16 植物における フェアリー化合物の生合成経路に関する研究 (口頭発表の部)
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(2) 0 P95[aĚ#ĢÚōƀ"ƕ0İĽ (a ƛ²Ɩ`Œƃ, b ƛ²`?[a_İ, c ƛ²`ƃ, d ƛ²`Ġ, e ƛ²Ɩ`ƈ, f òĊ²`ƈ, g ƛĭ²`ŧ) a ŀð ´ķ , Æ ¿Ę a,b, sŨ ÐÁ a, ƅŨ ƍb a, şjĒ Ŧ c, tŭ ¨ d, Ƌŗ šµ b,d, ÚÇ Ķ b,d, óÅ Ģ e, Êk ĉã a,b, ĈÇ » f, ļk ŷ g, Ť âË g, ĄÄ Ć¢ a,b,e. Śë`īĪ ŠţƂĜ"ŕŢê"$÷ĀÒ"ƂĜ"<OAĩĢ0ğŽ$P95 [a[_?Ƥfairy ringsƥ ¡%1 0P95[a[_?ØſĚž AWZ B<CXDƤLepista sordidaƥťʼnz©ƞĔċ .ƚ1 2-azahypoxanthine (AHX)
(3) -& imidazole-4-carboxamide (ICA) $Ɲ¹c#ĸ"Ėƕ~"ŵ #øĚ "À ÚƓŹŃćÖ4ĵ 1,2)7N,AW=ł#ƒ4²É"¯ 1,3,4) (AHX $øĚz 2-aza-8-oxohypoxanthine (AOH) 'pż10 é AOH + AHX û!øĚÚƓŹŃćÖ4ĵ 5)Û$1. AHXICAAOH 4P95[aĚƤfairy chemicals; FCsƥ ŒĹ
(4) /û!øĚ"Ģ 0 é 0 5) ."7N" FCs 4Ġ0 AHX $ AHX--D-glucoside (AHXG)AOH $ 3 ĻƝ# AOH--D-glucoside (AOHG-1 AOHG-2AOHG-3) ICA $ ICA-riboside (ICAr)ICA-ribotide (ICAR)
(5) -& homocysteinyl ICAr (ICAr-1)glucosyl ICAr (ICAr-2) #ű 8 #pżģĚ4ƚ (¥ 1) 6). ¥ 1. FCs
(6) -&7N# FCs Ġ"- Ó.1 FCs pżģĚ ƣö$ïİĽ ĢĴŶ1Ě. .
(7) 16. FCs $û!<OA"+Ģ
(8) /û"ÚƓŹŃćÖ4ì 0# *FCs å!øĚS\Y_0 $<OAS\Y_ 0ŜÖŘ .1 0#ĢÚōƀ$î"eé!ĕ± (FCs Ú#ĩä 0 5-aminoimidazole-4-carboxamide-1--D-ribofuranosyl 5’-monophosphate (AICAR) $ Ƈ ÈQ[_pżōƀ"- ÃƑ' pż10 5-aminoimidazole-4-carboxamide (AICA) ' °á10 į.1 0AICA #.!0pżōƀ$é. "! ! (¥ 3)bæ FCs #b 0 AHX
(9) -& ICA $ AICA 4 Ɵz lIJƑ"-/¹Ú1AHX $."<B_H_:<CGaF (XOD) "- AOH ' °á10* 7-9)øĚz"
(10) +û#ōƀ4 / AICA pż10 rŸ4Ŀ #Ŏõ7N"
(11) AHX $ AICA .ĢÚ10 4Ŵé 5) FCs #ơÙÌùą#Ɣĩ qFCs # AHX AOH "ƕ 7N"
