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Effects of p-Vinylphenyl Glycosides and Other Related Compounds on the Oviposition Behavior of Ceratitis capitata

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Abstract

Elaphoside-A [p-vinylphenyl (β-d-glucopyranosyl)-(1→3)-β-d-allopyranoside], a Mediterranean fruit fly oviposition deterrent, was previously isolated from an Argentine collection of the fern Elaphoglossum piloselloides. In order to establish the structural requirements for the observed oviposition inhibition, we synthesized and characterized 4 known and 21 new aromatic glycosides structurally related to elaphoside-A. Their effects on the oviposition behavior of Ceratitis capitata females are discussed.

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Scheme 1
Fig. 1
Fig. 2.

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Notes

  1. Interchangeable signals.

  2. Duplicated signals due to the presence of the two C-1 epimers.

  3. See footnote 2.

  4. See footnote 1.

  5. See footnote 1.

  6. Known compound (Helferich and Höfmann, 1952; Ojika et al. 1984)

  7. See footnote 6.

  8. See footnote 2.

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Acknowledgments

We thank Ms. Y. Okamoto from Tokushima Bunri University for measuring the HR-MS spectra, Dr. M. Tanaka (TBU) for recording some of the NMR spectra, and Mr. J. Caram for drawing Fig. 2. C. Socolsky thanks Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) for a grant. Dr. N. D’Accorso is a research member of CONICET. This work was supported in part by a Grant-in-Aid for Scientific Research (B) N° 14403014 from the Ministry of Education, Science, Sports and Culture (Japan), CONICET, ANPCyT (project 06-13922), Universidad de Buenos Aires (UBA), and Consejo Nacional de Investigaciones de la Universidad Nacional de Tucumán (CIUNT), Argentina.

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Authors and Affiliations

  1. Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, Tucumán, 4000, Argentina

    Cecilia Socolsky & Alicia Bardon

  2. CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Tercer piso, Buenos Aires, 1428, Argentina

    Mirta L. Fascio & Norma B. D’Accorso

  3. Estación Experimental Agroindustrial Obispo Colombres, Av. William Cross 3150, Tucumán, 4101, Argentina

    Analia Salvatore & Eduardo Willink

  4. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan

    Yoshinori Asakawa

Authors
  1. Cecilia Socolsky
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  2. Mirta L. Fascio
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  3. Norma B. D’Accorso
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  4. Analia Salvatore
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  5. Yoshinori Asakawa
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  6. Alicia Bardon
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Correspondence to Alicia Bardon.

Appendix

Appendix

p-Ethylphenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Galactopyranoside (1)

High-resolution fast atom bombardment mass spectrum (HR-FAB-MS) m/z: 475.1599 [M + Na]+, calculated for C22H28O10Na: 475.1580; [α]D +251.8 (CHCl3, c 1.0 g/dl, 19.4°C); IR ν max [cm−1] (neat), 1,747, 1,608, 1,510, 1,371, 1,217, 1,070; 1H NMR (500 MHz, CDCl3), δ 6.98 (d, J = 8.8 Hz, H-2′, H-6′), 7.13 (d, J = 8.5 Hz, H-3′, H-5′), 2.60 (q, J = 7.5 Hz, H-1″), 1.21 (t, J = 7.5 Hz, H-2″), 5.73 (d, J = 3.6 Hz, H-1), 5.28 (dd, J = 10.9, 3.7 Hz, H-2), 5.58 (dd, J = 11.0, 3.4 Hz, H-3), 5.53 (dd, J = 3.4, 1.1 Hz, H-4), 4.37 (t, J = 6.6 Hz, H-5), 4.13 (dd, J = 11.2, 6.3 Hz, H-6a), 4.07 (dd, J = 11.2, 7.2 Hz, H-6b), 2.16, 2.07, 2.02, 1.94 (s, CH 3C=O); 13C NMR (125 MHz, CDCl3): δ 154.4 (C-1′), 116.8 (C-2′, C-6′), 128.9 (C-3′, C-5′), 139.0 (C-4′), 28.1 (C-1″), 15.8 (C-2″), 95.1 (C-1), 67.9 (C-2), 67.6 (C-3), 68.0 (C-4), 67.1 (C-5), 61.5 (C-6), 170.4, 170.3, 170.2, 170.0 (C=O), 20.74, 20.69, 20.64, 20.58 (CH3C=O).

