関: 8,11,14-eicosatrienoic acid、DHLA

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"
a unit of magnetic field strength equal to one-hundred-thousandth of an oersted
the 3rd letter of the Greek alphabet
a herd of whales

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
ガンマ(ギリシア語アルファベットの第3字Γ,γ;英語のG,gに相当)
(特に女性の)魅力的な脚,すんなりした脚

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/11/03 21:06:56」(JST)

wiki en

Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω−6 fatty acid. In physiological literature, it is given the name 20:3 (ω−6). DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product of linoleic acid (18:2, ω−6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.^[1]^[2]

Biological effects

The eicosanoid metabolites of DGLA are:

Series-1 thromboxanes (thromboxanes with 1 double-bond), via the COX-1 and COX-2 pathways.
Series-1 prostanoids, via the COX-1 and COX-2 pathways.^[3]
A 15-hydroxyl derivative that blocks the transformation of arachidonic acid to leukotrienes.^[4]

All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of arachidonic acid (AA), which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA competes with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.

Taken orally in a small study, DGLA produced antithrombotic effects.^[5] Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.^[6] Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.^[7]

Borage is a rich source of γ-linolenic acid—the dietary precursor to DGLA.

References

^ Horrobin, D. F., 1990a. Gamma linolenic acid. Rev. Contemp. Pharmacother. 1, 1-45
^ Huang, Y.-S. and Mills, D. E. (Eds.), 1996. Gamma-linolenic acid metabolism and its roles in nutrition and medicine. AOCS Press, Champagne, Illinois, 319 pp.
^ Fan, Yang-Yi and Robert S. Chapkin (9 September 1998). "Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition". Journal of Nutrition 128 (9): 1411–4. PMID 9732298. http://jn.nutrition.org/cgi/content/full/128/9/1411. Retrieved 2007-10-16.
^ Belch, Jill JF and Alexander Hill (January 2000). "Evening primrose oil and borage oil in rheumatologic conditions". http://www.ajcn.org/cgi/content/full/71/1/352S. Retrieved February 12, 2006.
^ Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-γ-linolenic acid in man". British Medical Journal 2 (6100): 1441–1444. doi:10.1136/bmj.2.6100.1441. PMC 1632618. PMID 338112. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1632618/.
^ Johnson MM, Swan DD, Surette ME et al. (1997). "Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. PMID 9237935.
^ Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH (August 2000). "Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans". J. Nutr. 130 (8): 1925–31. PMID 10917903.

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English Journal

Lipidomic analysis reveals a radiosensitizing role of gamma-linolenic acid in glioma cells.

Antal O1, Péter M2, Hackler L Jr3, Mán I3, Szebeni G3, Ayaydin F4, Hideghéty K5, Vigh L2, Kitajka K6, Balogh G2, Puskás LG7.
Biochimica et biophysica acta.Biochim Biophys Acta.2015 Sep;1851(9):1271-82. doi: 10.1016/j.bbalip.2015.06.003. Epub 2015 Jun 16.
Previous studies have demonstrated that gamma-linolenic acid (GLA) is effective against glioma cells under both in vitro and in vivo conditions. In the present study we determined how GLA alone or in combination with irradiation alters the fatty acid (FA) and lipid profiles, the lipid droplet (LD) c
PMID 26092623

Epoxyeicosatrienoic acids regulate macrophage polarization and prevent LPS-induced cardiac dysfunction.

Dai M1, Wu L1, He Z1, Zhang S1, Chen C1, Xu X1, Wang P1, Gruzdev A2, Zeldin DC2, Wang DW1.
Journal of cellular physiology.J Cell Physiol.2015 Sep;230(9):2108-19. doi: 10.1002/jcp.24939.
Macrophages, owning tremendous phenotypic plasticity and diverse functions, were becoming the target cells in various inflammatory, metabolic and immune diseases. Cytochrome P450 epoxygenase 2J2 (CYP2J2) metabolizes arachidonic acid to form epoxyeicosatrienoic acids (EETs), which possess various ben
PMID 25626689

Cytokines, angiogenic, and antiangiogenic factors and bioactive lipids in preeclampsia.

