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61h Symposium an Renewable Resources
The oil of L. campestre contains 35 % linolenic acid and 23 %
erucic acid. The seed is coated by a mucilage, that expands in
contact with water. The amount of ash and dietary fibres are
higher, while the content of oil (22 %) and crude protein (24 % of
the dry matter) are lower, compared to Brassica oil-seeds. New
crops that do not cross and recombine with Bras-sica species, are
needed for increased cultivation to supply the demand of
alternatives to fossil oil products in our society.
204
Unusual seed oil fatty acids in the plant kingdom
Unusual seed oil fatty acids in the plant kingdom
Kurt Aitzetmüller Institute for Chemistry and Physics of Lipids,
BAGKF, Münster, Germany
Keywords: Unusual fatty acids, phylogeny, new sources, plant
kingdom
Abstract
The biosynthetic potential of higher plants for the synthesis of
unusual fatty acid structures - which may eventually be of interest
to the chemical industry- is considerable /1/. Phylogenetic
considerations based on gas chromatographic "seed oil fatty acid
fingerprints" - in combination with an available data collection -
are essential for the search for, and disco-very of, new sources of
unusual fatty acids. This is illustrated in the pre-sent paper by
way of several examples taken from the published litera-ture and
from own investigations.
Over the last 25 years, literature data and data from own
investigati-ons have been collected regarding the fatty acid
composition of seeds and seed oils from higher plants, including
many wild species. This collection currently contains literature
references and data from about 6,000 plant species. A selective
parallel collection of capillary gas chromatographic fatty acid
"fingerprints" of seeds of wild species has also been established
/2,3/. Under standardized GLC conditions, these finger-prints show
the presence and elution sequence of unusual fatty acid com-ponents
in the gas chromatograms of seed oils. They can be used for
phy-logenetic and chemotaxonomic studies regarding the evolution
and distribution of unusual - and possibly technically interesting
- fatty acids in the plant kingdom / 5-9 / . In this way, a number
of new fatty acids and unusual fatty acid patterns has been
discovered, which will be shown and discussed.
205
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6th s . ymposium on Renewable Resources
I~ another project, the present manual data collection will be
transfor-med mto a computer-searchable data base and will be made
availabl · :nterne~. Details of this _rroject, which will also
permit a search for pa:~~~ atty ac1d structures, will be described
elsewhere.
Poster
The present p.oster was originally submitted as an oral
commun:ation and the orgaruzers were informed that the material may
not be suitable a~ a poster. To make the best of it, it was decided
to simply present here _ as a poster - a numb~r of stru~tures
(selected examples only) of fatty acids that can be found m seed
mls of higher plants. Shown below are· Struc-ture ~schematic),
"shorthand notation" and level found (exampl~s onl area-Yo of t~tal
seed fatty acids in GLC, as found in natural seed oils). y,
The vanous fatty acid structures shown below should be "f d f th
ht" f h . oo or
oug o~ syi:it ehe organic chemists working in the chemical and
pharmaceuhcal mdustries. An electronic data base will be available
in ~bou~ two years. In the field of renewable resources, this may
help to idenhfy sources .of genes and enzymes for plant breeding,
gene transfer, and enzyme des1gn to produce tailormade fats.
Acknowledgement
The aut~or ~s .indebted to Ms. Miriam' Schmitz for providing the
formulae and mamtammg the Institute's data collection. This work
was supported by Fachagentur Nachwachsende Rohstoffe, Gülzow
Germany (G t FNR FKZ 97NR193). , ' ran
206
Unusual seed oil fatty acids in the plant kingdom
References
References to published papers related to the "seed oil fatty
acids / rene-wable resources data collection" of the Institute for
Chemistry and Phy-sics of Lipids: /1/ Aitzetmüller, K.: Was können
Pflanzen eigentlich alles? In: Eierdanz, H . (Editor):
Perspektiven Nachwachsender Rohstoffe in der Chemie. VCH,
Weinheim; 1996; pp. 209-217.
