- Extracts with liver-X-receptor modulators, compounds and their use in weight control and treatment of disorders of lipid metabolism
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The invention relates to the use, or methods (especially with regard to animals, especially human, that are in need of such treatment) comprising the use, of an extract and/or one or more natural compounds from plants or parts of plants, respectively, from a genus selected from the group consisting of Schisandra, Illicium, Kadsura, Steganotaenia and Magnolia, alone or as supplement, as active ingredient in the regulation of body weight and/or fat loss and/or for the management of obesity, either in humans or in animals, to the use of said extract and/or natural compound(s) or mixtures in the manufacture of a pharmaceutical or nutraceutical formulation for the regulation of body weight and/or fat loss and/or for the management of obesity either in humans or in animals. The above extract and/or compound(s) can further be used to reduce one or more adverse metabolic parameters in a subject, such as the blood cholesterol level, especially the "bad" low density lipid (LDL) cholesterol. The invention relates also to said extract and/or compound(s) for use in the treatment or in the preparation of a medicament for the treatment of obesity and/or elevated blood cholesterol, as well as their preparation. It also relates to pharmaceutical or nutraceutical formulations comprising said extract and/or natural compound(s) which are useful in the regulation of body weight and/or fat loss and/or for the management of obesity.
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- Regio- and stereoselective 12-O-demethylation of schizandrin into gomisin T, an important intermediate to gomisin A, by Mortierella sp. (TM-I1104)
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A strain TM-I1104 identified as Mortierella sp. was discovered from soil as the most efficient fungus, which converted schizandrin into gomisin T in 91% regioselectivity by microbial 12-O-demethylation. Under optimum conditions, the yield of gomisin T reached around 80%. The faculty of 12-O-demethylation was specific on (+)-schizandrin (natural form) and the optical purity of gomisin T converted from (±)-schizandrin was 96% ee.
- Kanatani, Hirotoshi,Terabayashi, Susumu,Takeda, Shuichi,Li, Wei,Koike, Kazuo,Nikaido, Tamotsu
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p. 8467 - 8470
(2007/10/03)
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- Total Synthesis of (+)-Isoschizandrin Utilizing a Samarium(II) Iodide-Promoted 8-Endo Ketyl-Olefin Cyclization
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The 13-step synthesis of (+)-isoschizandrin reported herein features a samarium(II) iodide-promoted 8-endo ketyl-olefin coupling to assemble the eight-membered ring present in the target concomitantly with the required functionality and stereochemistry. In constructing (+)-isoschizandrin as a single atropisomer, the synthesis utilizes a kinetic resolution of a seven-membered lactone using a CBS-oxazaborolidine.
- Molander, Gary A.,George, Kelly M.,Monovich, Lauren G.
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p. 9533 - 9540
(2007/10/03)
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- Synthesis of optically pure gomisi lignans: The total synthesis of (+)-schizandrin, (+)-gomisin A, and (+)-isoschizandrin in naturally occurring forms
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The total syntheses of (+)-schizandrin (1), (+)-gomisin A (2), and (+)-isoschizandrin (3) having natural configurations were accomplished. Optically pure butyrolactones ((-)-9, (-)-31) were transformed to α-benzylidenebutyrolactones ((+)-10, (+)-32, (+)-35). By a highly efficient iron(III) perchlorate-mediated oxidative coupling reaction of 10, 32, and 35, the key intermediates with biphenyl skeletons ((-)-11, (-)-33) were constructed with high stereoselectivity. Several methods for the stereoselective introduction of the C6-hydroxyl group were examined. For the synthesis of schizandrin and gomisin A, the Mukaiyama hydration reaction of (-)-11 and(-)-33 provided the desired products with satisfactory selectivity. For the synthesis of isoschizandrin, the stereoselective epoxidation of allylic alcohol (+)-48 was successfully utilized taking advantage of its conformational features.
- Tanaka,Mukaiyama,Mitsuhashi,Maruno,Wakamatsu
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p. 4339 - 4352
(2007/10/02)
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- Synthesis of (±)-dibenzocyclooctadiene lignans, (±)-schizandrin, (±)- gomisin A and their stereoisomers, utilizing the samarium-Grignard reaction
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Several (±)-dibenzocyclooctadiene lignans, (±)-schizandrin (1a) (±)- gomisin A (1b), and their stereoisomers 2a and 2b, were synthesized by the samarium-Grignard reaction of the phenylpropyl bromides 4 and the phenylacetone derivative 5 to give the erythro and threo-butanols 6 and 7 followed by oxidative aryl-aryl coupling reaction of each butanol.
