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石黒浩二 , 吉元 誠, 田仁人*, 高垣Q也*
E 45 F Nippon Shokuhin Kagaku Kogaku Kaishi Vol. /., No. +, ./D.3 (,**1) G×ÉCH 45 [email protected] Ó»hrTÀºaUrÓ»Àº@ IZORPJ T [email protected] dêã[email protected] ÅÚ [email protected] ~XW*@ æ¶Ï³* Ãä^«WÎ@SòÎÄHmç×ÉÃâ ÑB¬Î×É¡C * »ø±ú¹Tµ ´[email protected] IZORPJ uÛÄbZrcDnw¸§ÄT aXs`OrA »V¡egzCdcfÃ\]¤mqÅeÁ js`OrA ¯[email protected] Ó»eÁjsrüd zC]¤[email protected] }zó [email protected] ¡ó [email protected] }z|yó E.,/-diCQA, -,/-diCQA, -,.-diCQAF Roh}z|yó E-,.,/-triCQAF dcf} Hypotensive E#ect of Sweetpotato Tops Koji IshiguroL, Makoto Yoshimoto, Masahito Tsubata* and Kinya Takagaki* National Agricultural Research Center for Kyushu Okinawa Region, 00/+B, Yokoichi, Miyakonojo, Miyazaki 22/B**3+ * Toyoshinyaku, Co., Ltd., 1B,2 Yayoigaoka, Tosu, Saga 2.+B***/ BBBBBBBBBBBB Sweetpotato tops exhibited angiotensin I-converting enzyme (ACE) inhibitory activity, with di#erent levels of activity in the constituent parts of the tops. Leaves showed the highest activity, while that of stems and petioles was much reduced. Since there appeared to be a relationship between ACE inhibitory activity and the total content of the ca#eoylquinic acids in the constituent parts, the ACE inhibitory activity of each ca#eoylquinic acid was analyzed. -,.,/-tri-O-ca#eoylquinic acid (-,.,/triCQA) showed the strongest activity, followed by -,.di-O-ca#eoylquinic acid (-,.-diCQA), and .,/-di-O-ca#eoylquinic acid (.,/-diCQA). Spontaneously hypertensive rats (SHR) which were orally administered sweetpotato tops exhibited dose-dependent suppression in blood pressure increases in comparison with the control group. These results suggest that sweetpotato tops have a hypotensive e#ect in SHR, which is at least in part due to the ACE inhibitory activity of ca#eoylquinic acids. (Received Aug. ,/, ,**0 ; Accepted Oct. +-, ,**0) Keywords : sweetpotato tops, Suioh, angiotensin I-converting enzyme (ACE) inhibitory activity, spontaneously hypertensive rats (SHR), ca#eoylquinic acids BADAC : }¡Ó»@ [email protected] x¡|¡¡ I ©¾å i EACEF jµº\@ æÕ¢÷gL [email protected] }zó·r zó·rÆaNq EY [email protected] WspfzC ]¤eoráóñº/[email protected] ᩤÛñº[email protected] ~¡î¬nR½ [ñº[email protected] Roháñº1F dce_O`ªèY`U ]A }zó·rfxam[email protected] -,.,/-triCQA f·@` Áº\gQeæOWbm²pSed^`Or1FA }z ó·re_O`[email protected] [email protected] ¡`]½[ñº[email protected] áB HIV ñº[email protected] áªLñº+*[email protected] ao Cjµº\++F dce_O`mªèXs`OrA ®×É[email protected] yÓ»f`ºC½esZrXp dr`Áº\ß®fÖMf¦¿bY`@ WsjasNbY `OdS^]æÕ¢esZr½[ß®öÙuök]A j [@ Ó»RohÓ»zC]¤eorx¡| ¡¡ I ©¾åi EACE : EC-...+/.