182265-17-4Relevant academic research and scientific papers
Studies on the constituents of Lonicera species. X. Neolignan glycosides from the leaves of Lonicera gracilipes var. glandulosa MAXIM.
Matsuda, Noriko,Kikuchi, Masao
, p. 1676 - 1679 (1996)
Four new 8-O-4'-neolignan glycosides, 4,9,9'-trihydroxy-3,3'-dimethoxy- 8-O-4'-neolignan-7-O-β-D-glucopyranosides [7S,8S-threo form (1) and 7S,8R- erythro form (2)], 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'- neolignan-3'-O-β-D-glucopyranoside (3
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.
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
Wu, Hao-Yue,Ke, Jia-Ping,Wang, Wei,Kong, Ya-Shuai,Zhang, Peng,Ling, Tie-Jun,Bao, Guan-Hu
, (2019/11/03)
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.
Glycosides from the root of Iodes cirrhosa
Gan, Maoluo,Zhang, Yanling,Lin, Sheng,Liu, Mingtao,Song, Weixia,Zi, Jiachen,Yang, Yongchun,Fan, Xiaona,Shi, Jiangong,Hu, Jinfeng,Sun, Jiandong,Chen, Naihong
experimental part, p. 647 - 654 (2009/04/04)
Seven new neolignan glycosides (1-7), two arylglycerol glycosides (8, 9), and 18 known glycosides have been isolated from an ethanolic extract of the root of Iodes cirrhosa. Their structures including absolute configurations were determined by spectroscop
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.
