Prenylated isoflavonoids from Rhynchosia edulis

Four new prenylated isoflavones, rhynedulins A-C (1-3) and rhynedulinal (4), were isolated by bioassay-guided fractionation of the dichloromethane bark extract of Rhynchosia edulis. Five previously described compounds, scandenal, ulexin B, cajanone, cajanin, and cyclochandalone, were also isolated. These isoflavonoids showed weak inhibitory activity towards rhodesain, the major cathepsin-L like protease in Trypanosoma brucei. They also have weak antiproliferative activity towards MCF-7 cells.     

New Isoprenylated Xanthones from Cudrania tricuspidata

A phytochemical investigation of the roots of Cudrania tricuspidata afforded three new isoprenylated xanthones, cudratricusxanthones N–P ( 1 – 3 , resp.), together with five known compounds, 4 – 8 . The structures of the new compounds were elucidated by extensive spectroscopic analyses.     

Two new isoflavonoids from Bowdichia virgilioides

Two new isoflavonoids 7,8,4'-trimethoxyisoflavone and 7,8,4'-trimethoxyisoflavanone and calycosin (7,3'-hydroxy-4'-methoxyisoflavone) were isolated from the wood of the leguminous tree Bowdichia virgilioides by usual chromatographic procedures. Besides these compounds the pterocarpane (-)-maackianin, isoliquiritigenin (4,2',4'-trihydroxychalcone), and the hydrobenzylfurane derivative bowdenol were also obtained. The structures of these new compounds were determinated by MS and 1D and 2D NMR spectral analysis.     

Neuroprotective constituents from the fruits of Maclura tricuspidata

Cudraisoflavone L ? T (1–11), cudradihydrochalcone A (12), and cudrabibenzyl A (13), together with 41 known constituents, were isolated from the fruits of Maclura tricuspidata (formerly known as Cudrania tricuspidata). Their structures were determined by spectroscopic and chemical methods including electronic circular dichroism. All isolated compounds were evaluated for their neuroprotective effects against 6-hydroxydopamine (6-OHDA)-induced cell death in human neuroblastoma SH-SY5Y cells, of these six compounds exhibited activities with EC₅₀ values of 4.5–18.6 μM. Furthermore, the neuroprotective effects against oxygen glucose deprivation (OGD)-induced cell death of all isolated constituents, together with 37 previously reported isoflavones were evaluated. Four compounds showed neuroprotective activities with EC₅₀ values of 3.5–11.9 μM.     

Synthetic and modified isoflavonoids

Water-soluble diethanolamine and morpholine salts of derivatives of 1,3-benzodioxole, 1,4-benzodioxane, and 1,5-benzodioxepane analogs of isoflavones have been synthesized.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 306–312, May–June, 1998.     

Two new isoflavonoids from the rhizomes of Belamcanda chinensis

Two new isoflavonoids, 6-methoxy-5,7,8,4'-tetrahydryoxyisoflavone (1) and 4'-methoxy -5,6-dihydroxyisoflavone-7-O-β-D-glucopyranoside (2), were isolated from the rhizomes of Belamcanda chinensis (L.) DC. Their structures were elucidated by extensive spectroscopic evidence including ID NMR, 2D NMR, MS and IR spectra.     

Isoflavonoid Profiling and Estrogen-Like Activity of Four Genista Species from the Greek Flora

As part of our ongoing research on phytoestrogens, we investigated the phytochemical profile and estrogen-like activities of eight extracts from the aerial parts of four Genista species of Greek flora using estrogen-responsive cell lines. Ethyl acetate and methanolic extracts of G. acanthoclada, G. depressa, G. hassertiana, and G. millii were obtained with accelerated solvent extraction and their phytochemical profiles were compared using ultra-high-performance liquid chromatography-high-resolution mass spectrometry (uHPLC-HRMS). Fourteen isoflavonoids, previously isolated from G. halacsyi, were used as reference standards for their identification in the extracts. Thirteen isoflavonoids were detected in both extracts of G. acanthoclada and G. hassertiana, while fewer and far fewer were detected in G. millii and G. depressa, respectively. The ethyl acetate extracts of G. hassertiana and G. acanthoclada displayed 2.45- and 1.79-fold higher, respectively, estrogen-like agonist activity in Ishikawa cells compared to MCF-7 cells at pharmacologically relevant concentrations. Both these extracts, but not that of G. depressa, contained mono- and di-O-β-d-glucosides of genistein as well as the aglycone, all three of which are known to display full estrogen-like activity at lower-than-micromolar concentrations. The possibility of using preparations rich in G. hassertiana and/or G. acanthoclada extracts as a potentially safer substitute for low-dose vaginal estrogen for menopausal symptoms is discussed.     