+F jµöÙuä^]A Wfï@ yÓ»g¡£¨eÀºXsrWbmk Xsr][email protected] ¡£¨e ACE jµº\uoY]A j]@ yÓ»eoræÕ¢÷gL ESHRF esZ rÕ¢OK½[öÙe_O`m¦\`ªèZrA [email protected] FEGH @ ö Ä yÓ» E@± IZORPJF [email protected] ÑB¬Î ×É¡CP×ÉËeRO` ,**, eíY]A A¸Y]Ó»[email protected] »V¡@ Ó¡@ Roh»§¡e¤ÂY] mfuÔ¼[email protected] ACE jµöÙeÌöY]A [email protected] ¡£ ¨f¼lEŹçg»V¡ -,[email protected] Ó¡ -,[email protected] Roh» §¡ -..,A aN^]A yÓ»fÔ¼l¥¯f 2*A {CyG ©u[email protected]¼Ü[email protected] HEPES wC E*.+ M HEPES, *.M NaCl, pH 2.-F ev¾[email protected] ACE jµº\oºföÄb Y]A SHR esZrÕ¢OK½[öÙ[email protected] cDºe{aY y EIpomoea batatas L.F g²ë¡fÀºT¦ ]öÄuÌY]A yÓ»hruZ E31KF e + [email protected] Ó»¡g¯TéagibvcÀºXs`OdO ¤ÀU}[email protected] ¡¡JÁuä[email protected] ÇÆÝ@ ¢¼l [email protected] x[email protected] x}u¥agÓ»¡mSXs`OrA Y]Ý[email protected] ¥¯eY]mfu£öÙeºO]A ®f¦¡fu¥[email protected] Ó»xf»§¡uÊl£nÉQ£@ }£dcbY`SY`[email protected] »V¡g d¨¼iTÁ A ö µ }zó·rÆf HPLC eoroj]g ACE jµ js`OremSStp[+F,[email protected] QVknÒ°TÍO][email protected] º\oeRO`ôºY] CA gÉÞIµàλø±ú[email protected] NjqÀºXs`WdS^]A Ð@ »V¡fS°T³f ChA gú[email protected] ó EQAF g}yú[email protected] M22/B**3+ ÈðØPõ«õz 00/+B, * M2.+B***/ ì°Ø|_õ´`TÇ 1B,2 L È¿e ECorresponding authorF .,/-diCQA, -,/-diCQA, -,.-diCQA Roh -,.,/-triCQA g ûpTtÂY]mf.F uºO] EY +FA ACE öµgÉÞ Iµàλø±úa Eʶ¾[email protected] Âù[email protected] Bachem AG a rB}±ºÙº´æ Z /. ¾ Z + Ü ,**1 t + Ñ 46 D 46 E T + [email protected] QA : xâ@ CA : vsâ@ ChA : z¡¡|¢â@ .,/odiCQA : .,/ooOovsuqxâ@ -,/odiCQA : -,/ooOov suqxâ@ -,.odiCQA : -,.ooOovsuqxâ@ -,../otriCQA : -,.,/ooOovsuqxâ a Hippuryl-L-histidyl-L-leucine DHip-His-LeuE mãS NaOH m¯M\xªmcäSXÖ@ *.,A a OC o XA ¨m +* @l f¯S\@ ì¬] +/ ÁxªRVXA @ vsânWÂaTd +/ @l a -.0 M ¢âmf¯[email protected] qz¡ BTd~V vsânWad[email protected] ³Æ`ÞSX ] HPLC S\ DMPA-3-**E NfcÌ×Td~VS\ DCS-3-*E ~P `fhÚZXA [email protected] ¸~PwK©a¿o]~ aqw_q¢{x¢{¢B qËahϽQ /* mg ` +* ml a 2*A t B DCS-3-**PC : ibKà÷KE mK\@ -0* nm a .E Bm¯[email protected] / ÁE]]îSXA + /**Hg, +* Á Åw_`fiÌ×Çg D.,* nm ¤a×møÆTi× ©C[email protected] ûJmo~q *../ @m a PTFE ¢ øÆp B L-., mãE DSxE mTdSXA ~¢ ¢p B]k³[email protected] Wa +* @l m HPLC `^sSXA aYlh` HEPES nBaemf¯[email protected] maPà HPLC [email protected]Ò[email protected] v ; YMC-Pack ODS-AM AM--*, mÚZXüÝaÌ×Çg DCE m}¢¡B^SXA d D+/*H..0 mm [email protected] ¦lR : AE *.,A [email protected] yâNfc [email protected] ACE ÛN¨aYlh` HEPES nBmf¯S BE B@ õ@Ò ; ,A B D*C+/ min, qz XüÝaÌ×Çgm~¢¢z DSBLxE ^SXA ~ p[email protected] ,J./A B D+/C/* min, o{t¢[email protected] ¢f¯m«ë@ ~¢éD`fiÌ×ÇgmI U ; + [email protected], v¬g ; .