p-Ethylphenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Glucopyranoside (2)

High-resolution chemical ionization mass spectrum (HR-CI-MS) m/z: 453.1775 [M + H]+, calculated for C22H29O10: 453.1761; 1H NMR (500 MHz, CDCl3): δ 7.00 (d, J = 8.6 Hz, H-2′, H-6′), 7.13 (d, J = 8.4 Hz, H-3′, H-5′), 2.60 (q, J = 7.6 Hz, H-1″), 1.21 (t, J = 7.6 Hz, H-2″), 5.70 (d, J = 3.8 Hz, H-1), 5.03 (dd, J = 10.2, 3.6 Hz, H-2), 5.70 (t, J = 9.8 Hz, H-3), 5.15 (t, J = 9.9 Hz, H-4), 4.14 (ddd, J = 10.3, 4.5, 2.2 Hz, H-5), 4.25 (dd, J = 12.3, 4.6 Hz, H-6a), 4.06 (dd, J = 12.3, 2.3 Hz, H-6b), 2.06, 2.05, 2.04, 2.04 (s, CH 3CO); 13C NMR (125 MHz, CDCl3): δ 154.1 (C-1′), 116.5 (C-2′, C-6′), 128.8 (C-3′, C-5′), 139.0 (C-4′), 28.0 (C-1″), 15.7 (C-2″), 94.3 (C-1), 70.4 (C-2), 70.1 (C-3), 68.3 (C-4), 67.8 (C-5), 61.6 (C-6), 170.5, 170.1, 169.6 (C=O), 20.66, 20.59, 20.57, 20.54 (CH3C=O).

p-Ethylphenyl α-d-Galactopyranoside (3)

High-resolution electron impact mass spectrum (HR-EI-MS) m/z: 284.1258 [M]+, calculated for C14H20O6: 284.1260; [α]D +222.5 (MeOH, c 1.0 g/dl, 20.3°C); IR ν max [cm−1] (neat), 3,366, 1,609, 1,511, 1,228, 1,080, 1,032; 1H NMR (500 MHz, MeOH-d4): δ 6.97 (d, J = 8.9 Hz, H-2′, H-6′), 7.11 (d, J = 8.9 Hz, H-3′, H-5′), 2.58 (q, J = 7.6 Hz, H-1″), 1.19 (t, J = 7.6 Hz, H-2″), 5.43 (d, J = 3.2 Hz, H-1), 3.96–3.91 (overlapping signals, H-2, H-3, H-5), 3.98 (dd, J = 2.8, 1.1 Hz, H-4), 3.71 (dd, J = 11.4, 5.7 Hz, H-6a), 3.67 (dd, J = 11.4, 6.6 Hz, H-6b); 13C NMR (50 MHz, MeOH-d4): δ 156.9 (C-1′), 118.4 (C-2′, C-6′), 129.6 (C-3′, C-5′), 139.5 (C-4′), 29.1 (C-1″), 16.4 (C-2″), 100.0 (C-1), 70.1 (C-2)Footnote 1, 71.4 (C-3)1, 70.8 (C-4), 73.0 (C-5), 62.5 (C-6).

p-Ethylphenyl α-d-Glucopyranoside (4)

HR-FAB-MS m/z: 307.1174 [M + Na]+, calculated for C14H20O6Na: 307.1158; 1H NMR (500 MHz, D2O): δ 6.98 (d, J = 8.7 Hz, H-2′, H-6′), 7.13 (d, J = 8.7 Hz, H-3′, H-5′), 2.47 (q, J = 7.5 Hz, H-1″), 1.04 (t, J = 7.5 Hz, H-2″), 5.46 (d, J = 3.6 Hz, H-1), 3.58 (dd, J = 9.8, 3.6 Hz, H-2), 3.78 (t, J = 9.4 Hz, H-3), 3.38 (t, J = 9.6 Hz, H-4), 3.65 (ddd, J = 9.7, 4.7, 2.5 Hz, H-5), 3.63–3.60 (overlapping signals, H-6a, H-6b); 13C NMR (125 MHz, D2O): δ 154.8 (C-1′), 118.2 (C-2′, C-6′), 129.9 (C-3′, C-5′), 140.5 (C-4′), 28.2 (C-1″), 16.0 (C-2″), 98.2 (C-1), 71.9 (C-2), 73.8 (C-3), 70.2 (C-4), 73.2 (C-5), 61.1 (C-6).

