Plant Antimutagenic Agents, 2. Flavonoids

Wall, Monroe E.; Wani, Mansukh C.; Manikumar, Govindarajan; Abraham, Philip; Taylor, Harold; Hughes, Thomas J.; Warner, Janet; McGivney, Robert

doi:10.1021/np50060a006

Cited by 97 publications

(60 citation statements)

References 9 publications

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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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“…Recent research has conˆrmed that plant ‰avo-noids inhibit the mutagenicity induced by chemical mutagens. [36][37][38][39][40][41] Nakasugi et al 42) reported that apigenin, hispidulin, genkwanin, and cirsimaritin in carqueja showed strong antimutagenic activities against Trp-P-2. Samejima et al 43) reported that luteolin, which is contained in peppermint, sage, and thyme, showed a strong antimutagenic eŠect against Trp-P-2.…”

Section: Discussionmentioning

confidence: 99%

Antimutagenic Activity of Flavonoids fromChrysanthemum morifolium

Miyazawa

Hisama

2003

Bioscience, Biotechnology, and Biochemistry

196

113

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A methanol extract from the ‰ower heads of Chrysanthemum morifolium showed a suppressive eŠect on umu gene expression of the SOS response in Salmonella typhimurium TA1535 W pSK1002 against the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide). The methanol extract was re-extracted with hexane, chloroform, ethyl acetate, butanol, and water. The ethyl acetate fraction showed a suppressive eŠect. Suppressive compounds in the ethyl acetate fraction were isolated by silica gel column chromatography and identiˆed as the ‰avonoids acacetin (1), apigenin (2), luteolin (3), and quercetin (4) by EI-MS, IR, and 1 H and 13 C NMR spectroscopy. Compounds 1-4 suppressed the furylfuramide-induced SOS response in the umu test. Compounds 1-4 suppressed 60.2, 75.7, 90.0, and 66.6z of the SOS-inducing activity at a concentration of 0.70 mmol W ml. The ID 50 (50z inhibitory dose) values of 1-4 were 0.62, 0.55, 0.44, and 0.59 mmol W ml. These compounds had the suppressive eŠects on umu gene expression of the SOS response against other mutagens, 4-nitroquinolin 1-oxide (4NQO) and N-methyl-N?-nitro-N-nitrosoguanidine (MNNG), which do not require liver-metabolizing enzymes. These compounds also showed the suppression of SOS-inducing activity against the other mutagens a‰atoxin B 1 (AfB 1 ) and 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), which require liver-metabolizing enzymes, and UV irradiation. In addition to the antimutagenic activities of these compounds against furylfuramide, Trp-P-1 and activated Trp-P-1 were also assayed by the Ames test using S. typhimurium TA100.

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“…is increasingly becoming a strong contender for cancer management. Coumarins, flavonoids, sesquiterpene lactones and edotides may be the principles in VA that are responsible for its anticancer activity [44][45][46].…”

Section: Vernonia Amygdalina (Va)mentioning

confidence: 99%