Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapum-genistae

Andary, Claude; Wylde, Renée; Laffite, Colette; Privat, G.; Winternitz, F.

doi:10.1016/s0031-9422(00)82429-2

Cited by 243 publications

(123 citation statements)

References 8 publications

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“…The separation was performed by Sephadex LH-20 chromatography. Analysis by 1 H NMR and 13 C NMR could identify these two compounds unequivocally, when compared with literature data 13,14 .…”

Section: Resultsmentioning

confidence: 73%

“…The characterization of the constituents of the less polar triterpene mixture as well as of the more polar constituents was simplified by the assignment of the carbon atoms in the 13 C NMR. As the chemical shift of a sp 2 carbon atom is very characteristic for each triterpenoid skeleton, 13 C NMR spectroscopy has been very frequently employed for the structural analysis of triterpene mixtures 11 . To distinguish carbon types (multiplicity), the attached proton test (APT) was used.…”

Section: Resultsmentioning

confidence: 99%

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Dirhamnosyl flavonoid and other constituents from Brillantaisia palisatii

et al. 2003

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Recebido em 17/7/02; aceito em 10/4/03 DIRHAMNOSYL FLAVONOID AND OTHER CONSTITUENTS FROM Brillantaisia palisatii. A mixture containing sitosterol and stigmasterol; a new triterpene 3-epi-ursolic acid; another triterpene mixture comprising α-amyrin, β-amyrin and lupeol; verbascoside, a phenylpropanoid glycoside; and lespedin, a glycosyl flavonoid, were isolated. The less polar compounds (steroids and triterpenoids) were isolated from the hexane partition of the crude ethanolic extract while the more polar ones (phenylpropanoid glycoside and glycosyl flavonoid) were isolated from the ethyl acetate partition of the same extract. The structures of all compounds were established using modern spectrometric methods of elucidation. The spectroscopic data of Lespedin, a rare dirhamnosylflavonol with hypotensor activity and of the triterpene, 3-epi-ursolic acid, are also reported.

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Section: Resultsmentioning

confidence: 73%

Section: Resultsmentioning

confidence: 99%

Dirhamnosyl flavonoid and other constituents from Brillantaisia palisatii

et al. 2003

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“…The fraction eluted with MeOH was repeatedly subjected to column chromatography using silica gel and octadecylsilyl silica gel, then by preparative HPLC-ODS to afford 18 compounds (1-18). Thirteen were known compounds; shanzhiside methyl ester (1), 8-O-acetylshanzhiside methyl ester (barlerin) (2), 6-O-acetylshanzhiside methyl ester (3), 6,8-O,Odiacetylshanzhiside methyl ester (acetylbarlerin) (4) (Damtoft et al, 1982;Byrne et al, 1987), ipolamiide (9) (Damtoft et al, 1984b), ipolamiidoside (10) (Byrne et al, 1987), phlorigidoside B (11) , forsythoside B (13) (Endo et al, 1982), verbascoside (14) (Andary et al, 1982), poliumoside (15) (Andary et al, 1985), (+)-lyoniresinol 3a-O-b-glucopyranoside (16) (Achenbach et al, 1992), (3R)-1-octen-3-yl-b-primeveroside (17) (Yamamura et al, 1998) and benzyl alcohol b-(2 0 -O-b-xylopyranosyl) glucopyranoside (18) (Sudo et al, 2000) by physical data and spectroscopic evidences.…”

Section: Resultsmentioning

confidence: 99%

Iridoid glucosides from Barleria lupulina

2001

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“…Protection of a particular functional group of an organic compound is not only necessary for the modification of properties of the remaining functional groups but also for the synthesis of newer derivatives of great importance. Various methods for acylation of carbohydrates and nucleosides have so far been developed and employed successfully [4][5][6][7][8]. Of these, the direct acylation method is considered as one of the most effective [8,9] for selective acylation of carbohydrates.…”

Section: Introductionmentioning

confidence: 99%

Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

Kawsar

Mymona

Asma

et al. 2015

ILCPA

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ABSTRACT.This study was carried out to regioselective myristoylation of methyl α-Dglucopyranoside (1) using the direct acylation method gave the corresponding methyl 6-Omyristoyl-α-D-glucopyranoside (2) in fair yield. A number of 2,3,4-tri-O-acyl derivatives (3-15) of this 6-O-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The reaction conditions are reasonably simple and yields were very good. The structures of the title compounds (2-15) were established by using analytical, physicochemical techniques and spectroscopic data (IR and 1 H-NMR). All the synthesized compounds were employed as test chemicals for in vitro antimicrobial functionality test against Gram-positive Bacillus subtilis, Staphylococcus aureus, Gram-negative Escherichia coli, Pseudomonas aeruginosa bacteria and plant pathogenic fungi Aspergillus niger and Candida albicans. For comparative studies, antimicrobial activity of standard antibiotics, Ampicillin and Nystatin were also carried out against these microorganisms. The study revealed that the tested samples exhibited moderate to good antibacterial and antifungal activities. It was also observed that the test substances were more effective against fungal phytopathogens than those of the human bacterial strains. Encouragingly, a number of tested chemicals showed nearest antibacterial and antifungal activities with the standard antibiotics employed.

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Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapum-genistae

Cited by 243 publications

References 8 publications

Dirhamnosyl flavonoid and other constituents from Brillantaisia palisatii

Dirhamnosyl flavonoid and other constituents from Brillantaisia palisatii

Iridoid glucosides from Barleria lupulina

Infrared, <sup>1</sup>H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-α-D-Glucopyranoside Derivatives: Assessment of Antimicrobial Effects

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