한국응용과학기술학회지 (Journal of the Korean Applied Science and Technology)

  • 제25권4호
  • /
  • Pages.446-458
  • /
  • 2008
  • /
  • 1225-9098(pISSN)
  • /
  • 2288-1069(eISSN)
한국응용과학기술학회 (The Korean Society of Applied Science and Technology)
권호 표지
DOI QR코드

DOI QR Code

감마지방산 : 리뷰

Gamma fatty acid : A review

  • 박병성 (강원대학교 동물생명공학과)
  • 발행 : 2008.12.31
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Essential fatty acids (EFA) are fatty acids that must be obtained from the diet because they can not be biosynthesized by human or animals. Gamma fatty acids contain gamma-linolenic acid (GLA, 18:3n-6) and dihomo-gamma-linolenic acid (DHGLA, 20:3n-6) as intermediate metabolites of linoleic acid (LA, 18:2n-6), which is an EFA found in vegetable oils. GLA is an important essential fatty acid that is required by human and animals to function normally. Recently, studies have indicated that GLA may be an essential component of the cell membrane, as well as an active component of dietary supplements and medicine. GLA must beadministered through the diet because it is converted into DHGLA in the body quickly and completely. DHGLA is a key material involved in the metabolism of LA. GLA is biosysthesized by the rate limiting step of ${\Deltac}^6$-desaturase, which is an enzyme that desaturates LA, there by allowing it to be converted into DHGLA via chain elongation. In addition, DHGLA exerts bioactive effects via action as a precursor of eicosanoid series 1. Breast milk contains an abundant amount of GLA; however, GLA is also available directly in evening primrose oil, black currant seed oil, borage oil and hemp seed oil. In addition, GLA enriched animal and plant can be produced using biotechnology, and highly pure GLA can be extracted using supercritical fluids, such as supercritical carbon dioxide, which will allow economically feasible production of GLA for use in medicines.

키워드

참고문헌

  1. D. Murphy, Gamma-linolenic acid, Biological Sciences Review., 11, 19 (1998)
  2. L. Allen, Fats of the land, Biological Sciences Review., 9, 17 (1996)
  3. D. F. Horrobin, Gamma-linolenic acid, Rev. Contemp. Physol., 1, 41 (1990)
  4. P. James and M. D. Carter, Gamma-linolenic acid as a nutrient, Food Tech., June, 72 (1988)
  5. J. L. Guil-Guerrero, J. C. Lopez-Martinez, R. Navarro-Juarez, and F. Gamma-linolenic acid from Cape Verdian Boraginaceae Gomez-Mercado, Natural Product Research., 20, 9(2006) https://doi.org/10.1080/14786410500166402
  6. D. E. Barre, Potential of evening primrose, borage, black currant, and fungal oils in human health, Ann. Nutr. Metab., 45, 47 (2001) https://doi.org/10.1159/000046706
  7. Y. Xu and Y. Xiao, Study progress on ${\gamma}$-linolenic acid. Food Science., 26, 508 (2005)
  8. O. Sayanova, Gamma-linolenic acid, Biol. Sci. Rev., 11, 19 (1998)
  9. R.S. Chapkin, C. C. Miller, S. D. Somers, and K.L.Erickson, Ability of monohydroxyeicosatrienoic acid (15-OH-20:3) to modulate macrophage arachidonic acid metabolism, Biochem. Biophys. Res. Commun., 153, 799 (1988) https://doi.org/10.1016/S0006-291X(88)81166-5
  10. T. L. Frankel and J. P. Rivers, The nutritional and metabolic impact of gamma-linolenic acid on cats deprived of animal lipid, Br. J. Nutr., 39, 227 (1978) https://doi.org/10.1079/BJN19780029
