Studies on the Differentiation Inducers of Myeloid Leukemic Cells from Citrus Species.

Sugiyama, Satoko; Umehara, Kaoru; Kuroyanagi, Masanori; Ueno, Akira; Taki, Takao

doi:10.1248/cpb.41.714

Cited by 64 publications

(42 citation statements)

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“…Therefore, nobiletin exhibited more potency compared with kojic acid, by approximately two-fold. Nobiletin is a polymethoxyflavonoid occurring exclusively in Citrus fruits, 10) and has been reported to induce the differentiation of mice myeloid leukemia cells, 12) to exhibit antiproliferative activity toward a human squamous cell carcinoma cell line, 13) to exert anti-mutagenic activity, 14) and to suppress the induction of matrix metalloproteinase-9 and prostaglandin E 2 release. 15) In addition, nobiletin inhibits the combined endotoxin and cytokine-induced expression of nitric oxide synthesis and cyclooxygenase-2 proteins, and suppresses the formation of tumor promoter-induced edema 16) and papilloma 17) in mice.…”

Section: Resultsmentioning

confidence: 99%

Nobiletin as a Tyrosinase Inhibitor from the Peel of Citrus Fruit.

Sasaki

Yoshizaki

2002

Biological & Pharmaceutical Bulletin

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Tyrosinase catalyzes the oxidation of tyrosine and certain diphenolic intermediate products to quinines, which polymerize to give rise to melanin. 1) Tyrosinase inhibitors are used in depigmentation drugs and whitening cosmetics, 2,3) whereas compounds that increase melanogenesis may protect human skin from ultraviolet irradiation damage.4) The tyrosinase metabolic pathway also seems to be involved in the antimelanoma effects of some tyrosinase analogues.2) These substances are oxidated by tyrosinase, generating reactive oquinone with cytotoxic potential.2,5) Therefore, tyrosinase may be a useful target in the fields of hyperpigmentation and cosmetic materials. 6)Flavonoids and hydroxycinnamates, major constituents of the human diet, are powerful electron-donating anti-oxidants, the catechol moiety being one of the main structural features responsible for their antioxidant activities.7,8) Several flavonoids, stilbenes and related 4-substituted resorcinols, were tested for their inhibitory activity against tyrosinase to clarify the structure-activity relationship.9)The present study was under-taken to search for tyrosinase inhibitors in the peel of Citrus fruit. It has been used not only in traditional Chinese medicines but also as a skin whitening and skin-moisturized agent in Japanese folk medicines. Citrus fruit contains several biologically active components, e.g., limonoids and their glycosides, glyceroglycolipids, alkaloids such as synephrine, and several flavonoids in a large amount. Thus, the components of the peel of Citrus fruit are expected to provide valuable material to prevent skin pigmentation. MATERIALS AND METHODS Chemicals and General MaterialsMushroom tyrosinase, l-dopa, was purchase from Nakalai Tesque (Kyoto), and kojic acid from Tokyo Kasei Co. (Tokyo). Silica gels (Wakogel C-200) were purchased from Wako Chemical, Inc., Ltd. (Kyoto). Plant materials were purchased from Uchida Wakanyaku Co. (Niigata, from China).General Procedures Melting point was determined on a Yanagimoto micromelting point apparatus and is uncorrected. A Perkin Elmer 1600 series FTIR spectrophotometer was used for the measurement of IR spectrum. Mass spectrum (MS) was taken on a JEOL DX-303 mass spectrometer. Proton nuclear magnetic resonance (NMR) spectrum was recorded with JEOL EX-270 spectrometer, and chemical shifts are given in d (ppm) with tetramethylsilane as an internal standard (s: singlet, d: doublet, dd: double doublet).Extraction and Isolation The peel of Citrus fruit (3.5 kg) was extracted twice with methanol (8 l) at room temperature. Removal of solvent in vacuo gave 952.2 g of methanol extract. The extract was dissolved in water and distributed three times between chloroform (1 l), giving a chloroform extract (31.6 g). The water-soluble residue was partitioned three times between ethyl acetate (1 l) and H 2 O (1 l). After removal of the solvent in vacuo, the ethyl acetate extract (27.3 g) was column chromatographed on silica gel (Wakogel C-200) using n-hexane and n-hexane-acetone, giving colorless needles,...

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Section: Resultsmentioning

confidence: 99%

Nobiletin as a Tyrosinase Inhibitor from the Peel of Citrus Fruit.

