Abstract
Since most of the ACE inhibitory drugs are peptides, this chapter deals with exploration of ACE inhibitory activities for some enzymatically synthesised l-alanyl, l-valyl, l-leucyl, l-isoleucyl, l-proline, l-phenylalanine, l-tryptophan and l-histidine esters of carbohydrates and glycosides of n-octanol, phenolic glycosides of guaiacol, eugenol, curcumin, vanillin, N-vanillyl-nonanamide, dl-dopa, dopamine and vitamin glycosides of retinol, thiamin, riboflavin, pyridoxine, ergocalciferol, cholecalciferol and α-tocopherol. A few glycosides were also tested for antioxidant activities. These results exhibiting both the phenolic and vitamin glycosides holding promising potential as antioxidants and ACE inhibitors are discussed in terms of structure–function relationship between these compounds and those of the commercially known inhibitors.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Azuma K, Nakayama M, Koshioka M, Ippoushi K, Yamaguchi Y, Kohata K, Yamauchi Y, Ito H, Higashio HJ (1999) Phenolic antioxidants from the leaves of Corchorus olitorius L. Agric Food Chem 47:3963–3966
Cooke JWB, Hayes D, Henson RA, Hermitage SA, Ward RA, Whitehead AJ (2003) Process for the preparation of 4-substituted phenylalanyl ester derivatives. PCT Int Appl WO 2003068725:A2 (CA 138 180345)
Cushman DW, Cheung HS (1969) A simple substrate for assay for dog lung angiotensin converting enzyme. Fed Proc 28:3019
Cushman DW, Cheung HS (1971) Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung. Chem Pharmacol 20:1637–1638
Dae-Gill K, Yong-Sup L, Hyoung-Ja K, Yun-Mi L, Ho-Sub L (2003) Angiotensin converting enzyme inhibitory phenylpropanoid glycosides from Clerodendron trichotomum. J Ethnopharmacol 89:151–154
Dai F, Miao Q, Zhou B, Yang L, Liu ZL (2006) Protective effects of flavanols and their glycosides against free radical induced oxidative hemolysis of red blood cells. Life Sci 78:2488–2493
De Lima DP (1999) Synthesis of angiotensin converting enzyme (ACE) inhibitors an important class of anti-hypertensive drugs. Quim Nova 22:375–381
Deloffre L, Sautiere PE, Huybrechts R, Hens K, Vieau D, Salzet M (2004) Angiotensin converting enzyme inhibition studies by natural leech inhibitors by capillary electrophoresis and competition assay. Eur J Biochem 271:2101–2106
Einstein Charles R, Ponrasu T, Sivakumar R, Divakar S (2009) Angiotensin converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides. Biotech Appl Biochem 52:177–184
Hyuncheol O, Dae-Gill KC, Hun-Taeg L, Ho-Sub L (2003) Four glycosides from the leaves of Abeliophyllum distichum with inhibitory effects on angiotensin converting enzyme. Phytother Res 17:811–813
Johnston CI (1992) Renin-angiotensin system: a dual tissue and hormonal system for cardiovascular control. J Hypertens 10:13–26
Kamath V, Rajini PS, Lohith K, Somashekar BR, Divakar S (2006) Angiotensin Converting enzyme inhibitory activity of amino acid esters of carbohydrates. Int J Biol Macromol 38:89–93
Kefalas P, Kallithraka S, Parejo I, Makris DP (2003) A comparative study on the in vitro antiradical activity and hydroxyl free radical scavenging activity in aged red wines. Food Sci Technol Int 9:383–387
Kim SK, Byun HG, Park PJ, Shahidi F (2001) Angiotensin I converting enzyme inhibitory peptides purified from bovine skin gelatin hydrolysate. J Agric Food Chem 49:2992–2997
Kim WD, Kaneko S, Park GG, Tanaka H, Kusakabe I, Kobayashi H (2003) Purification and characterization of α-galactosidase from sunflower seeds. Biotechnol Lett 25:353–358
Li GH, Le GW, Yong-Hui S, Shrestha S (2004) Angiotensin I–converting enzyme inhibitory peptides derived from food proteins and their physiological and pharmacological effects. Nutr Res 24:469–486
Lohith K, Vijayakumar GR, Somashekar BR, Sivakumar R, Divakar S (2006) Glycosides and amino acyl esters of carbohydrates as potent inhibitors of Angiotensin Converting Enzyme. Eur J Med Chem 41:1059–1072
Michaud A, Williams TA, Chauvet MT, Corvol P (1997) Substrate dependence of angiotensin I-converting enzyme inhibition captopril displays a partial selectivity for inhibition of N-acetyl-seryl-aspartyl-lysyl-proline hydrolysis compared with that of angiotensin I. Mol Pharmacol 51:1070–1076
Moon JH, Terao J (1998) Antioxidant activity of caffeic acid and dihydrocaffeic acid in Lard and human low-density lipoprotein. J Agr Food Chem 46:5062–5065
Moon YH, Lee JH, Jhon DY, Jun WJ, Kang SS, Sim J, Choi H, Moon JH, Kim D (2007) Synthesis and characterization of novel quercetin-β-d-glucopyranosides using glucansucrase from Leuconostoc mesenteriodes. Enzyme Microb Technol 40:1124–1129
Mullally MM, Meisel H, FitzGerald RJ (1996) Synthetic peptides corresponding to a lactalbumin and β-lactoglobulin sequences with angiotensin-I-converting enzyme inhibitory activity. J Biol Chem 377:259–260
Portes E, Gardrat C, Castellan A (2007) A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids. Tetrahedron 63:9092–9099
Potier P, Maccario V, Giudicelli MB, Queneau Y, Dangles O (1999) Gallic esters of sucrose as a new class of antioxidants. Tetrahedron Lett 40:3387–3390
Roche M, Dufour C, Mora N, Dangles O (2005) Antioxidant activity of olive phenols Mechanistic investigation and characterization of oxidation products by mass spectrometry. Org Biomol Chem 3:423–429
Vermeirssen V, Van-Camp J, Verstraete W (2002) Optimization and validation of an angiotensin-converting enzyme inhibition assay for the screening of bioactive peptides. J Biochem Biophys Methods 51:75–87
Villano D, Fernandez-Pachon MS, Moy ML, Troncoso AM, Garca-Parrilla MC (2007) Radical scavenging ability of polyphenolic compounds towards DPPH free radical. Talanta 71:230–235
Wu JY, Liu SW (2002) Influence of alcohol concentration on lipase-catalyzed enantioselective esterification of racemic naproxen in isooctane under controlled water activity. Enzyme Microb Technol 26:124–130
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2013 Springer India
About this chapter
Cite this chapter
Divakar, S. (2013). ACE Inhibition and Antioxidant Activities of Enzymatically Synthesised Aminoacyl Esters and Glycosides. In: Enzymatic Transformation. Springer, India. https://doi.org/10.1007/978-81-322-0873-0_11
Download citation
DOI: https://doi.org/10.1007/978-81-322-0873-0_11
Published:
Publisher Name: Springer, India
Print ISBN: 978-81-322-0872-3
Online ISBN: 978-81-322-0873-0
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)