  11. M. S. Manku, N. Morse-Fisher, and D. F. Horrbin, Changes in human plasma essential fatty acid levels as a result of administration of linoleic acid and gamma-linolenic acid, Eur.J. Clin. Nutr., 42, 55 (1988)
  12. J. L. Deferne and D. P. West, Antithrombotic potential of dihomo-gamma-linolenic acid in man, Br. Med. J., 2, 1441 (1996)
  13. R. R. Brenner, Nutritional and hormonal factors influencing desaturation of essential fatty acids, Progr. Lipid Res., 20, 41 (1982)
  14. Y. Y. Fan and R. S. Chapkin, Importance of dietary gamma-linolenic acid in human health and nutrition, J. Nutr., 128, 1411 (1998)
  15. P. Borgeat, M. Hamberg, and S. Samuelsson, Transformation of arachidonic acid and homo gamma linolenic acid by rabbit polymorphonuclear leucocytes. Monohydroxy acids from novel lipoxygenase, J. Biol. Chem., 251, 7816 (1976)
  16. M. M. Johnson, D. D. Swan, M. E. Surette, J. Stegner, T. Chilton, A. N. Fontech, and F. H. Chilton, Dietary supplementation with ${\gamma}$-linolenic acid alters fatty acid content and eicosanoid production in healthy human, J. Nutr., 127, 1435 (1997)
  17. M. T. Clandinin, J. E. Chappel, and T. Heim, Do low weight infants require nutrition with chain elongation-desaturation products of essential fatty acids? Progr.Lipid Res., 20, 901 (1982)
  18. M. A. Crawford, Estimation of essential fatty acid requirements in pregnancy and lactation, Progr. Food Nutr. Sci., 4, 75 (1980).
  19. R. A. Gibson and G. M. Kneebone, Fatty acid composition of human colostrum and mature breast milk, Am. J. Clin. Nutr., 34, 252 (1981) https://doi.org/10.1093/ajcn/34.2.252
  20. G. Harzer, M. Haug, I. Dieterich, and P. R. Gentner, Changing patterns of human milk lipids in the course of lactation and during the day, Am. J. Clin. Nutr., 37, 612 (1983) https://doi.org/10.1093/ajcn/37.4.612
  21. R. T. Holman, L. Smythe, and S. Johnson, Effect of sex and age on fatty acid composition of human serum lipid, Am. J. Clin. Nutr., 32, 2390 (1979) https://doi.org/10.1093/ajcn/32.12.2390
  22. H. Traitler and H. Winter, Fatty acid patterns in organ lipids in response to dietary black currant seed oil rich in gamma-linolenic acid, Progr. Lipid Res., 25, 255 (1986) https://doi.org/10.1016/0163-7827(86)90053-6
  23. C. Leicer, D. Ribnicky, and A. Pouler, The composition of hempseed oil and its potential as important source of nutrition, J. Nutra. Func. Med. Food., 2, 35 (2000) https://doi.org/10.1300/J133v02n04_04
  24. B. D. Oomash, M. Busson, and D. V. Godfrey, Characteristics of hemp seed oil, Food Chem, 76, 33 (2002) https://doi.org/10.1016/S0308-8146(01)00245-X
  25. D. F. Horrobin, Nutritional and medical importance of gamma-linolenic acid, Lipid Res., 31, 163 (1992) https://doi.org/10.1016/0163-7827(92)90008-7
  26. O. Ciferri and O. Tiboni, The biochemistry and industrial potential of Spirulina, Ann. Rev. Microbiol., 39, 503 (1985) https://doi.org/10.1146/annurev.mi.39.100185.002443
  27. Y. S. Huang and D. E. Mills, ${\gamma}$-Linolenic acid metabolism and its roles in nutrition and medicine, Free Radical Biology and Medicine., 23, 351 (1997) https://doi.org/10.1016/S0891-5849(97)10002-8
