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

▶
bioflavours
SMART_READER_LITE
LIVE PREVIEW

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

Oct 09, 2023 133 likes •301 views

Bioflavours Terpenes and related compounds Prof. Dr. Jrgen Rabenhorst A collaborative MOOC-Project by: part of the Terpenes L-Menthol Geraniol Patchoulol D-Limonene Valrie Chansigaud; Pogostemon cablin, CC BY-SA 3.0 Different groups

slide-1
SLIDE 1

Bioflavours

Terpenes and related compounds

  • Prof. Dr. Jürgen Rabenhorst

A collaborative MOOC-Project by: part of the

slide-2
SLIDE 2

Terpenes

D-Limonene Geraniol Patchoulol L-Menthol

Valérie Chansigaud; Pogostemon cablin, CC BY-SA 3.0

slide-3
SLIDE 3

Different groups of Terpenes

Isopren unit (C5H8) Monoterpenes (C10H16) Sesquiterpenes (C15H24) Di‐terpenes (C20H32) Tri‐terpenes (C30H49) Tetra‐terpenoids (C40H57)

slide-4
SLIDE 4

Mevalonate pathway and MEP pathway

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

slide-5
SLIDE 5

Monoterpenes and Flavour profile

D‐Limonene

  • Sweet,
  • orange,
  • citrus,
  • fruity

R(‐)carvone

  • spearmint,
  • sweet

L‐Menthol

  • cooling,
  • mentholic,
  • minty

S(+)carvone

  • caraway
slide-6
SLIDE 6

Sesquiterpenes and Flavour profile

Nootkaton

  • grapefruit,
  • citrus

Valencene

  • sweet,
  • fresh,
  • grapefruit,
  • juicy
slide-7
SLIDE 7

(-)-patchoulol

Reaction products of Patchoulol synthase

(+)-germacrene A pogostol guaia-4,11-diene α-guaiaene α-bulnesene α-patchoulene γ-patchoulene trans-β-caryophyllene α-humulene

slide-8
SLIDE 8

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]

α-humulene synthase α-humulene Mevalonic acid pathway Acetyl-CoA farnesyl-pyrophosphate

slide-9
SLIDE 9

Sandelwood oil

β‐Santalole α‐Santalole

Garg, sandalwood, CC BY-SA 4.0

slide-10
SLIDE 10

Carnosic acid, Carnosol and Cis‐Abienol

Bierfaß, rosemary, CC BY-SA 3.0

Cis‐Abienol Carnosic acid Carnosol

slide-11
SLIDE 11

Ambrein and Ambroxide

Ambroxide Ambrein

OH

slide-12
SLIDE 12

Ambrein synthesis

[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]

Process – facts:

  • > 100 mg/L
  • Alicyclobacillus acidocaldarius

squalene 3-deoxyachilleol (+)-ambrein 8a-hydroxypolypoda-13,17,21-triene

  • noceranoxide

14-hydroxyonocera-8(26)-ene

O H H H OH H OH OH

slide-13
SLIDE 13

Carotene Degradation Products

β-Damascenone α-Ionone β-Ionone β-Irone α-Irone

slide-14
SLIDE 14

Synthesis of Ionone

O O O H OH

+ +

+ O2

α-Ionone ε-Ionone α-Ionone

[US2018251796 (A1)]

ε-Carotene

slide-15
SLIDE 15

A collaborative MOOC-Project by: part of the