Maillard-type reactions in food - Perspectives and ... · 2007-09-04 Nestle PTC Orbe / I. Blank /...

2007-09-04 Nestle PTC Orbe / I. Blank / 9th Maillard Munich 1

Maillard-type reactions in food

- Perspectives and constraints -

9th International Symposium on the Maillard Reaction,

Munich, September 1–5, 2007

Imre Blank

Nestlé Product Technology Centre, Orbe, Switzerland

2

Definition of the “Maillard reaction”

The “Maillard reaction” is a special case of the amino-carbonyl reactions of reducing sugars and amino acids or derivatives thereof

→ Amine assisted carbohydrate degradation

Goal: Better control of the Maillard reaction cascade

☺ Aroma

☺ Taste

☺ Colour

☺ Antioxidants

☺ Health benefits

☺ Texture

� Nutritional value loss

� Shelf-life issues

� Toxic compounds

∆T


(Hodge, 1953)

The Maillardreaction cascade

�Amino-carbonyl reaction

�Dehydration

�Enolisation

�Decarboxylation

�Cyclisation

�Hydrolysis

�Oxidation

�Reduction

�Retro-aldol reaction

�Radical reaction

�Disproportionation

�Canizzaro reaction

�Retro-Claisen reaction

�Acyloin reaction

�Baeyer-Villiger rearrangement

�Benzilic acid rearrangement

�and others …


OH

OH

NH

O

COOHOH

OH

O

NH

O

COOHOH

OH2

OH

O

OH OH

CH2OH

OH

O

OH O

CH3OH

O

O

OH OH

CH3

NH2

COOHOH

2

OH

OH

OH

N

OH

OHCOOH

OH

OH

OH

NH

OH

OHCOOH

OH

OH

OH

NH

O

OHCOOH

O

OH

OH

NH

OH

OHCOOH

OH2OH

2

O

OH

OH

OH

OH

OHNH

2COOH

I

OH

OH

OH

NOH CH

2

CO2

OH

OH

OH

NH2

OH

OH2

CH2

O

OH2

OH

O

OH

OH

OH

NH

COOH

CH2

N

N

COOH

CH2

COOH

e-

OH2

CH2

N

N

COOH

CH2

COOH

+.

OH

OH

NH

+

OH

COOHOH

OH

OH

O

O

OH

O CHOOH

H+

H+

OH2

OH2

NH2

COOH

OH2

NH2

COOH

OH

OH

N

O

OH

OHCOOHO

OH OH

OH

COOHNOH

O

OH OH

OH

CH2

N

O

OH OH

OH

NH2

OH

OH

O

O

OH

OH

IX

X

XI

O2/Me2+

OH2

CO2 OH

2,

OH2

CH2

O

(Davidek et al., 2002)

Means of control

• Composition

• Concentration

• pH

• Catalyst

• Heat load (t, T)

• Redox state

• React. medium

• Physical state

• Structure

• Molecular

organisation

• Moisture

• Water activity

• …(pH > 6)

(pH < 6)

Oxidation

Decarboxylation

Dehydration 2,3-Enolisation

1,2-Enolisation

Retro-aldol

OH

OH

OH

NH

OH

COOHOH


12 Symptoms of the Maillard reactionA highly complex system

• Lowering of pH

• Increasing reducing power

• Decreasing solubility

• Chelation of metals

• Production of fluorescence

• Production of colour and discoloration

• Production of flavour and off-flavour

• Production of water

• Production of carbon dioxide

(H.E. Nursten)

• Loss of vitamin C activity

• Loss of biological value of protein

• Production of toxicity

Chemistry

Physico-chemistry

Biochemistry


in-vitro in-vivo in-food

Analyticsnon-volatilesvs. volatiles

InteractionsMaillard / lipids /

polyphenols

Mechanismsmajor vs. minor

pathways

Food physicswater activity /food structure

Outline of the presentation

Positive effects

Aroma formation

→ Structured fluids

Taste chemistry

→ Taste, modulators

Protection

→ Antioxidative activity

Positive effects

Aroma formation

→ Structured fluids

Taste chemistry

→ Taste, modulators

Protection

→ Antioxidative activity

Pleasure

Pleasure

Health

PleasurePleasure

PleasurePleasure

HealthHealth

Negative effects

Loss of nutritional value

→ Lysine blockage

Shelf-life issues

→ Browning

Process contaminants

→ Acrylamide

Negative effects

Loss of nutritional value

→ Lysine blockage

Shelf-life issues

→ Browning

Process contaminants

→ Acrylamide

Nutrition

Quality

Safety

NutritionNutrition

QualityQuality

SafetySafety

How to control the Maillard reaction cascade ?