p-Ethylphenyl 2,3,6,2′,3′,4′,6′-Hepta-O-Acetyl-α-Lactoside (5)

HR-EI-MS m/z: 740.2523 [M]+, calculated for C34H44O18: 740.2527; [α]D +83.3 (CHCl3, c 1.0 g/dl, 20.1°C); IR ν max [cm−1] (neat), 1,747, 1,510, 1,369, 1,217, 1,047; 1H NMR (600 MHz, CDCl3): δ 7.00 (d, J = 8.5 Hz, H-2″, H-6″), 7.12 (d, J = 8.5 Hz, H-3″, H-5″), 2.60 (q, J = 7.6 Hz, H-1″′), 1.21 (t, J = 7.6 Hz, H-2″′), 5.60 (d, J = 3.6 Hz, H-1), 4.95 (dd, J = 10.3, 3.7 Hz, H-2), 5.69 (dd, J = 10.2, 9.6 Hz, H-3), 3.84 (t, J = 9.7 Hz, H-4), 4.05 (ddd, J = 10.1, 4.6, 1.9 Hz, H-5), 4.42 (dd, J = 12.0, 1.9 Hz, H-6a), 4.14 (dd, J = 12.1, 4.8 Hz, H-6b), 4.50 (d, J = 7.9 Hz, H-1′), 5.12 (dd, J = 10.3, 7.9 Hz, H-2′), 4.96 (dd, J = 10.4, 3.5 Hz, H-3′), 5.36 (dd, J = 3.6, 1.1 Hz, H-4′), 3.89 (td, J = 7.3, 1.1 Hz, H-5′), 4.16 (dd, J = 11.2, 6.4 Hz, H-6′a), 4.09 (dd, J = 11.2, 7.3 Hz, H-6′b), 2.17, 2.09, 2.08, 2.05, 2.04, 2.02, 1.96 (s, CH 3C=O); 13C NMR (150 MHz, CDCl3): δ 154.2 (C-1″), 116.5 (C-2″, C-6″), 128.8 (C-3″, C-5″), 138.9 (C-4″), 28.0 (C-1″′), 15.8 (C-2″′), 94.3 (C-1), 70.68 (C-2), 69.8 (C-3), 76.2 (C-4), 68.7 (C-5), 61.7 (C-6), 101.0 (C-1′), 69.1 (C-2′), 71.0 (C-3′), 66.6 (C-4′), 70.73 (C-5′), 60.9 (C-6′) 170.32, 170.30, 170.1, 170.0, 169.7, 169.6, 169.1 (C=O), 20.8, 20.7, 20.62, 20.58, 20.57, 20.4 (CH3C=O).

p-Ethylphenyl α-Lactoside (6)

HR-EI-MS m/z: 446.1790 [M]+, calculated for C20H30O11: 446.1788; [α]D +126.3 (MeOH, c 1.0 g/dl, 20.0°C); IR ν max [cm−1] (neat), 3,387, 1,610, 1,510, 1,373, 1,227, 1,070, 1,020; 1H NMR (600 MHz, MeOH-d4): δ 7.05 (d, J = 8.7 Hz, H-2″, H-6″), 7.11 (d, J = 8.8 Hz, H-3″, H-5″), 2.58 (q, J = 7.6 Hz, H-1″′), 1.19 (t, J = 7.6 Hz, H-2″′), 5.42 (d, J = 3.7 Hz, H-1), 3.62 (dd, J = 9.8, 3.7 Hz, H-2), 3.98 (dd, J =  9.7, 8.8 Hz, H-3), 3.67 (dd, J = 9.9, 8.7 Hz, H-4), 3.79 (t, J = 3.3 Hz, H-5), 3.87 (dd, J = 12.2, 3.6 Hz, H-6a), 3.74 (dd, J = 12.3, 3.5 Hz, H-6b), 4.38 (d, J = 7.7 Hz, H-1′), 3.56 (dd, J = 9.7, 7.7 Hz, H-2′), 3.49 (dd, J = 9.8, 3.3 Hz, H-3′), 3.82 (dd, J = 3.3, 0.7 Hz, H-4′), 3.60 (ddd, J = 7.5, 4.7, 0.9 Hz, H-5′), 3.80 (dd, J = 11.4, 7.5 Hz, H-6′a), 3.71 (dd, J = 11.5, 4.6 Hz, H-6′b); 13C NMR (150 MHz, MeOH-d4): δ 156.6 (C-1″), 118.1 (C-2″, C-6″), 129.7 (C-3″, C-5″), 139.6 (C-4″), 29.1 (C-1″′), 16.5 (C-2″′), 99.2 (C-1), 73.1 (C-2), 73.4 (C-3), 80.6 (C-4), 77.2 (C-5), 62.6 (C-6), 105.2 (C-1′), 72.7 (C-2′)1, 74.9 (C-3′), 70.4 (C-4′), 72.6 (C-5′)1, 61.6 (C-6′).

