The oligosaccharides of some Japanese legumes. I. Preliminary experiments by paper chromatography.-香川大学学術情報リポジトリ

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Preliminar’y Experiments by Paper’Chromatography.

TeiitiNARASAKI(Laboratory of AgriculturalProducts Technology) and Sin’itir6KAWAMURA(Laboratory of BiologicalChemistry)

(Received October・3l,1957)



Conceringthe oligosaccharides of the soybean,KAWAMURA(1)repclrted that the soybean contained SaCChaIOSe,raffinose,and stachyose”A sample of the soybean contained theminthe amounts of3L7,10, and3.2%,工eSpeCtively(2)。HASEGAWA et al(3)reportedthatthe soybean,kidney bean,aSparaguS bean, and pea showed the presence of a】1these three oligosacchaIides by paper chromatography… KAWAMURA,

TuBOI,and NAI(AMURA(4)could asce工tain that also the broad bean showedthe pIeSenCe Of the same three Oligosaccharides.Now paper chromatogIaphy was appliedto see the distribution of the oligosaccharidesin the fivelegumes,ieadzukibean,mung,kidney bean,aSParaguS bean,and sword bean

M A T E R]A L S The fivelegumes used as the samp】e were as fo1lows: l一Adzuki.,bean,PhalSeOlus chrysanihos,’’azuki”inJapanese


3.Kidnやy bean,P.vulgaris,”ingen・mame’’ 4小 Asparagus bean,ⅥgnaSeSquipedalis,’’sasage”. 5Sword bean,Canavalia gladiata,†’natamame”

They wer・e allpurchased on the market,Werein exce11ent conditions,and were stated to have complete

germinating abilities.They are the samelegumes as usedin the study of starches byKAWAMURA,TuBOI, and Huz王Ⅰ(5),Who gave the analyses reproducedin Tablel.

Tablel‖ Analyses oflegumesuSed(5)

Moisture Crude protein 14小55 21‖27 1443 22..03 1459 22.05 1433 21,27 1481 24.C6 63 25 eO A rJ 二 ■Yト ニ ﹁︼ ︰ .− Crude N”free 董at ex七ⅠaCt OeO 52 40 0小91 5498 ].い44 53.22 134 54.45 138 5232 1Adzukibean 2.Mung 3.Xidney bean 4 Asparagus bean 5SwoId bean

Theselegumes were dehulled and pulverizedThe sugars were extracted from20g of themwith 200m1 5〕%ethanolby allowingto stand for about2小5hours at700with occasionalshaking.The extract was fil・ te工ed with sintered glass filter,the filtrate was evaporated to drynessin vacuo below50O on a wateI・bath, and the resulting thin f’ilm of the sugars was taken upin 5 mlof 5〕% ethanolAfter filtration thisis ready to be applied to paper chromatography


Tech..Bull.FacAgI.Kagawa Univ”



AMaTaius.One・dimensionalchromatographicapparatus of Te・y6Fiiter Paper Col(Tokyo) Papern Paper strip of T6y6No.5つ(2cm x 40cm)

Two soIvent systems were used:

SoIvont AA mixture of n・butanol,aCetic acid,and water(4:l:2,V/V)was shakenin a separating funneland the upperlayeIWaS uSed after allowing to separatein†o twolayers.

SoIvent B.A mixture of phenoland water(u:3,Wt/wt)

ColoY reagenis。Ammoniacalsilver nitIate(8)and panisidine phosphate(7)weIe employed

Procedure。The sugar solution,5■・10ILl,WaS SpOtted on paper strip with amic王OpipetteThe chromato・ grams were developed foIabout2〇hours with soIvent A and about24 hours with soIvent B at constant temperature of22±lO C。The double development was made with soIvent A”Following the development of

the ch【OmatOgram,the sugars on the strips were revealed by use of the spray reagents and each spot was identified by comparing eheir colors and Rf values with those of standaId sugars


As shownin Tables2and3,allsamp】es oflegumes contained no reducing sugaI。The presence of SaCCharose,raffinose,StaChyose,and one or two more unidentiiied oligosacchazideswasfound.Swordbean Seem声d to contain another unidenti董ied oiigosaccha工ide over the spot of raffinose on the chromatogIam

AccoIdingto DupERON(8),the distribution of saccharose,raffinose,and stachyoseis considerably wide The oligosaccharides corresponding tolower R董Values thanthe R董Of stachyose not detectedin the cases

Of the soybean and broad bean might be pentasaccharide and hexasaccharide.CouRTOIS,et al(9).found VerbascSeOrtrigalactosidosaccharoseintheseedsoflentil,alfalfa,andvetch(a11belongingtoLegumino− Sae).They(10)further found the existence of ajugose or tetragalactosidosaccharosein vetch seeds

Thusitis very probable that the mung contains these two higher oligosacchaIides(Verbascose and ajugo・

Se),SWOrd bean contains verbascose,and the adzukibean,kidney bean,and asparagus bean contain either


The above findings were reported by KAWAMURA(11〉ltis veryinteresting to note that very recently G‡RI(11)reported the existence ol qaccharose,raffinose,StaChyose,and verbascosein green gram (Phaseolus Yadiatus),Whichis undeIStOOd to beidenticalwith mungin this report