7

Mechanistic AspectsMechanistic AspectsMechanistic AspectsMechanistic Aspects


“Peeling-off” mechanism of αααα-glucanto 1,4-dideoxyhexosulose

(Kroh & Schulz, 2001; Hollnagel & Kroh, 2002)

Solid-state MR conditions


3,4-Dideoxypentosulose from oligosaccharides (1,4-glycosides)

(Mavric et al. 2004; Mavric & Henle, 2006)

New imidazolinone resulting from

the reaction of peptide-bound

arginine and oligosacccharides

with 1,4-glycosidic linkages

Nδδδδ-[5-(3-Hydroxypropyl)-4-oxo-imidazolon-2-yl]-L-ornithine (PIO)


3-Deoxypentosulose: A new majorαααα-dicarbonyl from oligosaccharides

(Kroh & Schulz, 2001; Hollnagel & Kroh, 2002)

3-deoxypentosulose

(Aqueous milieu)

Oxidation or

H-abstraction

11

Aroma GenerationAroma GenerationAroma GenerationAroma Generation

12

Norfuraneol as key intermediate to generate various functionalities

CHO

CH-OH

(CH-OH)2

CH2-OH

Pentose

∆∆∆∆T

O

OH O

C2 + C3

Sugar fragments

∆∆∆∆T

CHO

CH-OH

(CH-OH)3

COOH

Uronic acid

∆∆∆∆T

CHO

CH-OH

(CH-OH)2

CH2-O-P

Pentose-5-P

∆∆∆∆T

Colour

OO

O

OH O

O

O

O

OH O

O

Antitumor agent

O

O

Sulphur

Aroma

O

SH

source

Taste

O

ON

N

H


Means of control: Use of mesophases as reaction medium

Micelles (L2 phase) Lamellar phase Cubic phase

Monoacylglyceride

(Monoolein)

+H2O

Hexagonal phase

CH2OH

CH

CH2O

OH

O

Self-assembly structures (structured fluids) based on monoglycerides

Cubic phase:

• highly viscous

• very large interface

• thermodynamically stable

• polar and apolar solubilisation sites


Norfuraneol (ug/mmol xyl)

750851

1095

2188

0

500

1000

1500

2000

2500

Buffer Lamellar Cubic Hexagonal

Xylose degradation and norfuraneol formation depend on mesophase

Residual xylose (%)

63

4540

47

0

25

50

75

100

Buffer Lamellar Cubic Hexagonal

(pH 6, 70 °C, 7 h)

(Davidek et al., 2004)

� Higher yields – Concentrated flavor precursor systems� Higher stability – Protection of odorants generated� More specificity – Reactions at the interface (regio-selectivity)

3x


Reaction conditionsReaction conditions

L-Cysteine (6.7 mmol)

D-ribose (20 mmol)

Phosphate buffer (10 mL, pH 5)

1 g aq. solution + 4 g monoglyceride

Flavour extracted with diethylether

and analysed by GC/FPD and MS

Structured FluidStructured Fluid

Dimodan PV/water (80:20) cubic phase

(Vauthey et al., 2000)

Ribose+

Cysteine

100°C

4 h

Products

0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34

44

46

48

50

52

54

56

58

60

O

SH

H2O

O

S

O

S

O

S

O

S

0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34

60

80

100

120

140

160

180

200

220

240

O

SH

O

SH CP

O

S

O

S

O

S

O

S

Time (min)

Structured fluids used as micro-reactors in flavour generation

16

Taste ChemistryTaste ChemistryTaste ChemistryTaste Chemistry


Taste-active molecules identified in Maillard reaction samples

N

OH

N

OH

Tressl et al.(1985)

Bitter

O

N

O

N

Ottinger et al.(2001)

Cooling

Pabst et al.(1984)

Bitter

OOH

OH

N

OOH

N

N

Frank et al.(2001)

