37 Nippon Shokuhin Kagaku Kogaku Kaishi Vol. //, No. /,,-3,.. (,**2) 239 * * Cultivar Variation and Anthocyanins and Rutin Content in Sweet Cherries Prunus avium L. Tetsuya Sugawara and Kiharu Igarashi* Yamagata Research Institute of Technology, Shaonai Testing Facility,,/ Sakuragi, Oshikiri-shinden, Mikawa-machi, Yamagata 331 +-,+ * Faculty of Agriculture, Yamagata University, +,- Wakaba-machi, Tsuruoka, Yamagata 3312/// Major anthocyanins in +- sweet cherry ( Prunus avium L.) cultivars that were grown on a farm of the Yamagata General Agricultural Research Center were identified and quantified to determine the relationship between anthocyanin and flavonoid (rutin) content with identical sugar moiety. The anthocyanins in sweet cherry Prunus avium L. cv Benisayaka fruit with deep red skin and flesh were characterized. Anthocyanins were purified from the / acetic acid soluble fraction of fruit purified by Diaion HP-,* and Sephadex LH-,* column chromatography and HPLC, followed by determination of the chemical structure of + +- anthocyanin content by HPLC and ESI-MS spectrometry, and by H, CNMR analysis. Five types of anthocyanins were identified ; cyanidin---rutinoside and cyanidin---glucoside were the major anthocyanins of the fruit. Peonidin and pelargonidin---rutinoside were minor anthocyanins. Cyanidin---sophorosidg FW and showed higher correlation (R *. 31) with content of cyanidin---rutinoside, a major also was present. Concentrations of cyanidin---rutinoside in Japanese sweet cherries ( 1 cultivars) ranged from not detected (n.d.) to 1-. 2 mg per +** g of fresh weight (FW), with the highest content observed in cv Benisayaka. As the flavonoid of fruit, rutin also was detected in +- cultivars, with content ranging from *. 1, 21. mg per +** anthocyanin in sweet-type cherry. (Received Nov. 3,,**1 ; Accepted Feb. +,,**2) Keywords : cherry, anthocyanin, rutin, quantification :, 2** t +2 1, 2 0 + Prunus L. +33+ subgenus Cerasus sub- genus Padus,* +- Prunus avium L. Prunus cerasus L.,, - / 331 +-,+,/ * 3312/// +,- Corresponding authorsugawarate@pref.yamagata.jp
240 // /,**2 / 38 0 / A vv B+* /* vv./ B,* /* 1* +*. mlmin, SPD+* AV, /+* /-* nm - -. + Brix +2 0,0 /** g, / /** ml / 2 *** /..l /,. / A /** ml Napoleon DIAIONHP-,*, l Jabouley 1 +/. l / 2* Conpactlambert Greatbigarreau,* ml Van Redglory Mertonfavrite Seneca 0 Sephadex LH-,mmi.d3** Brix mm,/ // 2*. mlmin, ph, HPLC B +* ml HPLC, HPLC Inertsil PREP-ODS,* mm AM-- i.d.,/* mm, GLScience 0.* ml / 2 *** ph min HPLC ph ph HPLC,,2* nm -0* nm /+* nm / g 32 2* +** ml *.*/ / 2 ***,*,.,. / A / HPLC *./. m HPLC - HPLC HPLC +- / +** ml C, / / A vv D, /* *./. m HPLC +* D D HPLC LC-+*,/.* 0* 2* A HPLC Mightysil RP- +.* mlmin,2* -0* nm +2.. 0 mm i.d.,/* mm, HPLC 0.* mlmin.* A +* / HPLC
