97133-59-0Relevant articles and documents
Isolation and structural characterization of four diastereomeric lignan glycosides from Abies holophylla and their neuroprotective activity
Cha, Joon Min,Lee, Tae Hyun,Subedi, Lalita,Ha, Young Jun,Kim, Hye Ryeong,Kim, Sun Yeou,Choi, Sang Un,Kim, Chung Sub
, (2020/12/02)
Diastereomers are a type of a stereoisomer and they are often isolated as a mixture due to their similar physical properties. Through HPLC technique, we isolated four stereoisomeric lignan glycosides, holophyllosides A–D (1–4), from the trunk of Abies holophylla Maxim. which were first isolated as a mixture 25 years ago. The planar structures of 1–4 were characterized by conventional 1D and 2D NMR data analysis and their stereochemistry was determined via empirical comparison of their 13C NMR chemical shifts and 3JH-H coupling constants with the reported values, enzymatic hydrolysis followed by LC-MS analysis, and ECD experiment. Of the four stereoisomers isolated, only compounds 1, 3, and 4 showed moderate neuroprotective activity by inducing NGF secretion in C6 cells whereas 2 did not. This study highlights again the stereochemical importance of molecules in their biological and pharmaceutical application.
Neolignan glycosides from Symplocos caudata
Huo, Changhong,Liang, Hong,Zhao, Yuying,Wang, Bin,Zhang, Qingying
, p. 788 - 795 (2008/09/19)
A phytochemical investigation of the roots of Symplocos caudata Wall (Symplocaceae) resulted in isolation and characterization of four optical isomers of a neolignan glycoside (1-4), a lignan lactone glycoside (5), a phenylpropanoid glycoside (6), as well as two known compounds (7, 8). Their structures were elucidated as (7S,8S)-threo-7,9,9′-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-4-O-β-d-glucopyranoside (1), (7R,8R)-threo-7,9,9′-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-4-O-β-d-glucopyranoside (2), (7R,8S)-erythro-7,9,9′-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-4-O-β-d-glucopyranoside (3), (7S,8R)-erythro-7,9,9′-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-4-O-β-d-glucopyranoside (4), 8R,8′R-matairesinol-4-O-β-d-xylopyranosyl-(1 → 2)-O-β-d-glucopyranoside (5), 1-O-[β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6), matairesinoside (7), and (R)-1-O-(β-d-glucopyranosyl)-2-[2-methoxy-4-(ω-hydroxypropyl)-phenoxyl]-propan-3-ol (8) on the basis of spectroscopic data (1D and 2D NMR, MS and CD) and chemical evidence.
The Constituents of Conifer Needles. Dilignol Glycosides from Pinus massoniana Lamb.
Lundgren, Lennart N.,Shen, Zhaobang,Theander, Olof
, p. 241 - 248 (2007/10/02)
Seventeen dilignol glycosides and two arylglycerols have been isolated and identified from Pinus massoniana Lamb. needles.They consisted of two α-L-rhamnopyranosides of 2,3-dihydro-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-7-methoxy-5-benzofuranpropanol; two α-L-rhamnopyranosides and a β-D-glucopyranoside of 2,3-dihydro-7-hydroxy-2-(4'-hydroxy-3'-methoxyphenyl)-3-hydroxymethyl-5-benzofuranpropanol; an α-L-rhamnopyranoside, two β-D-glucopyranosides and a β-D-xyloparanoside of 1-(4'-hydroxy-3'-methoxyphenyl)-2--1,3-propanediol; an α-L-rhamnopyranoside and a β-D-glucopyranoside of 1-(4'-hydroxy-3'-methoxyphenyl)-2--1,3-propanediol; a β-D-xylopyranoside, a β-D-glucopyranoside and an α-L-arabinofuranoside of (+)-isolariciresinol; a β-D-glucopyranoside and a β-D-xylopyranoside of (-)-seco-isolariciresinol and a β-D-glucopyranoside of (+)-pinoresinol.The two arylglycerols were 1-(4-hydroxyphenyl)-1,2,3-propanetriol and 1-(4-hydroxy-3-methoxyphenyl)-1,2,3-propanetriol.In this communication, we describe the identification of a series of dilignol glycosides and two arylglycerols, isolated together with some flavonoids 1 and a new lignan, 2 from Pinus massoniana Lamb.
