Glycosides and amino acyl esters of carbohydrates as potent inhibitors of angiotensin converting enzyme

Lohith, K.; Vijayakumar, Giriyapura R.; Somashekar, Bhandya R.; Sivakumar, Ramaiah; Divakar, Soundar

doi:10.1016/j.ejmech.2006.04.005

Cited by 18 publications

(10 citation statements)

References 26 publications

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“…To validate the specificity of the ACE-inhibitory activity found for glycosides 1 and 2 , the test assay was performed with their single components malic acid, gentiobiose, and glucose, respectively. However, none of these compounds showed any significant ACE-inhibitory activity, thus confirming the prime importance of the glycosidic bond as proposed earlier for synthetic glycosides such as eugenyl O -β- d - glucoside and vanillyl O -β- d -mannoside, respectively …”

Section: Resultssupporting

confidence: 81%

Activity-Guided Discovery of (S)-Malic Acid 1′-O-β-Gentiobioside as an Angiotensin I-Converting Enzyme Inhibitor in Lettuce (Lactuca sativa)

Lagemann

Dunkel

Hofmann

2012

J. Agric. Food Chem.

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Angiotensin-converting enzyme (ACE), playing a crucial role in the renin angiotensin aldosterone system, is well-known to catalyze the conversion of the decapeptide angiotensin I into the physiologically active octapeptide angiotensin II, triggering blood pressure increasing mechanisms. To meet the demand for natural phytochemicals as antihypertensive agents in functional food development, extracts prepared from a series of vegetables were screened for their ACE-inhibitory activity by means of a LC-MS/MS-based in vitro assay. By far the highest ACE inhibition was found for a lettuce extract, in which the most active compound was located by means of activity-guided fractionation. LC-MS, NMR spectroscopy, and hydrolysis experiments followed by ion chromatography led to the unequivocal identification of the ACE inhibitor as the previously not reported (S)-malic acid 1'-O-β-gentiobioside. This glycoside represents a novel class of ACE-inhibiting phytochemicals with a low IC(50) value of 27.8 μM. First incubation experiments in saliva and aqueous hydrochloric acid demonstrated the stability of (S)-malic acid 1'-O-β-gentiobioside against salivary glycosidases and stomach acid.

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Section: Resultssupporting

confidence: 81%

Activity-Guided Discovery of (S)-Malic Acid 1′-O-β-Gentiobioside as an Angiotensin I-Converting Enzyme Inhibitor in Lettuce (Lactuca sativa)

Lagemann

Dunkel

Hofmann

2012

J. Agric. Food Chem.

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“…Pure D-sorbitol exhibits a strong, broad band appearing at 3500-3200 cm -1 , which is assigned to the stretching vibration of the hydroxyl group. 34 The band shifted to 3420-3350 cm -1 in the unwashed sample prepared in the presence of D-sorbitol. The presence of the O-H group in the unwashed nickel nanoparticles revealed that the hydroxyl group of D-sorbitol interacted with nickel nanoparticles. No characteristic bands of D-sorbitol were observed in the FTIR spectra of the ethanol-washed sample.…”

Section: Resultsmentioning

confidence: 95%

“…Pure d -sorbitol exhibits a strong, broad band appearing at 3500−3200 cm −1 , which is assigned to the stretching vibration of the hydroxyl group . The band shifted to 3420−3350 cm −1 in the unwashed sample prepared in the presence of d -sorbitol.…”

Section: Resultsmentioning

confidence: 98%

Effect of Organic Modifiers on the Structure of Nickel Nanoparticles and Catalytic Activity in the Hydrogenation of p-Nitrophenol to p-Aminophenol

Wang

Yin

et al. 2009

Langmuir

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Spherical nickel nanoparticles with different sizes and different structures were prepared starting from nickel oxalate and using hydrazine hydrate as a reductant in the presence of citric acid, cetyltrimethylammonium bromide, Tween 40, and d-sorbitol as organic modifiers. The size and structure of the resultant nickel nanoparticles were affected by using different organic modifiers. All of the nickel nanoparticles showed higher catalytic activity and selectivity than the conventional raney Ni catalyst in the hydrogenation of p-nitrophenol to p-aminophenol. Although the catalytic activities of the resultant nickel nanoparticles generally increased with decreasing particle size, the structure of nickel nanoparticles also had an important impact on the catalytic activity.

