Tyrosinase inhibitory effects and inhibition mechanisms of nobiletin and hesperidin from citrus peel crude extracts

Zhang, Chongwei; Lü, Yanhua; Lin, Tao; Tao, Xinyi; Su, Xiaochun; Wei, Dongzhi

doi:10.1080/14756360600953876

Cited by 45 publications

(28 citation statements)

References 39 publications

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“…To identify the active component, the CH-ext was fractionated by solvent extraction to give a hexane-solu- Thus it was found that these two fractions were flavanone glycoside-rich fractions in which naringin and neohesperidin were major flavanones, and narirutin as well as hesperidin were minor flavanones. These results are in accordance with the reports 6,7) that some flavanone glycosides exhibit tyrosinase inhibitory activities. The tyrosinase inhibitory activities of naringin, neohesperidin, narirutin, and hesperidin are shown in Table 2.…”

Section: Resultssupporting

confidence: 94%

“…7) In the previous study on seasonal variation in several Citrus fruit extracts in the relationship between anti-allergic activity and the content of flavanone glycosides, we reported that unripe C. unshiu fruit extract showed more potent activity than that of ripe fruit, and that the flavanone glycoside content in unripe fruit extract was richer than that in the ripe extract. 10) During the course of our preliminary comparative screening for mushroom tyrosinase inhibitory activity of 50% ethanolic extracts obtained from C. hassaku fruit collected monthly in July, August, September, October, and November, we found that the extract obtained from unripe fruit collected by thinning out in July showed the most potent activity (data not shown) as in the case of the anti-allergic activity of C. unshiu fruit extract.…”

Section: Resultsmentioning

confidence: 86%

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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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Section: Resultssupporting

confidence: 94%

Section: Resultsmentioning

confidence: 86%

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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“…13) In this paper, considering utilization of the unripe fruit of C. hassaku collected by thinning, we focused on the in vitro effects of CH-ext on rabbit platelet aggregation, rat erythrocyte aggregation, and the fibrinolytic system. As shown in Table 1, CH-ext concentration-dependently inhibited both platelet aggregation and erythrocyte aggregation; CH-ext also showed concentration-dependent fibrinolysis activity as depicted in Table 1.…”

Section: Resultsmentioning

confidence: 99%

Effects of Unripe Citrus hassaku Fruits Extract and Its Flavanone Glycosides on Blood Fluidity

Itoh

Masuda

Naruto

et al. 2010

Biological & Pharmaceutical Bulletin

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Citrus fruits are widely consumed in Asian countries, especially in Japan. Some Citrus species, such as Citrus unshiu MARKOVICH and Citrus hassaku HORT ex T. TANAKA originate in Japan. Both species have been shown to possess various biological activities such as anti-allergy, tyrosinase inhibitory and anti-melanogenesis activities through recent extensive research. 1,2) Our previous reports 1,2) described that the 50% ethanolic extract (CH-ext) obtained from C. hassaku unripe fruits collected in July possessed significant anti-melanogenesis activity with potent tyrosinase inhibitory activity. In addition, CH-ext inhibited the allergic symptoms in vivo and degranulation of mast cells obtained from rat peritoneal showing its potent anti-allergic activity. Thus, CH-ext is expected to be a functional material possessing both skinwhitening and anti-allergy effects and a useful ingredient for cosmetics and/or supplements.The brightness of skin may be influenced by infraorbital dark circles around the eyes and skin darkness. From an antiaging point of view, these factors are recognized as unfavorable for many women. Thus, many cosmetic products to reduce these symptoms have been launched by Japanese cosmetic-related companies. One of the ways to improve infraorbital dark circles around the eyes and skin darkness is the enhancement of blood fluidity, since the murkiness is said to be due to the blood stasis ("Oketsu" in Japanese, a term in oriental medicine) in specific areas of the body. The treatment of Oketsu can be achieved by invigorating blood circulation and eliminating blood stasis. The enhancement of blood fluidity may lead to the improvement of skin problems resulting from unsmooth circulation or stagnation of blood. From the study of blood fluidity, it is known that blood platelet hyperactivity results in platelet adhesion to the vessel wall. Thus platelet hyperactivity is one of the most essential factors responsible for thrombosis, and the incidence of Oketsu, and for cardiovascular, cerebrovascular, and peripheral vascular diseases. 3) Many investigations for antiplatelet agents from natural resources have therefore been carried out to prevent platelet dysfunction. 4) Recently, it has been reported that hesperetin, an aglycone of hesperidin which is a constituent of Citrus fruits, inhibited rabbit platelet aggregation induced by collagen and arachidonic acid, and that the cellular mechanism for the antiplatelet activity of hesperetin was mainly mediated by the inhibition of phospholipase (PL)C-g2 phosphorylation and cyclooxygenase-1 activity. 5) A group of antioxidants of the flavonoid family has been reported to inhibit platelet aggregation in vitro and ex vivo, and human studies have also suggested that a diet high in flavonoids may inhibit platelet aggregation in vivo. 5) These reports prompted us to examine the antiplatelet activity of CH-ext, since there is no report on antiplatelet effects of C. hassaku. First, we examined in vitro antiplatelet activity of CH-ext by an assay of the inhibitory effect ...

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“…For instance, it is reported that the IC 50 value of naringin and hesperidin were 1.9 mM (Itoh et al, 2009) and 16.08 mM (Zhang et al, 2007), respectively. The tyrosinase inhibition potency of nobiletin has also been reported (Sasaki & Yoshizaki, 2002).…”

Section: Introductionmentioning

confidence: 99%

Tyrosinase inhibitory components of immature calamondin peel

Lou

2012

Food Chemistry

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Tyrosinase inhibitory effects and inhibition mechanisms of nobiletin and hesperidin from citrus peel crude extracts

Cited by 45 publications

References 39 publications

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

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

Effects of Unripe Citrus hassaku Fruits Extract and Its Flavanone Glycosides on Blood Fluidity

Tyrosinase inhibitory components of immature calamondin peel

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