Das UN1.
Nutrition (Burbank, Los Angeles County, Calif.).Nutrition.2015 Sep;31(9):1083-95. doi: 10.1016/j.nut.2015.03.013. Epub 2015 Apr 29.
Preeclampsia is a low-grade systemic inflammatory condition in which oxidative stress and endothelial dysfunction occurs. Plasma levels of soluble receptor for vascular endothelial growth factor (VEGFR)-1, also known as sFlt1 (soluble fms-like tyrosine kinase 1), an antiangiogenic factor have been r
PMID 26233865

Japanese Journal

Dihomo-gamma-linolenic acid levels and obesity in patients with type 2 diabetes

Diabetology international 6(3), 206-211, 2015
NAID 40020601092

Effects of Docosahexaenoic Acid on the Endothelial Function in Patients with Coronary Artery Disease

Journal of Atherosclerosis and Thrombosis 22(5), 447-454, 2015
NAID 130005071052

Effects of Docosahexaenoic Acid on the Endothelial Function in Patients with Coronary Artery Disease

Journal of Atherosclerosis and Thrombosis, 2014
NAID 130004700298

「DHLA」

Dihomo-γ-linolenic acid
	Other names cis,cis,cis-8,11,14-Eicosatrienoic acid; DGLA
Identifiers
CAS number	1783-84-2
PubChem	5280581
ChemSpider	4444199
Jmol-3D images	Image 1; Image 3
	SMILES CCCCCC=CCC=CCC=CCCCCCCC(=O)O (canonical) CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O (isomeric) ;
	InChI InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-; Key: HOBAELRKJCKHQD-QNEBEIHSSA-N InChI=1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-; Key: HOBAELRKJCKHQD-QNEBEIHSBE ;
Properties
Molecular formula	C20H34O2
Molar mass	306.48 g mol−1
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

ジホモγリノレン酸

関: 8,11,14-eicosatrienoic acid、dihomo-gamma-linolenic acid

「ジホモγリノレン酸」

　　[★]

英: dihomo-gamma-linolenic acid、DHLA
関: 8,11,14-エイコサトリエン酸

「8,11,14-eicosatrienoic acid」

　　[★]

8

関: DHLA、dihomo-gamma-linolenic acid

「linolenic acid」

　　[★]

リノレン酸

関: alpha-linolenic acid、linolenate

「gamma」

　　[★] γ ガンマ　　　

[0] Horrobin, D. F., 1990a. Gamma linolenic acid. Rev. Contemp. Pharmacother. 1, 1-45

[1] Huang, Y.-S. and Mills, D. E. (Eds.), 1996. Gamma-linolenic acid metabolism and its roles in nutrition and medicine. AOCS Press, Champagne, Illinois, 319 pp.

[2] Fan, Yang-Yi and Robert S. Chapkin (9 September 1998). "Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition". Journal of Nutrition 128 (9): 1411–4. PMID 9732298. http://jn.nutrition.org/cgi/content/full/128/9/1411. Retrieved 2007-10-16.

[3] Belch, Jill JF and Alexander Hill (January 2000). "Evening primrose oil and borage oil in rheumatologic conditions". http://www.ajcn.org/cgi/content/full/71/1/352S. Retrieved February 12, 2006.

[pmid338112-4] Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-γ-linolenic acid in man". British Medical Journal 2 (6100): 1441–1444. doi:10.1136/bmj.2.6100.1441. PMC 1632618. PMID 338112. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1632618/.

[pmid9237935-5] Johnson MM, Swan DD, Surette ME et al. (1997). "Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. PMID 9237935.

[pmid10917903-6] Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH (August 2000). "Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans". J. Nutr. 130 (8): 1925–31. PMID 10917903.

リンク元	「DHLA」「ジホモγリノレン酸」「8,11,14-eicosatrienoic acid」
関連記事	「linolenic acid」「gamma」

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案内

dihomo-gamma-linolenic acid