Four new prenylated flavonoids from the roots of Cudrania tricuspidata

Four new prenylated flavonoids, cudraflavanones E‐F (1–2) and cudraflavones F‐G (6–7), together with eight known compounds were isolated from the roots of Cudrania tricuspidata. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses, including 1D and 2D NMR, HRESIMS and CD. Copyright © 2013 John Wiley & Sons, Ltd.     

New cytotoxic cucurbitacins from the pericarps of Trichosanthes tricuspidata fruits

An extract of the fruits of Trichosanthes tricuspidata collected in North Vietnam was found cytotoxic in KB cells. A bioassay-guided fractionation led to the isolation of a series of cucurbitacins of which two are new: tricuspidatin and 2-O-glucocucurbitacin J. Their isolation and structure determination are described.     

Isolation and characterisation of bioactive isoflavonoids from the roots of Dalbergia horrida

The roots of Dalbergia horrida yielded two new isoflavanones, Dalhorridin (I) - 5,5'-dihydroxy-3',4'-methylenedioxy-5'-prenyl-6',6'-dimethyl-dihydropyrano(2',3' : 7,8)-isoflavanone and Dalhorridinin (II) - 5,7,5'-trihydroxy-3',4'-methylenedioxy-8-[5-methyl-2-(2-hydroxyisopropyl)-1,4-hexadienyl]isoflavanone along with two known isoflavones, Dalspinin and Dalspinosin. Preliminary biological screening of the enriched extract revealed that it showed analgesic, anti-inflammatory, CNS depressant and mild anti-bacterial properties.     

The rapid identification of isoflavonoids from Belamcanda chinensis by LC-NMR and LC-MS

The use of hyphenated LC-NMR and LC-MS techniques for the purpose of directly identifying the major constituents of Belamcanda chinensis was investigated. Reversed-phase isocratic chromatography was performed using an acetonitrile-water solvent system on a C18 column. The NMR spectrum yielded five main peaks, whose analysis revealed them to be 5, 6, 7, 3'-tetrahydroxy-4'-methoxyisoflavone (1), tectorigenin (2), iristectorigenin A (3), irigenin (4), and irisflorentine (5). The identification of these constituents was confirmed by performing LC-ESI-MS experiment. This study shows that hyphenated LC-NMR and LC-MS can be used for the rapid (70 min) identification of the isoflavonoids.     

Four new isoflavonoids from the stem bark of Erythrina variegata

Bioassay-directed fractionation of the stem bark extract of Erythrina variegata L. has resulted in the isolation of three new isoflavones: 5,4'-dihydroxy-8-(3,3-dimethylallyl)-2'-methoxyisopropylfurano[4,5:6,7]isoflavone (1), 5,7,4'-trihydroxy-6-(3,3-dimethylallyloxiranylmethyl)isoflavone (2), 5,4'-dihydroxy-8-(3,3-dimethylallyl)-2'-hydroxymethyl-2'-methylpyrano[5,6:6,7]isoflavone (3) and a new isoflavanone, 5,4'-dihydroxy-2'-methoxy-8-(3,3-dimethylallyl)-2',2'-dimethylpyrano[5,6:6,7]isoflavanone (4) together with seven known compounds, euchrenone b10 (5), isoerysenegalensein E (6), wighteone (7), laburnetin (8), lupiwighteone (9), erythrodiol (10), and oleanolic acid (11). The structures were determined on the basis of spectroscopic analyses and chemical evidence. The effect of these compounds on the proliferation of rat osteogenic sarcoma (UMR106) is also reported.     

Flavonoids from Carduus nutans

Zaporozh'e Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 3, p. 453, May–June, 1988.     

Flavonoids from Andrographis viscosula

Phytochemical investigation of the whole plant of Andrographis viscosula has led to the isolation of three new 2'-oxygenated flavonoids, (2R)-5-hydroxy-7,2',3'-trimethoxyflavanone (1), 7,2',5'-trimethoxyflavone (2), 5,7,2',3'-tetramethoxyflavone (3), and eight known flavones, 5,7,2'-trimethoxyflavone (4), 5,7,2',4',5'-pentamethoxyflavone (5), echioidinin (6), 5,2',6'-trihydroxy-7-methoxyflavone (7), 5-hydroxy-7,2'-dimethoxyflavone (8), echioidin (9), echioidinin 5-O-glucoside (10), and 5,2',6'-trihydroxy-7-methoxyflavone 2'-O-glucoside (11). The structures of 1-11 were elucidated by physical and spectral methods, including extensive 2D NMR studies. The presence of 2'-oxygenated flavonoids is apparently restricted to Andrographis species in Acanthaceae. Therefore, 2'-oxygenated flavonoids are regarded as chemotaxonomic markers of Andrographis genus in the Acanthaceae family.