90

60

26 11 22 13:15

30

399-4598 8304

90 60

172

26 11 22 13 15

30

13:15

13:20

13:55

14:30

14:50

15:25

16:00

16:2018:00

1.

1)

GC

2.

GC-O AEDAAroma Extract Dilution Analysis 2)

IEC

HPLC

GC-MS

MDGC-MS

RI

3.

AEDA

albedo-like 1FD 128sweaty

2FD 128

1

HPLC: 241

GC-MS1

1trans-4,5-epoxy-(E,Z)-2,7-decadienal

LAHPrilezhaev Lindlar Dess-Martin

Wittig 69.4%

1trans-4,5-epoxy-(E,Z)-2,7-decadienal3)

Katsuki-Sharpless 14S,5S4R,5R

96% ee-

gamma-DEX 2251l 4S,5S

>99% ee1(4S,5S)-trans-4,5-epoxy- (E,Z)-

2,7-decadienal4)

2

GC-O2

IEC

MDGC-MS1D: TC-WAX; 2D: InertCap 12

24-methyl-3-hexenoic acid

Jones 2

5%E8%Z

2(E)-4-methyl-3-hexenoic acid5)

12

4.

AEDApungent

3FD2433

33

MDGC-MS1D: TC-WAX; 2D: BETA DEX 2253

3 2,3- 2,5- 2,6-

dimethyl-1,4-cyclohexanedione

2,6-2,6-dimethylhydroquinoneO-Benkeser

31232,6-

3

cis3cis-2,6-dimethyl-1,4-cyclohexanedione

6)3

5.

1) McGorrin RJ (2012) in: Marsili R (ed) Flavor, Fragrance, and Odor Analysis 2nd edn. CRC

Press, Boca Raton. 2) Grosch W (1993) Trend Food Sci Tech 4:6873. 3) Miyazato H,

Hashimoto S, Hayashi S (2012) Eur Food Res Technol 235:881891. 4) Miyazato H,

Hashimoto S, Hayashi S (2013) Eur Food Res Technol 237:933942. 5) Miyazato H,

Hashimoto S, Hayashi S (2013) Flavour Frag J 28:6269. 6) Miyazato H, Nakamura M,

Hashimoto S, Hayashi S (2013) Food Chem 138:23462355.

1999 3 2001 3 2001 4 2014 3

Ralstonia solanacearum 200

R. solanacearum

EPS

PhcA phcA

PhcA PhcB

QS3-hydroxypalmitic acid methyl ester3-OH PAME

PhcS/PhcR

1 phc QS

3-OH PAME 20

R. solanacearum

1 phc QS

phc QS

QS

1. phc QS

phc QS

phcA

phcAOE1-1

phcA

5 OE1-1

ralfuranone A B

ralfuranone JL

2ralfuranone

ralfuranone R.

solanacearum

ralfuranone RalA ralA OE1-1

ralA

ralA ralfuranone ralfuranone

ralfuranone

R. solanacearum

ralA OE1-1 BF

ralA ralA BF

ralfuranone R. solanacearum BF

2. phc QS

phc QS S-

PhcB phcB EPS

phcB OE1-1

OE1-1 phcB QS

EPS phcB

OE1-1 phcB EPS OE1-1

2. Ralfuranone

O

O

ralfuranone A ralfuranone B

ralfuranone J ralfuranone K ralfuranone L

23

4 56

78

9

1011

12

1314

1

OE1-1

GC-MS LC-MS 3-OH PAME phcB

ralfuranone OE1-1 OE1-1

phcB ralfuranone R.

solanacearum

PhcB OE1-1

OE1-1 QS

QS

2002 3

2007 5

2007 6

2008 1

, . ,

,

, .

, , .

,

. .

Burkholdine

Burkholdines (Bks) Schmidt Burkholderia ambifaria 2.2N ,

.1 Xylocandin , occidiofungin

, -1,3-,

. ,

. D/L-

, .

Fmoc-, ,

.

, . ,

.2 ,

.

.

Callipeltin

CCR5 , callipeltin

. Callipeltin A3 B4 1996, Callipelta sp. ,

,

.

, .

. -Methoxytyrosine (MOY)5

pyroglutamic acid (pDME)6,7 4 ,

. N-Me , D-allothreonine (D-aThr)8 .

Fmoc-, .

.

, callipeltin B .9

. callipeltin

Hela , ,

, pDME .

.

