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Flavanonol Glucoside and Proanthocyanidins: Oviposition Stimulants for the Cerambycid Beetle, Monochamus Alteynatus

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Flavanonol Glucoside and Proanthocyanidins: Oviposition Stimulants for the Cerambycid Beetle, Monochamus Alteynatus J. Pesticide Sci. 24, 123-129 (1999) Original Article Flavanonol Glucoside and Proanthocyanidins: Oviposition Stimulants for the Cerambycid Beetle, Monochamus alteYnatus Masashi SATO, Syed Q. ISLAM, Shinobu AWATA and Toru YAMASAKI Department of Biochemistry and Food Science, Kagawa University, Miki-cho, Kagawa 761-0795, Japan (Received May 8, 1998; Accepted October 14, 1998) An oviposition stimulant for the cerambycid beetle, Monochamus alternatus, from an aqueous acetone extract of inner bark of Pinus densiflora, was identified as a flavanonol glucoside, (-)-2, 3-trans- dihydroquercetin-3'-O-a-D-glucopyranoside. Two dimeric proanthocyanidins, along with polymeric proanthocyanidins, were also isolated from the extract and identified as procyanidins B-1[epicatechin-(4 a->8')-catechin] and B-3 [catechin-(4a->8')-catechin]. In the presence of a fraction of the extract, a mixture of the polymers and either B-1 or B-3 stimulated oviposition of the female beetle. However, the glucoside, B-l, B-3 and the polymers were inactive alone. Key words: Monochamus alternatus, Pinus densiflora, oviposition stimulants, (-)-2, 3-trans-dihydro- quercetin-3'-O-a-D-glucopyranoside,procyanidins B-1 and B-3, polymeric proanthocyanidins. Methanol and water extracts of pine inner bark stimulat- INTRODUCTION ed oviposition of the female beetle in the presence of free Young adults less than ca. 14 days old of the ceram- moisture. 8) Recently, a flavan-3-ol, (+)-catechin, was bycid beetle, Monochamus alternatus, are attracted by isolated from a 70% aqueous acetone extract of the inner a-pinene. 1) The pathogenic pine wood nematode, Bur- bark of P. densiflora and characterized as an oviposition saphelenchus xylophilus, transfers from a young adult stimulant for the female beetle. 9) The present communi- (vector) to healthy pines through the feeding wound. 2,3) cation deals with a flavanonol glucoside and dimeric and The combination of the beetle and the nematode causes a polymeric proanthocyanidins, present in the inner bark high mortality rate of pines. Paraquat-induced light- of P. densiflora, as oviposition stimulants for the female wood is highly attractive to mature adults of the beetle. 1,4) beetle. The attractive principle of lightwood was identified as a synergistic mixture of the sesquiterpene alcohol ( + )- MATERIALS AND METHODS juniperol and the diterpene aldehyde (+)-pimaral. 5) 1. Instruments The monoterpene alcohol (+)-cis-3-pinen-2-ol, charac- UV spectra were measured with a Hitachi U-2000 teristic of lightwood, enhances male attraction by the spectrophotometer. Negative FAB-MS spectra were mixture. 6) Healthy pines are unattractive to the mature taken with a JEOL JMS-SX 102 mass spectrometer. adults. However, the mature adult-specific1 attractants, Compounds were separately dissolved into droplets of i.e., (+)-j uniperol and (+)-pimaral were also isolated glycerine (FAB liquid matrix) and bombarded with 6.0 from them. 5) Recently, a key compound, the sesquiter- keY atoms. The resulting secondary ions were accelerat- pene hydrocarbon (-)-germacrene D, was isolated from ed to 10.0 keY, and negative ions were recorded. 1H healthy Pinus densiflora and identified as a masking and 13CNMR spectra were recorded at 400 MHz and 100 substance, i.e., an agent inhibiting (suspending) MHz, respectively, on a JEOL JNM-A 400 spectrometer. locomotory movements towards the attractant source. 7) Spectra of 13C-1H/1H-1H COSYs and HMBC were also After landing on a Paraquat-treated pine - the light- taken with the spectrometer. All NMR measurements wood of which being devoid of the masking substance7) were performed at 30°C with TMS as an internal stan- or a nematode-infected pine, a mature adult of the female dard. Optical rotations were measured with a JASCO beetle moves to a favorable site for oviposition, cuts a J-20 polarimeter. characteristic slit in the outer bark, inserts her ovipositor into the inner bark through the slit and lays eggs. 124 日本 農 薬 学 会 誌 第24巻 第2号 平 成11年5月 2. Isolation of Compounds 1-3 and Polymeric (1. 5 X 28 cm) chromatography over Sephadex LH-20 Proanthocyanidins (Fig. 1). Ether solubles were removed from the 70% aqueous Fraction III (3.00g) was applied to a column (2. 5 X 70 acetone extract of off-white inner bark meal9) of P. cm) of Sephadex LH-20 and eluted using ethanol with a densiflora, and the resultant extract was divided into flow rate of 18 ml/h (Fig. 1). Eluates (20 ml each) were ethanol solubles and ethanol insolubles according to the collected. Materials (330 mg) were eluted with 1 range preceding paper. 