Bitter

O

O

N+

O

OH

O

OH

OH

OH

ON

COOHOH

COOHH

OH

OH

OH

OOH

N

COOK

COOK

H

Umami

Beksan et al.(2003)

Sugar + proline Xyl + Ala Sugar + glutamic acid


Identification of new bitter tastingmolecules: Indolizinium-6-olates

(Frank & Hofmann, 2001)

Fractionation -> Taste dilution analysis -> Identification (HPLC-MS, 2D-NMR)

O

O

N+

O

OH

O

(TT= 2.5x10-4 µµµµmol/kg water)

Model: xylose/alanine, pH 5, reflux, 3 h


Comparative Taste Dilution Analysis: Alapyridaine in beef bouillon

20

15

10

5

0

1 2 4 8

TD-factorsignal intensity [λ λ λ λ = 300 nm]

t [min]

8

3

1

2

45

6

7

9

10

taste threshold of

saccharose (50 mmol/L)20

15

10

5

0

1 2 4 8

TD-factorsignal intensity [λ λ λ λ = 300 nm]

t [min]

8

3

1

2

45

6

7

9

10

taste threshold of

saccharose (50 mmol/L)

(Hofmann et al., 2003)

N+

OH

OH

COO-

+

-

N

R COO

OH

OH

O

OH O

NH2

R COOHEtOH / H2O

Hexose

Maillard reaction

Alapyridaine (R= Me)


Natural taste enhancer found in beef bouillon: Alapyridaine

0

1

2

3

0

1

2

3

MSG MSG/Alapyridaine

GMP GMP/Alapyridaine

MSG/GMP

MSG/GMP/Alapyridaine

Inte

nsi t

y o

f u

mam

i n

ot e

0

1

2

3

4

5umami

sweet

sour

bitter

salty

astringent

0

1

2

3

4

5umami

sweet

sour

bitter

salty

astringent

0

1

2

3

4

5umami

sweet

sour

bitter

salty

astringent

A

0

1

2

3

4

5umami

sweet

sour

bitter

salty

astringent

0

1

2

3

4

5umami

sweet

sour

bitter

salty

astringent

0

1

2

3

4

5umami

sweet

sour

bitter

salty

astringent

B

N

OH

OH

COO-

+Glucose

+

Alanine

boiling

(Soldo et al., 2003; WO 03/022817 A1)


Taste modulators: Bitterness inhibitor

0

1

2

3

4

5

A B C D E

Bit

ter n

ess in

ten

sit

y

Samples

+0.02 mmol/L +

0.2 mmol/L

+2 mmol/L

+7 mmol/L

Co

ffee

Taste threshold

of salicine

TD factor

• Combinatorial approach

Pyridinium betaine libraries

• Fractionation, HILIC, cTDA

• Identification, synthesis

(Soldo & Hofmann, 2005; WO 03/022817 A1)

N

OH

OH

COO-

+Glucose

+

Glycine

heating

Glypyridaine

22

Protection Protection Protection Protection


Health benefits the Maillard reaction products: Recent results

K.-H. Wagner, S. Reichhold, K. Koschutnig, S. Chriot, C. Billaud

The potential antimutagenic and antioxidant effects of Maillard reaction

products used as “natural antibrowning” agentsMol. Nutr. Food Res. 2007, 51, 496 – 504

S. Ruhs, N. Nass, V. Somoza, U. Friess, R. Schinzel, R.-E. Silber, A. Simm

Maillard reaction products enriched food extract reduce the expression of

myofibroblast phenotype markersMol. Nutr. Food Res. 2007, 51, 488 – 495

M. Lindenmeier, V. Faist, T Hofmann

Structural and functional characterization of Pronyl-lysine, a novel protein modification in bread crust melanoidins showing in vitro antioxidative and

phase I/II enzyme modulating activity.

Journal of Agricultural and Food Chemistry (2002), 50, 6997-7006.

→ Antifibrotic → Antioxidative→ Antimutagenic → Chemopreventive

molecular

insight


Pronylated proteins in bread crust: Chemopreventive activity in-vitro

Lindenmeier et al. (2002, 2004)

… “pronylated” proteins as part of bread

crust melanoidins act as monofunctional

inducers of GST, serving as a functional

parameter of an antioxidant, chemo-

preventive activity in vitro.

