or orientin (4) (Li et al, 2009), apigenin-6-C-glucoside or isovitexin (5) (Leong et al, 2010), kaempferol 3-O-α-rhamnoside (6) (Fossen et al, 1999) and lupenone (7) (Prachayasittikul et al, 2010), respectively. Characterization of the sugar moieties from the mixture of quercetin 3-β-galactopyranoside (1) and quercetin 3-β-glucopyranoside (2) was performed according Cota et al 2008b.…”

Section: Resultsmentioning

confidence: 99%

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

Cota¹,

Siqueira²,

Oliveira³

et al. 2012

Rev. bras. farmacogn.

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Abstract:Many phenolic compounds such as xanthones, quinones and coumarins have been isolated from Kielmeyera species; however the presence of flavonoids have been showed in other genera in the Calophylleae tribe as Caraipa, Mesua and Calophyllum. Six known glycosidic flavonoids: quercetin 3-β-O-galactopyranoside (1), quercetin 3-β-O-glucopyranoside (2), quercetin 3-O-α-rhamnoside (3), luteolin 6-C-β-glucopyranoside (4), isovitexin (5), kaempferol 3-O-α-rhamnoside (6) and one triterpene, lupenone (7) were isolated, for the first time, from organic crude extract of Kielmeyera variabilis Mart. & Zucc., Calophyllaceae, leaves. The crude organic extract from K. variabilis leaves exhibited 95% of leishmanidal activity at 20 µg/mL on amastigote-like form of Leishmania (Leishmania) amazonensis in vitro model and only compound 3 showed 40-45% of growth inhibition at concentration ranging from 0.78 to 20 µg/mL. In addition, quercetin 3-O-α-rhamnoside (quercitrin) was found to be the major metabolite. Our results and previous reports suggest that synergistic effects of flavonoid glycosides are the cause of significant leishmanidal activity of the crude organic extract from K. variabilis leaves.

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Inhibitory Effects of Flavonoid Glycosides Isolated from the Peel of Japanese Persimmon (Diospyros kaki 'Fuyu') on Melanin Biosynthesis

Cited by 39 publications

References 12 publications

Inhibitory effects of flavonoid glycosides isolated from the peel of Japanese persimmon (Diospyros kaki Fuyu) on antigen-stimulated degranulation in rat basophilic leukaemia RBL-2H3 cells

Inhibitory effects of flavonoid glycosides isolated from the peel of Japanese persimmon (Diospyros kaki Fuyu) on antigen-stimulated degranulation in rat basophilic leukaemia RBL-2H3 cells

Characterization of Carotenoid Fatty Acid Esters from the Peels of the Persimmon <i>Diospyros kaki</i>

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

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