(12) 0¼Ö
(13) -&¼ƒ4« 5) ICA "ƕ $ơÙÌ!ùą!ĢĴŶ1 ! (¥ 1 "ĵƇ/Û$û! FCs #pżģĚ4¼ 0øĚ"
(14) 1.#Ě#Ģ#ìĖ+ĴŶ1 ! ĢÚōƀ#ůé4 ũ c 1.#Ě#Ģ#ĴŶ
(15) -&¼ƒ4ũ #$eþ 0*ń } ơÙÌ! FCs #őŗĪùą#Ɣĩ4ũ øĚz4 MeOH/H2O/HCOOHƨ15/4/1 #ж ÜƆĬ¦Ĭ;ZW 0 Oasis HLB (Waters) 4Ĥ ŁbāƘ#ƎŇū4ũ."#Đċ4ēŔ Ò 2% HCOOH "ĐůÎ7:_máƦƆĬVI>EYaL 0 Oasis MCX (Waters) "| 2% HCOOHMeOH5% NH4OH5% NH4OH (60% MeOH) ƜÿĐ0 FCs
(16) -&pżģĚ#Ħ4ũ#æą"
(17) 0¤Ğ $ 80%~95% /LC-MS/MS (Orbitrap) ô"
(18) ņÜĚ#Ŋ 150 #ÙÌ 0 4ĴŶ(¹ÚhŖẼxzZR\ [4-13C,2-15N]AHX
(19) -&[2,5-13C2]ICA 4ƎüďĚž Ĥ ô4ũ 2100 mg #7N . AHX (2.77 ± 1.13 ng g-1 FW in shoot22.1 ± 9.01 ng g-1 FW in root)AOH (7.80 ± 4.34 ng g-1 FW in shoot43.1 ± 11.8 ng g-1 FW in root)ICA (14.6 ± 2.27 ng g-1 FW in shoot20.3 ± 2.50 ng g-1 FW in root) #¼ƒ"Ú."# æą"- 7N©ƞŌś"
(20) AHXAOHG-2AOHG-3ICAICArICAR #ĢĴŶ11.#Ě#ĢÚōƀ7N"¸§0 é. !ğ§n#øĚ"
(21) +ô
(22) -&n#pżģĚ"
(23) +ùŲ4ũ 0 ICA ĢÚōƀ#ůé Û$7N"
(24) AHX AICA .ĢÚ1." AHX AOH "° á10åŮQ[_pżōƀ#¸§4Ŵ é (¥ 3) 5)ICA +û" AICA .¹Ú10*øĚz"
(25) + AICA .ĢÚ10 Ř [2,5-13C2]AICA 47N"/Ƅ(. ¥ 2. AICA . ICA '#°á. .
(26) 16. #7N#Üċ4 LC-MS/MS "| 2 [2,5-13C2]ICA ù1 .øĚz"
(27) ICA + AHX û" AICA .ĢÚ10 é. ! (¥ 2, 3)ğ§7N#Üċ . ICA ÚƐŋ#Ňū4Ɖ* 0 çį#Q[_pżōƀ"
(28) [THLz 0 IMP
(29) -& XMP $ IMP 5’-nucleotidase "- [TCLz 0 inosine
(30) -& xanthosine ' °á10 (¥ 3)#*ICAR . ICAr #°á"
(31) + IMP 5’-nucleotidase "-0ćÖ #ĴŶ4ũ 0. ¥ 3. çį#Q[_pżōƀ å"à¼ĢÚōƀ ½œĮƧçį#ōƀ ´œĮƧÏİĽ¾ ĩŭōƀ ıœĮƧà¼ĢÚōƀ ½œöƧïİĽ é. "!ōƀ ıœöƧÏİĽ¾ ĩŭĩŪč)#Q[_pżōƀ. .
