Prenylated flavonoids from Moghania philippinensis

Five prenylated flavonoids, 8-(1,1-dimethylallyl)genistein (1), 5,7,3',4'-tetrahydroxy-2',5'-di(3-methylbut-2-enyl)isoflavone (2), 5,7,3'-trihydroxy-2'-(3-methylbut-2-enyl)-4',5'-(3,3-dimethylpyrano)isoflavone (3), (2R)-5,2',4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4a) and (2S)-5, 2', 4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4b), were isolated from the roots of Moghania philippinensis. The structures of these compounds were determined on the basis of spectroscopic and chemical means.     

Mevalonate-derived proteins in liver regeneration

Sixteen hours after partial hepatectomy in the rat, the synthesis of mevalonate (MVA) is not committed to produce cholesterol and only partially utilized for dolichol formation. In order to investigate the fate of MVA in this replicative system, slices of the remaining liver were incubated with 5-³H-MVA. Labeled proteins from whole liver and purified nuclei were analyzed after extensive delipidation and separation by SDS-PAGE. Many MVA-derived proteins were identified at 16 hours, while only two labelled peptides were detectable at 24 hours. The radioactivity was localized in covalently bound lipid moieties. A highly labeled 26 kD peptide was detectable in the nucleus at 16 hours, suggesting its involvement in the cell cycle progression.     

Amorinin,A prenylated chromenoflavanone from Amorpha fruticosa

A diprenylated chromenoflavanone has been characterized from the root bark of Amorpha fruticosa.     

Mixtecacin,a prenylated flavanone and oaxacacin its chalcone from the roots of Tephrosia woodii

From the roots of Tephrosia woodii, a new Mexican Tephrosia species, a new prenylated flavanone, oaxacacin, and its chalcone, mixtecacin, have been isolated and their structures elucidated from their chemical properties and spectral data.     

苦参异戊烯基黄酮类化合物的化学,活性及其生物合成研究进展

综述苦参(Sophora flavecens Aiton.)异戊烯基黄酮类化合物的化学,活性及其生物合成研究进展。     

Prenylated hydroquinones: contact allergens from trichomes of Phacelia minor and P. parryi

Geranylgeranylhydroquinone and 1-oxofarnesylhydroquinone were identified as contact allergens in trichomes of Phacelia minor and P. parryi.     

Human α-synuclein modulates vesicle trafficking through its interaction with prenylated Rab acceptor protein 1

α-Synuclein has been implicated in the pathogenesis of Parkinson’s disease. Although it is highly conserved, its physiological function has not yet been elucidated in detail. In an effort to define the function of α-synuclein, interacting proteins were screened in phage display assays. Prenylated Rab acceptor protein 1 (PRA1) was identified as an interacting partner. A selective interaction between α-synuclein and PRA1 was confirmed by coimmunoprecipitation and GST pull-down assays. PRA1 and α-synuclein were colocalized in N2a neuronal cells. Cotransfection of α-synuclein and PRA1 caused vesicles to accumulate in the periphery of the cytosol in neuronal cells, suggesting that overexpression of α-synuclein hinders proper vesicle trafficking and recycling as a result of the interaction between α-synuclein and PRA1.     

New synthesis of artepillin C,a prenylated phenol,utilizing lipase-catalyzed regioselective deacetylation as the key step

We have synthesized artepillin C, a diprenylated p-hydroxycinnamate originally isolated from Brazilian propolis and exhibiting antioxidant and antitumor activities, from 2,6-diallylphenol. Replacement of the terminal vinyl with 2,2-dimethylvinyl group by olefin cross-metathesis and subsequent transformation yielded 2,6-diprenyl-1,4-hydroquinone diacetate. Candida antarctica lipase B-catalyzed deacetylation in 2-propanol regioselectively removed the less hindered acetyl group to give 2,6-diprenyl-1,4-hydroquinone 1-monoacetate. After triflation of the liberated 4-hydroxy group, a three-carbon side chain was introduced by palladium-mediated alkenylation with methyl acrylate. Final hydrolysis of the esters furnished artepillin C.     

Fungitoxic dihydrofuranoisoflavones and related compounds in white lupin,Lupinus albus

Chromatographic investigation of a methanolic extract of white lupin roots has revealed the presence of six new dihydrofuranoisoflavones (lupinisoflavones A-F). Three monoprenylated (3,3-dimethylallyl-substituted) isoflavones (wighteone, luteone and licoisoflavone A), two diprenylated isoflavones [6,3′-di(3,3-dimethylallyl)genistein (lupalbigenin) and 6,3′-di(3,3-dimethylallyl)-2′-hydroxygenistein (2′-hydroxylupalbigenin)] and two pyranoisoflavones (parvisoflavone B and licoisoflavone B) have also been isolated from the same source. In addition to genistein, leaf extracts of L. italbus contain 3′-O-methylorobol which is presumed to be the precursor of lupisoflavone [5,7,4′-trihydroxy-3′-methoxy-6-(3,3-dimethylallyl)isoflavone]. Probable biogenetic relationships between the prenylated, and dihydrofurano-and pyrano-substituted isoflavones in roots and leaves of L. albus are briefly discussed.