Candida rugosa lipase selectivity toward trans,cis- and cis,trans-conjugated linoleic acid isomers

European Food Research and Technology

Volumn 235, Issue 1, 2012, Pages 53-59

  Giua, Laura ^a   Cossignani, Lina ^a   Simonetti, Maria Stella ^a   Lombardi, Germana ^a   Blasi, Francesca ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Candida rugosa; Conjugated linoleic acid; l Menthyl esters; Selectivity

Indexed keywords

CANDIDA RUGOSA; CANDIDA RUGOSA LIPASE; CIS ISOMERS; CONJUGATED LINOLEIC ACID; ENZYMATIC ESTERIFICATION; ENZYMATIC METHODS; HEALTH EFFECTS; LIGHT-SCATTERING DETECTION; SIGMATROPIC REARRANGEMENTS; SILVER-ION HPLC; TRANS ISOMERS;

CANDIDA; CATALYST SELECTIVITY; ESTERIFICATION; ESTERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LINOLEIC ACID;

ISOMERS;

CANDIDA RUGOSA;

EID: 84862318084     PISSN: 14382377     EISSN: 14382385     Source Type: Journal    
DOI: 10.1007/s00217-012-1731-x     Document Type: Article

References (27)

1. Pariza MW (1997) Conjugated linoleic acid, a new recognized nutrient. Chem Ind 12: 464-466.
2. Ip C, Chin SF, Scimeca JA, Pariza MW (1991) Mammary cancer prevention by conjugated dienoic derivatives of linoleic acid. Cancer Res 51: 6118-6124.
3. Belury MA (2002) Inhibition of carcinogenesis by conjugated linoleic acid: potential mechanisms of action. J Nutr 132: 2995-2998.
4. Park Y, Albright KJ, Liu W, Storkson JM, Cook ME, Pariza MW (1997) Effect of conjugated linoleic acid on body composition in mice. Lipids 32: 853-858.
5. Koba K, Akahoshi A, Yamasaki M, Tanaka K, Yamada K, Iwata T, Kamegai T, Tsutsumi K, Sugano M (2002) Dietary conjugated linolenic acid in relation to CLA differently modifies body fat mass and serum and liver lipid levels in rats. Lipids 37: 343-350.
6. Lee KN, Kritchevsky D, Pariza MW (1994) Conjugated linoleic acid and atherosclerosis in rabbits. Atherosclerosis 108: 19-25.
7. McLeod RS, LeBlanc AM, Langille MA, Mitchell PL, Currie DL (2004) Conjugated linoleic acids, atherosclerosis, and hepatic very-low-density lipoprotein metabolism. Am J Clin Nutr 79: 1169-1174.
8. Ryder JW, Portocarrero CP, Song XM, Cui L, Yu M, Combatsiaris T, Galuska D, Bauman DE, Barbano DM, Charron MJ, Zierath JR, Houseknecht KL (2001) Isomer-specific antidiabetic properties of conjugated linoleic acid. Improved glucose tolerance, skeletal muscle insulin action, and UCP-2 gene expression. Diabetes 50: 1149-1157.
9. Iwakiri Y, Sampson DA, Allen KG (2002) Suppression of cyclooxygenase-2 and inducible nitric oxide synthase expression by conjugated linoleic acid in murine macrophages. Prostag Leukotr Ess 67: 435-443.
10. van Wijlen RP (2011) Long-term conjugated linoleic acid supplementation in humans-effects on body composition and safety. Eur J Lipid Sci Technol 113: 1077-1094.
11. Barrett KE, Green MR, Hu HL, Parmar P, Powell JR, Rawlings AV (2003) Skin care composition containing conjugated linoleic acid and a phenolic compound. US6551602.
12. Ha YL, Storkson J, Pariza MW (1990) Inhibition of benzo(a)pyrene-induced mouse forestomach neoplasia by conjugated dienoic derivatives of linoleic acid. Cancer Res 50: 1097-1101.
