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食衛誌 50(1) 16-21 (2009) 16 Fr» Vol. 50, No. 1 `ῐῬ ῷ ῲ῰ῨΎῧ ῝ῗ ! ΐ2008 # 7 29 %&'῔ )*+,1, ῍ -./01 123,1 45671 89´;<2 =>?3 5@ A1 B E1 Examination of Original Plant of Jamaica Quassia Extract, a Natural Bittering Agent, Based on Composition of the Constituents Atsuko T6961, ῍,Naoki SJ<>BDID1,Kyoko S6ID1,Takumi A@>N6B61,Masaharu AH6CDB62, Young Sook YJC 3,Takeshi Y6B6O6@>1 and Kenichi T6C6BDID1 1 National Institute of Health Sciences: 1ῌ18ῌ1 Kamiyoga, Setagaya-ku, Tokyo 158ῌ8501, Japan; 2 Nagoya City Public Health Research Institute: 1ῌ11 Hagiyama-cho, Mizuho-ku, Nagoya 467ῌ8615, Japan; 3 School of Life Science, Tokyo University of Pharmacy and Life Sciences, 1432ῌ1 Horinouchi, Hachioji, Tokyo 192ῌ0392, Japan; ῍ Corresponding author Jamaica quassia extract is a natural bittering agent used as a food additive in Japan. The main constituents of the extract have already been reported to be quassin and neoquassin. In this study, the di#erences in composition of the constituents among four Jamaican quassia extract products were analyzed by LC/MS. The results showed that the four products have similar compositions of their minor constituents, as well as their main constituents. We isolated four of the minor constituents that were commonly included in the four products, and identified them as 11 -dihydro-12-norneoquassin, canthin-6-one, 4-methoxy-1-vinyl-b-carboline and 4,9-dimethoxy-1- vinyl-b-carboline. The List of Existing Food Additives in Japan mentions that Jamaica quassia (Picrasma excelsa)isthe original plant from which Jamaica quassia extract is produced. However, we presume that Jamaica quassia extract may actually be made from appropriate plants other than Picrasma excelsa,since P. excelsa is listed as an endangered species by the International Union for Conservation of Nature and Natural Resources. We prepared hot water extracts from two other species of plants, Quassia