  28. D. Murphy, Genetically engineered plant oils, Biological Sciences Review., 6, 16 (1994)
  29. A. S. Reddy and T. L. Thomas, Expression of cyanbacterial ${\Delta}^6$-desaturase gene results in ${\gamma}$-linolenic acid production in transgenic plants, Nat. Biotechnol., 14, 639 (1996) https://doi.org/10.1038/nbt0596-639
  30. http://www.checkbiotech.org
  31. I. H. Cho and H. S. Sang, A study of separation of ${\gamma}$-linolenic acid with supercritical carbon dioxide, J. Korean Society of Industrial Application., 10, 97 (2007)
  32. J. Geppert, H. Demmelmair, G. Hornstra, and B. Koletzko, Co-supplementation of healthy women with fish oil and evening primrose oil increases plasma docosahexaenoic acid, ${\gamma}$-linolenic acid and dihomo-${\gamma}$-linolenic acid levels without reducing arachidonic acid concentrations. The British Journal of Nutrition., 99, 360 (2008)
  33. B. S. Park, Effect of dietary ${\gamma}$-linolenic acid on plasma lipid metabolism in rats, J. of Korean Oil Chemists, Soc., 19, 181 (2002)
  34. B. S. Park and V. A. Zammit, Effect of dietary oil containing ${\gamma}$-linolenic acid on the plasma lipid levels and thrombotic activity in rats, J. Nutr(Kor.)., 36, 889 (2003)
  35. J. Chaintreuil, L. Monnier, C. Colette, A. Orsetti, D. Spielmann, F. Mendy, and P. Crastes, Effects of dietary gammalinolenate supplementation on serum lipids and platelet function in insulin-dependent diabetic patients, Hum. Nutr. Clin. Nutr., 38C, 121 (1984)
  36. P. Kankaanpaa, K. Nurmela, and A. Erkkila, Polyunsaturated fatty acids in maternal diet, breast milk, and serum lipid fatty acids of infants in relation to atopy, Allergy., 56, 633 (2001) https://doi.org/10.1034/j.1398-9995.2001.00965.x
  37. C. A. Hederos and A. Berg, Epogam evening primrose oil treatment in atopic dermatitis and asthma, Arch. Dis. Child., 75, 494 (1996) https://doi.org/10.1136/adc.75.6.494
  38. A. Takwale, E. Tan, and S. Agarwal, Efficacy and tolerability of borage oil in adults and children with atopic eczema: randomised, double blind, placebo controlled, parallel group trial, Br. Med. J., 327, 1385 (2003) https://doi.org/10.1136/bmj.327.7428.1385
  39. D. Horrobin, Essential fatty acid metabolism and its modification in atopic eczema, American Journal of Clinical Nutrition., 71, 367S (2000) https://doi.org/10.1093/ajcn/71.1.367s
  40. S. Wright and J. L. Burton, Oral evening-primrose-seed oil improves atopic eczema, Lancet., 2, 1120 (1982)
  41. R. K. Furse, R. G. Rossetti, and R. B. Zurier, Gammalinolenic acid, an unsaturated fatty acid with anti-inflammatory properties, blocks amplification of IL-1 beta production by human monocytes, J. Immunol., 167, 490 (2001) https://doi.org/10.4049/jimmunol.167.1.490
  42. D. F. Horrobin, The role of essential fatty acids and prostaglandins in the premenstrual syndrome, J. Reprod. Med., 28, 465 (1983)
  43. J. Puolakka, L. Makarainen, L. Viinikka, and O. Ylikorkala, Biochemical and clinical effects of treating the premenstrual syndrome with prostaglandin synthesis precursors, J. Reprod. Med., 30, 149 (1985)