,

. .

1. Tawfik, K.; Schmidt, E. W.; et al. Org. Lett. 2010, 12, 664-666.

2. Konno, H.; Otsuki, Y.; Matsuzaki, K.; Nosaka, K. Bioorg. Med. Chem. Lett. 2013, 23, 4244-4247.

3. Zampella, A.; DAuria, M. V.; et al. J. Am. Chem. Soc. 1996, 118, 6202-6209.

4. DAuria, M. V.; Zampella, A.; Paloma, L. G.; Minale, L. Tetrahedron 1996, 52, 9589-9596.

5. Konno, H.; Aoyama, S.; Nosaka, K.; Akaji, K. Synthesis 2007, 3666-3672.

6. Konno, H.; Takebayashi, Y.; Nosaka, K.; Akaji, K. Heterocycles 2010, 81, 79-89.

7. Kikuchi, M.; Konno, H. Heterocycles 2014, 89, 1620-1631.

8. Kikuchi, M.; Konno, H. Tetrahedron 2013, 69, 7098-7101.

9. Kikuchi, M.; Konno, H. Org. Lett. 2014, 16, 4324-4327.

1994 3

1996 3

1999 3

1999 4

2000 9

2004 1

2004 10 /

2009 4

1998 -2000 , 2008 ,

2009 , 2011

,

AD

10 42

A422 3 2 ~ 24

2 x n-mer or 3 x n-mer

A42

A42

A42

A42

.A42

A42 2

A42 Glu22

Asp23

.1,2) AD Glu22 Asp23

.3) A42

ESRA42

Tyr10 Met35 15

A40 15~20.4) A42 C

Met C

C

A42

( 1).5) A42 A40

A42 2, 3

.6)

1 A42 6)

.

AD A42

A42

2

A42

22 E22P-A42

E22V-A42 11A1 .7)

22 4G8E22P-A42

E22V-A42

AD 11A1

A 11A1

11A1 AD A 3

.7) AD A

,8) 11A1 AD

11A1 A AD iPS ,9) AD ,10)

AD 11)

11A1 AD

2

AD

AD 3

A

11A1

2012 3 2014 4

US 8710193 B2 A

[1] Morimoto, A. et al., J. Biol. Chem. 2004, 279, 52781-52788. [2] Irie, K. et al., Mini-Rev. Med. Chem. 2007, 7, 1001-1008. [3] Murakami, K. et al., J. Biol. Chem. 2003, 278, 46179-46187. [4] Murakami, K. et al., ChemBioChem 2007, 8, 2308-2314. [5] Murakami, K. et al., J. Am. Chem. Soc. 2005, 127, 15168-15174. [6] Murakami, K. Biosci. Biotechnol. Biochem. 2014, 78, 1293-1305. [7] Murakami, K. et al., ACS Chem. Neurosci. 2010, 1, 747-756. [8] Murakami, K. et al., J. Biol. Chem. 2011, 286, 44557-44568. [9] Kondo, T. et al., Cell Stem Cell 2013, 12, 487-496. [10] Soejima, N. et al., Curr. Alzheimer Res. 2013, 10, 11-20. [11] Kulic, L. et al., Transl. Psychiatry 2012, 2, e183.

2002 3 2007 3 2004 4 2007 3 DC1 2007 4 SPD 2007 6 2008 3 UCLA2009 6 8 2009 10 2013 7

2005, 20102006IUPAC 20062008201220122013

http://www.asahibeer.co.jp/

http://www.amano-enzyme.co.jp/jp/

http://www.ichibiki.co.jp/

http://www.itoen.co.jp/

http://www.katokagaku.co.jp/

http://www.gifushellac.co.jp/

http://www.kinjirushi.co.jp/

http://www.skk-net.com/

http://www.pasconet.co.jp/

http://www.shinsei-ip.ne.jp/

http://www.taiyokagaku.com/

http://www.tsuji-seiyu.co.jp/

http://www.tokaibsn.co.jp/

http://www.nakahyo.co.jp/

http://www.nippongene.com/

http://www.nisshoku.co.jp/

http://www.fnsugar.co.jp/

http://www.bfsci.co.jp/

& http://www.pokkasapporo-fb.jp/

Mizkan-Holdings http://www.mizkan.co.jp/company/

http://www5.mediagalaxy.co.jp/meito/

http://www.yamamori.co.jp/

http://www.yomeishu.co.jp/

CSR