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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"
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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）』「2017/02/10 22:18:58」(JST)

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Gamma-linolenic acid or GLA (γ-Linolenic acid), (INN and USAN gamolenic acid) is a fatty acid found primarily in vegetable oils. When acting on GLA, 5-lipoxygenase produces no leukotrienes and the conversion by the enzyme of arachidonic acid to leukotrienes is inhibited.

Chemistry

GLA is categorized as an n−6 (also called ω−6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ω) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n−6). GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of α-linolenic acid, which is a polyunsaturated n−3 (omega-3) fatty acid, found in rapeseed canola oil, soy beans, walnuts, flax seed (linseed oil), perilla, chia, and hemp seed.

History

GLA was first isolated from the seed oil of evening primrose. This herbal plant was grown by Native Americans to treat swelling in the body. In the 17th century, it was introduced to Europe and became a popular folk remedy, earning the name king's cure-all. in 1919, Heiduschka and Lüft extracted the oil from evening primrose seeds and described an unusual linolenic acid, which they name γ-. Later, the exact chemical structure was characterized by Riley.^[1]

Although there are α- and γ- forms of linolenic acid, there is no β- form. One was once identified, but it turned out to be an artifact of the original analytical process.^[2]

Dietary sources

GLA is obtained from vegetable oils such as evening primrose (Oenothera biennis) oil (EPO), blackcurrant seed oil, borage seed oil, and hemp seed oil. GLA is also found in varying amounts in edible hemp seeds, oats, barley,^[3] and spirulina. Normal safflower (Carthamus tinctorius) oil does not contain GLA, but a genetically modified GLA safflower oil available in commercial quantities since 2011 contains 40% GLA.^[4] Borage oil contains 20% GLA, evening primrose oil ranges from 8% to 10% GLA, and black-currant oil contains 15-20%.^[5]

The human body produces GLA from linoleic acid (LA). This reaction is catalyzed by Δ⁶-desaturase (D6D), an enzyme that allows the creation of a double bond on the sixth carbon counting from the carboxyl terminus. LA is consumed sufficiently in most diets, from such abundant sources as cooking oils and meats. However, a lack of GLA can occur when there is a reduction of the efficiency of the D6D conversion (for instance, as people grow older or when there are specific dietary deficiencies) or in disease states wherein there is excessive consumption of GLA metabolites.^[6]

Source of eicosanoids

The seed oil of Oenothera biennis (evening primrose) is a source of GLA

From GLA, the body forms dihomo-γ-linolenic acid (DGLA). This is one of the body's three sources of eicosanoids (along with AA and EPA.) DGLA is the precursor of the prostaglandin PGH₁, which in turn forms PGE₁ and the thromboxane TXA₁. Both PGE1₁ and TXA₁ are anti-inflammatory; thromboxane TXA₁, unlike its series-2 variant, induces vasodilation, and inhibits platelet^[7] consequently, TXA₁ modulates (reduces) the pro-inflammatory properties of the thromboxane TXA₂. PGE₁ has a role in regulation of immune system function and is used as the medicine alprostadil.

Unlike AA and EPA, DGLA cannot yield leukotrienes. However, it can inhibit the formation of pro-inflammatory leukotrienes from AA.^[8]

Although GLA is an n−6 fatty acid, a type of acid that is, in general, pro-inflammatory, it has anti-inflammatory properties. (See discussion at Essential fatty acid interactions: The paradox of dietary GLA.)

Health and medicine

GLA has been promoted as medication for a variety of ailments including breast pain and eczema, in particular by David Horrobin (1939 – 2003), whose marketing of evening primrose oil was described by the British Medical Journal (BMJ) as ethically dubious – the substance was likely to be remembered as "a remedy for which there is no disease".^[9] In 2002 the UK's Medicines and Healthcare products Regulatory Agency withdrew marketing authorisations for evening primrose oil as an eczema remedy.^[10] Another single source suggests that Evening Primrose Oil with adjuvant vitamin E, may reduce breast pain.^[11]

