Lignan and neolignan glucosides, and tachioside 2′-O-4″-O-methylgallate from the leaves of Glochidion rubrum

Abstract

Thirteen compounds (1-13) were isolated from a MeOH extract of leaves of Glochidion rubrum. The structures of four new compounds were elucidated to be (-)-isolariciresinol 2a-O-beta-D-glucopyranoside (1), (7R,8S)- and (7R,8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan 7-O-beta-D-glucopyranosides (2 and 3, respectively), and tachioside 2'-O-4''-O-methylgallate (4) on detailed inspection of one- and two-dimensional NMR spectral data.

Anti-inflammatory effect of a triterpenoid from Balanophora laxiflora: results of bioactivity-guided isolation

“…S1), these compounds were identified as (21α)-22-hydroxyhopan-3-on ( 1 ) ( Tanaka and Matsunaga 1992 ), pinoresinol ( 2 ) ( Páska et al., 2002 ), salicifoliol ( González et al., 1989 ), ethyl caffeate ( 4 ) ( Etzenhouser et al. 2001a , 2001b ), 1- O - E -caffeoyl- β - d -glucopyranose ( 5 ) ( Chiou et al., 2011 ), (8S,7′R,8′S)-isolariciresinol 4-O-β- d -glucopyranoside ( 6 ) ( Yoshikawa et al., 1997 ), coniferin ( 7 ) ( Chen et al., 2005 ), (8R,7′S,8′R)-lariciresinol 4′-O-β- d -glucopyranoside ( 8 ) ( Kikuchi and Sugiyama 1993 ; Sugiyama and Kikuchi 1993 ), (8S,8′S)-secoisolariciresinol 9′-O-β- d -glucopyranoside ( 9 ) ( Yuan et al., 2002 ), (8R,8′R)-secoisolariciresinol 4-O-β- d -glucopyranoside ( 10 ) ( Yuan et al., 2002 ), (8S,7′R,8′S)-isolariciresinol 9-O-β- d -glucopyranoside ( 11 ) ( Cai et al., 2009 ), coniferyl aldehyde β- d -glucopyranoside ( 12 ) ( Kanchanapoom et al., 2001 ), 4-O-galloyl-1-O-E-caffeoyl-β- d -glucopyranose ( 13 ) ( Jiang et al., 2001a , b ), 6-O-galloyl-1-O-E-caffeoyl-β- d -glucopyranose ( 14 ) ( Aliotta et al., 1992 ; Kamiya et al., 2002 ), and deacetyl asperulosidic acid ( 15 ) ( Satake et al., 2002 ) ( Figure 2 ).

Figure 2 Chemical structure of compounds from Balanophora laxiflora (1–15).

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Phenolic constituents from twigs of Aleurites fordii and their biological activities

“…The other known compounds were identified as 7 R ,8 S -dihydrodehydrodiconiferyl alcohol 4- O -β-ᴅ-glucopyranoside ( 4 ) [ 26 ], icariside E 4 ( 5 ) [ 17 ], isomassonianoside B ( 6 ) [ 27 ], sakuraresinol ( 7 ) [ 28 ], selaginellol 4′- O -β-ᴅ-glucopyranoside ( 8 ) [ 21 ], 7 R ,8 R -4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8- O -4′-neolignan-7- O -β-ᴅ-glucopyranoside ( 9 ) [ 29 ], 7 R ,8 R -4,9,9′-trihydroxy-3,3′-dimethoxy-8- O -4′-neolignan ( 10 ) [ 30 ], 7 S ,8 S -4,9,9′-trihydroxy-3,3′-dimethoxy-8- O -4′-neolignan ( 11 ) [ 30 ], 7 R ,8 S -4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8- O -4′-neolignan-7- O -β-ᴅ-glucopyranoside ( 12 ) [ 29 ], 7 S ,8 R -4,7,9-trihydroxy-3,3′-dimethoxy-8- O -4′-neolignan-9′- O -β-ᴅ-glucopyranoside ( 13 ) [ 31 ], buddlenol A ( 14 ) [ 32 ], aleuritin ( 17 ) [ 33 ], fraxinol ( 18 ) [ 34 ], and 5,6,7-trimethoxycoumarin ( 19 ) [ 34 ] based on the comparison of their spectroscopic data and specific rotation with the reported data.…”

Theagalloflavic Acid, a New Pigment Derived from Hexahydroxydiphenoyl Group, and Lignan Oxidation Products Produced by Aerobic Microbial Fermentation of Green Tea

“…S2). Based on a comparison of spectroscopic data, the known compounds were identified to be 4-[(2R,3R)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl]-3,6-dihydro-6-oxo-(2R)-2H-pyran-2-carboxylic acid (4), 10) teadenol A (5), 11) 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid (6), 13) 2,4-dihydroxy-6-(4-hydroxybenzoyloxy)-benzoic acid (7), 13) 3-O-acetyl-(−)-epicatechin (8), 14) epiafzelechin (9), 15) cis-epigallocatechin-3-O-p-coumarate (10), 16) trans-epigallocatechin-3-O-p-coumarate (11), 16) procyanidin B4 (12), 17) epiafzelechin-(4β 8)-epicatechin-3-O-gallate (13), 18) epiafzelechin-(4β 8)-epicatechin (14), 19) procyanidin B-5 (15), 20) epiafzelechin-(4β 6)-epicatechin-3-O-gallate (16), 18) luteolin (17), 21) tricetin (18), 22) apigenin 6-C-β-glucopyranoside (19), 23) kaempferol (20), 24) quercetin (21), 24) myricetin (22), 25) dihydromyricetin (23), 26) (7R*,8S*)-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan (24), 27) 4-hydroxybenzoic acid (25), 4-hydroxybenzoic acid methyl ester (26), and p-coumaric acid (27). In this study, four major tea catechins were not purified.…”