39 : 241 + ph,, ph HPLC Brix mg+** g -42* *4*+,,41,4,+ /14- +4-* -42+ *4*,,+4+ *401 0041,4-/ -41* *4*+,+42,43,,** 14+3-430 *4*+,,42 *4,* /+42,4,- -430 *4*+ +141 *4*0 024+ 04*. Napoleon -4/. *4*+ +14. +4*, ++1.43, Jabouley -40* *4*- +-42 *4/- +3* +340 Conpactlambert -41, *4*+ +.4, *4*0 1+43-4,. Van -413 *4*+ +-43 *4+, 224+ 242, Redglory -41/ *4*+ +-42 *4*+ +-/ +34/ Mertonfavrite.4*2 *4*+ +/42 *4*+ +./ 24,+ Greatbigarreau.4*+ *4*+ +/43 *4*0 +3, 042* Seneca -40/ *4*+ +341 *4-, -01,.4* + - + No4 mz M +, -. + 0++ - 0++,..3 -..3 - /3/ - 0+*. 0-- / /13 - /13 0 0*3-0*3 + HPLC +- CNMR, -.,, 0 ZabspecQ mz M - kv 1 kv HPLC n mzmn + 0 - No + 0 + H +- C-NMR JNM-EX.** FT-NMR ESI-MS ESI-MS mz, ESI-MS + ph Brix + HPLC /+* nm, ph, + No., ESI-MS m ph -./.. + z..3 M m z,21 HPLC,* - No. - ESI-MS m z/3/ M mz,21 +- CNMR +** MHz CF-COOD-CD - OD + 3 TMS d ppm +0...1 C-, +./. 02 C- - +-0./+ C-. +/3. -1 C- / +*-. 11 C-0 +1*. 13 C- 1 3/..1 C- 2 +/1. 30 C- 3 ++-./, C-+* +,+..1 C- + ++2. 1+ C-, +.1. 02 C- - +/0. +- C-. M
242 // /,**2 / 40 ++1. 03 C- / +,2. 0, C- 0 ++,. 11 C- + 1.. 3+ C-, 11. 03 C- - 1+..1 C-. 12.,0 C- / 02.*1 C-0 - +*,.., C- + 1,.*3 C-, 1,. 1 C- - 1.. +0 C-. - - 1*.*3 C- / +2. ++ C-0 Seneca 1 - O, 2 - +* 2 - Goncalves 23 HPLC, Greatbigarreau Jabouley HPLC No. - - - Seneca ESI-MS No. + - +0, mg+** g, - mz 0++ mz 03 mg+** g,21 No. / mz /13-1-. 2 mg+** mz,1+ No. 0 g, - +..- mg+** g mz0*3 mz Seneca -*+ 0++ - /13-3* - 0*3 - - -. - mg+** g - -, - O *4/03 *4+1* *4*,- *4**. *4,,2 *4*/* nd 4 1-42 *4.1 +.4- *4+.* Napoleon Jabouley Conpactlambert Van Redglory Mertonfavrite Greatbigarreau Seneca *4-.* *4*0- nd 4 nd 4 nd 4 *4/33 *4*.1 *4*,1 *4**- 014, 04.+ 14+2 *401-04+* +4.2 *4+-* *4*-* 340* *42. *4+3, *4*,, +.40 *4*+ +4+3 *4*,/.+4*.412,4,2 *4-+. 2*4/,4/-,42. *4*3* +0, 04,. 034*,4.3 + - - HPLC /+* nm No. + : - No., : - a : Jabouley, b : Greatbigarreau, c : Seneca
41 : 243. HPLC ESI-MS : HPLC -0* nm a : HPLC a ESI-MS mz 0*3 : MHM : mz-*+ 0 +- -. *2. 21. mg+** g / +- SenecaGreatbigarreauJabouley - - -, R *31. HPLC ESI-MS / HPLC, R *3/. 0 ESI-MS m z 0*3 : M+ CoA - po ocoa mz -*+ : M+,,., 0,.oto -
244 // /,**2 / 42 1 +- ++ B, +,. - - +- - - +- - +- / HP,* LH,* HPLC HPLC, ESI-MS, H, + +- CNMR / - - - - - 1-1-. 2 mg+** g *1. 21. mg+** g +- -, R *31. + +2,**1, -2* -2/ +33. - Wanng, H., Nair, M.G., Stransburg, G.M., Booren, AM. and Gray, J.I., Antioxidant polyphenols from tart cherries (Prunus cerasus), J. Agric Food Chem.,.1, 2.* 2.. ( +333).. Seeram, N.P., Momin, R.A., Nair, M.G. and Bourquin, L. D., Cycloxygenase inhibitory and antioxidant cyanidin glycoside in cherries and berries, Phyto-medicine., 2, -0, -03 (,**+). / Blando, F., Gerardi, C. and Nicoletti, I., Sour Cherry (Prunus cerasus L) Anthocyanins as Ingredients for Functional Foods, J. Biomed Biotecnol., /,,/-,/2 (,**.). 0 /,/.,/0,**+ 1 Wang., H., Nair, M.G., Iezzoni, A.F., Strasburg, G.M., Booren, A.M. and Gray, J.I., Quantification and characteri- zation of anthocyanins in Balaton Tart cherries, J. Agric Food Chem.,./,,//0,/0* ( +331). 2 Goncalves, B., Landbo, A.K., Knudsen, D., Silva, A.P., Moutin-ho-Pereira, J., Rosa, E. and Meyer, A.S., E# ect of ripeness and postharvest storage on the phenolic profiles of Cherries (Prunus avium L), J. Agric Food Chem., ++, /,- /-* (,**.). 3 Branka, Mozetic., Polonca, Trebse.,Janez Hribar., Deterxycunamic mination and quantitation of anthocyanins and hydro- acids in di# erent cultivars of sweet cherries (Prunus avium L.) from Nova Gorica Region (Slovenia), Food Teachnol. Biotecnol.,.*,,*1,+, (,**,). +* +* +,+ +33- ++ p.,3,*** +, p. -*,*** +- p. -* -+,*** +3 ++ 3,*, +