Lignoids from the fruit of three Virola species

doi:10.1016/S0031-9422(00)82577-7

Phytochemistry

Volume 24, Issue 8, 1985, Pages 1865-1866

https://doi.org/10.1016/S0031-9422(00)82577-7 Get rights and content

Abstract

The fruits of Virola peruviana contain, besides i 1-phenyl-1-1-(2′,6′-dihydroxyphenyl)-undecan-1-one and the neolignan 2,3-dimethyl-1,4-diveratryl-n-butan-1-ol, 3,4-methylenedioxycinnamyl alcohol. In contrast, the fruits of V. flexuosa and V. multinervia both contain oxidative dimers of cinnamyl alcohols such as asarinin, cubebin, dihydrocubebin and sesamin. The former contains additionally fargesin and O-methylpiperitol, besides 7,4′-dimethoxyflavone, and the latter contains additionally hinokinin.

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Lignans are a group of compounds consisting of dimers of phenyl propane units. They are found in diverse forms distributed in a variety of plants. Sesame lignans in particular are obtained from Sesamum indicum, a highly prized oilseed crop cultivated widely in many countries in the east. The plant is the main source of clinically important antioxidant lignans such as sesamin, sesamolin, sesaminol and sesamol. These lignans exhibit antihypertensive, anticancerous and hypocholesterolemic activities as well especially in humans due to which they have become compounds of tremendous research interest in recent times. Sesamin is synthesized from shikimic acid through phenylpropanoid pathway and metabolised into enterolignans which play a pivotal role in protection against several hormone related diseases. In this paper we present an overview of current status of research on sesame lignans with respect to the analytical methods employed, the biological activities and biosynthesis of sesame lignans.
Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass?
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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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Previous studies have shown chrysin, 7-hydroxyflavone and 7,4′-dihydroxyflavone to be the most potent flavonoid inhibitors of aromatase. However, very poor oral bioavailability is a major limitation for the successful use of dietary flavonoids as chemopreventive agents. We have recently shown that methylated flavones, including 5,7-dimethoxyflavone, 7-methoxyflavone and 7,4′-dimethoxyflavone, are much more resistant to metabolism than their unmethylated analogs and have much higher intestinal absorption. In this study, we examined these fully methylated flavones as potential aromatase inhibitors for the prevention and/or treatment of hormone-dependent cancers. Whereas 5,7-dimethoxyflavone had poor effect compared to its unmethylated analog chrysin, 7-methoxyflavone and 7,4′-dimethoxyflavone were almost equipotent to their unmethylated analogs with IC₅₀ values of 2–9 μM. Thus, some fully methylated flavones appear to have great potential as cancer chemopreventive/chemotherapeutic agents.
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Citation Excerpt :
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]. Also, 5,7-DMF is a natural product [45,46] highly abundant in pepper vine leaves.
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 human oral SCC-9 cancer cells, 5,7-dimethoxyflavone and 5,7,4′-trimethoxyflavone were both 10 times more potent inhibitors of cell proliferation (IC₅₀ 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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^☆: Part 26 in the series “The Chemistry of Brazilian Myristicaceae”. For Part see ref. [1]. Based on the Doctorate thesis of S. de H. C. and the M.S. thesis of D.F. presented to Universidade de São Paulo, 1983 and 1984, respectively.

¹: Present address: Departmento de Química, Universidade Federal de alagoas, 57000 Marceió, AL.

³: Present address: Instituto de Química, Universidade de Estadual Paulista, 14800 Araraquara, SP.

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Short reportsLignoids from the fruit of three Virola species☆

Abstract

Phytochemistry

Phytochemistry

J. Pharm. Sci.

Tetrahedron Letters

Phytochemistry

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Lloydia

Short reports
Lignoids from the fruit of three Virola species☆