Sasaki

Yoshizaki

2002

Biological & Pharmaceutical Bulletin

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“…Isosinensetin (6) (3′,4′,5,7,8-pentamethoxyflavone) is one of polymethoxyflavones widely distributed in Citrus plants (Machida and Osawa, 1989;Mizuno et al, 1991;Sugiyama et al, 1993;Hirata et al, 2009). Although C. unshiu leaves contained several additional polymethoxyflavones, two positional isomers of 6 isolated during fractionation in the present study, namely tangeritin (4′,5,6,7,8-pentamethoxyflavone) and sinensetine (3′,4′,5,6,7,-pentamethoxyflavone), were inactive when compared at the same dose (5 μg/strip) in the presence of sugars (1+2+3).…”

Section: Discussionmentioning

confidence: 99%

Larval Feeding Stimulants for a Rutaceae-Feeding Swallowtail Butterfly, Papilio xuthus L. in Citrus unshiu Leaves

2011

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Larvae of a swallowtail butterfly, Papilio xuthus L., feed exclusively on plants of the family Rutaceae, including various Citrus crops. Larvae were strongly stimulated to feed on paper strips impregnated with ethanolic extracts of host-plant leaves. Stimulation of feeding on extracts of Citrus unshiu leaves required a mixture of chemicals including sugars (D: -glucose, D: -fructose, and D: -sucrose), a betaine [(-)-stachydrine], a cyclic peptide (citrusin I), a polymethoxyflavone (isosinensetin), and the lipids 1-linolenoylglycerol, 1-linoleoylglycerol, 1-octadecenoylglycerol, 1-stearoylglycerol, and 1,2-dilinolenoyl-3-galactosyl-sn-glycerol. When these compounds were assayed individually, few larvae consumed test strips. However, larvae readily chewed the test strips treated with a mixture of all compounds, indicating that host recognition by P. xuthus larvae is mediated by a specific combination of both primary and secondary substances. Comparison of 11 stimulant components with 10 compounds from C. unshiu leaves previously reported as stimulant components for oviposition by P. xuthus adult females revealed only one compound, stachydrine, as an ingredient in common. While the larval feeding-stimulant mixture is dominated by nutrients and other compounds of general significance for primary metabolism, the component oviposition stimulants are mostly secondary substances, including flavonoid glycosides, protoalkaloids, a cyclitol, and a betaine, that have restricted distributions in plants. Reliance by adult females on unique profiles of secondary compounds presumably reflects the need to locate and recognize specific host-plant species within a diverse flora. Since the initial host choice for the larvae is made typically by the ovipositing female, however, unique secondary compounds may be less important for larval feeding than are compounds useful for indicating food and microhabitat quality once on the host plant.

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“…Many natural products, such as flavone aglycones [1][2][3], flavone glycoside [4], limonoids [5], coumarin [6], and acridone alkaloid derivatives, have been reported in citrus plants. Highly methoxylated flavonoids found in the peel of citrus species have been reported as cell differentiators [7]. Many kinds of dimeric coumarin derivatives, dimeric acridone alkaloids and acridone-coumarin dimers isolated from citrus plants have been used as cancer chemopreventive agents [8].…”

Section: Introductionmentioning

confidence: 99%

Flavonoid glycosides and limonoids from Citrus molasses

et al. 2007

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Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice production. This molasses is expected to be a useful source of organic compounds such as flavonoids and limonoids. To elucidate a use for this molasses waste, we isolated and identified its organic constituents. Two new flavanonol glycosides were isolated from tangerine orange molasses, along with several flavonoids such as hesperidine, narirutin, eriodictyol, 3',4',5,6,7,8-hexamethoxy-3-O-beta-D-glucopyranosyloxyflavone, and 3',4',5,6,7,8-hexamethoxy- 3-beta-D-[4-O-(3-hydroxy-3-methylglutaloyl)]-glucopyranosyloxyflavone, and limonoids such as limonin, nomilin, and cyclic peptide, citrusin III. The structures of the new flavanonol glycosides were determined as (2R,3R)-7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-aromadendrin and 7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-3,3',5,7-tetrahydroxy-4'-methoxyflavanone by means of spectral analyses using (1)H-NMR, (13)C-NMR, and 2D-NMR. Of these compounds, flavanone glycoside, hesperidin and narirutin were isolated as the main constituents. Thus, molasses is a promising source of flavonoid glycosides.

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Studies on the Differentiation Inducers of Myeloid Leukemic Cells from Citrus Species.

Cited by 64 publications

References 0 publications

Nobiletin as a Tyrosinase Inhibitor from the Peel of Citrus Fruit.

Nobiletin as a Tyrosinase Inhibitor from the Peel of Citrus Fruit.

Larval Feeding Stimulants for a Rutaceae-Feeding Swallowtail Butterfly, Papilio xuthus L. in Citrus unshiu Leaves

Flavonoid glycosides and limonoids from Citrus molasses

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