Chemotaxonomy of the genus Citrus based on polymethoxyflavones.

Mizuno, Mizuo; Iinuma, Munekazu; Mitsuharu, Ohara; Tanaka, Toŝhiyuki; Iwamasa, Masao

doi:10.1248/cpb.39.945

Cited by 34 publications

(29 citation statements)

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“…For example, 5,7,4'-TMF is a citrus flavonoid [39], also present in other plants used in folk medicine [40,41]. 7,4'-DMF has been identified in fruits and leaves from neotropical nutmeg species [42,43] as well as from propolis [44].…”

Section: Discussionmentioning

confidence: 99%

Cancer chemopreventive properties of orally bioavailable flavonoids—Methylated versus unmethylated flavones

Walle

Kawamori

et al. 2007

Biochemical Pharmacology

197

175

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Poor oral bioavailability has been a major limitation for the successful use of dietary flavonoids as cancer chemopreventive agents. In this study, we examined fully methylated flavones as promising improved agents. In the humanoral SCC-9 cancer cells, 5,7-dimethoxyflavone and 5,7,4'-trimethoxyflavone were both ten times more potent inhibitors of cell proliferation (IC 50 values 5-8 μM) than the corresponding unmethylated analogs chrysin and apigenin. Flow cytometry indicated that both methylated flavones arrested the SCC-9 cells in the G1 phase with a concomitant decrease in the S phase, dramatically different from the unmethylated analogs, which promoted G2/M phase arrest. Both methylated compounds inhibited the proliferation of two other cancer cell lines with very little effect on two immortalized normal cell lines. Examination of additional flavone structures indicated that methylated flavones in general have antiproliferative properties. Finally, we demonstrated that 5,7-dimethoxyflavone, in contrast to its unmethylated analog chrysin, was well absorbed and had high oral bioavailability as well as tissue accumulation in vivo in the rat. Thus, fully methylated flavones appear to have great potential as cancer chemopreventive/ chemotherapeutic agents, in particular in oral cancer.

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Section: Discussionmentioning

confidence: 99%

Cancer chemopreventive properties of orally bioavailable flavonoids—Methylated versus unmethylated flavones

Walle

Kawamori

et al. 2007

Biochemical Pharmacology

197

175

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show abstract

“…Second, these methoxyflavones are present in plants that are less utilized commercially for human consumption compared to the polymethoxyflavones. For example, 5,7,4′-TMF, although present in a Citrus species [71], also is present in other plants used in folk medicine [72,73]. 7,4′-DMF has been identified in fruits and leaves from neotropical nutmeg species [74,75] as well as from propolis [76].…”

Section: Where Can the Methoxylated Flavones Be Found?mentioning

confidence: 99%

Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass?

Walle

2007

Seminars in Cancer Biology

263

181

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Dietary flavonoids and other polyphenols show great potential as cancer chemopreventive agents in cell culture studies. This does not translate well into in vivo activity, because of extensive conjugative metabolism of these compounds in the intestine and liver. This paper presents a review of a flavonoid subclass in which all hydroxyl groups are capped by methylation. This results in dramatically increased metabolic stability and membrane transport in the intestine/liver, thus improving oral bioavailability. The methoxyflavones also show increased cancer chemopreventive properties. At the cancer initiation stage, bioactivation of polyaromatic hydrocarbon carcinogens and binding to DNA are markedly diminished through effects on CYP1A1/1B1 transcription but also through direct interactions with the proteins. At the cancer promotion stage, the proliferation of cancer cells, but not normal cells, is inhibited with greater potency than with the unmethylated flavones. Limited mechanistic experiments, such as of effects on cell cycle regulation, indicate that the mechanisms of methoxyflavone activities are unique, including aromatase inhibition. The cancer preventive effects and mechanisms of the polymethoxyflavones, such as tangeretin and nobiletin, are discussed in comparison. It is concluded that the methoxyflavones have properties that may make them particularly useful as cancer chemopreventive agents.

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“…Amongst them, polymethoxyflavones (PMFs) show chemopreventive potential in antimutagenic and antitumor properties (Li, Lambros, Wang, Goodnow, & Ho, 2007;Li et al, 2009aLi et al, , 2009bWalle, 2007). Various Citrus species present different composition of PMFs (Green, Wheatley, Osagie, St. A. Morrison, & Asemota, 2006;Hirata et al, 2009;Li, Pan, et al, 2007;Mizuno, Iinuma, Ohara, Tanaka, & Iwamasa, 1991). Ponkan, the fruit of Citrus reticulata Blanco cv.…”

Section: Introductionmentioning

confidence: 99%

The methoxyflavones in Citrus reticulata Blanco cv. ponkan and their antiproliferative activity against cancer cells

Chen

2010

Food Chemistry

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Chemotaxonomy of the genus Citrus based on polymethoxyflavones.

Cited by 34 publications

References 0 publications

Cancer chemopreventive properties of orally bioavailable flavonoids—Methylated versus unmethylated flavones

Cancer chemopreventive properties of orally bioavailable flavonoids—Methylated versus unmethylated flavones

Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass?

The methoxyflavones in Citrus reticulata Blanco cv. ponkan and their antiproliferative activity against cancer cells

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