(32) 16. AHX`AOH ĢÚōƀ#ůé AHX
(33) -& AOH 47N"Ġ0 ¥ 1 "ĵĚ"pż10 4é. "bæ FCs úƈƝwøĚS\Y_#b 0B7K ;7M_$[THLz"ƆĪ"°á1,(çį#Q[_pżōƀ $ [THLzĢÚ
(34) -&pż"ƕf 0#*FCs "
(35) +û" [THLz4ōĥ ĢÚ10ōƀ!3ĢĴŶ1 0 ICAR # n " AHX
(36) - & AOH # Ɵ z ! / 0 AHX-ribotide (AHXR)
(37) - & AOH-ribotide (AOHR) 4ōĥĢÚōƀ#¸§4Ř (AHXR $ AICAR " NO 4o0 ĢÚ10 Ř AICAR " NO ĩĢ (NOC5) 4Č 2 AHXR #ĢÚĴŶ1#*øĚ"
(38) + AICAR . AHXR 0 $ AOHR 4ō AHXAOH 'pż10ōƀ¸§0 ĵ£ 1 (¥ 3) (AWZB<CXD $Q[_ġ4ì0Ě"À SES[TC\ Õ4ũ adenine phosphoribosyltransferase (APRT) "- AICAR . AICA ' °á10 4Û$é. " 0 10)# APRT "ƝwÕ4۶ 0Ɛŋ hypoxanthine-guanine phosphoribosyltransferase (HGPRT) į.1
(39) /SES[TaE#o`ŝƚÕ"- hypoxanthine IMP
(40) -& guanine GMP #ƆĪ!Ĭi°áÕ4۶ 0 (¥ 3)7N"
(41) +@OW׫ . 1 ĻƝ# HGPRT ƌv·¸§0 ĴŶ1
(42) /#ƌv· AHX AOH . AHXR
(43) -& AOHR '#°á"ƕf 0ŜÖ4Ř ² Şť4Ĥ ĨĻĩğ4ũ Ó.17Nĥñ# HGPRT (OsHGPRT) "ªž AHXAOH
(44) -& phosphoribosyl diphosphate 4 Õ4ũ 21 .#[THLz#ĢÚ4ĴŶAOHR $åŮĚ /OsHGPRT "- AHX
(45) -& AOH #°á۶10 é. !(HGPRT $SE S[TC\Õ4ƆĪ"ũ *7N"
(46) +Û༠AHXR AOHR . AHXAOH '#Úōƀ#¸§ĵ£1bƎ# FCs
(47) -&pż ģĚ"
(48) ç"xzZR\z#¹Ú"Ú
(49) /OsHGPRT "- å !xzZR\z4Ú0Ja\ Ĥ 0 .!0pżōƀ#ůé íÑ 0. ¥ 4. B7K;7M_#Əň. ÿ"AHX
(50) -& AOH 4øĚ"Ġ0 ?\ACL'pż10 é. ! 0 . (¥ 1)øĚz"1.#Ě4Əň0Ɛŋ¸ §0 Ř FCs Ɲwúƈ4ì0B7K;7M_ $ľŋ·"?\. .
(51) 16. AaEŎƏňz¸§# 3 x"Ŏ0?\ACL$ů1 0#"À 7 x
(52) -& 9 x"Ŏ 0?\ACL$ů1! « 1 0 (¥ 4) 11)úƈ?\AC\Ǝx
(53) -&ňƁĺ#ěÔƝw 0 .B7K;7M_4Əňz0Ɛŋ"- FCs +û"Əňz'p ż10ŜÖ4Ř cytokinin-N-glucosyltransferase 0 UGT76C2 4²Şť4Ĥ ĨĻĩğćÖŵƠ4ũAHX
(54) -& AOH "À0ňƁ ĺćÖ$ĵ! # .øĚz"
(55) AHX
(56) -& AOH 4ěĨ Ī"Əň0Ɛŋ¸§0 Ř 7N#©ƞŌś .ňƁĺƐŋ#¼4ŵ )7N©ƞŌś#Üċ4 40%
(57) -& 70%#ēÌ ƜÿijƑ5_YM8WăĂ 4ũ 70%ijƑ5_YM8WăĂĦ4ÍƗ7:_má>^UK?ZP6a Ħ4ũ 2bƎ#ĐĦ"
(58) AOH . AOHG-2
(59) -& AOHG-3 ' #°áćÖĴŶ1#*ćÖÓ.1Ħ4."ÎƗ7:_má >^UK?ZP6a
(60) -&@\ĔƊ>^UK?ZP6a"|ğ§1.#Ɛ ŋćÖ4ßü"Ħ4ũ 0 ŒÝ ïİĽ$øĚ"
(61) 0pżģĚ
(62) -&Ɛŋ#¼4+ "FCs #ĢÚ`pż ōƀ#ůé4ŵ)#īĪ#*"å!ơÙÌùą#Ɣĩ4ũ #æ ą"- FCs #Ģƒé#pżģĚ 0 AOHG-2AOHG-3ICAr ICAR #ĢøĚ * ĴŶ1(øĚ"
(63) å!Q[_pżōƀ "- FCs
(64) -&pżģĚĢÚ10 4é. "7N#ƌv· . Ó OsHGPRT 4Ĥ 0 P95[aĚ#ĢÚ"ƕf 0 Ř . 10åŮĚ AOHR #Ú"Ú P95[aĚ$ơĎyĎgę¬! #û!EK]E"À øĚ" řÖ4f 0."P95[aĚ4Ġ0 "- EK]Eġ®d #Ņ,ÂƢ! #ƒ4ŐÞ0 ƃ{Ě#ĞĪ`º¼Ī|ŏí Ñ1 0 Řãĝ 1) Choi, J.-H. et al. ChemBioChem 11, 1373Ʀ1377 (2010) 2) Choi, J.-H. et al. J. Agric. Food Chem. 58, 9956Ʀ9959 (2010) 3) Asai, T. et al. Jpn. Agric. Res. Quart. 49, 45Ʀ49 (2015) 4) Tobina, H. et al. Field Crop Res. 162, 6Ʀ11 (2014) 5) Choi, J.-H. et al. Angew. Chem. Int. Ed. 53, 1552Ʀ1555 (2014) 6) óÅĢ., Ł 58 ¤³ėìýĚŲźuŻđŬèƙ, 303Ʀ307 (2015) 7) Kang, U. et al. J. Am. Chem. Soc. 100, 651Ʀ652 (1978) 8) Wang, Y. et al. Bioorg. Med. Chem. Lett. 6, 185Ʀ188 (1996) 9) Ikeuchi, K. et al. Org. Biomol. Chem. 12, 38136Ʀ3815 (2014) 10) Suzuki, T. et al. Sci. Rep. 6, 39087 (2016) 11) Letham, D. et al. Annu. Rev. Plant Physiol. 34, 163Ʀ197 (1983). .
