Phenolic Compounds fromViburnum cylindricum

Abstract

Three novel quinic acid esters, i.e., neochlorogenic acid methyl ester (1), cryptochlorogenic acid methyl ester (2), and chlorogenic acid methyl ester (3), were isolated from Viburnum cylindricum. Their structures were determined by spectroscopic analysis. Viburnum cylindricum is distributed in tropical Asia, which has been used as folk medicine to treat different diseases, such as cough, diarrhea, rheumatoid arthritis, and tumefaction [8]. A literature search revealed that no previous phytochemical and pharmacological study has been undertaken of this species. As part of ongoing phytochemical and pharmacological investigations of the genus Viburnum, we collected the stems and leaves of V. cylindricum from Kunming in Yunnan province. From the AcOEt extract, three new quinic acid esters besides several known compounds were isolated: neochlorogenic acid methyl ester 1 ) (1), cryptochlorogenic acid methyl ester

Chemical constituents from the leaves of Ilex paraguariensis inhibit human neutrophil elastase

“…Thus, the structure of 1 was elucidated as 5-methoxymethyl-1-[2-(4-hydroxyphenyl)-ethyl]-1H-pyrrole-2-carbaldehyde, and named as pyrrolezanthine-6-methyl ether. Other known compounds were identified as caffeine (2) (Elisabeth et al, 1991), theobromine (3) (Zhao et al, 2007), p-hydroxy cinnamic acid (4) (Kuo et al, 2007), caffeic acid methyl ester (5) (Oh et al, 1996), 3, 4-dihydroxybenzoic acid (6) (Ban et al, 2007), caffeic acid (7) (Kim et al, 2007), quercetin (8) , neochlorogenic acid methyl ester (9), cryptochlorogenic acid methyl ester (10), chlorogenic acid methyl ester (11) (Zhu et al, 2005), 3, 5-dicaffeoylquinic acid methyl ester (12) (Choi et al, 2003), 3, 4-dicaffeoylquinic acid methyl ester (13), 3, 5-dicaffeoylquinic acid (14), 4, 5-dicaffeoylquinic acid methyl ester (15), 3, 4-dicaffeoylquinic acid (16) (Basnet et al, 1996;Tatefuji et al, 1996), rutin (17) and kaempferol 3-Orutinoside (18) (Han et al, 1996) by direct comparison of their physical and spectral data with those reported in the literature.…”

Medicinal Flowers. XXXX.¹⁾ Structures of Dihydroisocoumarin Glycosides and Inhibitory Effects on Aldose Reducatase from the Flowers of <i>Hydrangea macrophylla</i> var. <i>thunbergii</i>

“…The aqueous layer was further extracted with 1-butanol (1-BuOH) to give a 1-BuOH (12.5%) and a H 2 O (11.0%) soluble fraction. The EtOAc-and 1-BuOH-soluble fractions were subjected to normal-phase and reversed-phase silica gel column chromatography and repeated HPLC to give florahydrosides I (1, 0.068%) and II (2, 0.014%), thunberginol (3R)-thunberginol I 4′-O-β-d-glucopyranoside (10, 0.056%), 18) (+)-3-(4-methoxyphenyl)-8-hydroxy-3,4-dihydroisocoumarin (11, hydrangenol monomethyl ether, 0.011%), 19) phyllodulcin (12, 0.19%), 20,21) hydrangenol 8-O-β-d-glucopyranoside (13, 2.87%), 16,18) thunberginol G 3′-O-β-d-glucopyranoside (14, 0.16%), 16,22) hydrangenol (15, 4.79%), 23,24) thunberginol G (16, 0.067%), 5,25) neochlorogenic acid (17, 0.075%), 26,27) 29) chlorogenic acid (20, 0.054%), 30) chlorogenic acid methyl ester (21, 0.049%), 9,31) taxiphyllin (22, 0.076%), 8,32,33) umbelliferone glucoside (23, 0.11%), 34,35) α-morroniside (24, 0.021%), 36) trans-p-coumaric acid (0.013%), 30,37) and shikimic acid (0.36%) 38) (Fig. 1 C-NMR spectra of 1 were superimposable on those of (3R)-thunberginol E [(3R)-3,4-dihydro-6,8-dihydroxy-3-(3-hydroxy-4-methoxyphenyl) isocoumarin], 22) except for the signals around the 8-position, while the proton and carbon signals due to the dihydroisocoumarin part including glycoside moiety were very similar to those of…”

Phenolic compounds fromScorzonera latifolia(Fisch. & Mey.) DC.

“…The structures of the known compounds were established conclusively by UV, ESI-MS, 1-D and 2-D NMR spectra analyses and comparison with literature data (Pauli, Poetsch, & Nahrsted, 1998;Sar|, 2010;Tatefuji et al, 1996;Zhang et al, 2000;Zhu, Dong, Wang, Ju, & Luo, 2005).…”