Studies on the Constituents of Sophora Species. IV. : Constituents of the Root of Sophora angustifolia SIEB. et ZUCC. (1)

Komatsu, Manki; Tomimori, Tsuyoshi; Hatayama, Katsuo; Mikuriya, Naoko

doi:10.1248/yakushi1947.90.4_463

Cited by 32 publications

(11 citation statements)

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“…The resulting ethyl acetate extract was further fractionated by high-speed countercurrent chromatography (HSCCC) and medium pressure liquid chromatography (MPLC) to obtain the flavonoid constituents. The structures of the flavonoids 1 ± 6 were determined with UV, IR, mass and NMR spectroscopy in comparison to published data [2], [3], [13], [14], [15], [16], [17], [18]. 1 [2,4,6,7 ± 3 H]-Estradiol (89 Ci/mmol) ([ 3 H]-E2) was obtained from Amersham Bioscience Europe (Freiburg, Germany).…”

Section: Methodsmentioning

confidence: 99%

Binding of Flavonoids fromSophora flavescensto the Rat Uterine Estrogen Receptor

Hillerns

2005

Planta med

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Prenylflavonoids and lavandulylflavonoids were isolated from the roots of Sophora flavescens Aiton (Fabaceae). The ability of 8-prenylkaempferol (1), kushenol X (2), norkurarinone (3), leachianone A (4), kushenol C (5), maackiain (6) and a root-extract of S. flavescens to displace 17beta-estradiol (E2) from rat uterine estrogen receptor (ER) was determined. Relative binding affinities (RBA) of prenylated flavonoids were weak with RBA values between 0.004 and 0.072. A lavandulyl or prenyl group at the position 8 enhanced binding to rat uterine ER.

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Section: Methodsmentioning

confidence: 99%

Binding of Flavonoids fromSophora flavescensto the Rat Uterine Estrogen Receptor

Hillerns

2005

Planta med

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“…[16] 226°C). ; 3 mL) in CH 3 OH (20 mL) was stirred at reflux for 2 h. After this time, the mixture was cooled to room temperature, and poured into ice-water.…”

Section: -Prenylkaempferol (13)mentioning

confidence: 98%

The First Total Synthesis of Sophoflavescenol, Flavenochromane C, and Citrusinol

et al. 2015

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The first total syntheses of sophoflavescenol (1), flavenochromane C (2), and citrusinol (3) were achieved. These three naturally occurring prenylated or prenyl‐cyclized flavonoids have important biological activities such as cytotoxicity against some cancer cell lines, or are lead compounds for the treatment of erectile dysfunction. Starting from 2,4,6‐trihydroxyacetophenone and substituted benzaldehydes, the synthesis involved methoxymethyl protection, aldol condensation, cyclization, oxidation with dimethyldioxirane, O‐prenylation, microwave‐assisted Claisen rearrangement, deprotection, cyclization of the prenyl group, and dehydrogenation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone. The overall yields of 1, 2, and 3 were 23, 17, and 16 %, respectively. All compounds were characterized by 1H and 13C NMR spectroscopy and MS. The key step of the synthetic route was a regioselective microwave‐assisted Claisen rearrangement to form an 8‐prenylated flavonoid from a 5‐O‐prenylflavonoid.

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“…Freudenberg and Hartmann, 1954. Hatayama and Komatsu, 1971Komatsu et al, 1970. Komatsu et al, 1969b.…”

Section: Acacia Longifoliamentioning

confidence: 99%

Flavanones and Dihydroflavonols

Bohm¹

1975

The Flavonoids

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Studies on the Constituents of Sophora Species. IV. : Constituents of the Root of Sophora angustifolia SIEB. et ZUCC. (1)

Cited by 32 publications

References 0 publications

Binding of Flavonoids fromSophora flavescensto the Rat Uterine Estrogen Receptor

Binding of Flavonoids fromSophora flavescensto the Rat Uterine Estrogen Receptor

The First Total Synthesis of Sophoflavescenol, Flavenochromane C, and Citrusinol

Flavanones and Dihydroflavonols

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