- Neolignan glycosides from Symplocos caudata
-
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.
- Huo, Changhong,Liang, Hong,Zhao, Yuying,Wang, Bin,Zhang, Qingying
-
-
Read Online
- Isolation and structural characterization of four diastereomeric lignan glycosides from Abies holophylla and their neuroprotective activity
-
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.
- Cha, Joon Min,Lee, Tae Hyun,Subedi, Lalita,Ha, Young Jun,Kim, Hye Ryeong,Kim, Sun Yeou,Choi, Sang Un,Kim, Chung Sub
-
-
- Discovery of Neolignan Glycosides with Acetylcolinesterase Inhibitory Activity from Huangjinya Green Tea Guided by Ultra Performance Liquid Chromatography-Tandem Mass Spectrometry Data and Global Natural Product Social Molecular Networking
-
Global Natural Product Social feature-based networking was applied to follow the phytochemicals, including nine flavonoid glycosides, six catechins, and three flavonols in Huangjinya green tea. Further, a new 8-O-4′-type neolignan glycoside, camellignanoside A (1), and 15 known compounds (2-16) were isolated through a variety of column chromatographies, and the structure was elucidated extensively by ultra performance liquid chromatography-quadrupole-time-of-flight-tandem mass spectrometry, 1H and 13C nuclear magnetic resonance, heteronuclear single-quantum correlation, heteronuclear multiple-bond correlation, 1H-1H correlation spectroscopy, rotating frame nuclear Overhauser effect spectroscopy, and Nuclear Overhauser effect spectroscopy, and circular dichroism spectroscopies. Compounds 1 and 2 showed acetylcolinesterase inhibition activity, with IC50 = 0.75 and 0.18 μM, respectively.
- Wu, Hao-Yue,Ke, Jia-Ping,Wang, Wei,Kong, Ya-Shuai,Zhang, Peng,Ling, Tie-Jun,Bao, Guan-Hu
-
-
- Studies on the Glycosides of Epimedium grandiflorum MORR. var. thunbergianum (MIQ.) II
-
Two new glycosides of ionone derivatives, icarisides B3 (2) and B4 (3), as well a new phenylethanoid glycoside, icariside D1 (4), and two new lignan glycosides, icarasides E1 (12) and E2 (13), have be
- Miyase, Toshio,Ueno, Akira,Takizawa, Nobuo,Kobayashi, Hiromi,Oguchi, Hiroko
-
p. 3713 - 3719
(2007/10/02)
-
- The Constituents of Conifer Needles. Dilignol Glycosides from Pinus massoniana Lamb.
-
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.
- Lundgren, Lennart N.,Shen, Zhaobang,Theander, Olof
-
p. 241 - 248
(2007/10/02)
-