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zatwt LepidopteraScienc6e6(1)1:5-18,May2015
Diffi}ren icne the odors emitted by male adults of two subspecies of the swallowtail butterfl lylyasa
(Papilionidae)
aloinous
Takao IToH i) and Hisash i6MuRA 2)
i) Graduat Sechoo lof Integra tAerdt sand Science Hsi,roshim Uaniversi Htiyg,ashi-Hirosh i7m3a9,-852 1Japan
2) Department of Biofunctiona lScienc eand Technolog yG,raduat eSchoo lof Biospher eScience H,iroshima
University,Higashi-Hiroshima,739-8S28Japan
Abstract Male adults of the two subspecies, Byasa alcinous alcinous and B, a, loochooan aex,hibit strong musk-
lik eodors which are slightly differe nftrom each ether in the odor profil peerceivabl bey the human nose. Using wild-
caught males, the chemical compositions of these edors were investiga btye dmeans of gas chromatography-mass
spectrometry. Among 1 1 compounds identif iferdom the male odors, seven sesquiterpenes were approximately 3 to
1O times more abundant in B. a. alcinous than in B. a. toochooana ,while 6-methyl-5-hepten-2-o anned linaloo wlere
detect eodnly from B, a, loochooan aT,hese qualitat ianvde quantitat diivfeferenc eisn particul acromponents are
considered to be responsible fo rthe slight differe nicn emale odors betwee nthe two subspecies.
Key wordsByasa atcinous, GC-MS analyses, male odor, Papilionidae.
Introduction inhabitsMiyakoisland bradanus
miyakoensis and
Ibontu ittst hnee orowdfo irewmi eioeltfls c ahk apnriaoecwtrneir id bsttuhitcat t oedaho rarn sfvu(,mel bMbyeSretieinn c1i o ed1ft1eh 8enme 7atrfl8iei,)f rai ,sr aeewdtdpiuodflrettatr idiKisyn nfuhofstaehb rusie itnSgi nscsabielkefatiincwsda ehn.e Ditin um nsri uatibsshnlpeg ea vctiniched iseans li c,ttaohyluoc ruiognsfhoe u ts ohtf eh a esin donmuvo tyrehpashekotrlunios ggphiaacitarmlit a ooonnffa
vianr itethye m aolfe vo loatdthiolreesi rc(omBpooupndpsr 16 9,84) , Male adults of ssoo me chhaevmiec raelal izceodmp otnhenat tsmale o fad uoldtosrs of o fth Be ysaubssap ebcuietste arlfcilnio euwses,
rsAapnencgdieeesr osl sufosaenc tory cu e2ssp0e c0fi7fOi;cr Nmai teviobnlgaetir lde(ie n,cgom gpHo.ounn,dsda20 e0t8 a)als,, , Gs2he0onr0ut6-s; aontdhe r,l oTohceh ohuomaan nas mneolsle sios miewn hgatener da ilrfatfheerre snetn lstiytoi veeac hto
Bpyoasssa eis s cshoan reeat c otafle,r ,it shtei cf aomd oorus,s gIrno au fp b siertn e waghl,oi,ci hn g pmaalpe e r ai,dt uwlatss tihnet esr]iegsh ttt oc hiannvgees toifg asm tetelhles ,c heImit cmaulst cboemp, ostihteiroenfor ea, nodf
shown that wild-caught males of Byasa (Atrophaneurroedaloar)tsiv eof atmohuen ttswo soufbs ptehcei esche moifca Blya scoam paolnciennot"ss. oIfn tthhee
alcinous alcinous emlitin aal sotor6ol-n,gme otdhoryl -co5n-sihsteipngte no-f2-onper,esen sttudy, wild-caught males of B, a, atcinous and B.
papinhrndeennde byor melmaairngcnzieanlstndat e cloohfdmy eptohdhn yeeea nd hntedi,n dt whoifan gt ms palhe (enH yoodlonra,cde a1It,9oa8cl0ad)le.ihzy edaset , tthhee atg.ha esI vcooholracotmhialoteoo gacronampa phwoyen-remenatss ssub joefc ttsephdee c etxtrtoor masecottlrsvye nwe tr(e Gex Cetxr-aamcMitnSieo)dn. a nbdy
Up to the presen tf,iv esubspecies of Byasa alcinous have Material asnd methods
beendescribeidnJapan,There Byasa
aUtmceinn oou,s 1(92K9l)u ,B g.1 ,a 8. 3I6o) o,Bc. hao. oyaan ka(u as,Rrheoi tmahnsac (h Eai1l8slc9iadn6 o,k)ua s,niBd. Mcaaptluere dadu latts O(okfNi Bnya3aw)saa I asllcainndo uisn Alproiolc 2h0o1o4a nan ad(N tf=hr oo4sem) woefr Be.