*[email protected] Óõw_ ; -,0 nm m [email protected] }¢¡B`XTiÌ×g [email protected]+**G KXA |öå^S\@ CA, ChA, .,/-diCQA, -,/-diCQA, móë^SX¡`NK\@ `Me`Ì×gOÔùT -,.-diCQA Nfc -,.,/-triCQA m[email protected] ¹H`[K\Ó iy¥]@ ACE »GÔùO /*A mèT^Paxª¨] Mmà[email protected] dSXA A ACE O·»GTd ACE O·»Gb ACE å`f~a»GTd+,E m 30 Î a~¢ugm IC/* [^SXA [email protected] + ~¢`[K \ , x][email protected] Qjm - µÚ[email protected] É[máõSXA B УûúFز qz¡ B`\Td°v_ð`¶ S\TdSXA ~qËmK\¤afL`S\@ Уû [email protected] ßAL§qz¡ B DHellma ïKE a¹ úFز`[K\ÓkSXA [email protected] . òaGa SHR rs`@ ~¢ /* @l [email protected] Qjg` *.*+ U/ml DrB@B¼ê´ïE 3 {mÕÊç DMF : ACE +** @l mf¯S\@ -1I `\ +* Á q¢xB ut¢ ÛÙȼê´ïE ] + òÁp®SXA p® SXA WaÖ@ ,/ @l aÃí¨ D,/ mM Hip-His-LeuE Ö@ zÀÐêélÐ£Í D¡¢ïKE mK\У mf¯[email protected] -1I `\ .* ÁxªRVXA +** @l a *./ N [email protected] QañôÄУaÉ[Omj^_ifL` - è½@ñ : {ubd°ºÁa C 47 D 47 «cQSZA È[email protected] YdL[d + «cRZÇe CMF : y A zwÂ^Dód ACE ëä x}¹V·©ÊÍD s{ubRZP zwÂ^Dó CCA, ChA, .,/-diCQA, -,/-diCQA, -,.- +A [email protected] `bqnLcI»VZƳÇes_MZ«s diCQA Nnf -,.,/-triCQAD Nnf QA d ACE ëä +A ü«`[email protected] C`c -A [email protected] `bqnLcRZÇe sïûVZA zwÂ^DóeKXrl¨K ACE ë sI»VZƳÇes_MZ«s -A ü«`VZA i äsÉ[email protected] Àläd¨O\Z -,.,/-triCQA d IC/* e ,2.1 [email protected] Ãpd + «eôÛ«`[email protected] RZÇes_MZA @M _J\Z CN -DA ðK^@ -,.-diCQA CIC/* : -1./ @[email protected] ƳÇeA_ÄOo [email protected] [email protected] ,+ G[cdÎÒ¥ .,/-diCQA CIC/* : .+.* @[email protected] ChA CIC/* : /-.* @[email protected] -,/- °sïûVZA [email protected] A_¥¢ø@ KXrd«clF¦ diCQA CIC/* : 1+.- @[email protected] CA CIC/* : 2/./ @MD dÕ_J\ WgQÞõU[email protected] óÑîNnféfd¿ Z CN -DA [email protected] QA c ACE ëÁaeHkorbO\ZA lHkorbO\ZA B {ubcnq SHR côWq°ÝÚcã µ C B®Öd ̳B}eSªGMÔ´¿[email protected] °ÝÚcãÆ³ È[email protected] {ubcnq SHR côWq°ÝÚc c]K^[email protected] ÅKd|vwt ESPSS for Windows ãµs±ÜVZA bêósçÐacúæVZÆec +*.*.1JF saK^ Dunnet dòÑLXcnp]¿d± [email protected] zwÂ^DóP\ +A [email protected] £irZA bsI» û C pH*.*/D s¸\ZA VZÇes_MZ«[email protected] ôÛ«`LV^@ ]¿ CpH ,@ ]XVQ *.*/D eHkorbO\[email protected] °ÝÚP¡mO`b @ {ubd ACE ëä [email protected] Yd¬¶e +A ü«np -A ü«_öQO\Z {ubd 2*A x} BùÓc]K^@ Cá ,DA ACE ëäsïûVZA bdP_ ACE ëä [email protected] Z [ [email protected] YdäebødP_b\ZA bàP ßO÷JËOoEorZ~cnq ACE ëdW PÀl¨R CIC/* : *.+0+ [email protected]@ ðK^P CIC/* : *..+* ¼eòâ[email protected] ñdßOøåQcnq ACE ëdW [email protected]@ bTP CIC/* : *.1,+ [email protected] dÕ_J\Z CN ¼heÙbK+.D+/DA Y²§[email protected] {ubNnf +DA 2*A x} BùÓceòfdzwÂ^Dó Cá bc£irq .,/-diCQA, -,/-diCQA, -,.