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Isoswertiajaponin 2''-O-beta-arabinopyranoside and other flavone-C-glycosides from the Antarctic grass Deschampsia antarctica.

The major falvonoid constituents of the Antarctic grass, Deschampsia antarctica, are shown to be the C-glycosylfavones, isoswertiajaponin (7-O-methylorientin) 2''-O-beta-arabinopyranoside and orientin. These are accompanied by lower levels of orientin 2''-O-arabinopyranoside, isoswertisin (7-O-methylvitexin) 2''-O-beta-arabinopyranoside, acylated derivatives, isoswertisin, isoswertiajaponin and tricin. A preliminary study suggests that the overall level of flavonoids in Deschampsia increases during the Antarctic mid-summer.

Antarctic Regions↗

An 8-hydroxylated external flavone and its 8-O-glucoside from Becium grandiflorum.

The major vacuolar flavonoid of a greenhouse-grown plant of Becium grandiflorum has been identified as the 8-O-glucoside of isothymusin (5,8,4'-trihydroxy-6,7-dimethoxyflavone), while the major external flavonoids in the diethyl ether surface wash of the same plant are found to be isothymusin and cirsimaritin (5,4'-dihydroxy-7,8-dimethoxyflavone). Although isothymusin is already known as a conversion product of thymusin (5,6,4'-trihydroxy-6,7-dimethoxyflavone) formed by means of the Wessely-Moser rearrangement, this is the first report of isothymusin as a plant constituent, both as aglycone and glycoside. The biogenetic and chemotaxonomic implications of the occurrence of these flavonoids in B.grandiflorum are briefly discussed.

Chromatography, High Pressure Liquid↗

Antimycobacterial flavones from Haplopappus sonorensis.

Crude extracts of Haplopappus sonorensis (A. Gray) S.F. Blake (Asteraceae), showed activity against Mycobacterium tuberculosis H(37)Rv. By assay-guided fractionation, 5-hydroxy-3,7,4'-trimethoxyflavone (1). 5,7-dihydroxy-3,4'-dimethoxyflavone (2). and 5,4'-dihydroxy-3,7-dimethoxyflavone (3). were identified as the antimycobacterial principles. Compound 2 was the most active compound.

Antitubercular Agents↗

Phytochemical flavones isolated from Scutellaria barbata and antibacterial activity against methicillin-resistant Staphylococcus aureus.

A crude extract prepared from Scutellaria barbata D. Don (Lamiaceae) was analyzed in the effort to discover antibacterial compounds against high-level strains of methicillin-resistant Staphylococcus aureus (MRSA). Apigenin and luteolin were isolated from the plant as active constituents against the bacteria. These flavonoid congeners were selectively toxic to S. aureus, including the MRSA and methicillin-sensitive S. aureus strains.

Anti-Bacterial Agents↗

Eupatilin, a pharmacologically active flavone derived from Artemisia plants, induces apoptosis in human promyelocytic leukemia cells.

Extracts of the whole herb of Artemisia asiatica Nakai (Asteraceae) have been used in traditional oriental medicine for the treatment of inflammation, cancer and other disorders. In the present work, we have evaluated the apoptosis-inducing capability of eupatilin (5,7-dihydroxy-3,4,6-trimethoxyflavone), a pharmacologically active ingredient of A. asiatica, in cultured human promyelocytic leukemia (HL-60) cells. Thus, eupatilin exhibited concentration-dependent inhibitory effects on viability and DNA synthesis capability of HL-60 cells. The anti-proliferative effect of eupatilin was attributable to its apoptosis-inducing activity as determined by characteristic nuclear condensation, in situ terminal end-labeling of fragmented DNA (TUNEL), release of mitochondrial cytochrome c into cytoplasm, proteolytic activation of caspases-9, -3, and -7, and cleavage of poly(ADP-ribose)polymerase. Eupatilin-induced HL-60 cell apoptosis does not appear to be mediated via alteration in Bcl-2/Bax-2. Taken together, the above findings suggest that eupatilin has chemopreventive and cytotoxic effects.

Antineoplastic Agents↗