13. Park Y, Storkson JM, Albright KJ, Liu W, Pariza MW (1999) Evidence that the trans-10, cis-12 isomer of conjugated linoleic acid induces body composition changes in mice. Lipids 34: 235-241.
14. Park Y, Albright KJ, Storkson JM, Liu W, Cook ME, Pariza MW (1999) Changes in body composition in mice during feeding and withdrawal of conjugated linoleic acid. Lipids 34: 243-248.
15. De Deckere EAM, van Amelsvoort JMM, McNeill GP, Jones P (1999) Effects of conjugated linoleic acid (CLA) isomers on lipid levels and peroxisome proliferation in the hamster. Brit J Nutr 82: 309-317.
16. Nagao K, Inoue N, Wang YM, Hirata J, Shimada Y, Nagao T, Matsui T, Yanagita T (2003) The 10 trans, 12 cis isomer of conjugated linoleic acid suppresses the development of hypertension in Otsuka Long-Evans Tokushima fatty rats. Biochem Biophys Res Commun 306: 134-138.
17. Haas MJ, Kramer KG, McNeill G, Scott K, Foglia TA, Sehat N, Fritsche J, Mossoba MM, Yurawecz MP (1999) Lipase-catalyzed fractionation of conjugated linoleic acid isomers. Lipids 34: 979-987.
18. McNeill GP, Rawlins C, Peilow AC (1999) Enzymatic enrichment of conjugated linoleic acid isomers and incorporation into triglycerides. JAOCS 76: 1265-1268.
19. Nagao T, Shimada Y, Yamauchi-Sato Y, Yamamoto T, Kasai M, Tsutsumi K, Sugihara A, Tominaga Y (2002) Fractionation and enrichment of CLA isomers by selective esterification with Candida rugosa lipase. JAOCS 79: 303-308.
20. Nagao T, Yamauchi-Sato Y, Sugihara A, Iwata T, Nagao K, Yanagita T, Adchi S, Shimada Y (2003) Purification of conjugated linoleic acid isomers through a process including lipase-catalyzed selective esterification. Biosci Biotechnol Biochem 67: 1429-1433.
21. Shimada Y, Hirota Y, Baba T, Kato S, Sugihara A, Moriyama S, Tominaga Y, Terai T (1999) Enzymatic synthesis of L-menthyl esters in organic solvent-free system. JAOCS 76: 1139-1142.
22. Kobayashi T, Nagao T, Watanabe Y, Yamauchi-Sato Y, Negishi S, Shimada Y (2006) Enrichment of CLA isomers by selective esterification with l-menthol using Candida rugosa lipase. JAOCS 83: 93-99.
23. Li Z, Wang Y, Li J, Wang P, Wei W, Gao Y, Fu C, Dong W (2010) Dual response surface-optimized synthesis of l-menthyl conjugated linoleate in solvent-free system by Candida rugosa lipase. Bioresour Technol 101: 1305-1309.
24. Christy AA, Xu Z, Harrington PB (2009) Thermal degradation and isomerisation kinetics of triolein studied by infrared spectrometry and GC-MS combined with chemometrics. Chem Phys Lipids 158: 22-31.
25. Maurelli S, Blasi F, Cossignani L, Bosi A, Simonetti MS, Damiani P (2009) Production and structural analysis of triacylglycerols containing capric acid and conjugated linoleic acid isomers obtained by enzymatic acidolysis. J Sci Food Agric 89: 2595-2600.
26. Blasi F, Giua L, Lombardi G, Codini M, Simonetti MS, Damiani P, Cossignani L (2011) Improved HRGC separation of cis, trans CLA isomers as Diels-Alder adducts of alkyl esters. J Chrom Sci 49: 379-383.
27. Destaillats F, Angers P (2002) Evidence for [1, 5] sigmatropic rearrangements of CLA in heated oils. Lipids 37: 405-408.