(65) 16. Studies on Biosynthetic Pathway of Fairy Chemicals in Plants Hirohide Takemuraa, Jae-Hoon Choia,b, Akinobu Itoa, Ryoichi Kondoa, Kaoru Yogosawac, Keiji Fushimid, Hideo Dohrab,d, Rei Narikawab,d, Nobuo Matsuzakie, Hirofumi Hiraia,b, Tomohiro Asakawaf, Makoto Inaig, Toshiyuki Kang, Hirokazu Kawagishia,b,e (aGraduate school of Integrated Science and Technology, Shizuoka University, bRIGST, Shizuoka University, cFaculty of Agriculture, Shizuoka University, dFaculty of Science, Shizuoka University, eGraduate School of Science and Technology, Shizuoka University, f. Institute of Inovative Science and Technology, Tokai University, g. School of Pharmaceutical Science, University of Shizuoka). “Fairy rings” is the phenomenon in which turfgrass grows or dies in a circle. In previous reports, we discovered that fairy rings were induced by 2-azahypoxanthine (AHX) and imidazole-4-carboxamide (ICA) produced by one of the fairy rings forming fungi, Lepista sordida. AHX is metabolized to 2-aza-8-oxohypoxanthine (AOH) in plants. AHX, ICA and AOH are named fairy chemicals (FCs). Furthermore, we proved the existence of endogenous FCs and succeed in isolation and structural determination of some metabolites of FCs. Thus, we thought that the pathway producing them in plants was a novel purine pathway. However, the biosynthetic pathway of FCs in plants has not been disclosed completely. The precursor of FCs in chemically synthesis is 5-aminoimidazole-4-carboxamide (AICA) and we have found AHX is biosynthesized from AICA in plants. In feeding experiments with stable isotope-labeled AICA, it was revealed that ICA was also biosynthesized from AICA in plants. Furthermore, we developed a new detection and quantification method of FCs and succeed in quantification the endogenous content of that. In addition, by using this method, we found that FCs metabolites (two kinds of AOH--D-glucosides, ICA-riboside, and ICA-ribotide) endogenously exist in rice. AHX-ribotide, presumptive precursor of AHX, is chemically synthesized from AICA-ribotide and NO donor (NOC5). We found that AHX-ribotide was converted from AHX by hypoxanthine-guanine phosphoribosyltransferase obtained from rice, and a novel compound, AOH-ribotide, was also converted from AOH by the enzyme.. .
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