9) Sephadex LH-20 (25-100, um, Phar- of eluate nos. 57-73. Most (250 mg) of them were re- macia Biotech) column (2. 5 X 70 cm) chromatography of chromatographed over Sephadex LH-20 (2. 5 X 70 cm) by ethanol solubles afforded fractions I and IL9) Adsorbed subsequent elutions with aqueous methanol[50% (600 materials of the ethanol solubles were recovered by elu- ml)-> 60% (1000 ml)] with a flow rate of 60 ml/h. Ten- tion with 70% aqueous acetone as fraction III (Fig. 1). ml eluates were collected. Eluate nos. 115-135 and 140- Compound 1 and (+)-catechin were separated from 151 gave 2 (79 mg) and 3 (40 mg), respectively. These fraction IL9) These compounds were purified by a com- compounds were purified with Zorbax ODS and Se- bination of preparative HPLC over Zorbax ODS (5, um, phadex LH-20. Adsorbed materials of fraction III were 9.4 X 250 mm, Rockland Technologies) and column purified according to the procedure of Porter et al. 10,11) Fig. 1 Isolation scheme of compounds 1-3 and polymeric proanthocyanidins. The yields based on an oven-dried inner bark are shown in parentheses. Journal of Pesticide Science 24 (2) May 1999 125 and recovered as polymeric proanthocyanidins (1.64g) were prepared by applying aqueous methanol solution by elution with 70% aqueous acetone. (s) to each 3 X 3-cm piece of filter paper (No. 526, Advantec Toyo). The dose (D mg) of a sample per 3. Enzymatic Hydrolysis of Compound 1 piece was determined according to its yield (s% shown in The hydrolysis of 1(100 mg) was achieved in water (16 Fig. 1) based on an oven-dry weight of inner bark: D = ml) with a-glucosidase (34 mg) (containing ca. 50% Fs/(100- s), where F was a mean oven-dry weight (278 bovine serum albumin and a small amount of glutathione mg) of a piece of filter paper. Moisture contents of the as stabilizers, from sweet almonds, Funakoshi) at 28°C test substrates were kept at a level between 25% and 35% for 8. 5 h. The reaction mixture (white suspension) was on a wet basis. Results were given as follows: Oviposi- applied to a Sephadex LH-20 column (2.0 X 28 cm) and tion response (%) =100 X no. which oviposited/no. sub- eluted using water (950 ml) and then 50% aqueous mitted. Comparisons of the results were conducted with methanol (600 ml) with a flow rate of 55 ml/h. Ten-ml a one-way ANOVA followed by a Turkey-Kramer eluates were collected. A sugar was obtained from multiple comparison test. eluate nos. 6-8 and purified by ascending development on a paper (No. 514A, Advantec Toyo) with the organic RESULTS layer of a mixture of ethyl acetate/pyridine/water (2:1: 1. Identification of Compounds 1-3 2). Yield: 32 mg. Eluate nos. 130-142 provided an 1.1 Compound 1 aglycone la (57 mg). This compound was isolated in the form of a white amorphous solid. It was positive to the methanolic 4. Bioassay ferric chloride and the phenol/sulfuric acid tests. Approximately 120 female adults of M alternatus, Acetylation of 1 gave eight methyl (-OCOCH3) singlets being attracted to paraquat-treated pines, were collected in the 1H NMR spectrum, suggesting eight free hydroxyl in mid-July, 1996-1997, held in individual containers4) groups in the molecule. A deprotonated molecular ion and submitted to assays during the following three ([M-H] -) was observed at m/z 465 in the negative weeks. FAB-MS spectrum of 1. The UV spectrum of 1 hinted The bioassay procedure was virtually identical with at a certain flavanonol, 12 i. e., AMeOHmax nm (log 6): 290 that9) described previously. Individual test substrates (band II, 4. 27), 326 (band I, sh, 3. 84). The enzymatic Table 1 'H and 13C NMR data of compounds 1 and la. a) Measured in methanol-d 4. 126 日本農薬学会誌 第24巻 第2号 平成11年5月 1 R: f-D-glucopyranosyl 1a R: H 2 3 hydrolysis of 1 yielded a sugar and an aglycone la. The singlets in the 1H NMR spectrum, suggesting ten free free sugar was confirmed to be D-glucoseon the basis of hydroxyl groups in the molecule. Both 1H and 13C twelve singlets including singlets at 93.0 ppm due to NMR spectra (Table 2) indicated that 2 consisted of a 2, a-anomer and at 96.8 ppm due to j3-anomerin the 13C 3-cis and 3,4-trans epicatechinunit (the upper unit) and NMR (D20) spectrum. The UV spectrum of la was a 2,3-trans catechin unit (the lower unit), and that both similar to that of 1, i. e, AMeOHmax nm (loge): 289 (bandunits II, were bonded together by a 4,8'-linkage. The addi- 4.30), 328 (band I, sh, 3.84). The 13CNMR spectra of tional NMR spectra (1H-1H/13C-1HCOSYs and DEPT) la (Table 1) coincided with the previous 13C NMR were also used to elucidate the structure. The previous data13)of (+)-2, 3-trans-dihydroquercetin. The [a]24Dof 'H'7"8 and 13018)NMR data of procyanidin B-1 support- la was+20.0 (MeOH, c=0.85) {[a]? = + 19.4 (MeOH, ed the structure elucidation of 2.
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