/2/ Aitzetmüller, K.: Capillary GLC Fatty Acid Fingerprints of
Seed Lipids -A Tool in Plant Chemotaxonomy? J. High Resol.
Chromatogr. 16, 488-490 (1993).
/3/ Aitzetmüller, K.: Fatty Acid Patterns of Ranunculaceae Seed
Oils: Phylogenetic Relationships. Plant Syst. Evol. [Suppl.] 9,
229-240 (1995).
/4/ Aitzetmüller, K. and Tsevegsüren, N.: Seed Fatty Acids,
"Front-End"-Desatura-ses and Chemotaxonomy - A Case Study in the
Ranunculaceae. J. Plant Physiol. 143, 538-543 (1994).
/5/ Aitzetmüller, K. : Seed Fatty Acids, Chemotaxonomy and
Renewable Resources. In: Oils-Fats-Lipids 1995: Proceedings of the
2lst World Congress of the Interna-tional Society for Fat Research,
The Hague, 1995. Vol. 1. P. J. Barnes & Associa-tes,
Bridgwater; 1996; pp. 117-120.
/6/ Aitzetmüller, K.: Agonandra Seed Oil - An Excellent Source
of a Truly Multi-functional Fatty Acid. Fett-Lipid 100, 21-23
(1998).
/7 / Aitzetmüller, K.: An Unusual Fatty Acid Pattern in Eranthis
Seed Oil. Lipids 31, 201-205 (1996).
18/ Tsevegsüren, N. and Aitzetmüller, K.: Unusual t.5cis-Fatty
Acids in Seed Oils of Cimicifuga Species. J. High Resol.
Chromatogr. 20, 237-241 (1997).
/9 / Aitzetmüller, K., Tsevegsüren, N. and Vosmann, K.: A new
allenic fatty acid in Phlomis (Lamiaceae) seed oil. Fett-Lipid 99,
74-78 (1997). .
/10/ Aitzetmüller, K., G. Werner and N. Tsevegsüren: Screening
of Seed Lipids for y-Linolenic Acid: Capillary Gas-Liquid
Chromatographie Separation of 18:3 Fatty Acids with t.5- and
t.6-Double Bonds. Phytochem. Anal. 4 (1993) 249-255.
/11/ Aitzetmüller, K. and G. Werner: Stearidonic acid (18:4w3)
in Primulajlorindae. Phytochemistry 30 (1991) 4011-4013.
/12/ Tsevegsüren, N. and K. Aitzetmüller: y-Linolenic Acid in
Anemone spp. Seed Lipids. Lipids 28 (1993) 841-846.
/13/ Aitzetmüller, K.: Seed oil fatty acids in the Labiatae.
Lamiales Newsletter (Kew /London) 5 (1997) 3-5.
/14/ Spitzer, V., K. Aitzetmüller and K. Vosmann: The seed oil
of Bernardia pulchella (Euphorbiaceae) - A rich source of vernolic
acid. J. Amer. Oil Chem. Soc. 73 (1996) 1733-1735.
/15/ Tsevegsüren, N., K. Aitzetmüller and G. Werner: Fatty Acids
of Some Central Asian Labiatae. Lamiales Newsletter (Kew /London) 5
(1997) 6-8.
/16/ Aitzetmüller, K.: M-, t.5- und t.6-Fettsäuren. In:
Schlimme, E. (Ed.), Ernäh-rungs-physiologische Eigenschaften von
Lebensmitteln, Schriftenreihe des Bun-
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6th Symposium on Renewable Resources
desministeriums für Ernährung, Landwirtschaft und Forsten, Reihe
A: Ange-wandte Wissenschaft; Heft 445. Landwirtschaftsverlag,
Münster (1995) 2-13.
/17 / Aitzetmüller, K.: Pflanzliche Öle: Namen von Ölen und
Fetten und ihre botani-sche Herkunft - Vegetable Oils of the World:
Names of Oils and Fats and their Botanical Source. Fat Sei.
Techno!. 97 (1995) 539-544.
