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13 Nippon Shokuhin Kagaku Kogaku Kaishi Vol. /., No.3,.*+.*/ (,**1) 401 * * Changes in the Color and Pigmentation of Fermented Benikoji-rice Drink Gok

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(1)2 13 3. Nippon Shokuhin Kagaku Kogaku Kaishi Vol. /., No. 3, .*+º.*/ (,**1) »QR¼. 401.  

(2)     *. 

(3)  *     . Changes in the Color and Pigmentation of Fermented Benikoji-rice Drink Goki Maeda, Kenichi Higa and Junsei Taira*. Okinawa Industrial Technology Center, +,ῌ, Suzaki, Uruma, Okinawa 3*.ῌ,,-. * Department of Biosciences Technology, Okinawa National college of Technology, 3*/ Henoko, Nago, Okinawa 3*/ῌ,+31 ῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍ Benikoji-rice fermentation drink is made from fermentation of Genus Monascus with boiled rice, but the strong dark red colors give nasty impressions, causing lose the consumer’s interest. To dissolve the problems Genus Monascus was fermented under the various fermentative conditions such as boiled-rice water volume (ῌ of +** g-raw rice), temperature and humidity, and their colors were measured by colorimeter. The pigment extract were also analyzed by HPLC and LC/MS spectrometry and four pigments of rubropunctamine and monascorubramine as purple colors, and monascin and ankaflavin as yellow colors were estimated. The contents of former purple pigments decreased with increasing of temperature, humidity and boiled rice water volume, but not the latter yellow pigments were a#ected by humidity conditions. The di#erence in pigment compositions due to fermentative conditions changed color index of lightness, chromaticity, saturation and hue, and then colors varied from dark red colors to blight red colors. These results indicated that the pigment compositions with various fermentative conditions can control the color of Benikoji-rice fermentation. (Received Jan. +/, ,**1 ; Accepted Jun. 1, ,**1) Keywords : Monascus, rubropunctamine, monascorubramine, ankaflavin, Benikoji fermentation.  : . !"#$% &'() !*% +,-*.  /. 01 2Monascus ,.3 45678

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(11) @M. )a K.3/3 CDbc;EFId e?N@. 4L=”9 /™š4>ŒTvw> 9 / @. >!";EFJTH #fP0 1@RSTOg. ›VyJO//œžO?\4Ÿ@y=@>cSTH. 9UVEFJT dimerumic acid bh^ijk?*lm9.    . InTopi$% qrs9&ST'tu(4)STv w4*Px9yFJT0313H z{@|+f@},k~@. +

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(16) M·¤´N ¸ 3*/. OP¹ 2Corresponding author3 taira@okinawa-ct.ac.jp. ,  . :A«>/My=:94(`_(¬lm9GE F (@4­®­¯u 2EC-.-HHP, M[ °M3 > .2 ±² /;<=H /0 :†H 28

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(18) ´Bµ¶·¶¸¹ C /. º C 3 » ,**1 D 3 ¼. 402 Table +.  14 . Color characteristics of Benikoji-rice fermentation under the fermentative conditions. Fermentative conditions. Lightness. Chromaticity. Saturation. Hue. Color value. Constant. Variable. L*. a*. b*. C*. h. OD.30. Temperature, ./²C Humidity, 32ῌ. Rice water (ῌ) +-+00 ,**. -24-³*4. .*40³*4+ .-4.³*4.. --43³*4, -,43³*4+ -*43³*4-. -.40³*40 -14.³*4, -24,³*4+. .24.³*4.342³*4+ .34+³*4,. *40,³*4**4.1³*4*+ *4-/³*4*,. +42-³*4*2 +4/*³*4*, +4*1³*4*-. Rice water, +--ῌ Humidity, 32ῌ. Temperature (²C) -/ .* ./. -,4/³*4/ -.42³*4. -24-³*4.. --41³*4. --43³*4, --43³*4,. ,/4*³+4, ,243³*41 -.40³*40. .+43³+4* ..40³*40 .24.³*4-. +4*3³*4*0 *421³*4**40,³*4*-. ,411³*4++ ,420³*4++ +42-³*4*2. Rice water, +--ῌ Temperature, ./²C. Humidity (ῌ) 3* 32. -04-³*42 -24-³*4.. -.4/³*4* --43³*4,. -+4*³+4, -.40³*40. .04.³*42 .24.³*4-. *42*³*4*0 *40,³*4*-. ,4+-³*4+2 +42-³*4*2. +. Boiled rice water volume (ῌ of +** g-raw rice)4 Each value is the mean³SE (n@-)4. +. -/ .* ./  3* 32ῌ 

(19) .