… pronyl-L-lysine in bakery products is

strongly dependent on the manufacturing

conditions as well as the recipe.→ Addition of casein and glucose (5-10%)→ Sourdough fermentation


Pronylated proteins: Chemopreventive activity in-vivo

Somoza et al. (2005)

… the main systemic effects of dietary malt, bread crust, and pronyl-

BSA were demonstrated to be the enhanced antioxidant capacity and

the particulate increase in chemo-preventive enzymes.

Bread crust: GST (kidney)


5

(Marko et al., 2003)

Beneficial effects of the Maillard reaction: Inhibiting tumor growth


Health effects of Maillard reaction products: Status COST Action 919

“The results obtained for intestinal degradation, and respective implications for gut

health, absorption, and further health effects, such as antioxidant activity, chemo-

preventive activity, and antimutagenic activity, clearly demonstrate that at least

some of the dietary MRPs and melanoidins are health-promoting, while others may

be not.

The challenge for future studies is the chemical characterization of harmful and

beneficial compounds for their structure-specific health effects and the optimization

of food processing technologies for a selective formation of health beneficial MRPs

and melanoidins.”

(V. Somoza,

Mol. Nutr. Food Res.

2005, 49, 663-672)

(Somoza, 2005)

28

Interactions with Lipid OxidationInteractions with Lipid OxidationInteractions with Lipid OxidationInteractions with Lipid Oxidation


Maillard reaction vs. lipid oxidation

“… both reactions are so interrelated that they should be considered simultaneously

to understand the products of the Maillard reaction

in the presence of lipids and vice versa, and should be included in one general pathway

that can be initiated by both lipids and carbohydrates.”


Flavour Heat-inducedchemicals

Antioxidants

(Zamora & Hidalgo, 2005)

Interactions between the Maillard

reaction and lipid oxidation


2-Alkylpyridine

Phenylacetaldehyde

(Reaction: 37 °C, overnight)

Flavour formation: Strecker-type

degradation by 4,5-epoxy-2-elkenals

pHopt ~ 7

(Hidalgo & Zamora, 2004)


Colour development: Formation

of 2-(1-hydroxyalkyl)-pyrroles

(Reaction: 37 °C, overnight)2-(1-Hydroxyalkyl)pyrrole derivatives are highly reactive

and tend to easily undergo polymerisation reactions


- CO2

- CO2


Highermelanoidin-like

polymers

Colour formation by polymerisation

of pyrrole derivatives

Methylene-bridged polypyrroles

(Zamora & Hidalgo, 2005; Tressl et al. 1998)

2-(1-Hydroxyalkyl)pyrrole


• Protein modifications: second. + tert. structure, denaturation, dimerisation

• Increased oxidative stress: εεεε-N-pyrrolylnorleucine (Pnl), loss of lysine

BSA + Epoxyheptenal,

pH 7.4, 37 °C

Pnl


Structural modifications of proteins

by epoxyalkenals

Michael adduct of

4,5-epoxy-2-heptenal

with histidine

Polymeric pyrrole cross-links

formed by reaction of lysine

with 4,5-epoxy-(E)-2-heptenal

35

Interactions with PolyphenolsInteractions with PolyphenolsInteractions with PolyphenolsInteractions with Polyphenols


Formation of Strecker aldehydes from polyphenol-derived quinones

4-Amino-1,2-benzoquinone (6): putative intermediate

in the formation of Strecker aldehydes (0.03-0.4

mol%) from polyphenols under oxidative conditions.

(Rizzi, 2006)

Y = amino acid residue, R = alkyl group; [O] = molecular oxygen


Trapping of reactive Maillard intermediates by polyphenols

(Totlani & Peterson, 2006; Noda & Peterson, 2007)

Glc/Gly

1,2,3-THB

Me-Gallate

EGCG, ECG, 1,3,5-THB

Epicatechin

O

O

O

OH

OOH

OH

OH

OH

OH

OH

O

OOH

OH

OH

OH

OH

Epicatechin

O

O

(Electrophilic aromaticsubstitution reaction,

hydroxyalkylation)


Polyphenols interfere in the Maillard reaction

• Epicatechin: Quenching of sugar fragmentation products (pressure cooking)

Trapping agent of 3-deoxy-2-hexosulose (roast conditions)