a(H.o Fnmrisyauhkohuen,ssiSsth oi1k9r0o f8k()eu.O rmS,uobtKsopy e,u1cs9i6he0 usa)li,c siannloduas nB di. sna,h,a bbirt amsdaiannl"ys acH.a ipatglucarinesoduhs ic-o cHoio nr=s os o hwcreiir telmy aai rcn avJpat uuaelrt e yadHnid ro roS soebhptiatmienae mUdbn ei 2vr0e1r4s wi(itlT dyi-hne
inhabit sYakushi manad Ta negash iymaakuisshlimaanndas, 2-nd generatio fnor B, a, loochooan aan,d 2-nd and 3-rd
loochooa na inhabit s Oakndin awa to Amami islands, gcoellneectreadt biuo tfntoser rBf, iai .c eoasutlcdin onuost) ,b e Adlettheorumgihn te hdpe raegcesis eofly,
Authors'E-mail:[email protected],[email protected]
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16 T. IToH and H. 6MuRA
both of B. a, loochooan aand B. a, alcinous seemed tQ be cedar Cedrus attantica (Pranar6m International,
relatively fresh .Judging from the degree of freshness, Belgium). Quantitat ievsteimates of individual
we estimated that the male adults of B. a. Ioochooana, compounds were carried out through comparison of the
were aged 2 to 4 days after ec]osion. For thi sreason, we peak intens iwtityh tha tof authentic standard of linalool
used laboratory-re amraleed adults 2 to 4 days after obtained from [Ibky oChemica lIndustry.
eclosion fbr subspecies B. a, alcinous, Butterfli weesre
individua lflryoze nto death at -20 OC and the whole Result sand discussion
bodies of adults were soaked in 3 mL of purified [[btiaoln fromthe
ids1uni0 b cvsOaehCc,qluuooe nrt Tolahymnede t ftchohianelcnnete nett rro f aeta1oden0rdd, 0 3cp o Lnmeci xenutn,nrtdarec arttseT d ah ween rit etoer xIo tgeireasnmc smtt sehstadrni e aaw1met rme eLlaty aie.xn tIFraioc gtos, c 1wh ,a coshTro ohaimea ndta aeonmgdanrj atoBmris. c facab.o lm r aobplbocotniaetnino hntusesudbs mpcaeolcneiteas i and e(udl petxs iet ran aa r1ctekt 1hss) e h ooo.fTdwBonh.re
msausbsjec tsepdec ttroo mGeCt-erMS c oaGunpaClle-ydsMeSs w iustihng a aS Shhiimmaaddzz u GuQCP-51070A0 macao jrrornreoslp eoccnoudmlipanorgnent tio o ans hcooownbessdpeircv ueaodu swea k aft rp aemglamzke c no t2rir6oe2sn p aotan ndmdilnzg t2h 0att2o
gas chromJa&toWgrapSh.cie ntifiDcB- 1anafluysseesd -wesriel piecraformed in the EI mass spectrum, The differen coef 60 mass units
cu42hctwosoi03ehlimt 0lounpheCmgais nr Oue Ci ,aa(omn n gf a2 s(miAa tiualO thnjlt. h eehi sec2ceasnam mtrmto5rpTl oietlaiDtcretehes nsre2tt ir g5oa nm×a0nw adseOa1 Cl. r , ar5e)Ctn d ,diomos m,vm s(eerp pnasTOloi i s.ubttainnl2enkdegdm5 syp s psreClom maarywhts aese eftr ioeumifn rli sjeim1p c eedtp0 ca cthercOrClti/Ianaomipcnentg ikddilrunu lfsaewsaiiismtr tn ysebhrogt)yfdyo,, dactsswohuuideregbtdrtgshe isepeptp serotritcnmsihodeeeeinsds ntetmeoo nh lodcat ef hetcf t uetBrhol of,eaop rtm arplah rencet ie s fhfndoeeaorco" nearsmltgc ymiol omenucifeaa l s n antagaot n tifrdio od ooiao Cnucnrao eipfotg f7.y snlu HtaCboTh2ts2eseht6Hd ait 0n4tsi i cw0 2esoocoT2e.nbs , s h qaepoiruetfv ie na tmattdaelviiohrzeknprce se ata ng6,ewtei0oin,ng
Jesaspenatn i)a la nodil ss eosfq uyilt aernpge-nyelan hg yCdarnoacnagr ab oodnors aptares e anntd i An ttlhaes aa7lm7coi1u nnotnugs. off o rC TBih,e7 H a2c, o6mtp0o2 ounpodecr hooneo c aomnra rlaeaesnpd own ad3si7n g4e3s tni gmtao t fepdoer atBko, b1a.e0
eeA*vb'm=Do-=t-co=sRsc
s 10 15
e
5 le IS
Retentiontime(min>
Fig ,1 ,Ibta lion chromatograms of dichlorometh aexntreact of Byas aalcinous loochooan aand B. a. alcinous wild
males. The par tof chrematogram of B, a toochooan (aupp etrrace) embedded as a dotted-I isqnuaere part is
enlarged by 10 times .Eleve ncompounds were identif iase 6d-methyl-5-hepten- (21-o) nn,oenanal (2) l,inalool
(3) d,ecanal (4) a,-copaene (5) a,-himachalene (6 )y,-himachalene (7) f, i-himachale n(e8 )i, -cadine n(e9),
sesquiterpene alcohol CisHMO (10 )an,d acetylated sesquiterpene Ci7H2602 (11).
