548-29-8Relevant academic research and scientific papers
Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities
Sampei, Mana,Arai, Midori A.,Ishibashi, Masami
, p. 651 - 654 (2018/04/16)
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
Synthetic transformation of hydroxymatairesinol from Norway spruce (picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol
Eklund, Patrik,Sillanpaeae, Reijo,Sjoeholm, Rainer
, p. 1906 - 1910 (2007/10/03)
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.
(+)-Isolarisiresinol 3a-O-sulphate from leaves of Myrsine seguinii
Zhong, Xi-Ning,Ide, Toshinori,Otsuka, Hideaki,Hirata, Eiji,Takeda, Yoshio
, p. 1777 - 1778 (2007/10/03)
From leaves of Myrsine seguinii, (+)-isolarisiresinol 3a-O-β-D- glucopyranoside and 3a-O-sulphate were isolated. Their structures were elucidated by spectroscopic analyses.
Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG)
Schoettner, Matthias,Gansser, Dietmar,Spiteller, Gerhard
, p. 529 - 532 (2007/10/03)
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
LIGNAN GLYCOSIDES FROM PARSONSIA LAEVIGATA
Abe, Fumiko,Yamauchi, Tatsuo
, p. 1737 - 1742 (2007/10/02)
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.
THE SYNTHESES OF (R)-(+)-β-VANILLYL-γ-BUTYROLACTONE AND OF CHIRAL LIGNANS THEREFROM
Brown, Eric,Daugan, Alain
, p. 1169 - 1172 (2007/10/02)
(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.
DILIGNOL GLYCOSIDES FROM NEEDLES OF PICEA ABIES
Lundgren, Lennart N.,Popoff, Thomas,Theander, Olof
, p. 1967 - 1970 (2007/10/02)
(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.