amara (American quassia, Surinam quassia) and P. quassioides (‘Nigaki’ in Japanese), and investigated their constituents by LC/MS. The results showed that the compositions of the constituents in the Jamaica quassia extract products resembled those in the extract derived from Q. amara. These findings suggest that Jamaica quassia extract products are probably made from Q. amara. (Received July 29, 2008) Key words: ῲ῰ῨΎῧ Jamaica quassia extract; FGῷ food additive; bittering agent; ῲ῰ῨΎῧ Picrasma excelsa; ῧ῱ῳ῭KL Quassia amara; ῭KL Picrasma quassioides ῍ῌ Ῥ῍2 ῎῎.Mῌ῕῭KLῸ ῲ῰ῨΎ ῲ῰ῨΎῧMῌ ῷOP῍1 Q ῧ (Quassia excelsa SW.) ῼ`ΊM0ῡΰῌ ῟ RῘῥ῞VῤXYZ[ 1 ῜῟^ΰῌ `Ίb Ῑ῞ῢῥΊῠ῟^ῤ῍ Mῧ (quas- cῙ῞ῠfVῢῥ῞Vῤ῍ ῷOPQRGiῳῪ sin (1)) ¡ῡ¢΅Ῡῧ (neoquassin (2)) ῟^ῤ῍¥ c¦RῘῥ῞Vῤ (Fig. 1)῍ ῍ klm ῲ῰ῨΎῧcῙ῞ῦῖn©ªῚῤG 1 nopqGFGrs uv῏x158ῌ8501 yz{|*}῿ fΌ 1ῌ18ῌ1 ῍1 ¬s­®¯° 120 ± ῑῷOPῒ ´ 8 # 4 16 2 O ῵rs uv῏x467ῌ8615 O ῵ ῿5 % (1996). 1ῌ11 ῍2 ¬s­sΏrs῾·ª¸ ῑ¹ 1 ῷOPQRGi 3 yzqῸῺsῸῺ῏x192ῌ0392 yz{ῴ, ῳῪῬῒ ´ 8 # 5 23 %ῌ rῶ° 56 ± (1996). 1432ῌ1 February 2009 X. IJKῶΌΌ Nῴ῱# *ῧ;ῧ.;<῜ _ῷ 17 ῑ῏ 1. ῐ X. IJKῶΌΌ Nῴ῱# ῠ ῕Quassia Extract, +, 3 ῑ 4 ῠῐ ῠ AῒDῌ B C Ώ9+,ῠῩ ῭S-῍? ῌ ῝ 2Ῠ῕=ΰ῍ ῺΏCXM῜ =Ῠῌ ῴ Ό ῺΏ Q. amara ῕῕Y?Z; mn\Z$῜ Fig. 1. Structures of major constituents1),quassin (1) and neoquassin (2), in Jamaica quassia extract mndῑῼ ῏ 0056῍94TN? ῜ῲῪ ῺΏ P. quassioides ῕῕Y?Z; mn\Z$῜ mnd ῌ ῠΎῨ Quassia Extract ῙῚῘ ῠῩ ῑῼ ῏ 0054῍79TS? ῕ῳ` 1cmOῌ Ῐ῍ Quassia Extract ῴΌ῜ῲῪ EU ῩῐΎ a 2s΅? 2ῌ ῡῢ ῕Y?Z; cmn\Z$ ῞ῘῨῙ῍ ῝ ῲῐΎ ῜ mndῑ)ῶmne῜ῲῪ` mneῲp ῲ Ῡῌ 14 ῾ 17 ῾ ῾! 10 kg 7 *h=ῨῙΰῤ῟ῌ Ῡῌ ῜ (=Ῠ$Ῑΰ῍ Ῥ kg ῩῘῥΰ῎3῍ ῠ῞$%ῩῘ&῝ῳῌ &ῬῩ ΰῌ (JP) ῺΏ=Ῠῷ῿῾jZῲp=ΰ ῔*+,῞ῗ-.ῌ Ὶῗ-῝ῥΰ῞ῌ /. ΐ ῺΏ M῔ 2$Ῑΰ῍ Ῡ0Ῑ12῎ῠ&῝ῳ,3 4῞῞56$ῬῥῨ 2. ῐ Ῑ78ῨῙ῍ ῼῴNd῜ῲῪ ῸῼῴNd *ῡ$X=Ῠῌ Ό 9ῌ : CFR῎4 (The Code of Federal Regulations) ¡ῶ Dῼ῕£?ῑῠ ῼῴNdZ ῕ῴΌ ῺΏ Q. ῌ “Quassia” ;<῜ =Ῠ Picrasma excelsa amara ῝ῳ kῠῐ ῼῴNd 51.1ῖ ῜ῲῪ ῸῼῴN ῕Quassia excelsa Ώ9῜ ? ῜ῲῪ Quassia amara L. d 43.8ῖ¤i 94.7ῖ s@ ῕HPLC (UV 250¥40 nm) ῕ ῺΏCῴΌ ῺΏῌ !D F ῺΏ? ῞GH lῢn*o?? 2$Ῑΰ῍ Ό¡Fῼ K ´¡§῵ῑῌ ῨῙ῍ =ΰ῞ῥῨῌ 8῞:ῠIJKῶΌ Silica gel 60 ῕Merck ῑῠῌ p 63ῒ200 mm, Cat. Ό Nῴ῱# ῠ ;<=Ῠ P. excelsa O Q. No. 7734? 