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Odors of two subspecies of Byasa alcinous 17
Ilabl e1 ,Chemica lcomposition of scent substances in the extract of Byasa alcinous loochooana and B. a. alcinous wild male.
No, Compounds IM](min)Amount 1 Individua [lng m,ean ± SD]
B. a. Ioochooan (aN = 4) B, a. alcinous (N = 3)Identificationa
12345667-8M9e10t1h1yl-5-hepten-2-one 4.66.66,6862610,6711112,5712.012,312,41ND4,,b46155.7 StdStdStdStdStdStdStdStdStd
±
NonanalLinaloolDecanala ± 180 ± 18ND,9
134 7210
±
63 233
± ±
-Copaene 75 5754
± ±
722 9295
a-Himachalene ± ±
y -Himachalene ±1123 ±4060
3-Himachalene 104 10447
± ±
6-Cadinene 8132 82411
± ±
sesquiterpenealcoholCisH240 ± 101 ± 124
acetylatedsesquiterpeneCi7H2602 771 ± 709 3743 ± 3686
a Std, identificat biaosned on authentic standards.
bNotdetected.
showed a mass fragmentati osnimilar to that of Ci7H2602 the male scent of B. a, atcinous has been described
whose molecular ion was cletect eatd mlz 220. It follows previousl y(Honda 1,980) ,these compounds were not
from these observations that this compound is a detecte din the extracts of the same species, The reason
sesquiterpene alcohol with the molecular formula of for thi sdiscrepanc yis unclear, but it may be due to the
CLsH240 ,the deacetylated alcohol of Ci7H2602. differenti ahlost-plan tusage of wild-caught males.
Moreover, chemical components corresponding to peaks Interesting lpyh,enylacetaldehyd eand benzaldehyde,
1, 2, 3, 4, 5, 6, 7, 8, and 9 were identifi etod be 6-methyl- previousl ryeported as the predominan tand minor
5-hepten-2-on en,onanal, linalo odle,cana la ,-copaene, yolatiles of B, a, alcinous (Honda 1,980), were not
a -, y -, and 6 -himachalene asn,d i -cadinen ere,spectively detecte din the presen tstudy. Since these cornpounds
([[hb l1)e. Although the seven sesquiterpene compounds were not detecte din the odor of laboratory-rea rBe. da.
