cc-by: tobias kind (2008) algal and bacterial lipids 2008 research seminar tobias kind...
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CC-by: Tobias Kind (2008)
Algal and bacterial lipids2008
Research Seminar
Tobias Kindfiehnlab.ucdavis.edu
http://fiehnlab.ucdavis.edu/staff/kind/Metabolomics/LipidAnalysis/
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Free to share, copy, remixby attribution: Tobias Kind (FiehnLab)
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 bacteriaand 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
doi:10.1016/j.chroma.2005.08.011
Nine double bondsin crustacea (not algae)
Maximum chain lengths
Neutral Lipids: Chain length C40
Glycolipids: Chain length C30−36, C50−58, C74−82
Phospholipids: common up to C40 FA
Glycosylglicerides in algae
MGDG
DGDG
SQDG
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Other lipid classes found in algae
Source: Natural Product Updates (RSC)
Sulfonoglycolipids
Oxylipins
Galactolipids
Aminoglucoglycerolipids
Acyl lipids in algae
DGDG - digalactosyldiacylglycerolDGTA - diacylglycerylhydroxymethyltrimethylalanineDGTS - diacylglyceryltrimethylhomoserineDPG - diphosphatidylglycerol (cardiolipin)MGDG - monogalactosyldiacylglycerolSQDG -sulfoquinovosyldiacylglycerolPC - phosphatidylcholinePE - phosphatidylethanolaminePG - phosphatidylglycerolPI - phosphatidylinositol
Source: Membrane Lipids in Algae; John L. Harwood; Springer Verlag
List of common plant and algal glycosylglycerides
See also Guschina and Harwood; Lipids: Chemical Diversityhttp://dx.doi.org/10.1002/9780470048672.wecb292
Common SQDG and MGDG and DGDD species in Arabidopsis
Source: Welti, Wang (2004): Lipid species profiling: a high-throughput approach to identifylipid compositional changes and determine the function ofgenes involved in lipid metabolism and signaling http://dx.doi.org/10.1016/j.pbi.2004.03.011
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
Common SQDG and MGDG and DGDD species in algae
913.6 DGDG (32:1) + Na+911.6b DGDG (32:2) + Na+941.6a DGDG (34:1) + Na+939.6a DGDG (34:2) + Na+937.6a DGDG (34:3) + Na+931.6 DGDG (34:6) + Na+929.6b DGDG (34:7) + Na+959.6 DGDG (36:6) + Na+975.6 DGDG (36:6) + K+957.6 DGDG (36:7) + Na+
756.6a DGTS (34:3) + Na+734.6a DGTS (34:3) + H+690.5 DGTS (34:3) - CO2754.6a DGTS (34:4) + Na+732.6a DGTS (34:4) + H+688.5 DGTS (34:4) - CO2
749.5 MGDG (32:2) + Na+739.5 MGDG (32:5) + Na+741.5 MGDG (32:6) + Na+785.5 MGDG (34:6) + K+769.5 MGDG (34:6) + Na+797.5 MGDG (36:6) + Na+813.5 MGDG (36:6) + K+793.5b MGDG (36:8) + Na+819.5 MGDG (38:9) + Na+861.5 SQDG (34:3, sodium salt) + Na+ 839.5 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) 143–155VIELER Astrid ; WILHELM Christian ; GOSS Reimund ; SÜSS Rosmarie ; SCHILLER Jürgen ;
Algae in the dark
Source: THE HIDDEN LIFE OF ALGAE UNDERGROUNDWerner 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/