Seven New Phenolic Glucosides from Viburnum cylindricum

Abstract

Seven new phenolic glucosides, 2′‐O‐acetylhenryoside (1), 2′,3′‐di‐O‐acetylhenryoside (2), 2′,6′‐di‐O‐acetylhenryoside (3), 2′,3′,6′‐tri‐O‐acetylhenryoside (4), 2′,3′,4′,6′‐tetra‐O‐acetylhenryoside (5), 2‐[(2,3‐di‐O‐acetyl‐β‐D‐glucopyranosyl)oxy]‐6‐hydroxybenzoic acid (6), and 6‐hydroxy‐2‐[(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyl)oxy]benzoic acid (7), were isolated from the leaves and stems of Viburnum cylindricum, along with 26 known compounds (henryoside=2‐(β‐D‐glucopyranosyloxy)‐6‐hydroxybenzoic acid [2‐(β‐D‐glucopyranosyloxy)phenyl]methyl ester). The structures of the new compounds were established on the basis of chemical and spectroscopic evidences.

Recent Advance on Chemistry and Bioactivities of Secondary Metabolites from Viburnum Plants: An Update

“…One novel lupane triterpenoid 47 and one known compound 7 were isolated from Viburnum grandiflorum [19] . And some other known pentacyclic triterpenoids were found, including 8 , 14 , 19 , 20 , 25 , 30 and 49 from Viburnum cylindricum , [20] 13 from Viburnum setigerum , [21] 22 and 42 from Viburnum sambucinum , [22] 26 and 46 from Viburnum foetidum var. ceanothoides , [23] as well as 48 from Viburnum erosum [24] …”

“…Cyperenol acid ( 126 ) and spathulenol ( 127 ), possessing significant neuroprotective activities against H 2 O 2 ‐induced damage in SH‐SY5Y cells, as well as isololiolide ( 133 ) were isolated and identified from the leaves of V. odoratissmum [10] . In addition, a guaiane‐type sesquiterpenoid 128 was found in V. cylindricum [20] . Besides compounds 129 and 130 isolated from the roots of Viburnum lancifolium , [39] the other megastigmane‐type sesquiterpenoids including 135 and 136 from V. erosum , [24] 138 from V. foetidum var.…”

“…ceanothoides , among which, compound 218 exhibited strong inhibition against estrogen biosynthesis with IC 50 values of 1.5 μM [47] . And (+)‐licarin A ( 211 ) was reported from V. cylindricum [20] . Besides the novel norneolignan glycoside ( 208 ), [60] ten dihydrobenzofuran neolignan constituents 216 , 220 – 225 , 227 – 229 were found in V. fordiae fruits.…”

“…Besides, eight known compounds were isolated from the species V. erosum var. erosum ( 291 ), [17] V. cylindricum ( 293 , 311 and 314 ), [20,37] V. foetidum var. ceanothoides ( 295 ), [23] V. lancifolium ( 296 and 315 ) [39] and V. plicatum Thunb.…”

Compounds from Viburnum sargentii Koehne and Evaluation of Their Cytotoxic Effects on Human Cancer Cell Lines

“…The genus Viburnum is known to be rich in iridoid glycosides, characterized by a sugar moiety at C-11 and an isovaleroyl group at C-1 (Valeriana-type iridoids) that have been isolated from several Viburnum species [ 7 , 8 , 9 , 10 , 14 , 21 ]. In addition, the known phytochemical studies carried out on Caprifoliaceae species have revealed triterpenoids [ 11 ], phenolic compounds [ 12 ] and benzofuran-type lignans [ 13 ]. Phytochemical studies on V. sargenti have documented the occurrence of Valeriana-type iridoid glucosides: 7,10,2’-triacetylsuspensolide F, 1, and viburnoside IV and V [ 14 ].…”