• Phenolic chemistry alters the mechanisms of the Maillard reaction

→ Need for a better understanding of Maillard chemistry in processed food

Co

nc

en

tra

tio

n (

µµ µµg

/mm

ol

glu

co

se

)

16

12

4

8

0

N

N

OH

O

OO

�� Glc/Gly

�� Glc/Gly/EC

N

N

O

O

N

N

O

O

O

O

O

OH

NH

O

(Totlani & Peterson, 2005; 2007)

Maillard precursors

Modified composition

OOH

OH

OH

OH

OH


Trapping of key odorants (thiols) by polyphenols via oxidative coupling

(Müller & Hofmann, 2007)

The loss of 2-furfurylthiol during coffee storage is mainly due to the oxidative coupling

of the odorant to hydroxyhydroquinone (2), giving rise to the conjugates 9 and 10.

40

Loss of Nutritional Value: Lysine Blockage Loss of Nutritional Value: Lysine Blockage Loss of Nutritional Value: Lysine Blockage Loss of Nutritional Value: Lysine Blockage


Loss of lysine during storage of skim milk powder

Uptake of moisture

Threonine

Leucine

Valine

Isoleucine

Phenylalanine

Lysine

Methionine

Histidine

Arginine

Tryptophan

Am

ino

acid

s (

%)

Cystine

Storage (d)

(Henry & Kon, 1948)

Changes in content of essential amino

acids during storage

0

1

2

3

4

5

6

0 0.1 0.2 0.3 0.4 0.5 0.6

Water activity (aw)

Re

ac

tiv

e l

ys

ine

(g

/16

gN

)

0

5

10

15

20

25

30

35

40

Ly

sin

e b

loc

ka

ge

(%

)

Reactive Lys

Blocked Lys

0 %

0 %

0 – 2 %

0 – 2 %

5 – 10 %

5 – 10 %

20 – 50 %

Freeze-drying

Pasteurization

UHT sterilization

Spray-drying

Spray-dried formula

HTST sterilization

Roller-drying

Blocked lysineHeat process

(Finot & Hurrell, 1983)


-60

-40

-20

0

20

40

60

80

100

0 10 20 30 40 50 60 70 80 90 100

Total solids [%]

Te

mp

era

ture

[°C

]

Milkpowder

Fresh milk

concentration

pasteurisation

drying

atomisation

homogenisation

after-drying

after-cooling

Manufacturing of milk powder

Tf

Ts

Solution (emulsion)

Lactose crystals and solution

Ice and solution

Glassy

state

Tg

(Vuataz, 2002)

43

ShelfShelfShelfShelf----life Issues: Browning of Milk Powderlife Issues: Browning of Milk Powderlife Issues: Browning of Milk Powderlife Issues: Browning of Milk Powder


Shelf-life issues:Browning of milk powder

Issue:

Browning of milk powder was extensively detected under hot climatic conditions

Spontaneous nucleation and crystal formation is possible above the Tg

in a certain range which depends on (T – Tg)

glassyVisco-

elasticTg

Heat orWater addition

Glass transition(reversible)

crystalline

Crystallisation(irreversible)

Mechanism: Recrystallisation of an amorphous powder


-60

-40

-20

0

20

40

60

80

100

0 10 20 30 40 50 60 70 80 90 100

Total solids [%]

Te

mp

era

ture

[°C

]

Solution

(emulsion)

Ice and solution

Glassy

state

Ts

Tf

Tg

10 min.

1 h.

1 d.

Rubbery stateLactose crystals

and solution

Risk of lactose crystallisation during storage (water uptake)

(Vuataz, 2002)

visco-elastic region

T > Tg : spontaneous

nucleation (β-from)

glassy solid region

T < Tg : no risk

of crystallisation


Risk of heat

shocks in hot

countries

1 hour WM

20

30

40

50

60

70

80

90 91 92 93 94 95 96 97 98 99 100

Total Solids [%]

Te

mp

era

ture

[°C

]

10 min. 1 day Tg5 min.

1 w

eek 1

mon

th

Risk of lactose crystallisation during storage (heat shock)


Means of control: Adjust water content and/or limit heat shock

The temperature increases up to 65°C

for a short time (less than one day), due

to transport conditions or sun exposure

during unloading of containers.

