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Table 5 Glucosinolate hydrolysis products (nmol/g fresh weight, mean ± SD) of P. novae-zelandiae and P. cheesemanii

From: Transcript and protein profiling identify candidate gene sets of potential adaptive significance in New Zealand Pachycladon

Glucosinolates

Isothiocyanates

  

Nitriles/epithionitriles

 
 

compound

mean ± sd

%

compound

mean ± sd

%

P. novae-zelandiae

      

S-2-OH-3-butenyl

goitrin

1394 ± 698

12.4

2OH3but-CN

590 ± 100

5.3

    

epithio-2OH3B-I

2446 ± 397

21.8

    

epithio-2OH3B-II

2269 ± 371

20.2

allyl

allyl-ITC

1622 ± 668

14.4

epithio-allyl

1868 ± 450

16.6

3-butenyl

3-but-ITC

162 ± 45

1.4

-

-

 

3MTP

3MTP-ITC

449 ± 226

4

3MTP-CN

67 ± 27

0.6

3MSOP

3MSOP-ITC

30 ± 41

0.3

-

-

 

4MTB

4MTB-ITC

210 ± 122

1.9

4MTB-CN

22 ± 14

0.2

4MSOB

4MSOB-ITC

58 ± 48

0.5

-

-

 

8MTO

8MTO-ITC

27 ± 9

0.2

-

-

 

9MTN

9MTN-ITC

28 ± 6

0.2

-

-

 
 

all

 

35.3

all

 

64.7

P. cheesemanii

      

S-2-OH-3-butenyl

goitrin

5115 ± 981

60.7

2OH3but-CN

32 ± 15

0.4

allyl

allyl-ITC

3261 ± 997

38.7

epithio-allyl

4 ± 2

0.1

3-butenyl

3-but-ITC

9 ± 4

0.1

-

-

 
 

all

 

99.5

all

 

0.5

  1. Note that P. novae-zelandiae is capable of converting its main glucosinoalates (S-2-hydroxy-3-butenyl and allyl) into its corresponding nitriles ((S)-3-hydroxy-pent-4-enenitril) and epithionitriles (diastereomers 1 and 2 of (S)-3-hydroxy-3-((R, S)-thiiran-2-yl)propanenitril, 2-((R, S)-thiiran-2-yl)ethanenitril) whereas P. cheesemanii is not. Despite minor glucosinolates being converted to isothiocyanates in P. novae-zelandiae, 65% of its glucosinolate breakdown products are nitriles/epithionitriles. In P. cheesemanii, 99.5% of glucosinolates are converted to isothiocyanates indicating nitrile/epithionitrile forming activity in P. novae-zelandiae but not P. cheesemanii.
  2. Abbreviations: goitrin, goitrin; allyl-ITC, 2-propenylisothiocyanate; 3-but-ITC, 3-butenylisothiocyanate; 3MTP-ITC, 3-methylthiopropylisothiocyanate; 3MSOP-ITC, 3-methylsulfinylpropylisothiocyanate; 4MTB-ITC, 4-methylthiopropylisothiocynate; 4MSOB-ITC, 4-methylsulfinylbutylisothiocyanate; 8MTO-ITC, 8-methylthiooctylisothiocyanate; 9MTN-ITC, 9-methylthiononyl-isothiocyanate; 2OH3but-CN, S-3-hydroxy-pent-4-enenitrile; epithio-2OH3B-I, diastereomer 1 of (S)-3-hydroxy-3-((R, S)-thiiran-2-yl)propanenitril; epithio-2OH3B-II, diastereomer 2 of (S)-3-hydroxy-3-((R, S)-thiiran-2-yl)propanenitril; epithio-allyl, 2-((R, S)-thiiran-2-yl)ethanenitril; 3MTP-CN, 4-methylthiobutanenitrile; 4MTB-CN, 5-methylthiopentanenitrile.