The Australian Wine

Research Institute

Pepper and spice in Shiraz:

what influences rotundone

levels in wines?

Leigh Francis

Tracey Siebert

Mark Solomon

Gerard Logan (University of Auckland)

The Australian Wine

Research Institute Gas chromatography-mass spectrometry

The Australian Wine

Research Institute

The Australian Wine

Research Institute (-)-Rotundone

By GC-MS-O, rotundone was established as the

principal aroma impact compound for pepper

aroma in grapes and wine.

O • Identity confirmed with reference

compound (Symrise)

• 1H and 13C NMR, ORD

• GC-MS-O, co-injections

• Quantification using SIDA

O

D

D

D D

D

Wood, C.; Siebert, T. E.; Parker, M. et al. J. Agric. Food Chem. 2008, 56, 3738-3744

Siebert, T. E. et al. J. Agric. Food Chem. 2008, 56, 3745-3748

Cyperus rotundus, nut grass weed

The Australian Wine

Research Institute

How potent is rotundone?

8 ng/L in water 16 ng/L in red wine

20 to 25% of the panellists were anosmic to rotundone

Wood, C.; Siebert, T. E.; Parker, M. et al. J. Agric. Food Chem. 2008, 56, 3738-3744

aroma detection threshold

The Australian Wine

Research Institute

Aroma detection threshold of the black pepper

compound Rotundone, in red wine, is 16 ng/L

0

1

2

3

4

5

6

7

8

9

10

Nu

mb

er

of

pa

ne

llis

ts

0.4 3.2 9.4 28.1 84.2 250 760 > 4000

Concentration (ng/L)

0

1

2

3

4

5

6

7

8

9

10

Nu

mb

er

of

pa

ne

llis

ts

0.4 3.2 9.4 28.1 84.2 250 760 > 4000

Concentration (ng/L)

The Australian Wine

Research Institute

16 7

37

11 11

39 28

97

32 33

161 152

75

10

25 16 3 10 3 4 11 2

35

3

38

9

0

20

40

60

80

100

120

140

160

180

Ad

ela

ide

Hill

s

Cla

ren

don

Hill

s

Co

on

aw

arr

a

Ge

elo

ng

Gra

mp

ians

Ma

ce

do

n

Ran

ge

s

McL

are

n

Va

le

Ya

rra

Va

lley

Ad

ela

ide

Hill

s/Y

arr

a

Mo

rnin

gto

n

Pe

nin

sula

Ta

sm

ania

Ya

rra

Va

lley

Ba

rossa

V

alle

y

Go

ulb

urn

V

alle

y

Ruth

erg

len

Can

be

rra

D

istr

ict

Fra

nkla

nd

Riv

er

Region/Variety

Rotu

ndo

ne (

ng/L

)

AWRI TR #180 (June 2009)

Rotundone in Australian wines

The Australian Wine

Research Institute Australian cool climate Shiraz

The Australian Wine

Research Institute New Zealand

Gimblett Gravels (400 Ha), Hawke’s Bay, New Zealand

• 39°37’ S, 176°44’ E

• 1435 GDD (Base 10°C) (17 year

average)

• 803mm rainfall (21 year average)

• 2188 hours of sunshine/year

• 14.5°C mean temperature all year

• Omahu Gravel Soil

• Maritime with a little continentality

The Australian Wine

Research Institute

Rotundone in other commercially

available Shiraz wines

220

240

260

200

16 7

37

11 11

39 28

97

32 33

161 152

75

10

25 16

0

20

40

60

80

100

120

140

160

180

Ad

ela

ide

Hill

s

Cla

ren

don

Hill

s

Co

on

aw

arr

a

Ge

elo

ng

Gra

mp

ians

Ma

ce

do

n

Ran

ge

s

McL

are

n

Va

le

Ya

rra

Va

lley

Region

Rotu

ndone (

ng/L

)

Ca

nb

err

a

Dis

tric

t

Gre

at

So

uth

ern

New

Zea

lan

d

Haw

ke

’s B

ay

The Australian Wine

Research Institute

0

20

40

60

80

100

120

140

160

180

Ro

tun

do

ne (

ng

/L)

Vintage

Shiraz/Viogner wines - same winery & style

Variability across vintages: Canberra District

The Australian Wine

Research Institute

Rotundone is only present in the

skin

Skin: rotundone

Seeds: not detected

Pulp: not detected

Photograph by Eric Wilkes

The Australian Wine

Research Institute

Rotundone increases during late

stage ripening

0

5

10

15

20

25

30

Veraison Midway Harvest

Ro

tun

do

ne

(n

g/k

g o

f b

err

ies

)

Ripening timepoint

2009 AH 1127

2009 AH 2626

Adelaide Hills Shiraz berries during ripening

The Australian Wine

Research Institute

0

10

20

30

40

50

60

70

0 2 4 6 8 10 12 14

Ro

tun

do

ne

(n

g/k

g o

f b

err

ies

)Sampling point (weeks)

2009 NZ ME

2010 NZ CR

Ver Mid

Har

↓ ↓

↓

Rotundone increases during late

stage ripening

NZ Hawke's Bay Syrah berries during ripening

Vine management may impact rotundone concentration

0

5

10

15

20

25

30

Veraison Midway Harvest

Ro

tun

do

ne

(n

g/k

g o

f b

err

ies

)

Ripening timepoint

2009 AH 1127

2009 AH 2626

Adelaide Hills Shiraz berries during ripening

The Australian Wine

Research Institute

Does vine management affect

rotundone levels?

