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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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/