Notes and references

^ Yung-Sheng Huang, Vincent A. Ziboh (2001). Gamma-Linolenic Acid: Recent Advances in Biotechnology and Clinical Applications. AOCS Press. p. 259. ISBN 1-893997-17-0. Retrieved 2007-12-07.
^ Eckey, EW (1954). Vegetable Fats and Oils (volume 123 of American Chemical Society monograph series). Reinhold. p. 542.
^ Qureshi A.A., Schnoes H. K., Din Z. Z., Peterson D.M., et al. (1984). "Determination of the structure of cholesterol inhibitor II isolated from high-protein barley flour (HPBF)". Fed. Proc. 43 (7): 2626.
^ Nykiforuk, C.; Shewmaker, C. (19 August 2011). "High level accumulation of gamma linolenic acid in transgenic safflower (Carthamus tinctorius) seeds". Transgenic Research. 21 (2): 367–81. doi:10.1007/s11248-011-9543-5. PMID 21853296.
^ Flider, Frank J (May 2005). "GLA: Uses and New Sources" (PDF). INFORM. 16 (5): 279–282. Archived from the original (PDF) on 2014-01-12.
^ Horrobin DF (From the Efamol Research Institute. Kentville. Nova Scotia. Canada) (1993). "Fatty acid metabolism in health and disease: the role of delta-6-desaturase" (pdf). Am. J. Clin. Nutr. 57 (5 Suppl): 732S–736S; discussion 736S–737S. PMID 8386433.
^ King, Michael W. "Introduction to the Eicosanoids". The Medical Biochemistry Page. 1996–2013 themedicalbiochemistrypage.org, LLC. Retrieved 23 July 2013.
^ Belch JJ, Hill A (2000). "Evening primrose oil and borage oil in rheumatologic conditions". Am. J. Clin. Nutr. 71 (1 Suppl): 352S–6S. PMID 10617996. Retrieved 2007-12-07. DGLA itself cannot be converted to LTs but can form a 15-hydroxyl derivative that blocks the transformation of arachidonic acid to LTs. Increasing DGLA intake may allow DGLA to act as a competitive inhibitor of 2-series PGs and 4-series LTs and, thus, suppress inflammation.
^ Richmond, C. (2003). "David Horrobin". BMJ. 326 (7394): 885. doi:10.1136/bmj.326.7394.885.
^ Williams, H. C (2003). "Evening primrose oil for atopic dermatitis: Time To Say Goodnight". BMJ. 327 (7428): 1358–9. doi:10.1136/bmj.327.7428.1358. JSTOR 25457999. PMC 292973. PMID 14670851.
^ "Vitamin E and Evening Primrose Oil for Management of Cyclical Mastaglgia: A Randomized Pilot Study" (PDF). Alternative Medicine Review. Retrieved September 19, 2015.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. アトピー性皮膚炎（湿疹）の治療 treatment of atopic dermatitis eczema
2. 更年期のほてり menopausal hot flashes
3. 急性呼吸窮迫症候群：新しい治療法 acute respiratory distress syndrome novel therapies in adults
4. 尿毒症性そう痒症 uremic pruritus
5. Treatment of dry eye in Sjögren's syndrome treatment of dry eye in sjogrens syndrome

English Journal

Effect of post harvest radiation processing and storage on the volatile oil composition and glucosinolate profile of cabbage.

