Structure-antioxidant activity relationships of flavonoids and phenolic acids

http://amborella.net/2010PlantSystematics/DATA/3-24-APG%202003%20Bot%20J%20Linn%20Soc%20APGII.pdf

An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II

Flavonoids are nearly ubiquitous in plants and are recognized as the pigments responsible for the colors of leaves, especially in autumn. They are rich in seeds, citrus fruits, olive oil, tea, and red wine. They are low molecular weight compounds composed of a three-ring structure with various substitutions. This basic structure is shared by tocopherols (vitamin E). Flavonoids can be subdivided according to the presence of an oxy group at position 4, a double bond between carbon atoms 2 and 3, or a hydroxyl group in position 3 of the C (middle) ring. These characteristics appear to also be required for best activity, especially antioxidant and antiproliferative, in the systems studied. The particular hydroxylation pattern of the B ring of the flavonoles increases their activities, especially in inhibition of mast cell secretion. Certain plants and spices containing flavonoids have been used for thousands of years in traditional Eastern medicine. In spite of the voluminous literature available, however, Western medicine has not yet used flavonoids therapeutically, even though their safety record is exceptional. Suggestions are made where such possibilities may be worth pursuing.

The Effects of Plant Flavonoids on Mammalian Cells:Implications for Inflammation, Heart Disease, and Cancer

Estimation of total flavonoid content in propolis by two complementary colorimetric methods

Antimicrobial activity of flavonoids

Flavonoids, such as daidzein and genistein, present in dietary plants like soybean, have unique chemical properties with biological activity relevant to cancer. Many flavonoids and polyphenols, including resveratrol in red wine and epigallocatechin gallate in green tea, are known antioxidants. Some of these compounds have estrogenic (and antiestrogenic) activity and are commonly referred to as phytoestrogens. A yeast-based estrogen receptor (ER) reporter assay has been used to measure the ability of flavonoids to bind to ER and activate estrogen responsive genes. Recently, estrogenic compounds were also shown to trigger rapid, nongenomic effects. The molecular mechanisms, however, have not been completely detailed and little information exists regarding their relevance to cancer progression. As a preliminary step toward elucidating rapid phytoestrogen action on breast cancer cells, we investigated the effect of 17-beta estradiol (E2), genistein, daidzein and resveratrol on the activation status of signaling proteins that regulate cell survival and invasion, the cell properties underlying breast cancer progression. The effect of these estrogenic compounds on the activation, via phosphorylation, of Akt/protein kinase B (Akt) and focal adhesion kinase (FAK) were analyzed in ER-positive and -negative human breast cancer cell lines. E2, genistein and daidzein increased whereas resveratrol decreased both Akt and FAK phosphorylation in nonmetastatic ER-positive T47D cells. In metastatic ER-negative MDA-MB-231 cells, all estrogenic compounds tested increased Akt and FAK phosphorylation. The inhibitory action of resveratrol on cell survival and proliferation is ER dependent. Therefore, all estrogenic compounds tested, including resveratrol, may exert supplementary ER-independent nongenomic effects on cell survival and migration in breast cancer cells.

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Flavonoid Effects Relevant to Cancer

Sixteen volatile compounds were identified from the n-hexane extract of the buds of Syzygium aromaticum by using gas chromatography-mass spectroscopy (GC-MS). The major components were eugenol (71.56 %) and eugenol acetate (8.99 %). The dichloromethane extract of the buds yielded limonin and ferulic aldehyde, along with eugenol. The flavonoids tamarixetin 3- O-b-D-glucopyranoside, ombuin 3-O-b-D-glucopyranoside and quercetin were isolated from the ethanol extract; identifications of all these compounds were established by chemical and spectroscopic methods including 1D and 2D NMR. This is the first report of limonin, ferulic aldehyde and these flavonoids from this plant. All extracts and the isolated flavonoids showed strong antioxidant activity against 1, 2-diphenyl picrylhydrazyl (DPPH). Among the tested extracts, the ethanol extract of the clove buds showed remarkable scavenging activity, as compared with synthetic antioxidants such as butylated hydroxyl toluene (BHT). The ethanol extract of clove showed remarkable hepatoprotective activity against paracetamol-induced liver injury in female rats.

ChemiCal Constituents of Clove ( Syzygium aromaticum, f am. Myrtaceae) and their antioxidant aCtivity

Ten aglycones and six glycosides of luteolin and apigenin were identified from the leaves of Salvia palaestina Bentham (Labiatae). Among them cirsimaritin showed a high activity against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, and Pseudomonas aeruginosa, while the others have little or no activity against the same bacterial strains.

Antibacterial activity studies of flavonoids from Salvia palaestina.

Methylated flavonols in Larrea cuneifolia

The restricted distributions of some classes of secondary metabolites in the angiosperms make them valuable taxonomic characters in assessing systematic relationships at higher levels of classification. Yet, for several reasons, secondary metabolites have not, until recently, been widely used as taxonomic characters above the family level. In this paper, the distributions of a number of classes of secondary compounds are discussed with reference to four recently published systems of higher angiosperm classification: Cronquist's of 1981, Dahlgren's of 1980, Takhtajan's of 1980 and Thome's of 1981. Some of the problems faced in choosing and using secondary metabolite data for systematic purposes (including the effects of our increasing understanding of their functional significance) are covered as well. Among the classes of secondary compounds treated here, benzylisoquinoline alkaloids, iridoids and be–talains are shown to be the most important systematic markers used at present at higher levels of classification, although glucosinolates, polyacetylenes and some other types of alkaloids are also demonstrated to be valuable criteria for making taxonomic judgments above the family rank. In addition, certain terpenoids, flavonoids, phenolics, cyanogenic glycosides and non–protein amino acids are illustrated to be of systematic use in particular cases.

Tom J. Mabry

Papers

Flavonoid Effects Relevant to Cancer

ChemiCal Constituents of Clove ( Syzygium aromaticum, f am. Myrtaceae) and their antioxidant aCtivity

Antibacterial activity studies of flavonoids from Salvia palaestina.

Methylated flavonols in Larrea cuneifolia

Secondary metabolites and the higher classification of angiosperms [Systematic use, taxonomic markers]