(20) XY8 f&' .** nm RA  -// nm 8f 8. - .   + g   / mL     -** ῌ  +. LC-+*A -‚[ /0 ƒ„  * †#1‡. !"#$ RECIPRO. SHAKER SR-,S, TAITEC  %& '(

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(23)  U  RA ˆk23&4‰9~U  ˆk2356 78Š  + 

(24) . +,-. / +* mm)0 ,* mm)12. XY&9 . /* mm ; CM-A32 MINOLTA  &3 %&. xy Table + &Š  L*  #5. 4  567 CR--** MINOLTA  8 L*  ;.  C*   ‹8Œ  \ Ž&9*1. 92:  ; ; a*  <; ; b* .   :&\‘ ./ 8Œ ’ +--ῌ .  5 C*  ; 4=>?2:  C*@. 32ῌ   5#1* Š  1\&. , +ῌ,. a* Ab*  ,. D+. @tan. B8 C h  ; 4*:  h. bῌa B?EF. * ‹8Œ ’ ‘ +00ῌ V &9#i“ ;‘” •.–<‘—‡8˜.•.#. / 

(25) .  ™C?  š <; b*  . G HH7 V-/0*  H . \‘ ./ 8 Œ ’ +--ῌ  32ῌ. * .30 nm IH  JK 0  . &=>. ‘  h  #G›œ ; a*   *3XY&* ž>Ÿi E3.  *../ ῌm LMNLOP8QR.  ž¡¢ ?£‰9¤#‘¥?  . %& ST +* ῌM retinoic acid RA . ¦§xy?E‹8Œ ’ +--ῌ 8 \ ./ #.  U  LCῌMS Esquire-***A WATERS . 32ῌ XY82¨  94=>?. * VWXY8

(26) * .  @‰9¤#‘ . HPLC XY : Z,[ ; Wakosil II /C+2 ..0 mm i.d),/*. ,  . mm Z,[\ ; .* !" ; *.2 mL ῌ min, ]# ;.  , LC # LC ῌ MS 8. *.+ῌ ^_ `.abac ,*d1*ῌ $e%ῌ-* !.

(27)  U  HPLC klua©,[#ª«AI¬. PDA f&' ; ,**ῌ0** nm.. -vka Fig. + A B &Š‰ f23U . MS XY : ghLi( ; jNkalL-mN()g. ­ghLˆk + : mῌz -/,.0 ®M-H¯D , : mῌz -2*.0. hLino "*p ; ,.2 kV, -qrL+s m ῌ z ;. ®M-H¯D - : mῌz -/1.0 ®M-H¯D . : mῌz -2/.0 ®M-H¯D . -**d.** tL*p ; .* eV.. Š C ~ˆkª«AI¬-vka ˆ. U  HPLC ,#u--vkaw,xy -z+, #{| } ~XY& €. , HPLC. k + # , ‘ -*0 .,* /-* nm & ˆk - # .  -3* nm &°>I¬ Š 1±E+,  LCῌMS ,

(28) * ª«AI¬.

(29)  15 . Fig. +. º»ῌ¼ : TUVWXY€n[. 403. Changes in the pigments of Benikoji-rice fermentation under the various fermentative conditions. + rubropunctamine, , monascorubramine, - monascin, . ankaflavin, uk unknown and retinoic acid (RA) as an internal standard (IS). (A) HPLC chromatogram of each pigment and (B) their UV spectra.. 

(30)  rubropunctamine. +--῍ gh ./v mh 32῍ WX‚ƒ*4 7. RP monascorubramine MR monascin MC . /EFG>„hi !5†8sa 9%&.  ankafavin AK  .  !". ;4‡ d 8sl-Cˆ?$!" @-. #$%&'()*+,-./0123. ‰n[8PŠhij‹‡Œ> Ž8. 

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(33)  -  . 4. ˆ?$! Table +". 7 MC  AK 89$:$;<=!#>?. @- WX‚ƒ8a .**“/-* nm ”•823C–A. $-" @- /0123?. B>+,?$-" / RP  MR 8—-. $!AB

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(36)  uk WX‚ƒ8. C+,?$-". !˜n[C™$ TUVWXYb€8z{. 7 AK  MC DEF4/8GH. š› !#>ˆ?$-" #Š8EF. IJ KLMNO8P EFCNOQR. 4IJs /noC TUVWXYb. S-"  TUVWXYZ[\]>^ -_8W. €‘~sTœ8n[?ž!†5. X`>`a TUVWXb8-cd8e>Ff. –8sl !#>ˆ?$-" '()*4 TUWX. !" @- WXghij8P EF4kl->. Y‰WX‚ƒ8lnŸ!#*€‘. mh8!no4pqrsl- Fig. , A". ~sT8€ *¡!#>sl-". / RP  MR DEF4 KLM WX. ¢£4 ¤ ¥ ¦xs!§ ‚ƒ* Monascus. ghmhij8P kt=!QRS-" u8g. anka FE¨8©. h ./v *kt>wJ MR 4pqr+,?$sl. §¬­®¯V¤ ¥ ¨\> Monascus. -" @- 7EF4xsamh 32῍ * E. anka FE¨8z{ / RP  MR E. F>yw8kt=!# /EF4mh. Fn[?ž-#S !+," @- ° 4I. n[8z{|}~= #CS?$- Fig. , B". ±² U³O´8aTU>NŸ!#ª«. i%& WX\]€>sKLM. >Ff!#ª«. !".  !+-" '()*4 KLVZ[µ[¶·¸¹?.