Banerjee A1, Variyar PS2, Chatterjee S1, Sharma A1.Author information 1Food Technology Division, Bhabha Atomic Research Centre, Mumbai 400 085, India.2Food Technology Division, Bhabha Atomic Research Centre, Mumbai 400 085, India. Electronic address: pvariyar@barc.gov.in.AbstractEffect of radiation processing (0.5-2kGy) and storage on the volatile oil constituents and glucosinolate profile of cabbage was investigated. Among the volatile oil constituents, an enhancement in trans-hex-2-enal was noted on irradiation that was attributed to the increased liberation of precursor linolenic acid mainly from monogalactosyl diacyl glycerol (MGDG). Irradiation also enhanced sinigrin, the major glucosinolate of cabbage that accounted for the enhanced allyl isothiocyanate (AITC) in the volatile oils of the irradiated vegetable. During storage the content of trans-hex-2-enal increased immediately after irradiation and then returned to the basal value within 24h while the content of sinigrin and AITC increased post irradiation and thereafter remained constant during storage. Our findings on the enhancement in potentially important health promoting compounds such as sinigrin and AITC demonstrates that besides extending shelf life and safety, radiation processing can have an additional advantage in improving the nutritional quality of cabbage.
Food chemistry.Food Chem.2014 May 15;151:22-30. doi: 10.1016/j.foodchem.2013.11.055. Epub 2013 Nov 18.
Effect of radiation processing (0.5-2kGy) and storage on the volatile oil constituents and glucosinolate profile of cabbage was investigated. Among the volatile oil constituents, an enhancement in trans-hex-2-enal was noted on irradiation that was attributed to the increased liberation of precursor
PMID 24423497

Functional Characterization of Polyunsaturated Fatty Acid Delta 6-Desaturase and Elongase Genes from the Black Seabream (Acanthopagrus schlegelii).

Kim SH, Park JS, Kim SY, Kim JB, Roh KH, Kim HU, Lee KR, Kim JB.Author information Rural Development Administration, National Academy of Agricultural Science, Seodun-Dong, Suwon, 441-707, Korea, sunheekim00@korea.kr.AbstractFatty acid delta 6-desaturase (D6DES) and elongases are key enzymes in the synthesis of polyunsaturated fatty acids (PUFAs) including arachidonic acid (ARA) and eicosapentaenoic acid (EPA) from microorganisms to higher animals. To identify the genes encoding D6DES and elongases for PUFAs, we isolated each cDNA with a high similarity to the D6DES and ELOVL5-like elongases of mammals and fishes via degenerate PCR and RACE-PCR from Acanthopagrus schlegelii. A recombinant vector expressing AsD6DES was subsequently constructed and transformed into Saccharomyces cerevisiae to test the enzymatic activity toward n-6 and n-3 fatty acids in the PUFA biosynthesis. The heterologously expressed AsD6DES produced γ-linolenic acid (GLA, C18:3 n-6) and stearidonic acid (STA, C18:4 n-3) at conversion rates of 26.3-35.6 % from exogenous linoleic acid (LA, C18:2 n-6) and α-linolenic acid (ALA, C18:3 n-3) substrates, respectively. When AsELOVL5 was expressed in yeast, it conferred an ability to elongate GLA to di-homo-γ-linolenic acid (DGLA, C20:3 n-6). In addition, AsELOVL5 showed an ability to convert ARA (C20:4 n-6) and EPA (C20:5 n-3) to dodecylthioacetic acid (DTA, C22:4 n-6) and docosapentaenoic acid (DPA, C22:5 n-3), respectively. In these results, the AsD6DES encodes a delta 6-fatty acid desaturase and the AsELOVL5 encoding a long-chain fatty acid elongase shows activity to enlongate C18Δ6/C20Δ5, but not C22.
Cell biochemistry and biophysics.Cell Biochem Biophys.2014 Mar;68(2):335-46. doi: 10.1007/s12013-013-9714-5.
Fatty acid delta 6-desaturase (D6DES) and elongases are key enzymes in the synthesis of polyunsaturated fatty acids (PUFAs) including arachidonic acid (ARA) and eicosapentaenoic acid (EPA) from microorganisms to higher animals. To identify the genes encoding D6DES and elongases for PUFAs, we isolate
PMID 24052399

Identification of saturated and unsaturated fatty acids released during microsomal incubations.

