Bioflavours Terpenes and related compounds Prof. Dr. Jrgen - PowerPoint PPT Presentation

Bioflavours Terpenes and related compounds Prof. Dr. Jürgen Rabenhorst A collaborative MOOC-Project by: part of the

Terpenes L-Menthol Geraniol Patchoulol D-Limonene Valérie Chansigaud; Pogostemon cablin, CC BY-SA 3.0

Different groups of Terpenes Isopren unit (C 5 H 8 ) Monoterpenes Sesquiterpenes Di‐terpenes Tri‐terpenes Tetra‐terpenoids (C 10 H 16 ) (C 15 H 24 ) (C 20 H 32 ) (C 30 H 49 ) (C 40 H 57 )

Mevalonate pathway and MEP pathway Acetyl-CoA Acetoacetyl-CoA Glycerine aldehyde PPP Pyruvate 1-Desoxy-D-xylulose-5-phosphat β-Hydroxy-β-Methylglutaryl-CoA 2C-Methyl-D-erythritol-4-phosphat 4-Diphosphocytidyl-2C-methyl-D-erythritol Dimethylallyldiphosphat Mevalonic acid 4-Diphosphocytidyl-2C-methyl-D-erythritol-2-Phosphate Mevalonate-5-phosphate 2C-Methyl-D-erythritol-2,4-cyclodiphosphat Isopentenylpyrophosphat Mevalonate-5-pyrophosphate 4-Hydroxy-3-methylbut-2-enyldiphosphat

Monoterpenes and Flavour profile R(‐)carvone L‐Menthol S(+)carvone D‐Limonene • spearmint, • cooling, • caraway • Sweet, • sweet • mentholic, • orange, • minty • citrus, • fruity

Sesquiterpenes and Flavour profile Valencene • sweet, Nootkaton • grapefruit, • fresh, • citrus • grapefruit, • juicy

Reaction products of Patchoulol synthase guaia-4,11-diene α -guaiaene α -bulnesene (+)-germacrene A pogostol α -humulene (-)-patchoulol trans-β-caryophyllene α - patchoulene γ-patchoulene

α‐Humulene Mevalonic acid pathway α -humulene synthase Acetyl-CoA farnesyl-pyrophosphate α -humulene Process – facts: • 60 mg/L • Recombinant E.coli [S. Alemdar, J. C. König, S. Hartwig, T. Frister, T. Scheper, S. Beutel (2017); Eng. Life Sci, 17; p. 900–907; DOI: 10.1002/elsc.201700043]

Sandelwood oil α‐Santalole Garg, sandalwood, CC BY-SA 4.0 β‐Santalole

Carnosic acid, Carnosol and Cis‐Abienol Bierfaß, rosemary, CC BY-SA 3.0 Cis‐Abienol Carnosol Carnosic acid

Ambrein and Ambroxide OH Ambroxide Ambrein

Ambrein synthesis OH squalene 3-deoxyachilleol (+)-ambrein H H H H OH Process – facts: O OH • > 100 mg/L onoceranoxide • Alicyclobacillus acidocaldarius 8a-hydroxypolypoda-13,17,21-triene 14-hydroxyonocera-8(26)-ene [A. Moser, G. A. Strohmeier, E. Leitner, T. J. Plocek, K. Vanhessche, H. Pichler (2018); Metabolic Engineering Communications 7; p. 900–907; DOI: 10.1016/j.mec.2018.e00077]

Carotene Degradation Products α-Ionone α-Irone β-Damascenone β-Irone β-Ionone

Synthesis of Ionone ε -Ionone ε -Carotene + O 2 O OH + + H O O α -Ionone α -Ionone [ US2018251796 (A1) ]

A collaborative MOOC-Project by: part of the