Fruit exposure

Leaf removal time

Crop load

Vine vegetative vigour

Clones

The Australian Wine

Research Institute

Clone and crop load

0

20

40

60

80

100

120

140

160

180

Chave 470 MS

Ro

tun

do

ne

(n

g/k

g)

Clone

NZ Hawke's Bay Syrah Clones

2010

2011

0

10

20

30

40

50

60

70

100% 50% 10%

Ro

tun

do

ne

(n

g/k

g)

NZ Hawke's Bay Syrah 2011 - Crop Load

The Australian Wine

Research Institute

Leaf removal

0

5

10

15

20

25

30

35

40

45

50

0% LR 100% LR 100% LR+SH

Ro

tun

do

ne

(n

g/k

g)

Leaf removal & shade

NZ Hawke's Bay Syrah 2011 – Leaf removal

0

10

20

30

40

50

60

17-Nov-10 11-Dec-10 10-Jan-11

Ro

tun

do

ne

(n

g/k

g)

Leaf removal date

NZ Hawke's Bay Syrah 2011 – Leaf removal

timing

The Australian Wine

Research Institute

Trunk Circumference: 163mm

LLN: 2.73

Gaps: 1.5%

The Australian Wine

Research Institute

Trunk Circumference: 129mm

LLN: 0.795

Gaps: 29%

The Australian Wine

Research Institute

0

20

40

60

80

100

120

140

160

180

200

B14 R14 B25 R11 B25 R19

Ro

tun

do

ne

(n

g/k

g)

Vineyard block and row

NZ Hawke's Bay Syrah - Vigour

high 2010

high 2011

low 2010

low 2011

0

20

40

60

80

100

120

140

160

180

200

B14 R14 B25 R11 B25 R19

Ro

tun

do

ne

(n

g/k

g)

Vineyard block and row

NZ Hawke's Bay Syrah - Vigour

high 2010

high 2011

low 2010

low 2011

Vigour

The Australian Wine

Research Institute

0

5

10

15

20

25

30

35

40

45

0 1 2 3 4 5 6 7 8 9 10 11 12 13 14

Rotu

ndone (

ng/L

)

Fermentation (Day)

Adelaide Hills Shiraz commercial fermentation 2009

1127

2626 - Tank 1

2626 - Tank 2

2626 - Tank 3

`

Time from inoculation (days)

Adelaide Hills Shiraz commercial fermentation 2009

Ro

tun

do

ne (

ng

/L)

Rotundone extraction during

winemaking

The Australian Wine

Research Institute

Rotundone extraction from berries

during winemaking

30

50

70

90

110

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

Ro

tun

do

ne

(n

g/L

)

Time from inoculation (days)

OT2

OT4

30

50

70

90

110

130

150

170

190

210

230

250

270

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

Ro

tun

do

ne

(n

g/L

)

Time from inoculation (days)

OT2 OT4

OT6 OT8

NZ Hawke's Bay Syrah commercial fermentation 2011

The Australian Wine

Research Institute

Can yeast affect rotundone levels

during fermentation?

0

500

1000

1500

2000

2500

3000

3500

4000

4500

Control 1631 796 1483 1555 1375

Ro

tun

do

ne

(n

g/L

)

AWRI Yeast

Fermentation in defined juice medium 2011

S. bayanus

The Australian Wine

Research Institute

Rotundone in French Pyrenees wines

Olivier Geffroy, IFV Sud-Ouest

2011 Graciano 11 - 18 ng/L

2011 Gamay 12 - 15 ng/L

2011 Pineau d'Aunis 66 - 200 ng/L

2008 Duras 95 ng/L

2012 Duras 26 ng/L

“Theoretical” optimum picking date

at day 45 after veraison

days

2011 Duras microvinification at 5 levels of maturity

Ro

tun

do

ne

(ng

/L)

IFV viticulture trials: 2011 2012

Irrigation / Elicitor / crop load 43-48 ng/L 29-36 ng/L

Control 37 ng/L 27 ng/L

Leaf removal 12 ng/L 12 ng/L

The Australian Wine

Research Institute

2012 Rotundone level in grapes

Role of:

• genome x environment?

• grape vine?

• in the soil, above surface?

• climate & climate change?

• terroir?

• 177 vines sampled

• 74 – 1081 ng/kg

• distinct spatial pattern

otherwise uniform TSS, TA, colour,...

Variability across the vineyard & vintages:

Nathan Scarlett, RWG; Rob Bramley, CSIRO; Damien Sheehan, MLG

The Australian Wine

Research Institute Conclusions and future directions

Viticulture parameters affected rotundone levels:

Picking date, clone, vigour, leaf removal & crop

load

Why does rotundone occur in Shiraz more often

than other cultivars?

Can rotundone be modulated during winemaking?

The Australian Wine

Research Institute Acknowledgements

The AWRI, a member of the Wine Innovation Cluster in Adelaide, research is financially supported by Australia's grape growers and winemakers through their investment body the Grape and Wine Research and Development Corporation, with matching funds from the Australian Government.

• The University of Auckland & EIT Hawke’s Bay

• Mission Estate Wines

• Craggy Range Vineyards

• Rob Bramley, CSIRO

• Darryl Catlin, Winemaker, and the winery and

laboratory staff of Shaw and Smith Wines

• Frank van de Loo, Mt Majura Vineyard

• Jim Lumbers, Lerida Estate and Lumbers

Consulting

• Dr Ayalsew Zerihun, Curtin University of

Technology

• Nathan Scarlett, Dan Buckle, Damien

Sheehan (Mt Langi Ghiran), Allen and Andrea

Hart (Treasury), Inca Pearce, Martin Wirper

(Orlando), Sue Hodder (Wynns Coonawarra

Estate)

• Symrise, Germany

AWRI

• Markus Herderich

• Mango Parker, Claudia Wood

• Flavour & Sensory Teams

• Radka Kolouchova