includi nCgi7H260 a2nd CisH24 0were common for the alcinous males that were fed on the fres hleave sof A,
extracts of the 2 subspecies, the amount of each d ebri sandA, liukiuens iwisthin 10 days after eclosion
compound contained in the extract of B. a. alcinous is A(Omura et al,, 2015) ,i tis most likel ytha tthe aromatic
approximately 3 to 10 times larger than in B, a. aldehydes reported in the previo usstudy are exogenous
Ioochooana in unit of yg per one male. Intra-subspecificsubstances (e. gor.i,ginated from thei rnectaring flowers)
differen icne each component was also ]arge .Further, or are biosynthesize dby males from 10 days after
both subspecies shared two aliphatic aldehydes, nonanal eclosion, It is recognized from Table 1 that there are
and decana lw,hich were firs tidentifie idn the male slight diffbrenc eisn the chemical compositions of male
scents of B, alcino"s, These results suggest that the adult odor of the two subspecies, which presumably
fiuctuat iion nthe amounts of aliphatic aldehydes and results in the slight differen coef the smells of the male
sesquiterpene components is relatively small for the male adults of the two subspecies alcinous and loochooana,
odors of the two subspecies of B. alcinous, On the other Sinc ea par tof the presen sttudy was carried out using
hand, 6-methyl-5-hepten-2-one and linaloo lwere wild-caught individual ss,eveTal components such as
detecte donly in the male extracts of B. a. Ioochooana, 6-methyl-5-hepten-2- oannde linalo oslhowed relatively
In the male odor of B, a, atcinous, the presen coef these large inter-subspec iafndic intra-subspec ivfariications in
terpenoid derivativ emasy be variable depending on the these male odors. More detaile adnd systematic studies
differen cien thei rfood plant s.The Aristoloch ipalants may be needed for the male adult odors of the two
are known to show considerable species-specificity in the subspecies using laboratory-rea rienddividua lfsed with
chemical composition of volatile compounds (Franciscodesignate fdood plants,
et al., 2008) .Larvae of B. a. toochooan amostly feed on
Aristoloch itaiukiuen s(iAsristolochi aatc Oekainea)wa References
Ictthseelb iaplnridse o,swrhe inAlcer eio sftt h6oo-slemo ceohft i hkBaya. elam-. n5af-lechrin eioipuns tHeo nuns-s eah2 nuA-d.ro ilnAsieltntoahlolouoc giohhnila A n d eWmraitseksl ocuhnon i,Jdc e,,2 , 0Ai0.n 7-a. KbM. uaBtloteer rgsfe-l xKJ ya.p .Ehruel]rs.o oBm inoNo,n.te .V2 r1be0lne: gas9ve6a4 n-ain9d7c 0 ha,fnedm aCl.e
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18 T．ITDH and H． OMuRA
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Yakushima． Z勿ん）7yrus 1：92−95．（In Japanes）e English presenti dnegscripti oonf a new subspecies）．
Francis，c Co， S，， G． B．Messiano， L． M ， X， Lopes， A， G Tinini，s Omura ， H．， T Noguchi and T． Nehira，2015． New oxygenated
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Aristotochi aspecies based on GC −MS and chemometric butterf， iByyasa o♂【〕inous alcinous ． Nat・Prod・Rθ∫・（in P「ess）
analyses of essential oils． Phytoche〃listr y69：168−175， Rothschi， lvdon W．，1986． On some new species of馳卿 o，1＞bv．
Fruhstorf， veorn H，，1908， Lepidopterologis cPδhlee−sM δle．1． Zool．3：421・425．
Neue ostasjatische Rhopaloceren． Ent． Zeits． Stutt8ar t22：
4647 ． 摘 要
Honda ， K．，1980． Odor of a papilioni dbutterfl， yodoriferQus
substances emitted by Atrophaneura alcinous alcinous ジャコ・ウアゲハ 2亜種の♂成虫が発する芳香の違い （伊藤
（Lepidopte；rPaapi旦ionid）a． eJ． Chem． Ecol．6：867−873． 隆夫 大村 尚）
Honda， Y ， K． Honda and H． Omura，2006． Major components in ジャコ ウアゲハ の沖縄亜種と本州亜種の♂成虫の発する芳
the hairpenci lsecretion Qf a butte且ry， Euploea m ”1（：iber 香のわずかな差を解明するため、野外採集した♂成虫を用
（Lepidoptetr， aDanaidae）；thei rorigins and male behavioral い てGC ・MS 分析を行っ た。 2亜種の♂の芳香から同定した
r1e0s4p3o−n1se0s5 3t，o pyrrolizidi nae豆kaloid．s∫Insec Pthンsiol．52： 1り1成も分本の州亜う種ち、に7お種いのてセ3ス〜キ10テ倍ルもペ多ンく化、合6・物metはhyl沖−縄5−亜he種pteよn−
Klug， E，1836， Papili oAlcinous sp． nov ． ln Hopfer， C． H．（ed．）， 2−one とlinalooはl沖縄亜種にのみ検出された。特定成分に
Neue oder weniger bekannt Sechmetterli dnegr eInsenkt−en おける質的 ・量的な違いが、2亜種の芳香のわずかな違い
Sammlung des KOnigll p 1，pl．1−4． Zoologischen Musei の原因と考えられた この違いは2亜種の食餌植物やそれ
der Universit aztu Berlin． と関係する成長過程で。 の生合成経路の差などによる可能性
Mtille，r R，1878． XX ． Note on Brazilia nEntomolog．y Trans． がある
Royal Entomo．l∫oo．五〇ndon 26：211−223． 。
N i ebNe，rEdsit，n rCga．m Mil， ．， JH， ．A ndde eVr（）sss， oMn，． VJ．． SBchhnnge， iEde． ，r HJe．d−Men． sLtars6sma，n cCe，． （Receive Ndovember 28，2014． Accepte dMarch 26，2015）
一
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