p-(1″-Hydroxyethyl)-Phenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Galactopyranoside (Mixture of Epimers 7)

HR-FAB-MS m/z: 491.1509 [M + Na]+, calculated for C22H28O11Na: 491.1529; IR ν max [cm−1] (neat), 3,481, 1,745, 1,608, 1,510, 1,371, 1,217, 1,066; 1H NMR (500 MHz, CDCl3): δ 7.04 (d, J = 8.6 Hz, H-2′, H-6′), 7.32 (d, J = 8.6 Hz, H-3′, H-5′), 4.87 (q, J = 6.4 Hz, H-1″), 1.48/1.47 (d, J = 6.5 Hz, H-2″)Footnote 2, 5.76 (d, J = 3.2 Hz, H-1), 5.28 (dd, J = 10.9, 3.6 Hz, H-2), 5.58 (dd, J = 10.9, 3.4 Hz, H-3), 5.53 (dd, J = 3.4, 1.0 Hz, H-4), 4.35 (t, J = 6.6 Hz, H-5), 4.12 (dd, J = 11.3, 6.3 Hz, H-6a), 4.07 (dd, J = 11.3, 6.6 Hz, H-6b)/4.07 (dd, J = 11.2, 6.6 Hz, H-6b)2, 2.17, 2.08, 2.03, 1.95 (s, CH 3CO); 13C NMR (50 MHz, CDCl3): δ 155.6 (C-1′), 116.7 (C-2′, C-6′), 126.7 (C-3′, C-5′), 140.5 (C-4′), 69.8/69.7 (C-1″)2, 25.18/25.16 (C-2″)2, 95.0 (C-1), 67.78 (C-2), 67.5 (C-3), 67.83 (C-4), 67.1 (C-5), 61.4 (C-6), 170.4, 170.3, 170.2, 170.0 (C=O), 20.7, 20.63, 20.59, 20.55 (CH3C=O).

p-(1″-Hydroxyethyl)-Phenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Glucopyranoside (Mixture of Epimers 8)

HR-FAB-MS m/z: 491.1509 [M + Na]+, calculated for C22H28O11Na: 491.1529; IR ν max [cm−1] (neat), 3,500, 1,751, 1,608, 1,508, 1,369, 1,219, 1,043; 1H NMR (500 MHz, CDCl3): δ 7.07 (d, J = 8.6 Hz, H-2′, H-6′), 7.32 (d, J = 8.6 Hz, H-3′, H-5′), 4.88 (q, J = 6.4 Hz, H-1″), 1.48/1.48 (d, J = 6.5 Hz, H-2″)Footnote 3, 5.73 (d, J = 3.8 Hz, H-1)/5.73 (d, J = 4.0 Hz, H-1)3, 5.04 (dd, J = 10.2, 3.7 Hz, H-2), 5.71 (t, J = 9.9 Hz, H-3), 5.16 (dd, J = 10.2, 9.5 Hz, H-4), 4.12 (ddd, J = 10.3, 4.4, 2.2 Hz, H-5), 4.25 (dd, J = 12.3, 4.5 Hz, H-6a), 4.05/4.04 (dd, J = 12.3, 1.9 Hz, H-6b)3, 2.06, 2.05, 2.04, 2.04 (s, CH 3CO); 13C NMR (125 MHz, CDCl3): δ 155.3 (C-1′), 116.5 (C-2′, C-6′), 126.7 (C-3′, C-5′), 140.6 (C-4′), 69.7/69.6 (C-1″)3, 25.2 (C-2″), 94.3 (C-1), 70.4 (C-2), 70.0 (C-3), 68.2 (C-4), 67.9 (C-5), 61.5 (C-6), 170.5, 170.14, 170.12, 169.6 (C=O), 20.7, 20.61, 20.57, 20.55 (CH3C=O).

