1. CC-by: Tobias Kind (2008) Algal and bacterial lipids 2008 Research Seminar Tobias Kind fiehnlab.ucdavis.edu http://fiehnlab.ucdavis.edu/staff/kind/Metabolomics/LipidAnalysis/ CC-by Free to share, copy, remix by attribution: Tobias Kind (FiehnLab)

2. 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/gkl83810.1093/nar/gkl838

3. 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

4. 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 bonds in crustacea (not algae)

5. Maximum chain lengths Neutral Lipids: Chain length C40 Glycolipids: Chain length C30−36, C50−58, C74−82 Phospholipids: common up to C40 FA

6. Glycosylglicerides in algae MGDG DGDG SQDG Source: Membrane Lipids in Algae; John L. Harwood; Springer Verlag

7. Other lipid classes found in algae Source: Natural Product Updates (RSC) Sulfonoglycolipids Oxylipins Galactolipids Aminoglucoglycerolipids

8. 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

9. List of common plant and algal glycosylglycerides See also Guschina and Harwood; Lipids: Chemical Diversity http://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 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 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 913.6DGDG (32:1) + Na+ 911.6bDGDG (32:2) + Na+ 941.6aDGDG (34:1) + Na+ 939.6aDGDG (34:2) + Na+ 937.6aDGDG (34:3) + Na+ 931.6DGDG (34:6) + Na+ 929.6bDGDG (34:7) + Na+ 959.6DGDG (36:6) + Na+ 975.6DGDG (36:6) + K+ 957.6DGDG (36:7) + Na+ 756.6aDGTS (34:3) + Na+ 734.6aDGTS (34:3) + H+ 690.5DGTS (34:3) - CO2 754.6aDGTS (34:4) + Na+ 732.6aDGTS (34:4) + H+ 688.5DGTS (34:4) - CO2 749.5MGDG (32:2) + Na+ 739.5MGDG (32:5) + Na+ 741.5MGDG (32:6) + Na+ 785.5MGDG (34:6) + K+ 769.5MGDG (34:6) + Na+ 797.5MGDG (36:6) + Na+ 813.5MGDG (36:6) + K+ 793.5bMGDG (36:8) + Na+ 819.5MGDG (38:9) + Na+ 861.5SQDG (34:3, sodium salt) + Na+ 839.5SQDG (34:3, sodium salt) + H+

10. Fatty acid compositions in algae Source: LIPIDS FROM THE MARINE ALGA Gracilaria verrucosa; S. V. Khotimchenko

11. Lipid compositions in algae Elsevier: Chemistry and Physics of Lipids 150 (2007) 143–155 VIELER Astrid ; WILHELM Christian ; GOSS Reimund ; SÜSS Rosmarie ; SCHILLER Jürgen ;

12. Algae in the dark Source: THE HIDDEN LIFE OF ALGAE UNDERGROUND Werner Reisser, Springer Verlag

13. Hydrocracking of B. Braunii Source: Hydrocracking of the oils of Botryococcus braunii to transport fuels

14. 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/