-diCQA Nnf +D P£ir^KZA Ydí£[email protected]¯ ìRZ +** g JZ -,.,/-triCQA d ACE ëÁaP×k^ÉUrZA zw [email protected] bàP_ 1 +** mg, P_ , 23, mg, bTP_ + -3, Â^Dógd ACE ëäe -,/-diCQA sØK^@ z mg _J\Z CN ,DA bP[email protected] ízwÂ^Dó£f wyu¤dâPîWqcÏ[email protected] ¨Rbq¬¶sÉV Pò[email protected] ACE ëäP¨KT`[email protected] zwÂ^D ZA [email protected] QA dj_e ACE ëäsÉUbO\ZT` ócnq ACE ëÁaPɾUrZA g g + HJMENUiC ACE cRSb IC/* [email protected]Ô´¿D ACE ëä QA CA ChA .,/-diCQA -,/-diCQA -,.-diCQA -,.,/-triCQA IC/* [email protected]Ô´¿D bà bT g , GLF\hfdC ACE cRSb *4+0+G*4*+, *4.+*G*4*,1 *41,+G*4*3- I/** 2/4/G+43 /-4*G+4/ .+4*G*43 1+4-G34, -14/G*40 ,241G+4- HJMENUiCGLF\hfdTk bà bT [email protected]+** g @¯ ìRZD CA ChA .,/-diCQA -,/-diCQA -,.-diCQA -,.,/-triCQA í£f ,3 + 0-+ -,- 0/0 ,13 +2* 1 +** N4D4 : Not Detected4 021-,1 + .*3 ,,* N4D4 , 23, +* .3. -,1 /*, /3 N4D4 + -3, ` , HJMENUiC SHR OIKBeADWP_^jaYQ £S´¾ß¾·û p /. À p + æ ,**1 + Õ 48 [email protected] Scg»¿\dzwyuÅb¢kVpS_PX [email protected] D C |TqZA àô±kà¤Ú¿\^jzwyuÅc @ Zbmp¿\i³cÐÞPinq]Kp D 48 E }uÒ²c 2*@ xCuG¬b ACE g»¿\PinqZA ¿\cÌTdÒ²sc¡^¤a /E0E A Æb ACE g»¿\Pinq]Kpr]_½Vp [email protected] DHECxz |{Cc IC/* P + .** @[email protected] DHEC [email protected] ²V@ Ò@ ²cK^J[ZA A 2*@ xCuG¬bÃgqpzwô«m x{z |{CP 3* @M, t{ b ACE g»¿\PinqZA ¿\cÌ[email protected] NNmX C A P ++/ @M, t{C B P ++* zwyuÅcZb½[email protected] -,.,/-triCQA, -,.-diCQA, @M, t~{CP -/ @M ^Jo @ } .,/-diCQA, ChA, -,/-diCQA, CA cK^J[ZA +.E uÒ²czwô«mdXqn_ } Qc ACE g»¿\[email protected] zwô«m¼c ACE g»®Ad ¦^[email protected] Ún B }uÒ²rçUZüºrcCUZ SHR dÒ ²c³»¢k~bÔQNPÁkObapÐÞ[email protected] P DHECx{z |{C [email protected] }uÒ²bmp SHR cÔQ b\K]X|[email protected] ACE ¿\¡_c÷áj~ Nµ[ÐÞ[email protected] zwô«m¼c ACE g»P§\c³ aÓeQbmpS_jâMnqpA ¨_XòTqZA +.E Mishima et al. +0E d~ómouGUZ -,.-diCQA, -,/-diCQA Nme -,.,/-triCQA c SHR bnV pq¸ÑÝúØ D+* [email protected] rã[email protected] Sqnczw ô«mdª£aÔQNµ[ܵ[email protected]@ [email protected] -,.,/triCQA cµ[ܵdíjÌKS_rèU]KpA z wô«mbmp SHR cÔQNµ[czd ¦^J[[email protected] £×Ëbmo¦nO_a[Z ACE g» ñ±[email protected] zwô«md SHR cÔQNrµ[U Zjc_X|TqpA }ucÒ²^dzwô«m¼d²Vbíj lRÃgq][email protected] -,.,/-triCQA d²Vch^ÖGTq p D ,EA ²Vd¶Pé^dJgo·±Tq]SaO[ [email protected] ¯^[email protected] E¶On}u² DzCE P wKÂSTq]QZA ª´²[email protected] zwô«m Pl»bÃgqp²VrbÎ~b·±VpS_Pª^ Jp_XòTqpA }uÒ²rçUZüºrMZ SHR [email protected] ±» ¢k~bÔQNPÁkO_apÐÞ[email protected] [email protected] Nm e [email protected] ³ÏcKWqbNK][email protected] ÇÂs /@ YJ^ cª£ìdinqaO[[email protected] [email protected] ³Ï^düº ºöOn 1 ¨Nme ,+ ¨cnOÏ_cìcª£¼¹ DpE [email protected] XqYq pI*.*01 Nme pI*.