p-(1″-Hydroxyethyl)-Phenyl α-d-Galactopyranoside (Mixture of Epimers 9)

HR-EI-MS m/z: 300.1210 [M]+, calculated for C14H20O7: 300.1209; 1H NMR (500 MHz, MeOH-d4): δ 7.12 (d, J = 8.5 Hz, H-2′, H-6′), 7.28 (d, J = 8.5 Hz, H-3′, H-5′), 4.77 (q, J = 6.5 Hz, H-1″), 1.40 (d, J = 6.5 Hz, H-2″), 5.47 (d, J = 3.0 Hz, H-1)/5.47 (d, J = 2.5 Hz, H-1)3, 3.96–3.93 (overlapping signals, H-2, H-3), 3.97 (dd, J = 2.5, 1.3 Hz, H-4), 3.92 (t, J = 6.3 Hz, H-5), 3.69 (dd, J = 11.3, 5.7 Hz, H-6a), 3.66/3.66 (dd, J = 11.4, 6.7 Hz, H-6b)3; 13C NMR (125 MHz, MeOH-d4): δ 157.9 (C-1′), 118.2 (C-2′, C-6′), 127.6 (C-3′, C-5′), 141.5 (C-4′), 70.44/70.40 (C-1″)3, 25.5 (C-2″), 99.8 (C-1), 70.0 (C-2)Footnote 4, 71.4 (C-3)4, 70.8 (C-4), 73.0 (C-5), 62.4 (C-6).

p-(1″-Hydroxyethyl)-Phenyl α-d-Glucopyranoside (Mixture of Epimers 10)

HR-EI-MS m/z: 300.1212 [M]+, calculated for C14H20O7: 300.1209; 1H NMR (500 MHz, MeOH-d4): δ 7.12 (d, J = 8.5 Hz, H-2′, H-6′), 7.28 (d, J = 8.6 Hz, H-3′, H-5′), 4.77 (q, J = 6.4 Hz, H-1″), 1.40 (d, J = 6.5 Hz, H-2″), 5.46 (d, J = 3.6 Hz, H-1), 3.56 (dd, J = 9.7, 3.7 Hz, H-2), 3.85 (t, J = 9.3 Hz, H-3), 3.43 (t, J = 9.3 Hz, H-4), 3.65 (ddd, J = 9.6, 4.6, 2.5 Hz, H-5), 3.72 (dd, J = 11.7, 2.1 Hz, H-6a), 3.68 (dd, J = 11.8, 4.6 Hz, H-6b); 13C NMR (125 MHz, MeOH-d4): δ 157.7 (C-1′), 118.0 (C-2′, C-6′), 127.7 (C-3′, C-5′), 141.5 (C-4′), 70.41/70.37 (C-1″)3, 25.5 (C-2″), 99.4 (C-1), 73.3 (C-2), 74.9 (C-3), 71.5 (C-4), 74.3 (C-5), 62.3 (C-6).

p-(1″-Acetoxyethyl)-Phenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Galactopyranoside (Mixture of Epimers 11)

