- Three new isoflavonoid glycosides from Lupinus luteus and L. polyphyllus x arboreus
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As part of our studies on leguminous plants, we examined the ingredients of Lupinus luteus L. and L. polyphyllus x arboreus hybrid, and three new isoflavonoid glycosides together with six known ones were isolated. They were determined to be 8-C-glucopyranosylgenistein 4'-O-glucopyranoside (1), 5-O-methylgenistein 4', 7-di-O-glucopyranoside (2), 2'-hydroxygenistein 4', 7-di-O-glucopyranoside (3) by spectroscopic and chemical methods. It was also shown that the isoflavonoid distributions in the two species were differed.
- Watanabe,Kinjo,Nohara
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- Total synthesis of apios isoflavones and investigation of their tyrosinase inhibitory activity
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Apios isoflavone glucosides 1 and 2 were synthesized for the first time via Friedel–Crafts reaction, Bischler–Napieralski-type cyclization, and phase-transfer catalyzed glycosylation as the key steps. In addition, aglycones 4 and 5 and related natural iso
- Asebi, Nana,Nihei, Ken-ichi
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- Total synthesis of the pyranocoumaronochromone lupinalbin H
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The pyranocoumaronochromone lupinalbin H was synthesized in three major steps, which involved preparation of 2′-hydroxygenistein by the Suzuki-Miyaura reaction, followed by oxidative cyclodehydrogenation into lupinalbin A. The final step was the regiospec
- Selepe, Mamoalosi A.,Drewes, Siegfried E.,Van Heerden, Fanie R.
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p. 8654 - 8658
(2011/12/01)
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- Facile synthesis of polyhydroxycoumaronochromones with quinones: Synthesis of alkylpolyhydroxy- and alkoxycoumaronochromones from 2′-hydroxyisoflavones
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4′,5,7-Trihydroxy- or 8-alkyl-4′,5,7-trihydroxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2′-hydroxyisoflavones with o-chloranil under mild conditions. By contrast, alkoxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2′-hydroxyisoflavones with DDQ.
- Tsukayama, Masao,Oda, Akihiro,Kawamura, Yasuhiko,Nishiuchi, Masaki,Yamashita, Kazuyo
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p. 6163 - 6166
(2007/10/03)
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- New 5-O-Methylisoflavones in the Roots of Yellow Lupin (Lupinus luteus L. cv. Barpine)
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In addition to 5-O-methylgenistein (1), a further investigation of the isoflavonoid constituents in roots of the yellow lupin (Lupinus luteus L. cv.Barpine) has yielded five new 5-O-methylisoflavones named barpisoflavone A (2), 5-O-methyl-lupiwighteone (3
- Tahara, Satoshi,Hashidoko, Yasuyuki,Ingham, John L.,Mizutani, Junya
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p. 1809 - 1820
(2007/10/02)
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- Synthesis of Licoisoflavone A and Related Compounds
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2',4',5,7-Tetrahydroxyisoflavone was partially benzoylated with benzoyl chloride to give 7-benzoyloxy-2',4',5-trihydroxyisoflavone.The condensation of the 7-(benzoyloxy)isoflavone with 2-methyl-3-buten-2-ol, followed by the hydrolysis of the resultant 3'-(3-methyl-2-butenyl)isoflavone gave licoisoflavone A.Its 5'-(3-methyl-2-butenyl) isomer was also synthesized from 5-benzoyloxy-2',4',7-trihydroxyisoflavone in a similar manner.
- Tsukayma, Masao,Fujimoto, Kunihiro,Horie, Tokunaru,Masumura, Mitsuo,Nakayama, Mitsuru
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p. 136 - 141
(2007/10/02)
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- SYNTHESES OF LICOISOFLAVONE A AND 5'-ALKENYL ISOMER
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2',4',5,7-Tetrahydroxyisoflavone was partially benzoylated with benzoyl chloride to give 7-benzoyloxy-2',4',5-trihydroxyisoflavone.The condensation of 7-benzoyloxyisoflavone with 2-methyl-3-buten-2-ol, followed by the hydrolysis of the resultant 3'-(3-met
- Tsukayama, Masao,Fujimoto, Kunihiro,Horie, Tokunaru,Yamashita, Yoshiro,Masumura, Mitsuo,Nakayama, Mitsuru
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p. 675 - 678
(2007/10/02)
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