Synthèses de 6-O-β-d-apiofuranosyl-β-d-glucopyranosides de monoterpényle

M'Bairaroua, Oubadjim.; Ton-That, T.; Tapiéro, C.

doi:10.1016/0008-6215(94)80057-x

Cited by 24 publications

(16 citation statements)

References 26 publications

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“…The values typically observed for apiose sugars are about 1 Hz for 1,2-trans linkages, and about 4-5 Hz for 1,2-cis linkages. 11,21 The observed 3 J 1,2 values (signals appearing as broad singlets) for 9 and 12 are consistent with formation of a 1,2-trans, or b-linkage. In addition, the 13 C-chemical shift values (about 111 ppm) for the anomeric carbons of the apiose residues of compounds 1 and 11 are in agreement with those found for 1,2-trans linkages in model compounds.…”

Section: Resultssupporting

confidence: 67%

“…1,2,3-Tri-O-acetyl-3-C-(benzyloxymethyl)-a/b-D D-erythrofuranose 4 was prepared from 2 by benzylation, followed by acetolysis and acetylation as described by Tapiéro. 11 Preparation of glycosyl bromide 5 by the treatment of 4 with hydrogen bromide in acetic acid was unsuccessful, proceeding with significant decomposition. Reaction of 4 with ethanethiol and a catalytic amount of SnCl 4 gave ethyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-a/b-D D-erythrofuranoside 6, as described by van Boom and co-workers.…”

Section: Resultsmentioning

confidence: 99%

“…of 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-a/ b-D D-erythrofuranoside 411 (1.829 g, 4.992 mmol) was dissolved in CH 2 Cl 2 (10.0 mL). p-Thiocresol (0.750 g, 6.039 mmol) in CH 2 Cl 2 (10.0 mL) was then added, followed by addition of BF 3 AEEt 2 O (0.90 mL, 7.3 mmol).…”

mentioning

confidence: 99%

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Synthesis of a disaccharide fragment of rhamnogalacturonan II

Buffet

Rich

McGavin

et al. 2004

Carbohydrate Research

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Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 99%

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Synthesis of a disaccharide fragment of rhamnogalacturonan II

Buffet

Rich

McGavin

et al. 2004

Carbohydrate Research

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“…In this study, purification of the EtOAc and n-BuOH fractions of Z. schinifolium stems by silica gel and YMC column chromatography afforded one new neolignan glycoside, zanthoxyloside A (1), and one newly monoterpenoid glycoside, zanthoxyloside B (2), together with 15 known glycosides (3)(4)(5)(6)(7)(8)(9)(10)(11)(12) and alkaloids (13)(14)(15)(16)(17). Their structures were elucidated as zanthoxyloside A (1), zanthoxyloside B (2), betulalbuside A (3), 13) 15) isopropyl apioglucoside (6), 16) benzyl 6-O-β-apiofuranosyl-O-β-glucopyranoside (7), 17) osmanthuside H (8), 18) coniferin (9), 19) syringin (10), 19) homovanillyl alcohol-4′-glycoside (11), 20) roseoside A (12), 21) skimmianine (13), 22) haplopine (14), 23) glycohaplopine (15), 24) norchelerythrine (16), 25) and nornitidine (17).…”

Section: Resultsmentioning

confidence: 89%

“…Their structures were elucidated as zanthoxyloside A (1), zanthoxyloside B (2), betulalbuside A (3), 13) 15) isopropyl apioglucoside (6), 16) benzyl 6-O-β-apiofuranosyl-O-β-glucopyranoside (7), 17) osmanthuside H (8), 18) coniferin (9), 19) syringin (10), 19) homovanillyl alcohol-4′-glycoside (11), 20) roseoside A (12), 21) skimmianine (13), 22) haplopine (14), 23) glycohaplopine (15), 24) norchelerythrine (16), 25) and nornitidine (17). 25) Compounds 4, 5, 8, 11, 15, and 17 were isolated from Z. schinifolium for the first time (Fig.…”

Section: Resultsmentioning

confidence: 99%

NF-κB Inhibitory Activities of Glycosides and Alkaloids from <i>Zanthoxylum schinifolium</i> Stems