HR-CI-MS m/z: 510.1757 [M]+, calculated for C24H30O12: 510.1737; 1H NMR (500 MHz, CDCl3): δ 7.04 (d, J = 8.5 Hz, H-2′, H-6′)/7.03 (d, J = 8.7 Hz, H-2′, H-6′)3, 7.30 (d, J = 8.5 Hz, H-3′, H-5′), 5.84/5.84 (q, J = 6.5 Hz, H-1″)3, 1.52/1.51 (d, J = 6.5 Hz, H-2″)3, 5.77/5.76 (d, J = 3.6 Hz, H-1)3, 5.28 (dd, J = 10.9, 3.7 Hz, H-2)/5.27 (dd, J = 11.0, 3.6 Hz, H-2)3, 5.57 (dd, J = 10.9, 3.5 Hz, H-3), 5.52 (d, J = 3.4 Hz, H-4), 4.33 (t, J = 6.8 Hz, H-5), 4.12 (dd, J = 11.2, 6.5 Hz, H-6a), 4.07 (dd, J = 11.2, 6.9 Hz, H-6b), 2.17, 2.06, 2.05, 2.05, 2.03 (s, CH 3CO); 13C NMR (50 MHz, CDCl3): δ 155.8 (C-1′), 116.6 (C-2′, C-6′), 127.6 (C-3′, C-5′), 136.3 (C-4′), 71.74/71.69 (C-1″)3, 22.0 (C-2″), 94.7 (C-1), 67.7 (C-2), 67.4 (C-3), 67.8 (C-4), 67.1 (C-5), 61.3 (C-6), 170.3, 170.2, 170.1, 170.0 (C=O), 21.3, 20.59, 20.55, 20.47 (CH3C=O).

p-(1″-Acetoxyethyl)-Phenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Glucopyranoside (Mixture of Epimers 12)

HR-CI-MS m/z: 510.1708 [M]+, calculated for C24H30O12: 510.1737; 1H NMR (500 MHz, CDCl3): δ 7.07/7.06 (d, J = 8.8 Hz, H-2′, H-6′)3, 7.30 (d, J = 8.8 Hz, H-3′, H-5′), 5.84/5.83 (q, J = 6.5 Hz, H-1″)3, 1.51 (d, J = 6.7 Hz, H-2″), 5.73/5.72 (d, J = 3.7 Hz, H-1)3, 5.04 (dd, J = 10.3, 3.6 Hz, H-2)/5.03 (dd, J = 10.2, 3.7 Hz, H-2)3, 5.70 (t, J = 9.9 Hz, H-3), 5.16 (dd, J = 10.1, 9.4 Hz, H-4)/5.15 (dd, J = 10.2, 9.5 Hz, H-4)3, 4.10 (ddd, J = 10.2, 4.3, 2.1 Hz, H-5), 4.25/4.24 (dd, J = 12.3, 4.3 Hz, H-6a)3, 4.05 (dd, J = 12.4, 2.0 Hz, H-6b), 2.17, 2.06, 2.04 (s, CH 3CO); 13C NMR (125 MHz, CDCl3): δ 155.7/155.6 (C-1′)3, 116.5 (C-2′, C-6′), 127.6 (C-3′, C-5′), 136.39/136.37 (C-4′)3, 71.8/71.7 (C-1″)3, 22.04/22.02 (C-2″)3, 94.20/94.15 (C-1)3, 70.4 (C-2), 70.0 (C-3), 68.3 (C-4), 68.0 (C-5), 61.5 (C-6), 170.5, 170.2, 170.11, 170.08, 169.5 (C=O), 21.3, 20.65, 20.58, 20.55 (CH3C=O).

p-Vinylphenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Galactopyranoside (13)

HR-EI-MS m/z: 450.1522 [M]+, calculated for C22H26O10: 450.1526; 1H NMR (500 MHz, CDCl3): δ 7.02 (d, J = 8.7 Hz, H-2′, H-6′), 7.35 (d, J = 8.7 Hz, H-3′, H-5′), 6.66 (dd, J = 17.8, 10.9 Hz, H-1″), 5.65 (dd, J = 17.6, 0.7 Hz, H-2″trans), 5.18 (dd, J = 10.9, 0.5 Hz, H-2″cis), 5.78 (d, J = 3.7 Hz, H-1), 5.29 (dd, J = 10.7, 3.7 Hz, H-2), 5.58 (dd, J = 10.8, 3.3 Hz, H-3), 5.53 (dd, J = 3.3, 1.0 Hz, H-4), 4.34 (td, J = 7.0, 0.9 Hz, H-5), 4.12 (dd, J = 11.3, 6.3 Hz, H-6a), 4.06 (dd, J = 11.3, 7.1 Hz, H-6b), 2.17, 2.08, 2.03, 1.94 (s, CH 3C=O); 13C NMR (125 MHz, CDCl3): δ 155.9 (C-1′), 116.8 (C-2′, C-6′), 127.4 (C-3′, C-5′), 132.7 (C-4′), 135.9 (C-1″), 112.9 (C-2″), 94.8 (C-1), 67.8 (C-2), 67.5 (C-3), 67.9 (C-4), 67.2 (C-5), 61.4 (C-6), 170.4, 170.3, 170.2, 170.0 (C=O), 20.7, 20.65, 20.61, 20.5 (CH3C=O).

