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Orixa Japonica Agric. Biol. Chem., 54 (5), 1265-1270, 1990 1265 Oviposition Deterrent of a Rutaceae-feeding Swallowtail Butterfly, Papilio xuthus, from a Non-host Rutaceous Plant, Orixa japonica Ritsuo ,Nishida, Takao Ohsugi,1 Hiroshi Fukami and Shuhei Nakajima* Pesticide Research Institute, Faculty of Agriculture, Kyoto University, Kyoto 606 Japan * Department of Agricultural Science, OkayamaUniversity, Tsushima, Okayama 700, Japan Received December 4, 1989 Females of the Rutaceae-feeding swallowtail butterfly, Papilio xuthus, do not oviposit on the rutaceous plant, Orixa japonica. A methanolic extract of O. japonica leaves was found to contain contact-chemical factors which deterred oviposition of the butterfly. Oneof the oviposition deterrent factors was isolated from a butanol soluble fraction, and determined to be quercetin 3-0-(2g-/?-d- xylopyranosylrutinoside). A large number of swallowtail butterfly mixing it with an extract of 0. japonica. We species feed exclusively on members of the describe here the isolation and identification plant family, Rutaceae, and the females lay of an oviposition deterrent contained in the eggs with great precision on their host plant leaves of O. japonica. leaves, detecting specific chemicals through their tarsal chemoreceptors.1'2) Papilio xuthus Results is one of the Rutaceae-feeding swallowtails, and the females have been stimulated to ovi- Gravid females of P. xuthus could be stimu- posit by contact with a piece of filter paper lated to lay eggs on a piece of filter paper treated with a methanolic extract of rutaceous treated with a methanolic extract of Citrus plants such as Citrus unshiu, C. natsudaidai, unshiu at a dose of0.03g ofleafequivalent per Poncirus trifoliata, Zanthoxylum piperitum.1 ^ filter paper (g.l.e./f.p.).3'4) The females, how- The oviposition stimulants of P. xuthus have ever, did not respond to a filter paper treated been isolated from the leaves of C. unshiu, and with a methanolic extract of Orixa japonica characterized as a mixture of 10 components, (0.1 g.l.e./f.p.). Moreover, a mixture of the including flavonoid glycosides, tryptamines Citrus extract (0.03 g.l.e./f.p.) and the Orixa and other polar substances.3~6) extract (0.1 g.l.e./f.p.) was strongly rejected by Although P. xuthus feeds on various kinds the females, which clearly indicated the pres- of rutaceous plants, the females do not ovi- ence of an oviposition deterrent(s) in the posit on the rutaceous plant, Orixa japonica. leaves of O. japonica. This suggested that leaves of O. japonica con- A methanolic extract of O. japonica was tained an oviposition deterrent(s), because the fractionated into ether, ethyl acetate, butanol oviposition stimulant activity of a methanolic and water layers by solvent extraction. The extract of C. unshiu was markedly decreased by oviposition deterrent activity was monitor- f Present address: Department of Chemistry, WakayamaMedical College, 651 Hironishi, Wakayama649-63, Japan. 1266 R. Nishida et al. Table I. 13C-NMRAssignments of Compound Y, Rutin and Methyl /?-d-Xylopyranoside in d6 -DlMETHYLSULFOXIDE ~.. Compound _ . Me C-Position ^ Rutin , . , Y xyloside Quercetin 2 1 56.29a 1 56.51a 3 132.94 133.27 Fig. 1. Separation Procedure and Oviposition Deterrent 4 177.25 177.31 Activity of Orixajaponica Fractions against Papilio xuthus 5 161.20 161.17 Females. 6 98.21 98.97 dose, 0.1 g.l.e. of Orixa fraction+0.03 g.l.e. of Citrus 7 163.77 163.98 extract. 8 93.39 93.51 9 155.75a 156.35a 10 103.91 103.91 ed by applying each fraction (0.1 g.l.e./f.p.) T 121.24b 121.13b 2' 115.17 115.17 together with a standard methanolic extract 3' 144.65 144.65 of C. unshiu (0.03 g.l.e./f.p.) by the filter pa- 4' 148.22 148.33 per bioassay described in the experimental 5' 116.04 116.20 section. The deterrent activity was split be- 6' 121.78b 121.51b tween the butanol and water layers (Fig. 1). Glucosyl 1 98.49 101. 