(37) ;–—ž—vŸ I /. º I 3 » ,**1 J 3 ¼. 404. Fig. ,. I 16 M. The pigment compositions of Benikoji-rice fermentation under the various fermentative conditions. (A) Distribution of monascin and ankaflavin as yellow colors. (B) Distribution of rubropunctamine and monascorubramine as purple colors. *, ῌ of RA peak area and **, boiled-rice water volume, ῌ of +** g raw rice..  

(38)   . MR ef ` MC - AK _.       . g("F _-#hi$. !" #$

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(40) *+,-./01 23. BC!-j./)  k . 4-56 . lY!Zm \- 01 %\ VW. 78 !9: &;<%= >.  ?./  BC!9) .  ? @>   4A. -  -='( NO &;<%=.  BCD !=E,='(F. \-,n&='. &G" ῏. ῎.  ? H IMonascs JKLM $

(41)  ? & @BC!9 NO%P &;<%= QF > R S S-=, TUP% ( =%'  VW   BC23>01 P%>  $

(42) X Y!Z[ BC \  -./ ] ^     5 _ rubropunctamine IRPM - monascorubramine IMRM Y!Z` monascin IMCM - ankaflavin IAKM a! b- $

(43) X.  Y!Z[,F=cd_ RP -. VWo

(44) &9 Hp 'q(( O) rs# Ituvw& xM  yFz{> ῍. ῌ. +M *|}+ ,~  €-. ‚ƒ/0 „ 1s †2 ‡3ˆ‰Š‹ŒŽ I4 5M pp. ...ῌ./2 I+313M ,M :6‘’ -"“!"@”>VW•@78–— 9˜™-š›:œ• ;žŸ -1 .*-ῌ.*3 I+33*M -M <  ¡ ¢ƒ=> 6?£/ ¤@¥A B¦§¨ Cƒ D© Eª- go «¬­F®¯°±‡²Œ³ Y´¯°µ¶·G ¸H—¹Ÿ /* ,2/ῌ,3+ I+33,M .M Endo, A. and Monacolin, K., A new hypocholesterolemic agent produced by a Monascus species., J. Antibiotics, -,, 2/,ῌ2/. (+313). /M Endo, A. and Monacolin, K., A new hypocholesterolemic.

(45)  17 . ”•ῌ– : YZzN—˜,™š9. agent that specifically inhibits --hydroxy---methylglutaryl coenzyme A reductase., J. Antibiotics, --, --.ῌ --0 (+32*). 0 Aniya, Y., Ohtani, I.I., Higa, T., Miyagi, C., Gibo, H., Shimabukuro, M., Nakanishi, H. and Taira, J., Dimerumic cid as an antioxidant of the mold, Monascus anka. Free Radic. Biol. Med., ,2, 333ῌ+**. (,***). 1 Taira, J., Miyagi, C. and Aniya, Y., Dimerumic acid as an antioxidant from the mold, Monusucus anka : the inhibition mechanisms against lipid peroxidation and hemeprotein-mediated oxidation. Biochem. Pharmacol., 0-, +*+3ῌ+*,0 (,**,). 2   

(46) ῌ     pp. +-1ῌ+.* +33-. 405. 3 !"# $%&'()*+,-. /0123456 7 89:;<=  ,+ pp. +3ῌ,/ ,**/ +* >?,-.@ABῌACDEFGH2IJKL@ 8DMN CMP IOPQ  .+ pp. /0ῌ0+ ,**0 ++ RSTU VW X YZ[\],^_`abcd,YZ [\]Jef8 ghiM ,**.ῌ-+-*,. j ,**. +, klm no  pqrst YZu Monascus anka sp. ,vwx&by(z{|,}~ € /+ 01ῌ 1+ ,**. +- ‚ƒ„ ‚†t ‡ˆ‰ŠZ‹Œa&)YZ,^Z € .2 20-ῌ200 ,**+. Žs +3  + / +/ ‘’ Žs +3  0 / 1 ‘“. ῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍῍.

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