  44. M. Soma, M. S. Manku, and D. F. Horrobin, The effects of hydrogenated coconut oil, safflower oil and evening primrose oil on development of hypertension and sodium handling in spontaneously hypertensive rats, Can. J. Physiol. Pharmacol., 63, 325 (1985) https://doi.org/10.1139/y85-059
  45. M. M. Engler and M. B. Engler, The effects of dietary evening primrose, black currant, borage and fungal oils on plasma, hepatic and vascular tissue fatty acid composition in the spontaneously hypertensive rat, Nutr. Res., 18, 1533 (1998) https://doi.org/10.1016/S0271-5317(98)00128-6
  46. P. Singer, W. Jaeger, S. Voigt, and H. Thiel, Defective desaturation and elongation of n-6 and n-3 fatty acids in hypertensive patients, Prostaglandins, Leucotr. Med., 15, 159 (1984) https://doi.org/10.1016/0262-1746(84)90173-2
  47. M. E. Marguerite, B. E. Mary, K. E. Sandra, and M. P. Steven, Dietary gamma-linolenic acid lows blood pressure and alters aortic reactivity and cholesterol metabolism in hypertension, J. Hypertension., 10, 1197 (1992) https://doi.org/10.1097/00004872-199210000-00013
  48. M. M. Engler, M. Schambelan, M. B. Engler, D. L. Ball, and T. L. Goodfriend, Effects of dietary gamma-linolenic acid on blood pressure and adrenal angiotensin receptors in hypertensive rats, Soc. Exp. Biol. Med., 218, 234 (1998) https://doi.org/10.3181/00379727-218-44292
  49. R. J. Head, P. L. McLennan, D. Raederstorff, R. Muggli, S. L. Burnard, and E. J. McMurchie, Prevention of nerve conduction deficit in diabetic rats by polyunsaturated fatty acids, Am J. Clin. Nutr., 71, 386S (2000) https://doi.org/10.1093/ajcn/71.1.386s
  50. H. Keen, J. Payan, and J. Allawi, Treatment of diabetic neuropathy with gamma-linolenic acid. The gamma-linolenic acid multicenter trial group, Diabetes Care., 16, 8 (1993) https://doi.org/10.2337/diacare.16.1.8
  51. G. A. Jamal, H. Carmichael, and A. J. Weir, Gamma-linoleic acid in diabetic neuropathy, Lanset., 1, 1098 (1986)
  52. J. J. Belch and A. Hill, Evening primrose oil and borage oil in rheumatologic conditions, Am. J. Clin. Nutr., 71, 352S (2000) https://doi.org/10.1093/ajcn/71.1.352s
  53. P. C. Calder and R. B. Zurier, Polyunsaturated fatty acids and rheumatoid arthritis, Curr. Opin. Clin. Nutr. Metab. Care., 4, 115 (2001) https://doi.org/10.1097/00075197-200103000-00006
  54. R. E. Kast, Borage oil reduction of rheumatoid arthritis activity may be mediated by increased cAMP that suppresses tumor necrosis factor-alpha, Int. Immunopharmacol., 1, 2197 (2001) https://doi.org/10.1016/S1567-5769(01)00146-1
  55. L. J. Leventhal, E. G. Boyce, and R. B. Zurier, Treatment of rheumatoid arthritis with black currant seed oil, Br. J. Rheumatol., 33, 847 (1994) https://doi.org/10.1093/rheumatology/33.9.847
  56. P. DeLuca, D. Rothman, and R. B. Zurier, Marine and botanical lipids as immunomodulatory and therapeutic agents in the treatment of rheumatoid arthritis, Rheum. Dis. Clin. N. Am., 21, 759 (1995)
  57. L. J. Leventhal, E. G. Boyce, and R. B. Zurier, Treatment of rheumatoid arthritis with gammalinoleic acid, Ann. Intern. Med., 119, 867 (1993) https://doi.org/10.7326/0003-4819-119-9-199311010-00001
  58. R. B. Zurier, R. G. Rossetti, E. W. Jacobson, D. M. DeMarco, N. Liu, Y. Temming, B. M. White, and M. A. Laposata, Gamma-linolenic acid treatment of rheumatoid arthritis. A randomized, placebo-controlled trial, rthritis Rueum., 39, 1808 (1996) https://doi.org/10.1002/art.1780391106