2$Ῑΰ῍ ῡ q ZῠΎῨ© sª amara ῞$ῙῳῨῙP῿&῞QΊῳ῞ῌ 'ῳ῝ ῘῙ HPLC $2$Ῑΰ῍ Ῡ-Ῑ῍ <(῜ )῞S-Tῌ ῡ ῱# ῩῘ ῠ *ῧ῰S-&῞,Ῠΰ`ῌ X. 3. ῔῕ IJKῶΌΌ Nῴ῱# /Y῎ ῏῜ῲῪῠ «)*ῡ ῑ῔´ῌ ῌ ¬­2$Ῑΰ῍ ῏῱\ῥ&]2 ^3῝ῳῌ ;< _ῷ῞56ῩῘ῍ $u®Ὺῼ K ´¡§/῏*ῡ (LC/MS): Waters 7ῒῳῌ &ῬῩIJKῶΌΌ Nῴ῱# ῏9 ῑῠ LC/MS system (LC: Alliance 2695; PDA: 2996 pho- %῜ῲῪ`aΰ/ ΰ` ;ῦ_ῷ=Ῠ 1 ῠῦῙ todiode array detector; MS: Quattro micro triple- Ῠ*ῡ=ῌ ΐ*῞ quassin ῕ῼῴNd? 21.4ῖ ῜ῲῪ quadrupole mass spectrometer)῍ neoquassin ῕ ῸῼῴNd?῕2 S&Ὺ hi ? 55.5ῖ *῔®Ὺῼ K ´¡§/῏*ῡ ῕*῔ LC/MS?῏ ῩῘ&2?j1) =ῨῙ῍ =῝=ῌ ῠ! kS Waters ῑῠ LC/MS-controlled preparative LC system @A῜ῲῪB*ῦῙῨῙῬῤ'ῳ῝Ῡ-Ῑ῍ ῡ (LC: 2525 binary high-pressure LC pump, 2767 one- &Ῡῌ mnῩῌ ῱# :Cῠ *ῐΎ2 bed injection-collection sample manager; PDA: 2996 o=ῌ : `aΰ/ ΰ` ;ῦE-Ί?2´ΰ` photodiode array detector; MS: ZQ-2000 single quad- ῌ 4 ῠ *ῧ2 LC/MS ῲp q=ῌ ῠ῰ rupole mass spectrometer)῍ r=Ῠs@ῨῙΰB* 4 ) tJ2'ῳ῝= ¯῍°rwD±ῼ ² (NMR): JEOL ECA 500 ῕ ΰ῍ ῬΰῴΌ ῺΏ Q. amara ῜ῲῪ ῺΏC ῺΏ ῴ῕£?ῠῌ 500 MHz?῍ NMR ³´Ό²N§ ῭ Ce Picrasma quassioides B:CC. * q2uῙῌ IJ XMῌ tetramethylsilane (TMS) 2$Ῑΰ῍ KῶΌΌ Nῴ῱# ῠ ;<ῦῙῨQv=ΰ῍ 4. LC/MS ῌ῍῎ῒΐ ῎3 “ :wEῺx2ῸῬΊΰ῝ `aῌ ;M xῙ4 IJKῶΌΌ Nῴ῱# ῠ ῕ ῑ ῠ῏ ῒ ? ῠῲ mn 19 ῾῵Py῎*Ῥmn?jῖ῔ {ST 3 4 A D ΌC|mn} ῑῑDῌ http://mhlw-grants.niph.go. 2 ῑ²z¶=Ῠ 5.0 mg/mL ῲ{=ῌ ῠ jp AῒC « 5 mL 2ῌ ῠ D 10 mL 2*ῡ|΅ῼ ῎4 Code of Federal Regulations, Title 21, PART 172ῌ =ΰ῍ ῺΏCXM῜ ῌ ῕ῳ` Oῌ a FOOD ADDITIVES PERMITTED FOR DIRECT ADDI- 1cm TION TO FOOD FOR HUMAN CONSUMPTION, Sub- 2s΅? Ῡ 0.3 g 2Dῼ·ῑῤ*¶¸ῌ k part FῌFlavoring Agents and Related Substances, “῏ ῠ῟ 2.0 mL 2Ίῌ ῟ῙῩ 90¹,40*῱#=ῌ 172.510 Natural flavoring substances and natural sub- ῌ º῞* =ῌ Ῑ « stances used in conjunction with flavors” http: //www. (10,000 rpm, 3 min) 20 mL gpoaccess.gov/cfr/index.html (4῍1῍08 Edition) 2|΅ῼ=ΰ῍ ῼῴNdZ ῑ²z¶=Ῠ 18 ¹º» Vol. 50, No. 1 1.5 mg/mL ῧῑ῟ῌ 10 mL ῳῡ῍ῧῘ῟῍ ῔῎ῒῑ LC ῎ ῴῌ XTerra RP18 (2.1 mm i. d. ῕ 150 1. LC/MS ῏ῒΐῙ῜ῐῗ῞Ί῕ mm, 5 mm, Waters); ῌ 0.2 mL/min; ῴῌ ´38&ῴῴ῿ῼ῏ῠῨ;ῤῌ qῡqῧ 30; Ὸ´ Ῠῌ ῌ 90 : 10(0 Ῐῦ|ῗῳῙ`Ὺῌ LC/MS ῧῬ`ῡῳῡ῍ min)!85 : 15(7ῑ22 min)!50 : 50(80ῑ95 min); $ Fig. 2aῑd ῧῩῌ PDA ῧῬ΅ UV 200ῑ600 nm ῤ+ %&'ῐ *&+,ῌ 200ῑ600 nm; +Ίῒῌ 257 ῟}~ῳ῟῍ 4 ; (AῑD) ΰῧῖ|ΰΰ nm. 37 ῡ (compound 1) ῖῬV 40 ῡῥ 41 ῡ (compound MS ῎ -ῐ.