Yang

Yan

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Zanthoxylum schinifolium is an aromatic shrub, the pericarp and leaves of which are widely used in culinary applications in East Asian countries. In the present study, one new neolignan glycoside, zanthoxyloside A (1) together with 16 known glycosides (2-12) and alkaloids (13-17), were isolated from methanol extract of the stems of Z. schinifolium. The absolute configuration of one known monoterpenoid glycoside (2) was determined. The structures of the isolated compounds were established by one dimensional (1D), 2D NMR and mass spectrometry. The nuclear factor-κB (NF-κB) inhibitory activities of the isolated compounds stimulated with tumor necrosis factor alpha (TNFα) were measured using a luciferase reporter system. Compounds 1, 5, 16, and 17 exhibited significant inhibition of NF-κB activation in a dose-dependent manner. Furthermore, compounds 1, 5, 16, and 17 inhibited TNFα-induced expression of inducible nitric oxide synthase (iNOS) and intercellular adhesion molecule-1 (ICAM-1) mRNA and dose-dependent inhibition of iNOS promoter activity.Key words Zanthoxylum schinifolium; Rutaceae; glycoside; alkaloid; nuclear factor-κB (NF-κB) inhibitory activity Zanthoxylum schinifolium SIEB. & ZUCC., which belongs to the Rutaceae family, is an aromatic plant, widely used as a pungent condiment and seasoning in Korea, China, Japan and other East Asian countries because of its unique aroma and taste.1) The leaves and seeds of Z. schinifolium have been used primarily for treatment of various types of pain, the common cold, diarrhea, and jaundice in traditional Chinese medicine. Pharmacological research on Z. schinifolium has focused on its inhibitory effect on monoamine oxidase and its anti-platelet, anti-diabetes, and anti-inflammatory activities. 2-4)Phytochemical studies on Z. schinifolium indicated the main constituents to be coumarins, essential oils, triterpenoids, monoterpenoids, steroids, and flavonoids. [5][6][7] Coumarins were shown to have significant platelet aggregation activity. Essential oils were found to have antioxidant activity and are used in skin care products. Alkaloids have various bioactivities such as antimicrobial effects. 8) Although there have been many investigations of the active constituents of Z. schinifolium, there have been no detailed reports of the isolation and structural elucidation of glycosides and alkaloids from the stems of this plant or their bioactivities.Nuclear factor-κB (NF-κB) represents a family of Rel domain-containing proteins, which includes five NF-κB units that can form 15 transcription factors through homo-and heterodimerization. NF-κB plays an important role in the transcriptional regulation of numerous cytokines and adhesion molecules. It is the most extensively studied transcription factor in the immune system. Known inducers of NF-κB activity are highly variable and include reactive oxygen species (ROS), tumor necrosis factor alpha (TNFα), interleukin (IL)-1β, bacterial lipopolysaccharides (LPS), isoproterenol, cocaine, and ionizing radiation. The activation of NF-...

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Synthese von dimeren Terpenglycosid‐Seitenketten aus cytotoxischen Saponinen

Reicheneder

Unverzagt

2004

Angewandte Chemie

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Professor Axel Zeeck zum 65. Geburtstag gewidmet Saponine sind Naturstoffe aus Pflanzen und marinen Organismen, die ein breites Spektrum biologischer Aktivitäten zeigen und z. B. gegen Krebserkrankungen wirksam sind. [1] Die meisten Saponine bestehen aus einem lipophilen Steroidoder Triterpengerüst und hydrophilen Oligosaccharid-Seitenketten. Die Strukturen der Saponine sind vielfältig, nur wenige aber enthalten eine zusätzliche MonoterpenglycosidSeitenkette (A, Schema 1), wie sie bei Julibrosiden, [2] Elliptosiden [3]

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Synthèses de 6-O-β-d-apiofuranosyl-β-d-glucopyranosides de monoterpényle

Cited by 24 publications

References 26 publications

Synthesis of a disaccharide fragment of rhamnogalacturonan II

Synthesis of a disaccharide fragment of rhamnogalacturonan II

NF-κB Inhibitory Activities of Glycosides and Alkaloids from <i>Zanthoxylum schinifolium</i> Stems

Synthese von dimeren Terpenglycosid‐Seitenketten aus cytotoxischen Saponinen

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