Bushee JL, Liang G, Dunne CE, Harriman SP, Argikar UA.Author information Department of Metabolism and Pharmacokinetics, Novartis Institutes for BioMedical Research Inc. , Cambridge, MA , USA and.AbstractAbstract 1. In vitro clearance in liver microsomes is routinely measured in drug discovery and development for new chemical entities. Literature reports indicate that long chain fatty acids such as arachidonic, linoleic and oleic acids may be released over a period of time during microsomal incubations. Some fatty acids have been shown to interfere with oxidative and conjugative reactions in microsomes, thus potentially inhibiting microsomal clearance of compounds. 2. The present study was aimed at deciphering the fatty acids present or released from microsomes. Analytical methods were developed to characterize and quantitatively assess the fatty acids without chemical derivatization in rat, monkey and human liver microsomes. Additionally, incubations with uridine-5'-diphosphoglucuronic acid (UDPGA) were utilized to trap the released fatty acids as their glucuronate esters, which were characterized and confirmed by high-resolution LC-MS/MS. 3. Our results indicate for the first time that timnodonic, trans-eicosenoic, gondoic, behenic, and nervonic acid were released during microsomal incubations. Additionally, α- and γ-linolenic, timnodonic, palmitoleic, linoleic, arachidonic, palmitic, oleic, and stearic acid were identified as their corresponding acyl-glucuronides in rat, monkey and human liver microsomes, providing the first direct evidence that the released fatty acids are capable of forming glucuronides under incubation conditions.
Xenobiotica; the fate of foreign compounds in biological systems.Xenobiotica.2014 Feb 6. [Epub ahead of print]
Abstract 1. In vitro clearance in liver microsomes is routinely measured in drug discovery and development for new chemical entities. Literature reports indicate that long chain fatty acids such as arachidonic, linoleic and oleic acids may be released over a period of time during microsomal incuba
PMID 24502389

Japanese Journal

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

Yamashita Kaoru,Higa Mariko,Kunishita Rieko [他]
Diabetology international 6(3), 206-211, 2015
NAID 40020601092

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

Yagi Shusuke,Aihara Ken-ichi,Fukuda Daiju,Takashima Akira,Hara Tomoya,Hotchi Junko,Ise Takayuki,Yamaguchi Koji,Tobiume Takeshi,Iwase Takashi,Yamada Hirotsugu,Soeki Takeshi,Wakatsuki Tetsuzo,Shimabukuro Michio,Akaike Masashi,Sata Masataka
Journal of Atherosclerosis and Thrombosis 22(5), 447-454, 2015
… Aim: The consumption of n-3 polyunsaturated fatty acids (PUFA), including docosahexaenoic acid DHA), reduces the incidence of cardiovascular events, and reduced serum levels of n-3 PUFA may be associated with an increased risk of cardiovascular events. …
NAID 130005071052

Fatty Acid Compositions of Silver Catfish, Pangasius sp. Farmed in Several Rivers of Pahang, Malaysia

Hashim Ridzwan B.,Jamil Elyna Fatinie,Zulkipli Farah Hanis,Daud Jamaluddin Mohd
Journal of Oleo Science advpub(0), 2015
… The present study evaluated fatty acid profiles of fish muscles in these two Pangasius sp. … The results showed MUFAs (Monounsaturated fatty acid) content was highest (35.0-44.4%) followed by SFA (Saturated fatty acid) [32.0-41.5%] and PUFAs (polyunsaturated fatty acids) [9.3-19.3%]. … Kanchong displayed higher palmitic acid (SFA; … In contrast, oleic acid (MUFA) revealed highest in P. …
NAID 130004800129

Related Pictures

★リンクテーブル★

リンク元	「γリノレン酸」
拡張検索	「dihomo-gamma-linolenic acid」
関連記事	「linolenic acid」「gamma」

「γリノレン酸」

**γ-Linolenic acid**
Names
	IUPAC name all-cis-6,9,12-octadecatrienoic acid
	Other names Gamma-linolenic acid, gamolenic acid, GLA
Identifiers
CAS Number	506-26-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28661
ChEMBL	ChEMBL464982
ChemSpider	4444436
ECHA InfoCard	100.107.263
IUPHAR/BPS	4710
PubChem	5280933
UNII	78YC2MAX4O
	InChI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- Key: VZCCETWTMQHEPK-QNEBEIHSSA-N ; InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- Key: VZCCETWTMQHEPK-QNEBEIHSBP ;
	SMILES O=C(O)CCCC\C=C/C\C=C/C\C=C/CCCCC ;
Properties
Chemical formula	C18H30O2
Molar mass	278.44 g·mol−1
Appearance	Colorless oil
Pharmacology
ATC code	D11AX02 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: gamma-linolenic acid
関: γ-リノレン酸

