- Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities
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Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca b
- Sampei, Mana,Arai, Midori A.,Ishibashi, Masami
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p. 651 - 654
(2018/04/16)
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- Synthetic transformation of hydroxymatairesinol from Norway spruce (picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol
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We have developed a method for the transformation of hydroxymatairesinol to optically pure (+)-lariciresinol and (+)-cyclolariciresinol via the hitherto unreported lignan 7-hydroxysecoisolariciresinol. The two naturally occurring isomers of hydroxymatairesinol were reduced with LiAlH4 to a mixture of two epimers of 7-hydroxysecoisolariciresinol, which were further selectively transformed to (+)-lariciresinol and (+)-cyclolariciresinol by an acid catalysed intramolecular cyclisation reaction. The structure of the major isomer of 7-hydroxysecoisolariciresinol was confirmed by X-ray crystallography and thereby also the absolute configurations of the two isomers of hydroxymatairesinol were unambiguously proven. Optical purities were determined by chiral HPLC-MS/MS and optical rotation measurements.
- Eklund, Patrik,Sillanpaeae, Reijo,Sjoeholm, Rainer
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p. 1906 - 1910
(2007/10/03)
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- (+)-Isolarisiresinol 3a-O-sulphate from leaves of Myrsine seguinii
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From leaves of Myrsine seguinii, (+)-isolarisiresinol 3a-O-β-D- glucopyranoside and 3a-O-sulphate were isolated. Their structures were elucidated by spectroscopic analyses.
- Zhong, Xi-Ning,Ide, Toshinori,Otsuka, Hideaki,Hirata, Eiji,Takeda, Yoshio
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p. 1777 - 1778
(2007/10/03)
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- Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG)
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Polar extracts of the stinging nettle (Urtica dioica L) roots contain the lignans (+)-neoolivil, (-)-secoisolariciresinol, dehydrodiconiferyl alcohol, isolariciresinol, pinoresinol, and 3,4-divanillyltetrahydrofuran. These compounds were either isolated f
- Schoettner, Matthias,Gansser, Dietmar,Spiteller, Gerhard
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p. 529 - 532
(2007/10/03)
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- LIGNAN GLYCOSIDES FROM PARSONSIA LAEVIGATA
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Bis-O-rhamnosides of lariciresinol, 5,5'-dimethoxylariciresinol, and secoisolariciresinol, and pinoresinolapiosyl(1->2)-glucoside were isolated from Parsonsia laevigata.Key Word Index - Parsonsia laevigata; Apocynaceae; lariciresinol; lignan rhamnoside; pinoresinol-apiosylglucoside.
- Abe, Fumiko,Yamauchi, Tatsuo
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p. 1737 - 1742
(2007/10/02)
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- THE SYNTHESES OF (R)-(+)-β-VANILLYL-γ-BUTYROLACTONE AND OF CHIRAL LIGNANS THEREFROM
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(R)-(+)-β-vanillyl-γ-butyrolactone was obtained in 4 steps including a resolution, from vanillin and dimethyl succinate, and was used for the total syntheses of 5 naturally occurring and optically active lignans such as (+)-isolariciresinol 20.
- Brown, Eric,Daugan, Alain
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p. 1169 - 1172
(2007/10/02)
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- DILIGNOL GLYCOSIDES FROM NEEDLES OF PICEA ABIES
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(2R,3R)-2,3-dihydro-2-(4'-hydroxy-3'-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranpropanol 4'-O-β-D-glucopyranoside , (2R,3R)-2,3-dihydro-7-hydroxy-2-(4'-hydroxy-3'-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranpropanol 4'-O-β-D-glucopyranoside and 4'-O-α-L-rhamnopyranoside, 1-(4'-hydroxy-3'-methoxyphenyl)-2--1,3-propanediol 1-O-β-D-glucopyranoside and 4'-O-β-D-xylopyranoside4, 2,3-bis-1,4-butanediol 1-O-β-D-glucopyranoside and (1R,2S,3S)-1,2,3,4-tetrahydro-7-hydroxy-1-(4'-hydroxy-3'-methoxyphenyl) -6-methoxy-2,3-naphthalenedimethanol α2-O-β-D-xylopyranoside have been isolated from needles of Picea abies and identified. - Keywords: Picea abies; Pinaceae; dilignol glycosides; dihydrodehydrodiconiferyl alcohol; ( - )-isolariciresinol.
- Lundgren, Lennart N.,Popoff, Thomas,Theander, Olof
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p. 1967 - 1970
(2007/10/02)
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