Table2.Deteこtion of oligosaccharides by papez chromatography with SOIvent A,BuOH・AcOH−H20(4:1:2)

Rf and size of spots fIOm Samples

Rf of standaId SugaI 2. Mung 5. SwoId bean Saccharose ? Rafiinose Stacbyose (Vezbascose?) (Ajugose?) 0‖24」十 0‖24」十 0.15 ± 0.13 十 0.〇フ 十 0小04 + 0.12 + 0“0フ + 0.04・+ ○り02 +・

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Vol‖ 9,Noい3(1958)

Table3。Detection of01igosaccharides by paper chromatography With soIvent B,PhOH・H20(17:3).


半The spot showed tailing towardlower R董 Value

R E F E R E N C E S (8)DupERON,R.:C¢∽♪f“㌢♂乃d.,241,.1乱フ・19 (1955) (9)CouRTOIS,J。E.,ARCHAMBAUr,A..,LEDIZE工, P.:β鋸〃.50C.(舶用.みよoJ.,38,351−8(1956) (10)+−,∴,+:乃≠dい,38,359・ 63(1956). nl)KAWAMURA,S.:SukeIOide kelkai.japanaj legumenacoj.Sciencaj Studoj(7nternaciaScienci・ Sta Asocio Esperantista),88−95(195プ) (12)GIRI,KA.:Transferases Synthesising Oligo・

SaCCharides from Molds,Animal Tissues,and Plants小Presented beforeInternationalSympoqium On Enzyme Chemistry,October22,1957“Kyoto UniveエーSity. (1)ⅩAWAMURA,Sin’itir6:7’ech・Bull,.Kagawa Agγ.CoJJ‖,4,65−71(1952) (2)+:./Ag㌢‖Cカβ∽小 50C../α♪α〝,28, 851・3(1954). (3)HASEGAWA,Masao,TAKAYAMA,T.,S王王IROYA, T“:動gaku(Science),21,593−4(1951) (4)ⅩAWAMURA,S.,TuBOI,Yosimi,NAKAMURA, HiIOSi:TβCゐβ〟JJ.∬αgαぴαAg㌢血C〃JJ.,8,2フ・ 31(1954).


,Huz王Ⅰ,Tamotu:乃査d′,7, 87・92(1955)り (6)PARTRIDGE,S.M。,WESTALL,R”G.,Biochem アリ,42,238−50(1948) (7)MuKHERJEE,S,SRIVASTAVA,H。C,Nature, 169,330(.1952)

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香川大学農学部学絹報告 豆類 の少糖類 に つ い て

Ⅰ ペーパークロマトグラフィー・による少糖顆の検出

楢 崎 丁 市,川 村信一郎

160 豆類の少糖成分としてほ,サッカロ−ス,ラフイノース,.スタキオ−・スが知られている(1 ̄4)・川村(5)ほ日本産の 各種豆類の澱粉について比較生化学的研究を行っているが,そこで使用されている豆類の中から5桂を選び,その少 糖顆をぺ−パ−クロマトグラフイ一により検索した. 使用したのほ,ア.ズキ,緑豆,インゲン豆,ササゲ,ナ・クマメの5種で,脱皮,粉砕後,50%温エタノ−ルで少糖 類を抽出した.展開ほブタノーールー酢酸一水(4:1:2)(2回)とフ,rノーーリレー水(1フ:3)で行い,アンモニア性硝 酸銀と♪・アニレジンで発色させた 単糖類ほどの試料からも検出されなかった.サッカロ−ス,ラフイノー・ス,スタキか−スほすべての試料から一様 に検出され,DupERON(8)の報告が確認された巾さらに・スタキオー・ヌよりRf値の小さい糖が⊥∼2種と,ナタマ・メで はラフイノ−スよりRf値の大きい未確認糖1種が検出された CouRTOIS√9)等は扁豆,ムヲサキクマゴヤシ㌧及びカラスノエンドクからトリガヲクトレドサッカロース,ペルパ スコーース,を発見し,さらに彼等(10)はテトラガテクトレドサッカロース,アジェ.ゴ−・ス,をカラスノーエンドクから 発見している,.これらの糖標晶が入手できなかったので確認ほできなかったが,筆者等の検出したスタキか−スより

Rf他の小さい2種の糖ほおそらくべル′ミスコーースとア汐ユゴ−スであろうい 従って緑豆はこれら2種を,ナダマメ

ほベルパスコ■−スを,他のアズキ,インゲン豆,及びササゲはこれらの内いずれか1種或ほ両方を含んでいるように 思われる.最近行われた国際酵素化学レンポジクムでGIRI(12)は朗α5♂OJ〟・ゞ7αdgαわ‘Sの種子中にサッカロ−ス,ラフ ィノ−ス,スタキオ−ス,の他にベルパスコーヌがあり,これらの少糖類がトランスガヲクトレデーションによりサ ッカローースから生ずることな報告したが,この豆は本報の緑豆に一一激する挙がわかった

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