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“…Phenolic glycosides found in a variety of fruits and vegetables have been studied extensively for their antioxidant properties [17,18]. Antioxidative action is reported to protect living organisms from oxidative damages, resulting in the prevention of various diseases such as cancer, cardiovascular diseases, diabetes and aging [19].…”

Section: Introductionmentioning

confidence: 99%

“…Poor solubility of aglycones in water as well as their pharmaceutical applications can be improved by glycosylation [17,23]. Similarly, glycosylation is also reported to improve the bioactivity of several vitamins besides enhancing water solubility [24,25].…”

Section: Introductionmentioning

confidence: 99%

Angiotensin‐converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides

Charles¹,

Ponrasu²,

Sivakumar³

et al. 2009

Biotech and App Biochem

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Amyloglucosidase from Rhizopus mould and beta-glucosidase from sweet almond were employed for the preparation of phenolic and vitamin glycosides of vanillin, N-vanillylnonanamide, DL-dopa, dopamine, curcumin, alpha-tocopherol (vitamin E), pyridoxine (vitamin B(6)), ergocalciferol (vitamin D(2)), thiamin (vitamin B(1)) and riboflavin (vitamin B(2)). Approx. 20 enzymatically prepared phenolic and vitamin glycosides were subjected to ACE (angiotensin-converting enzyme) inhibition activity measurements, and 14 glycosides were tested for antioxidant activities. Both phenolic and vitamin glycosides exhibited IC(50) values for ACE inhibition in the 0.52+/-0.03-3.33+/-0.17 mM range and antioxidant activities ranging from 0.8+/-0.04 to 1.18+/-0.06 mM. Comparable ACE inhibition values were observed between free phenols and vitamin glycosides. However, antioxidant activities of glycosides were, in general, lesser than those of free phenols. Best IC(50) value for ACE inhibition were observed for 11-O-(D-fructofuranosyl)thiamin (0.52+/-0.03 mM), 3-hydroxy-4-O-(6-D-sorbitol)phenylalanine (0.56+/-0.03 mM), 4-O-(beta-D-glucopyranosyl)vanillin (0.61+/-0.03 mM), 4-O-(D-galactopyranosyl)vanillin (0.61+/-0.03 mM) and pyridoxine-D-glucoside (0.84+/-0.04 mM). Similarly, best IC(50) values for antioxidant activity were observed for 1,7-O-(bis-beta-D-glucopyranosyl)curcumin (0.8+/-0.04 mM), 4-O-(beta-D-glucopyranosyl)vanillin (0.9+/-0.05 mM), 3-hydroxy-4-O-(beta-D-galactopyranosyl-(1'-->4)beta-D-glucopyranosyl)phenylalanine (0.9+/-0.05 mM), 20-O-(D-glucopyranosyl)ergocalciferol (0.9+/-0.05 mM) and dopamine-D-galactoside (0.93+/-0.05 mM).

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Glycosides and amino acyl esters of carbohydrates as potent inhibitors of angiotensin converting enzyme

Cited by 18 publications

References 26 publications

Activity-Guided Discovery of (S)-Malic Acid 1′-O-β-Gentiobioside as an Angiotensin I-Converting Enzyme Inhibitor in Lettuce (Lactuca sativa)

Activity-Guided Discovery of (S)-Malic Acid 1′-O-β-Gentiobioside as an Angiotensin I-Converting Enzyme Inhibitor in Lettuce (Lactuca sativa)

Effect of Organic Modifiers on the Structure of Nickel Nanoparticles and Catalytic Activity in the Hydrogenation of p-Nitrophenol to p-Aminophenol

Angiotensin‐converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides

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