ῌ 120; /Ῠ῝ῌ 350; / 2) Ῠ ῐῷῘ῞῰ῌ {῰῰ῷῼ ῒFig. 1 ΐ Ῠ῝῵. ῌ 400 L/hr; Ὼῐ῵.ῌ 50 L/hr; ῶ3 ῖῬV 'ῷῼ ῒ16 rῠΐῒFig. 1 ῐ῕5ῌ 3.0 kV; Ὼῐ῕5ῌ 30 V (ESI pos.); . ΐ Ῠΰῌ UV .ῷ (Fig. 3A-a, b) ῖῬV ῶ3῞6ῌ m/z 100ῑ1,000; SIM (Selected Ion Moni- MS .ῷ (Fig. 3B-a, b) ῥ ῎῟῝ῥῗ῭ῌ com- toring) [M῔H]῔ (ESI pos.). pound 1 ῳῷῼῌ compound 2 ῳ 'ῷῼ ῒ2 5. ῝ῗ῞ compounds 3῍6 ῐῚ῟ῌῘῙ rῠΐ ῥ"ΐ῟῍ $¡rῠῘ´38&ῴῴ῿ῼ ´38&ῴῴ῿ῼ῏ῠ; ῒ; Bΐ 25 g ῳ>? ῏ῠ;Ῠ¢qῡῤῡ῍ $¡rῠῨ ῐῷῤ£῟ ῾ 300 mL ῧῨA῟ῌ BῨCῡῳD5EF῟ῌ ῖ῭ Ῡ 4 ;ῤ¤¥'῟Ὶῌ Ῡ῞῰ῦῗῡ (Fig. ῰I῞ῳK; 300 mL ῧῨALῌ M 300 mL ῨOῶ 2aῑd)῍ §ῌ qῡῧῢ|ΰΎqῡ῟©ῳῡ῍ Fig. Ώῌ ῷRRSῌ >?῾ῖῬVWX ῐῤ[\ 2eῑh Ῡ Fig. 2aῑd ῳ{῰῰ª«῟ΰ῟ΎῨῤ ]ῌ]ῡ῜῏῟῍ ῷRRS῏]ῳD5Ὶ^῟ῌ `῍ ¬­Ῠ( Ῠqῡ ῐῷῘ+῞῰Ῐῌ {ῨῷR ῼῴΌῴ ῒῗ`῎ 45 mm; ῒ῞῎ 300 mm; a 8 ῸῩ 4 ;ῤ¤¥'῟ῚῩ῞῰ῦῗῡ b῎ ῷRRSῌcX ῐ 1:0!1:1, cX ῐῚ ῍ ῐῷῤ£Ῐ῟©῔«Ῑ|¢*ῦqῡ ῐῷῳ῞῭ ῳ. ῿ef&gῧh῜ 8 ῌjῤῨῌ k 2,200 ῧῡC`ῧ,+-ῳῡῥ῝῱ῌ ΰ 21 ῡῖῬ mLΐ ῧ῟῍ ]ῳῦ 10 mL lῢῡC῟ῌ LC/MS V 35 ῡῨ ῐῷῧῩ.­Ῠ¡rῠῘ°ῦῡΰῨ῟ΰῖ ῤn Xῐ῟ῦῘ῭ῌ qῡ compounds 3ῑ6 ῘῨ῟ ΅ῌ ῡ῟ΰ±`ῥ² ¡rῠ΅Ῠ ῐῷῤ£Ῡ³῞ MCῡῳrῲtῌ D5EF῟ῌ MqῡῨuῡCῡῳῖ ῗῡ῍ {῝ῤῌ ῐῷῤ£Ῐ῟©῔«ῙῚῌ ῗῢ ῐῷ ῍ ῖ῭῰uῡCῡῳvwῨῡx LC/MS ῤῡx ῧ´§῰`qῡῘ¢ῧ² Ῠ¡rῠῤ`ῥµ¶῞῰ ῳy΅ῢ῟ῌ u compounds 3ῑ6 ῳῖ῍ ῞῭ῧῌ {῰ ῐῷ 3 ῑ 6 (compounds 3 ῑ 6) ῧ ῐῥ῟῍ Com- ῭ῳῡx ODS ῴῳῩ| HPLC ῧῬ΅K;῟ῌ com- pounds 3ῑ6 Ῡῌ {῰῰ΰῠΊῤῦῚῌ UV ῖ pound 3 (2.2 mg), compound 4 (1.7 mg), compound 5 ῬV MS .ῷ Ύῌ 4 ;ῤ ῎`῝ῥῘῙ῞ (1.3 mg) ῖῬV compound 6 (1.5 mg) ῳῖ῍ ῦῖῌ NMR AῨ}~ῌ compound 3 Ῡῌ 16 2 ῒ3A ῖῬV 3Bΐ Ῠ rῠῤ`῝ῥῘῡῗῡ ῒL wΐ῍ ῞ LC/MS ῖ ῡx LC ῎ ῴῌ XTerra Prep RP18 (19 mm i.d. ῕100 mm, 5 mm, Waters); ῌ 10 mL/min; ῴ ῌ 30; abῌ ῌcX ῐ 7:3 (compound 3) ῖῬV 5:5(compound 5)ῌ ῌ 9:1(0 min)!8:2(7ῑ25 min)!5:5(60ῑ75 min) ῒcompound 4 ῖῬV compound 6ΐ῏ c&ῷ῿eῨ῝ῌ ῌ 8:2(v/v) (1.0 mL/min)ῌ $ %&'ῐ *&+,ῌ 210ῑ500 nm; +Ίῒῌ 257 nm.
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