14 The butanol layer was separated into three 2 81.48 74.00 fractions by a C18-reverse phase column as 3 76.60c 76.38c 4 70.48d 70.53d shownin Fig. 1, and the activity was recover- 5 75.79c 75.84c ed from fraction B. Fraction B was rechro- 6 66.42 66.91 matographed on the same C18-column, elut- Rhamnosyl 1 1 00.44 1 00.66 ing with a mixture of methanol, water and 2 70.2Id 70.32d acetic acid by gradually increasing the con- 3 69.56d 69.94d centration of methanol. The deterrent activity 4 71.78 71.78 was found mainly in the 35% methanol eluate, 5 68.15 68.15 although several other fractions also exhibit- 6 17.55 17.66 ed the activity to some extent. A deterrent Xylosyl 1 104.23 104.56 compoundY, tentatively named here, was iso- 2 73.62 73.08 lated from 35%eluate by means of high-per- 3 75.77c 76.39 formance liquid chromatography (HPLC) as 4 69.29 69.45 described in the experimental section. 5 65.39 65.50 The molecular weight of compoundY was S-Values with letters in the same column are inter- determined to be 742, since a prominent peak changable. was observed at mjz 743 (M++H) in its secondary ion mass spectrum. Uponmild hy- drolysis, compound Y produced rutin and coincided very well with those of methyl /?-d- xylose. UV spectra of compound Y under xylopyranoside. Since the 2G-carbon signal various condition exhibited very similar absorp- ofY was found atd 81.48, while that ofrutin tion maximato those of rutin (see Experimen- was observed at S 74.00, the xylose moiety tal section), suggesting Y to be a quercetin 3- was suggested to be attached at carbon 2 of <9-glycoside. Table I lists the 13C-NMR as- the glucose. signments of Yin comparison with those of In order to determine the xylosyl linkage, rutin and methyl jS-D-xylopyranoside. Five ex- compoundYwas converted to its peracetyl cess signals arising from the pentosyl moiety derivative, and the acylation shifts were exam- were revealed in the spectrum of Y, which ined in its ^-NMRspectrum compared with Oviposition Deterrent of Papilio xuthus 1267 Table II. ^-NMRSpectral Data of CompoundY Dodecaacetate and Rutin Decaacetate (Chemical Shifts, Multiplicities and J-Values in Hz) CompoundYdodecaacetate Rutin decaacetate Moiety Coupling (/) Coupling (/) Quercetin 7.26 d (2.5) 7.28 d (2.5) 6.80 d (2.5) 6.81 d (2.5) 7.81 d (2.0) 7.88 d (2.0). 7.33 d (8.7) 7.31 d (8.6) 7.90 dd (8.7, 2.0) 7.93 dd (8.6, 2.0) Glucosyl 5.87 d (7.8) 5.40 d (7.8) 3.86 dd (7.8, 9.6) 5.15 dd (7.8, 9.8) 5.25 t (-9.5) 5.25 t (-9.5) 5.00 t (-9.5) 4.92 t (-9.5) 3.61 ddd (9.5, 4.0, 3.0) 3.54 ddd (9.5, 5.6, 3.1) 3.30 dd (ll.0, 4.0) 3.24 dd (ll,0, 5.6) 3.66 dd (ll.0, 3.0) 3.49 dd (ll.0, 3.1) 1 Rhamnosyl 4.52 d (1.5) 4.49 bs 2 5.08 dd (3.4, 1.5) 5.06 bd (-3.4) 3 5.05 dd (10.0, 3.4) 5.05 dd (9.0, 3.4) 4 4.88 t (10.0) 4.92 t (-9.5) 5 3.60 dq (10.0, 6.3) 3.62 dq (9.5, 6.3) 6 0.89 d (6.3) 1.03 d (6.3) 1 4.79 d (5.5) 2 4.81 dd (7.0, 5.5) 3 5.10 t (7.0) 4 4.86 ddd (7.0, 6.0, 4.0) 5a 3.22 dd (13.0, 6.0) 5b 4.ll dd (13.0, 4.0) 2.40 2.41 2.32 2.32 2.31 2.31 2.28 2.27 2.08 2.12 2.04 2.06 2.03 2.00 2.02 2.00 2.01 1.93 2.00 1.91 1.90 1.82 that of peracetyl rutin. The assignments (Table proton signals between Y dodecaacetate (3 II) were given with the help of two- 3.86) and rutin decaacetate (3 5.15), which dimensional NMRanalyses (H-H COSYand clearly verified the xylosyl moiety to be at- C-HCOSYspectra). Most of the signals of tached to the 2-position of the glucose. The compoundY dodecaacetate gave values con- glucosyl anomeric proton of Y dodecaacetate sistent with the corresponding signals of rutin also showed a down field shift (zl<5 =0.47 ppm). decaacetate. Only one extreme difference The coupling constant of the xylosyl ano- (AS=1.29ppm) was observed with the 2G- meric proton of Y dodecaacetate (7=5.5 Hz) 1268 R. Nishida et al. Table III. Oviposition Deterrent Activity of an Orixa Extract and CompoundY Di scussion Sample (dose/filter paper) Inhibition The oviposition deterrent of Papilio xuthus contained in the leaves of Orixa japonica was Citrus extract 0% foundto be composedofa complexmixture of Citrus extract+ Orixa extract (0. 1 g.l.e.) 100% Citrus extract+compound Y (300 fig) 85% several compounds, in which a flavonoid tri- Citrus extract + rutin (300 fig) 10% glycoside Y was verified here as one of the major components. It is of great interest that a Citrus extract dose: 0.03 g.l.e., vV=20. flavonoid glycoside plays such a deterrent role, because some of the flavonoid glycosides have been characterized instead as positive ovipo- sition stimulants for Papilio xuthus 4) and two other closely related papilionid butterflies, P.
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