「dihomo-gamma-linolenic acid」

　　[★]

ジホモγリノレン酸

関: 8,11,14-eicosatrienoic acid、DHLA

「linolenic acid」

　　[★]

リノレン酸

関: alpha-linolenic acid、linolenate

「gamma」

　　[★] γ ガンマ　　　

[Huang-1] Yung-Sheng Huang, Vincent A. Ziboh (2001). Gamma-Linolenic Acid: Recent Advances in Biotechnology and Clinical Applications. AOCS Press. p. 259. ISBN 1-893997-17-0. Retrieved 2007-12-07.

[Eckey1954-2] Eckey, EW (1954). Vegetable Fats and Oils (volume 123 of American Chemical Society monograph series). Reinhold. p. 542.

[3] Qureshi A.A., Schnoes H. K., Din Z. Z., Peterson D.M., et al. (1984). "Determination of the structure of cholesterol inhibitor II isolated from high-protein barley flour (HPBF)". Fed. Proc. 43 (7): 2626.

[4] Nykiforuk, C.; Shewmaker, C. (19 August 2011). "High level accumulation of gamma linolenic acid in transgenic safflower (Carthamus tinctorius) seeds". Transgenic Research. 21 (2): 367–81. doi:10.1007/s11248-011-9543-5. PMID 21853296.

[5] Flider, Frank J (May 2005). "GLA: Uses and New Sources" (PDF). INFORM. 16 (5): 279–282. Archived from the original (PDF) on 2014-01-12.

[pmid8386433-6] Horrobin DF (From the Efamol Research Institute. Kentville. Nova Scotia. Canada) (1993). "Fatty acid metabolism in health and disease: the role of delta-6-desaturase" (pdf). Am. J. Clin. Nutr. 57 (5 Suppl): 732S–736S; discussion 736S–737S. PMID 8386433.

[7] King, Michael W. "Introduction to the Eicosanoids". The Medical Biochemistry Page. 1996–2013 themedicalbiochemistrypage.org, LLC. Retrieved 23 July 2013.

[Belch-8] Belch JJ, Hill A (2000). "Evening primrose oil and borage oil in rheumatologic conditions". Am. J. Clin. Nutr. 71 (1 Suppl): 352S–6S. PMID 10617996. Retrieved 2007-12-07. DGLA itself cannot be converted to LTs but can form a 15-hydroxyl derivative that blocks the transformation of arachidonic acid to LTs. Increasing DGLA intake may allow DGLA to act as a competitive inhibitor of 2-series PGs and 4-series LTs and, thus, suppress inflammation.

[dh-obit-9] Richmond, C. (2003). "David Horrobin". BMJ. 326 (7394): 885. doi:10.1136/bmj.326.7394.885.

[goodnight-10] Williams, H. C (2003). "Evening primrose oil for atopic dermatitis: Time To Say Goodnight". BMJ. 327 (7428): 1358–9. doi:10.1136/bmj.327.7428.1358. JSTOR 25457999. PMC 292973. PMID 14670851.

[pittedu-11] "Vitamin E and Evening Primrose Oil for Management of Cyclical Mastaglgia: A Randomized Pilot Study" (PDF). Alternative Medicine Review. Retrieved September 19, 2015.

v t e Lipids: fatty acids

Saturated	Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecanoic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Heptacosylic (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38)

ω−3 Unsaturated	α-Linolenic (18:3) Stearidonic (18:4) Eicosapentaenoic (20:5) Docosahexaenoic (22:6)

ω−6 Unsaturated	Linoleic (18:2) γ-Linolenic (18:3) Dihomo-γ-linolenic (20:3) Arachidonic (20:4) Adrenic (22:4)

ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Paullinic (20:1)

ω−9 Unsaturated	Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) Mead (20:3)

匿名

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案内

案内

gamma-linolenic acid