Skip to main content
Log in

Furan fatty acids: their role in plant systems

  • Published:
Phytochemistry Reviews Aims and scope Submit manuscript

Abstract

Furan fatty acids (F-acids) are heterocyclic fatty acids having a furan ring in their structure. Most existing studies on F-acids are related to either fish or other marine animals. Even though F-acids have been detected in many plant species, not much work has been done exclusively in plants of economic importance, especially oilseed crops. This review focuses mainly on the functions and roles of F-acids in plants. In plants, they are bound to phospholipids by substituting PUFA and function as free radical scavengers suggesting their role in defense against oxidative stress. Owing to their antioxidative property F-acids are highly unstable and their photooxidative products can contribute to the flavor of edible oils.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

EI mass spectrometry:

Electron ionization mass spectrometry

F-acids:

Furan fatty acids

PUFA:

Poly unsaturated fatty acids

References

  • Asada K (1999) The water-water cycle in chloroplasts: scavenging of active oxygen and dissipation of excess photons. Ann Rev Plant Physiol Plant Mol Biol 50:601–639

    Article  CAS  Google Scholar 

  • Batna A, Spiteller G (1994) Effects of soybean lipoxygenase-1 on phosphatidylcholines containing furan fatty acids. Lipids 29:397–403

    Article  CAS  PubMed  Google Scholar 

  • Batna A, Scheinkönig J, Spiteller G (1993) The occurrence of furan fatty acids in Isochrysis sp. and Phaeodactylum tricornutum. Biochim Biophys Acta 1166:171–176

    Article  CAS  PubMed  Google Scholar 

  • Belitz HD, Grosch W, Schieberle P (2009) Food chemistry, 4th edn. Springer, Berlin, vol 2, p 164

  • Boselli E, Grob K, Lercker G (2000) Determination of furan fatty acids in extra virgin olive oil. J Agric Food Chem 48:2868–2873

    Article  CAS  PubMed  Google Scholar 

  • Chander AK (2010) Characterization and oxidative stability of specialty plant seed oils. Dissertation, Aston University

  • Connor WE (2000) Importance of n-3 fatty acids in health and disease. Am J Clin Nutr 71:171–175

    Google Scholar 

  • Foyer CH, Noctor G (2000) Oxygen processing in photosynthesis: regulation and signaling. New Phytol 146:359–388

    Article  CAS  Google Scholar 

  • Glass RL, Krick TP, Sand DM, Rahn CH, Schlenk H (1975) Furanoid fatty acids from fish lipids. Lipids 10:695–702

    Article  CAS  PubMed  Google Scholar 

  • Gorst ACP, Puchta V, Spiteller G (1988) Investigations of the origin of furan fatty acids (F-acids). Lipids 23:1032–1036

    Article  Google Scholar 

  • Grosch W, Konopka UC, Guth H (1992) Characterization of off-flavors by aroma extract dilution analysis. In: St. Angelo AJ (ed) Lipid oxidation in food. American Chemical Society, Washington, pp 266–278

    Chapter  Google Scholar 

  • Guth H, Grosch W (1989) 3-Methylnonane-2,4-dione—an intense odour compound formed during flavour reversion of soya-bean oil. Fat Sci Technol 91:225–230

    CAS  Google Scholar 

  • Guth H, Grosch W (1991) Detection of furanoid fatty acids in soya-bean oil—cause for the light-induced off-flavour. Fat Sci Technol 93:249–255

    CAS  Google Scholar 

  • Guth H, Grosch W (1993) Furanoid fatty acids as precursors of a key aroma compound of green tea. In: Schreier P, Winterhalter P (eds) Progress in flavour precursor studies. Allured Publishing Corporation, Carol Stream, pp 401–407

    Google Scholar 

  • Guth H, Grosch W (1997) Stability of furanoid fatty acids in soybean oil. J Am Oil Chem Soc 74:323–326

    Article  CAS  Google Scholar 

  • Guth H, Zhang Y, Laskawy G, Grosch W (1995) Furanoid fatty acids in oils from soybeans lacking lipoxygenase isoenzymes. J Am Oil Chem Soc 72:397–398

    Article  CAS  Google Scholar 

  • Gutteridge JMC (1995) Lipid peroxidation and antioxidants as biomarkers of tissue damage. Clin Chem 41:1819

    CAS  PubMed  Google Scholar 

  • Hannemann K, Puchta V, Simon E, Ziegler G, Spiteller G (1989) The common occurrence of furan fatty acids in plants. Lipids 24:296–298