  59. C. M. Garcia, Gamma linolenic acid causes weight loss and lower blood pressure in overweight patients with family history of obesity, Swed. J. Biol. Med., 4, 8 (1986)
  60. M. C. Kruger and D. F. Horrobin, Calcium metabolism, osteoporosis and essential fatty acids: a review, Prog. Lipid Res., 36, 131 (1997) https://doi.org/10.1016/S0163-7827(97)00007-6
  61. D. F. Horrobin, Loss of delta-6-desaturase activity as a key factor in aging, Med, Hypothesis., 7, 1211 (1981) https://doi.org/10.1016/0306-9877(81)90064-5
  62. F. S. Kenny, S. E. Pinder, and I. O. Ellis, Gamma linolenic acid with tamoxifen as primary therapy tn breast cancer, Int. J. Cancer., 85, 643 (2000) https://doi.org/10.1002/(SICI)1097-0215(20000301)85:5<643::AID-IJC8>3.0.CO;2-Z
  63. J. A. Menendez, M. Barbacid, and S. Montero, Effects of gamma-linolenic acid and oleic acid on paclitaxel cytotoxicity in human breast cancer cells, Eur. J. Cancer., 37, 402 (2001)
  64. J. J. Van Doormal, I. G. Idema, F. A. J. Muskiet, I. A. Martini, and H. Doorenbos, Different effects of vitamin E-enriched evening primrose oil on erythrocyte vitamin E content and platelet function between normal and type I (insulin depend ent) diabetic men, Diabetologia., 29, A603 (1986)
  65. A. A. Qureshi, H. K. Schnoes, Z. Z. Din, and D. M. Peterson, Determination of the structure of cholesterol inhibitor II isolated from high protein barley flour, Fed. Proc., 43, 2626 (1984)
  66. S. Kanehara, T. Ohtani, K. Uede, and F. Furukawa, Undershirts coated with borage oil alleviate the symptoms of atopic dermatitis in children, Eur. J. Dermatol., 17, 448 (2007)
  67. C. H. Yen, Y. S. Dai, Y. H. Yang, L. C. Wang, J. H. Lee, and B. L. Chiang, Linoleic acid metabolite levels and transepidermal water loss in children with atopic dermatitis, Ann. Allergy Asthma Immunol., 100, 66 (2008) https://doi.org/10.1016/S1081-1206(10)60407-3
  68. P. C. Calder and E. A. Miles, Fatty acids and atopic disease, Pediatr. Allergy Immunol., 13, 29 (2000) https://doi.org/10.1034/j.1399-3038.13.s.15.2.x
  69. M. Worm and B. M. Henz, Novel unconventional therapeutic approaches to atopic eczema, Dermatology., 201, 191 (2000) https://doi.org/10.1159/000018487
  70. H. C. Williams, Editorial: Evening primrose oil for atopic dermatitis-time to say goodnight, Br. Med. J, 327, 1358 (2003) https://doi.org/10.1136/bmj.327.7428.1358
  71. M. M. Engler, J. W. Karanian, and N. Jr. Salem, Influence of dietary polyunsaturated fatty acids on aortic and platelet fatty acid composition in the rat, Nutr, Res., 11, 753 (1991) https://doi.org/10.1016/S0271-5317(05)80629-3
  72. C. L. Davies, M. Loizidou, and A. J. Cooper, Effect of gamma-linolenic acid on cellular uptake of structurally related anthracyclines in human drug sensitive and multidrug resistant bladder and breast cancer cell lines, Eur. J. Cancer., 35, 1534 (1999) https://doi.org/10.1016/S0959-8049(99)00181-1
  73. S. Ikushima, F. Fujiwara, S. Todo, and S. Imashuku, Gamma linolenic acid alters the cytotoxic activity of anticancer drugs on cultured human neuroblastoma cells, Anticancer Res., 10, 1055 (1990)