/18/ Aitzetmüller, K., G. Werner and S. A. Ivanov: Seed Oils of
Nigella Species and of Closely Related Genera. OCL- Oleagineux,
Corps Gras, Lipides 4 (1997) 385~3S8.
/19/ Tsevegsüren, N., K. Aitzetmüller and K. Vosmann: Unusual
fatty acids in Com-positae: r-Linolenic acid in Saussurea spp. seed
oils. J. High Resol. Chrornatogr. 20 (1997) 315-320.
/20/ Aitzetmüller, K.: Biologische Vielfalt und Nachwachsende
Rohstoffe auf dem Fettgebiet (Biodiversity and Renewable Resources
in the Fats and Oils Area). In: Welling, M. (Ed.), Biologische
Vielfalt in Ökosystemen - Konflikt zwischen Nut-zung und Erhaltung,
Schriftenreihe des BML, Reihe A: Angewandte Wissen-schaft. Köllen
Verlag, Bonn (1997) 302-304.
/21 / Aitzetmüller, K., N . Tsevegsüren and G. Werner: Seed Oil
Fatty Acid Patterns of the Aconitum-Delphinium-Helleborus Complex
(Ranunculaceae). Plant Systema-tics and Evolution 215 (1999)
37-47.
/22/ Aitzetmüller, K. and K. Vosmann: Cyclopropenoic Fatty Acids
in Gym-nosperms: The Seed Oil of Welwitschia. JAOCS 75 (1998)
1761-1765.
/23/ Aitzetmüller, K.: Komaroffia Oils - An Excellent New Source
of D.5-Unsaturated Fatty Acids. JAOCS 75 (1998) 1897-1899.
/24/ Ivanov, S. A. and K. Aitzetmüller: Untersuchungen über die
Tocopherol- und Tocotrienol-Zusammensetzung der Samenöle einiger
Vertreter der Apiaceae. Fat Sei. Techno!. 97 (1995) 24-29.
/25/ Ivanov, S. A. and K. Aitzetmüller: Untersuchungen über die
Tocopherol- und Tocotrienol-Zusammensetzung der Samenlipide einiger
Arten der bulgarischen Flora. Fett - Lipid 100 (1998) 348-352.
Numerous other · references to the published results of other
working groups are cited in the above papers. Readers are also
referred to the following standard reviews:
/26/ Gunstone,F. D.,J. L. HarwoodandF. B. Padley: The
LipidHandbook. 2nd Edition. /27 / Chapman & Hall, London (1994)
/28/ Badarni,.R. C. and K. B. Patil: Structure and occurrence of
unusual fatty acids in
minor seed oils. Progr. Lipid Res. 19 (1981) 119-153 /29 /
Hegnauer, R.: Chemotaxonomie der Pflanzen. Birkhäuser, Basel (1990)
/30/ Pohl, P. and H. Wagner: Fettsäuren im Pflanzen- und Tierreich
(eine Übersicht)
II: Trans-ungesättigte, Alkin-, Hydroxy-, Epoxy-, Oxo-,
Cyclopropan- und Cyclopropen-Fettsäuren. Fette, Seifen, Anstrichm.
74 (1972) 541-550
/31/ Srnith, C. R.: Occurrence of unusual fatty acids in plants.
In: Holman, R. T. (Ed.), Progr. Chem. Fats Other Lipids. Pergamon
Press, Oxford ( 1970) 137-177
208
Unusual seed oil fatty acids in the plant kingdom
Reference to formulas and data shown below: Seed oil fatty acids
/ renewable resources data collection of the Institute for
Chemistry and Physics of Lipids, Münster, Germany.
Address of the author:
Dir. u . Prof. Dr. Kurt Aitzetmüller, Institute for Chemistry
and Physics of Lipids, BAGKF, Piusallee 76, D-48147 Münster,
Germany. Tel.: 0251-43510, Fax: 0251-519275, e-mail:
[email protected]
Fig. 1-9: Collection of structural formulas (schematic),
"shorthand nota-tion" and levels found for various fatty acids
(examples only; % figures are area-% of total seed oil fatty acids
by
GLC).
209