*0- ^[email protected] +*@ Y J^cª£ìdinqZA FVKNLG c¦]Û@ } uÒ²[email protected] r®©º@ ©ï~Ca`cfð_U ]·±Tq][email protected] ©ï_U]cjL B bWs^K pA aF±bv_UZ}uÒ²¤rcCUZ SHR bNK]@ ÔQNPµ[TqpÐÞ[email protected] [email protected] v¸k³ßrzU]@ }uÒ²rR ~bcCVpS_^@ Ôä°kåÔ¬¡fcܵPÇ oTqpA }uÒ²bd uk bo z a`cz u@ E k K+ a`cù°\cª±]jl »bÃgq][email protected] Ĭ¡kêeUlLP¬¡a `cB¬¡ÜµjÇoTqpA B A +E ÊÙ `@ }u²c@ û@ ÍÉ [email protected] /[email protected] /,3C/-- D,**,EA ,E Md«@ ¥¦@ ¾§[email protected] { t§@ OsUl¹ë NmeÒ²sc@ wC@ ¥È]c |»@ Sh×@ //@ +C2 D+33+EA -E Ishiguro, K., Toyama, J., Islam, M.S., Yoshimoto, M., Kumagai, T., Kai, Y., Nakazawa, Y. and Yamakawa, O., Suioh, a new sweetpotato cultivar for utilization in vegetable greens. Acta Hort., 0-1, --3C-./ D,**.EA .E Islam, M.S., Yoshimoto, M., Yahara, S., Okuno, S., Ishiguro, K. and Yamakawa, O., Identification and Characterization of foliar polyphenolic composition in sweetpotato (Ipomoea batatas L.) genotypes. J. Agric. Food Chem., /*, -1+2C-1,, D,**,EA /E Islam, M.S., Yoshimoto, M. and Yamakawa, O., Distribution and physiological functions of ca#eoylquinic acid derivatives in leaves of sweetpotato genotypes. J. Food Sci., 02, +++C++0 D,**-EA 0E Yoshimoto, M., Yahara, S., Okuno, S., Islam, M.S., Ishiguro, K. and Yamakawa, O., Antimutagenicity of mono-, di-, and trica#eoylquinic acid derivatives islated from sweetpotato (Ipomoea batatas L.) leaf. Biosci. Biotech. Biochem., 00, ,--0C,-.+ D,**,EA 1E Yoshimoto, M., Kurata, R., Okuno, S., Ishiguro, K., Yamakawa, O., Tsubata, M., Mori, S. and Takagaki, K., Nutritional value and physiological functions of sweetpotato leaves. Acta Hort., 1*-, +*1C++/ D,**0EA 2E °®«[email protected] M¢UD÷@ T£¯õ@ yø¿@ }u uGbmpvCî c^]µ [@ S´ß@ [email protected] -+-C-+1 D+330EA 3E Mahmood, N., Moore, P.S., De Tommasi, N., De Simone, F., Colman, S., Hay, A. J. and Pizza, C., Inhibition of HIV infection by ca#eoylquinic acid derivatives. Antiviral Chemistry and Chemotherapy, ., ,-/C,.* D+33-EA +*E Peluso, G., De Feo, V., De Simone, F., Bresciano, E. and Vuotto, M.L., Studies on the inhibitory e#ects of caffeoylquinic acids on monocyte migration and superoxide ion production. J. Nat. Prod., /2, 0-3C0.0 D+33/EA ++E Matsui, T., Ebuchi, S., Fujise, T., Abesundara, K. J.M., Doi, S., Yamada, H. and Matsumoto, K., Strong antihyperglycemic e#ects of water-solble fraction of Brazilian propolis and its bioactive constituent, -,.,/-tri-Oca#eoylquinic acid. Biol. Pharm. Bull., ,1, +131C+2*- C 49 D @ : W^dShw´Lxkm³ C,**.DA Cheung, H.S. and Cushman, D.W. 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Acta Hort., 1*-, ,/[email protected],/0 C,**0DA +2D {²[email protected] ¤@ ¯pv@ ¹@ °º @ oFOMt´¨K¢uNQPc\ej [email protected] n}@ /*@ [email protected] C,**-DA +0D Cª +2 ¡ 2 y ,/ ¦@ ª +2 ¡ +* y +- ¶D AAAAAAAAAAAAAAAAAAAAAAAA