Identification and distribution of oxygenated fatty acids in Plantago seed lipids

JAOCS, Journal of the American Oil Chemists' Society

Volumn 91, Issue 8, 2014, Pages 1313-1322

  Smith, Mark A ^a   Zhang, Haixia ^a   Purves, Randy W ^a,b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Fatty acid methyl ester mass spectra; Isoricinoleic acid; MALDI TOF MS; Oxo fatty acid; Plantago lanceolata; Seed oil; Triacylglycerol estolide

Indexed keywords

BIOCHEMISTRY; GLYCEROL; LIPIDS; MASS SPECTROMETRY; MONOUNSATURATED FATTY ACIDS; OILS AND FATS; OLEIC ACID;

ESTOLIDES; MALDI TOF MS; MASS SPECTRA; PLANTAGO LANCEOLATA; SEED OIL;

SEED;

PLANTAGO; PLANTAGO CORONOPUS; PLANTAGO LANCEOLATA; PLANTAGO MAJOR; PLANTAGO NIVALIS; PLANTAGO OVATA; PLANTAGO SEMPERVIRENS;

EID: 84905117503     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-014-2478-2     Document Type: Article

References (27)

1. Harris CP (1927) Castor Oil as a Lubricant. Oil Fat Ind 4:11-14
2. Ogunniyi DS (2006) Castor oil: a vital industrial raw material. Biores Technol 9:1086-1091
3. Mutlu H, Meier MAR (2010) Castor oil as a renewable resource for the chemical industry. Eur J Lipid Sci Technol 112:10-30
4. Ahmad F, Schiller H, Mukherjee KD (1986) Lipids containing isoricinoleoyl (9-hydroxy-cis-12-octacedenoyl) moieties in seeds of Wrightia species. Lipids 21:486-490
5. Ahmad I, Singh J (1990) Surface active properties of sulphonated isoricinoleic acid. J Am Oil Chem Soc 67:205-208 (Pubitemid 20706005)
6. Lie Ken Jie MSF, Syed-Rahmatullah MSK (1991) Synthesis and properties of a novel 1-pyrroline fatty ester derivative from methyl isoricinoleate. J Chem Soc Perkin Trans 1(1991):421-424
7. Ahmad I, Lie Ken Jie MSF (2008) Oleochemicals from isoricinoleic acid (Wrightia tinctoria seed oil). Ind Eng Chem Res 47:2091-2095
8. Ahmed SM, Ahmad F, Osman SM (1985) Preparation and characterization of derivatives of isoricinoleic acid and their antimicrobial activity. J Am Oil Chem Soc 62:1578-1580 (Pubitemid 15609640)
9. Badami RC, Patil KB (1980) Structure and occurrence of unusual fatty acids in minor seed oils. Prog Lipid Res 19:119-153
10. Ronsted N, Chase MA, Albach DC, Bello MA (2002) Phylogenetic relationships within Plantago (Plantaginaceae): evidence from nuclear ribosomal ITS and plastid trnL-F sequence data. Bot J Linn Soc 139:323-338 (Pubitemid 34995779)
11. Samuelsen AB (2000) The traditional uses, chemical constituents and biological activities of plantago major L: a review. J Ethnopharmacol 71:1-21 (Pubitemid 30440649)
12. European Medicines Agency, Committee on Herbal Medicinal Products, 14 May 2013, Assessment report on Plantago ovata Forssk. Seminis tegumentum. EMA/HMPC/199775/2012
13. Stewart AV (1996) Plantain (Plantago lanceolata) - a potential pasture species. Proc NZ Grassl Assoc 58:77-86
14. Ronsted N, Franzyk H, Molgaard P, Jaroszewski JW, Jensen SR (2003) Chemotaxanony and evolution of Plantago L. Plant Syst Evol 242:63-82 (Pubitemid 38086236)
15. Ahmad MS, Ahmad MU, Osman SM (1980) A new hydroxyolefinic acid from Plantago major seed oil. Phytochemistry 19:2137-2139
16. Jamal S, Ahmad I, Agarwal R, Ahmad M, Osman SM (1987) A novel oxo fatty acid in Plantago ovata seed oil. Phytochemistry 26:3067-3069
17. Kunst L, Taylor DC, Underhill EW (1992) Fatty acid elongation in developing seeds of Arabidopsis thaliana. Plant Physiol Biochem 30:425-434
18. Puttick D, Dauk M, Lozinsky S, Smith MA (2009) Overexpression of a FAD3 desaturase increases synthesis of a polymethylene-interrupted dienoic fatty acid in seeds of Arabidopsis thaliana L. Lipids 44:753-757
19. Buser H-R, Arn P, Guerin P, Rauscher S (1983) Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts. Anal Chem 55:818-822 (Pubitemid 13546908)
20. Smith MA, Dauk M, Ramadan H, Yang H, Seamons LE, Haslam RP, Beaudoin F, Ramirez-Erosa I, Forseille L (2013) Involvement of Arabidopsis Acyl-coenzyme a desaturase-like2 (At2g31360) in the biosynthesis of very-long-chain monounsaturated fatty acid components of membrane lipids. Plant Physiol 161:81-96
21. Zhang H, Olson DJH, Van D, Purves RW, Smith MA (2012) Rapid identification of triacylglycerol-estolides in plant and fungal oils. Ind Crop Prod 37:186-194
22. Kleiman R, Spencer GF (1973) Gas chromatography-mass spectrometry of methyl esters of unsaturated oxygenated fatty acids. J Am Oil Chem Soc 50:31-38
23. Hecht S, Spiteller G (1998) Linoleic acid peroxidation products are metabolized by hydrogenation in porcine liver tissue. Eur Mass Spectrom 4:393-399
24. Shibahara A, Yamamoto K, Kinoshita A (2006) Mass spectral analysis of 10-hydroxy-octadec-12-enoic acid found in rice bran oil. J Rehabil Health Sci 4:49-52
25. Smith MA, Moon H, Chowrira G, Kunst L (2003) Heterologous expression of a fatty acid hydroxylase gene in developing seeds of Arabidopsis thaliana. Planta 217:507-516 (Pubitemid 36933287)
26. Smith MA, Zhang H, Forseille L, Purves RW (2013) Characterization of novel triacylglycerol estolides from the seed oil of Mallotus philippensis and Trewia nudiflora. Lipids 48:75-78
27. Fuchs B, Süß R, Schiller J (2010) An update of MALDI-TOF mass spectrometry in lipid research. Prog Lipid Res 49:450-475