- Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
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A new cyclic acetal (1) of marmin (6′,7′-dihydroxy-7- geranyloxycoumarin), two new cyclic acetals (5, 6) of 6′,7′- dihydroxybergamottin, and the known compounds marmin (2), 7-geranyloxycoumarin (3), bergamottin (4), and 6′,7′-dihydroxybergamottin (7) were
- Cesar, Thais B.,Manthey, John A.,Myung, Kyung
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- Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium
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We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), a-ionone (3), β-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/ H2O2/pyridine. The reactions, performed in CH2Cl2/H2O at 25 °C, have shown good regioand stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), 1H-, 13C-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects.
- Amato, Maria E.,Ballistreri, Francesco P.,Pappalardo, Andrea,Tomaselli, Gaetano A.,Toscano, Rosa M.,Sfrazzetto, Giuseppe Trusso
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p. 13754 - 13763
(2014/01/06)
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- SYNTHESIS OF SPIRO ORTHO ESTERS, SPIRO ORTHO CARBONATES, AND INTERMEDIATES
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Ortho esters and ortho carbonates can be produced by alkylating esters and carbonates with, for example, the hexafluorophosphate salt of a trialkyl oxonium ion. The spiro species are useful intermediates in the synthesis of complex organic molecules. Synt
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- Paradisin C: A new CYP3A4 inhibitor from grapefruit juice
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A new furanocoumarin derivative, paradisin C, was isolated from grapefruit juice as an inhibitor of cytochrome P450 (CYP) 3A4. Its stereochemistry was elucidated by spectroscopic methods. The stereochemistries of 17,18-dihydroxybergamottin and 17-epoxybergamottin were also elucidated.
- Ohta, Tomihisa,Maruyama, Takuro,Nagahashi, Minoru,Miyamoto, Yasuyo,Hosoi, Shinzo,Kiuchi, Fumiyuki,Yamazoe, Yasushi,Tsukamoto, Sachiko
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p. 6631 - 6635
(2007/10/03)
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