    Article  CAS  PubMed  Google Scholar 

  • Hasma H, Subramaniam A (1978) The occurrence of furanoid fatty acid in Hevea brasiliensis latex. Lipids 13:905–907

    Article  CAS  Google Scholar 

  • Isabelle AS (2002) Investigation on aroma active photooxidative degradation products originating from dimethyl pentyl furan fatty acids in green tea and dried green herbs. Dissertation, Swiss Federal Institute of Technology Zurich

  • Ishii K, Okajima H, Okada Y, Konishi H, Watanabe H (1989) Effects of phosphatidylcholines containing furan fatty acid on oxidation in multilamellar liposomes. Chem Pharm Bull 37:1396–1398

    Article  CAS  Google Scholar 

  • Johnson SM, Doherty SJ, Croy RRD (2003) Biphasic superoxide generation in potato tubers. A self-amplifying response to stress. Plant Physiol 131:1440–1449

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Kim HR, Ellamar JB (2013) Production methods of furan fatty acids. US Patent 8,426,620, April 2013

  • Liengprayoon S, Sriroth K, Dubreucq E, Vaysse L (2011) Glycolipid composition of Hevea brasiliensis latex. Phytochemistry 72:1902–1913

    Article  CAS  PubMed  Google Scholar 

  • Masanetz C, Grosch W (1998) Hay-like off-flavour of dry parsley. Z Lebensm Unters Forsch A 206:114–120

    Article  CAS  Google Scholar 

  • Masanetz C, Guth H, Grosch W (1998) Fishy and hay-like off-flavours of dry spinach. Z Lebensm Unters Forsch A 206:108–113

    Article  CAS  Google Scholar 

  • Mitei YC, Ngila JC, Yeboah SO, Wessjohann L, Schmidt J (2009) Profiling of phytosterols, tocopherols and tocotrienols in selected seed oils from Botswana by GC–MS and HPLC. J Am Oil Chem Soc 86:617–625

    Article  CAS  Google Scholar 

  • Morris LJ, Marshall MO, Kelly W (1966) A unique furanoid fatty acid from exocarpus seed oil. Tetrahedron Lett 7:4249–4253

    Article  Google Scholar 

  • Okada Y, Okajima H, Konishi H, Terauchi M, Ishii K, Liu IM, Watanabe H (1990) Antioxidant effect of naturally occurring furan fatty acids on oxidation of linoleic acid in aqueous dispersion. J Am Oil Chem Soc 67:858–862

    Article  CAS  Google Scholar 

  • Okada Y, Kaneko M, Okajima H (1996) Hydroxyl radical scavenging activity of naturally occurring furan fatty acids. Biol Pharm Bull 19:1607–1610

    Article  CAS  PubMed  Google Scholar 

  • Pande G, Akoh CC (2009) Antioxidant capacity and lipid characterization of six Georgia-grown pomegranate cultivars. J Agric Food Chem 57:9427–9436

    Article  CAS  PubMed  Google Scholar 

  • Rahn CHS, Krick DMTP, Glass RL, Schlenk H (1981) Synthesis of radioactive furan fatty acids. Lipids 16:360–364

    Article  CAS  Google Scholar 

  • Scheinkönig J, Spiteller G (1993) F-Säure-haltige Phospholipidmoleküle in Zuckerrohrzellen. Liebigs Ann Chem 1993:121–124

    Article  Google Scholar 

  • Spiteller G (2005) Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet? Lipids 40:755–771

    Article  CAS  PubMed  Google Scholar 

  • Triqui R, Reineccius GA (1995) Flavor development in the ripening of anchovy (Engraulis encrasicholus L.). J Agric Food Chem 43:453–458

    Article  CAS  Google Scholar 

  • Vetter W, Wendlinger C (2013) Furan fatty acids—valuable minor fatty acids in food. Lipid Technol 25:7–10

    Article  CAS  Google Scholar 

  • Vetter W, Laurie S, Wendlinger C, Matthes A, Smith AWT, Knight DW (2012) Determination of furan fatty acids in food samples. J Am Oil Chem Soc 89:1501–1508

    CAS  Google Scholar 

  • Yurawecz MP, Hood JK, Mossoba MM, Roach JAG, Ku Y (1995) Furan fatty acids determined as oxidation products of conjugated octadecadienoic acid. Lipids 30:595–598

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ibandalin Mawlong.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mawlong, I., Sujith Kumar, M.S. & Singh, D. Furan fatty acids: their role in plant systems. Phytochem Rev 15, 121–127 (2016). https://doi.org/10.1007/s11101-014-9388-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11101-014-9388-7

Keywords

Navigation