Temperature 65°C

30°C

12 h

Strategy:- Adapt the norm of water content to the risk of heat shock (T and duration)

- Better control the final water content of the processed powder

state of lactose

amorphous

crystallineAfter a certain delay (some hours), the

lactose crystallization is initiated and

rapidly achieved (in the beta anhydrous

or the alpha monohydrate form).

water activity

0.20

0.55

The water previously adsorbed on the

amorphous lactose is released, inducing

a large water activity increase (closed

can situation).

Time

browning

white

brownThe resulting high Aw is responsible for

the high rate of Maillard reaction, even

if the temperature is reduced to the

previous value.

48

Process ContaminantsProcess ContaminantsProcess ContaminantsProcess Contaminants

Mitigation Concepts for AcrylamideMitigation Concepts for AcrylamideMitigation Concepts for AcrylamideMitigation Concepts for Acrylamide


Agronomic

- Sugars

- Asparagine

- Sugars

- Asparagine

Agronomic Recipe

recipe…….……..

- NH4HCO3

- pH

- Minor ingredients

- Dilution

- Rework




- NH4HCO3

- pH

- Minor ingredients

- Dilution

- Rework

Recipe Process

Fermentation

Thermal input

Pre-treatment

Fermentation

Thermal input-

-

-

-

- Pre-treatment

Final Preparation

- Color endpoint

- Texture/flavour

- Product

storage/shelf life/consumer prep.

- Color endpoint

- Texture/flavour

- Product

storage/shelf life/consumer prep.

Final Preparation

� Guidance to assist in reducing AA levels in food

� Not meant as a formal prescriptive manual

� « Live » document

Means of control: Options to achieve acrylamide mitigation

(http://www.ciaa.be/documents/brochures/CIAA_Acrylamide_Toolbox_Oct2006.pdf)


Means of control: Potato crisps

Tools to try� Variety selection

� Storage conditions > 6°C

� Reconditioning

� Process management - color

� Formed crisp - partial potato replacement

� Blanching

� Vacuum frying

Future opportunities

� New varieties (sugar, storage qualities)

� Agricultural practices

� Potato varieties with lower Asn

� Asn-ase treatment: formed crisps

� Effect of Ca2+ addition –fabricated crisps

%

0 20 40 60 80 100

Storage Temp.

Frying Temp/Time

Colour Control

Variety Selection

Colour Sort

Recipe Change *

“Tools” used in acrylamide reduction for Potato

Crisps

AA reduction (%)


Means of control: Bread, bakery wares and breakfast cereals

Tools to try

� Ammonium bicarbonate replacement

� Fructose replacement

� Color / moisture specification change

� Oven condition optimization

� Substitution with < Asn raw materials

Future opportunities� Low Asn raw materials

� Agricultural practices

� Asparaginase

� Fermentation (e.g. yeast)

� Oven profile optimization

� Innovative processing

� Amino acid addition (e.g. glycine)

0

20

40

60

80

0 5 10 15 20

Time (min)

Asn

(m

g/1

00g

)

15°C / 50 ppm

30°C / 50 ppm

30°C / 10 ppm

Asn < 4.1 mg/100g after 5 min, using 10 mg/kg enzyme


Challenges ahead

� Toolbox concept shows different measures / combinations to achieve

moderate reductions

� In many food categories no reductions achieved so far (exhausting all

currently available options)

� Need to address urgently possible measures at agronomical level

No common solution !

Any mitigation measures must consider:

� Total product quality: The consumer is the judge

Quality is competitive

� Risk/benefit considerations:

� Understand the impact of mitigation steps on safety, nutrient profile

and organoleptic properties

� Position relevance of the suspected side effects of mitigation measures

� Quantify their potential impact


Outlook: To consider in future research on the “Maillard reaction”

Health & protection:• Evaluate and substantiate effects• Identify target molecules• Discover synergistic and

suppressive effects• Elucidate mechanisms of action• Extend from in-vitro to in-vivo

Food & pleasure:• Apply reaction kinetics / modelling• Elucidate reaction mechanisms• Establish mass balance (major /

minor fluxes)• Focus on low moisture MR• Develop concepts for mitigation• Extend from model studies to food

Nutritional effects

Pleasure & ConvenienceGeneral:• Break down complexity• Favour interdisciplinary science• Combine targeted and holistic

approach• Identify key (bio)active molecules

& transient intermediates

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