- Takeya,Ohguchi,Ara,Tobinaga
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p. 430 - 437
(2007/10/02)
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- Non-enzymic and enzymic oxygenations of a dibenzocyclooctadiene lignan, (±)-deoxyschizandrin: Implications for biosynthesis of the corresponding lignans
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Non-enzymic and enzymic oxygenation reactions of (±)-dibenzocyclooctadiene lignan, (±)-deoxyschizandrin (1) using a simple model system for mono-oxygenases Fe(MeCN)62+-Ac2O-H2O2 and rat liver S9 mix were investigated in connection with mammalian and plant metabolisms of the corresponding lignans. The non-enzymic reaction of 1 gave the two phenol acetates 4a and 5a and a quinone 6, and the enzymic reaction of 1 afforded several compounds for which three compounds characterized as 7, 8 and 9 were isolated. The latter results has implications for biosynthesis of these lignans.
- Takeya,Nakagawa,Ohguchi,Tobinaga
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p. 1694 - 1696
(2007/10/02)
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- The stereoselective first total synthesis of isoschizandrin having the natural configuration
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The total synthesis of isoschizandrin 1 having the natural configuration was accomplished confirming the structure of 1 in unambiguous manner. Starting from optically pure 9, allylic alcohol 11 was obtained in good yield, and was then converted into epoxide 12 stereoselectively. Finally, reductive C-O bond fission afforded the natural enantiomer of isoschizandrin 1.
- Tanaka,Itoh,Mitsuhashi,Maruno,Wakamatsu
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p. 605 - 608
(2007/10/02)
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- Synthesis of optically pure gomisin A and schizandrin: The first total synthesis of gomisin A and schizandrin having naturally occurring configurations
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The total synthesis of gomisin A and schizandrin having natural configurations were accomplished for the first time. The key feature of these syntheses is a highly efficient intramolecular oxidative coupling of the intermediates 9 and 21, which can be obtained as both enantiomers in optically pure forms. The manipulation of the lactone moieties of 7 and 22 afforded natural enantiomers of schizandrin and gomisin A.
- Tanaka,Mukaiyama,Mitsuhashi,Wakamatsu
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p. 4165 - 4168
(2007/10/02)
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- TWO LIGNANS FROM SCHISANDRA SPHENANTHERA
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Two new dibenzocyclooctadiene lignans, benzoylgomisin U and tigloylgomisin O were isolated from the fruits of Schisandra sphenanthera together with known lignans, gomisin U and epigomisin O.Their structures were determined by chemical and spectral studies.The structure of isoschizandrin was also revised by advanced chemical and spectral studies.
- Ikeya, Yukinobu,Sugama, Ko,Okada, Minoru,Mitsuhashi, Hiroshi
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p. 975 - 980
(2007/10/02)
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- The Constituents of Schizandra chinenzis BAILL. XV. Isolation and Structure Determination of Two New Lignans, Gomisin S and Gomisin T
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Two new dibenzocyclooctadiene lignans, gomisin S (1) and gomisin T (2) , were isolated from the fruits of Schizandra chinenzis BAILL. (Schizandraceae).On the basis of spectral methods and chemical transformations, the structures of 1 and 2 were elucidated as (6S,7S,8S,S-biar)-5,6,7,8-tetrahydro-1,2,10,11,12-pentamethoxy-6,7-dimethyl-3,8-dibenzocyclooctenediol and (6S,7S,R-biar)-5,6,7,8-tetrahydro-1,2,10,11,12-pentamethoxy-6,7-dimethyl-3,7-dibenzocyclooctenediol, respectively.Keywords - Schizandra chinenzis; Schizandraceae; dibenzocyclooctadiene; lignan; gomisin S; gomisin T; epigomisin O; (-)-gomisin K1
- Ikeya, Yukinobu,Kanatani, Hirotoshi,Hakozaki, Misako,Taguchi, Heihachiro,Mitsuhashi, Hiroshi
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p. 3974 - 3979
(2007/10/02)
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- The Constituents of Schizandra chinensis BAILL. IX. The Cleavage of the Methylenedioxyl Moiety with Lead Tetraacetate in Benzene, and the Structure of Angeloylgomisin Q
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A procedure for selective cleavage of the methylenedioxyl moiety with lead tetraacetate in dry benzene is described.Piperonylic acid methyl ester (5), 4-nitro-1,2-methylenedioxybenzene (6), 3,4-methylenedioxytoluene (7), 2,3-methylenedioxyanisole (8) and gomisin A (9) afforded protocatechuic acid (12), 4-nitrocatechol (13), 3,4-dihydroxytoluene(14), 2,3-dihydroxyanisole (15) and compound 16, respectively.The structure of angeloylgomisin Q isolated from the fruits of Schizandra chinensis BAILL. (Schizandraceae), was elucidated as 1 by using the above reaction.Keywords--cleavage of methylenedioxyl moiety; lead tetraacetate; Schizandra chinensis BAILL.; Schizandraceae; dibenzocyclooctadiene; lignan; angeloylgomisin Q
- Ikeya, Yukinobu,Taguchi, Heihachiro,Yoshioka, Itiro
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p. 2893 - 2898
(2007/10/02)
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