Algal and bacterial lipids
2008
Research Seminar
Tobias Kind
fiehnlab.ucdavis.edu
http://fiehnlab.ucdavis.edu/staff/kind/Metabolomics/LipidAnalysis/
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by attribution: Tobias Kind (FiehnLab)
CC-by: Tobias Kind (2008)
LIPIDS
Source: Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH, Murphy RC, Raetz CRH, Russell DW:
LMSD: LIPID MAPS structure database. Nucleic Acids Research 2007, 35(1):D527-D532. doi:10.1093/nar/gkl838
Odd and even chained lipids
Odd carbon chained alkanes are common in algae an bacteria
(examples V. furnissii or B. braunii)
Odd carbon chain fatty acids are common in algae and bacteria
and odd short chain fatty acids in animals
 Odd carbon chain fatty acids and alkanes are part of human diet
via diary products (bacteria in rumen) and fish and plant intake
Chain length and maximum degree of unsaturation
YYNGQLOFHNMZSC-GVKGLABJBC
[28:8(n-3)] FA
C28H40O2
octacosaoctaenoic acid
from microalgae
Nine double bonds
in crustacea (not algae)
doi:10.1016/j.chroma.2005.08.011
Maximum chain lengths
Neutral Lipids: Chain length C40
Glycolipids: Chain length C30−36, C50−58, C74−82
Phospholipids: common up to C40 FA
DGDG
SQDG
Source: Membrane Lipids in Algae; John L. Harwood; Springer Verlag
Glycosylglicerides in algae
MGDG
Other lipid classes found in algae
Sulfonoglycolipids
Aminoglucoglycerolipids
Oxylipins
Galactolipids
Source: Natural Product Updates (RSC)
Acyl lipids in algae
DGDG - digalactosyldiacylglycerol
DGTA - diacylglycerylhydroxymethyltrimethylalanine
DGTS - diacylglyceryltrimethylhomoserine
DPG - diphosphatidylglycerol (cardiolipin)
MGDG - monogalactosyldiacylglycerol
SQDG -sulfoquinovosyldiacylglycerol
PC - phosphatidylcholine
PE - phosphatidylethanolamine
PG - phosphatidylglycerol
PI - phosphatidylinositol
Source: Membrane Lipids in Algae; John L. Harwood; Springer Verlag
List of common plant and algal glycosylglycerides
Common SQDG and MGDG and DGDD species in Arabidopsis
Source: Welti, Wang (2004): Lipid species profiling: a high-throughput approach to identify
lipid compositional changes and determine the function of
genes involved in lipid metabolism and signaling
http://dx.doi.org/10.1016/j.pbi.2004.03.011
Common SQDG and MGDG
and DGDD species in algae
Source: Schiller (2007) The lipid composition of the unicellular green alga Chlamydomonas reinhardtii
and the diatom Cyclotella meneghiniana investigated by MALDI-TOF MS and TLC
http://dx.doi.org/10.1016/j.chemphyslip.2007.06.224
See also Guschina and Harwood; Lipids: Chemical Diversity
http://dx.doi.org/10.1002/9780470048672.wecb292
913.6
911.6b
941.6a
939.6a
937.6a
931.6
929.6b
959.6
975.6
957.6
DGDG (32:1) + Na+
DGDG (32:2) + Na+
DGDG (34:1) + Na+
DGDG (34:2) + Na+
DGDG (34:3) + Na+
DGDG (34:6) + Na+
DGDG (34:7) + Na+
DGDG (36:6) + Na+
DGDG (36:6) + K+
DGDG (36:7) + Na+
756.6a
734.6a
690.5
754.6a
732.6a
688.5
DGTS (34:3) + Na+
DGTS (34:3) + H+
DGTS (34:3) - CO2
DGTS (34:4) + Na+
DGTS (34:4) + H+
DGTS (34:4) - CO2
749.5
739.5
741.5
785.5
769.5
797.5
813.5
793.5b
819.5
861.5
839.5
MGDG (32:2) + Na+
MGDG (32:5) + Na+
MGDG (32:6) + Na+
MGDG (34:6) + K+
MGDG (34:6) + Na+
MGDG (36:6) + Na+
MGDG (36:6) + K+
MGDG (36:8) + Na+
MGDG (38:9) + Na+
SQDG (34:3, sodium salt) + Na+
SQDG (34:3, sodium salt) + H+
Fatty acid compositions in algae
Source: LIPIDS FROM THE MARINE ALGA Gracilaria verrucosa; S. V. Khotimchenko
Lipid compositions in algae
Elsevier: Chemistry and Physics of Lipids 150 (2007) 143–155
VIELER Astrid ; WILHELM Christian ; GOSS Reimund ; SÜSS Rosmarie ; SCHILLER Jürgen ;
Algae in the dark
Source: THE HIDDEN LIFE OF ALGAE UNDERGROUND
Werner Reisser, Springer Verlag
Hydrocracking of B. Braunii
Source: Hydrocracking of the oils of Botryococcus braunii to transport fuels
Conclusions
Expect everything!
Little is known about complex fatty acids and lipids/phospholipids
in algae and bacteria
Profiling/Fingerprinting of large sample sets is possible with
current analytical platforms
Current lipid profiling platforms screen only for common known
lipids and lipid classes
Structure ID requires advanced MS and NMR platforms
http://fiehnlab.ucdavis.edu/staff/kind/Metabolomics/LipidAnalysis/