p-Vinylphenyl 2,3,4,6-Tetra-O-Acetyl-α-d-Glucopyranoside (14)

HR-EI-MS m/z: 450.1534 [M]+, calculated for C22H26O10: 450.1526; 1H NMR (500 MHz, CDCl3): δ 7.05 (d, J = 8.7 Hz, H-2′, H-6′), 7.36 (d, J = 8.7 Hz, H-3′, H-5′), 6.66 (dd, J = 17.5, 10.9 Hz, H-1″), 5.65 (dd, J = 17.5, 0.7 Hz, H-2″trans), 5.19 (dd, J = 10.8, 0.7 Hz, H-2″cis), 5.74 (d, J = 3.7 Hz, H-1), 5.04 (dd, J = 10.3, 3.6 Hz, H-2), 5.70 (t, J = 9.9 Hz, H-3), 5.16 (t, J = 9.4 Hz, H-4), 4.11 (ddd, J = 10.3, 4.4, 2.2 Hz, H-5), 4.25 (dd, J = 12.3, 4.6 Hz, H-6a), 4.05 (dd, J = 12.3, 2.3 Hz, H-6b), 2.06, 2.05, 2.04, 2.04 (s, CH 3CO); 13C NMR (125 MHz, CDCl3): δ 155.7 (C-1′), 116.6 (C-2′, C-6′), 127.4 (C-3′, C-5′), 132.7 (C-4′), 135.8 (C-1″), 112.9 (C-2″), 94.2 (C-1), 70.4 (C-2), 70.0 (C-3), 68.3 (C-4), 68.0 (C-5), 61.6 (C-6), 170.5, 170.1, 169.6 (C=O), 20.7, 20.62, 20.60, 20.57 (CH3C=O).

p-Vinylphenyl α-d-Galactopyranoside (15)

HR-EI-MS m/z: 282.1097 [M]+, calculated for C14H18O6: 282.1103; [α]D +275.8 (MeOH, c 1.0 g/dl, 20.1°C); IR ν max [cm−1] (neat), 3,389, 1,629, 1,605, 1,508, 1,234, 1,082, 1,033; 1H NMR (500 MHz, MeOH-d4): δ 7.12 (d, J = 8.8 Hz, H-2′, H-6′), 7.35 (d, J = 8.8 Hz, H-3′, H-5′), 6.66 (dd, J = 17.7, 11.0 Hz, H-1″), 5.63 (dd, J = 17.5, 0.9 Hz, H-2″trans), 5.10 (dd, J = 11.0, 0.9 Hz, H-2″cis), 5.49 (d, J = 2.2 Hz, H-1), 3.89–3.84 (overlapping signals, H-2, H-3), 3.97 (dd, J = 1.8, 1.1 Hz, H-4), 3.91 (t, J = 6.3 Hz, H-5), 3.70 (dd, J = 11.4, 5.6 Hz, H-6a), 3.66 (dd, J = 11.4, 6.6 Hz, H-6b); 13C NMR (125MHz, MeOH-d4): δ 158.5 (C-1′), 118.3 (C-2′, C-6′), 128.3 (C-3′, C-5′), 133.4 (C-4′), 137.5 (C-1″), 112.4 (C-2″), 99.7 (C-1), 70.0 (C-2)Footnote 5, 71.4 (C-3)5, 70.8 (C-4), 73.1 (C-5), 62.4 (C-6).

p-Vinylphenyl α-d-Glucopyranoside (16)

HR-EI-MS m/z: 282.1102 [M]+, calculated for C14H18O6: 282.1103; 1H NMR (500 MHz, MeOH-d4): δ 7.11 (d, J = 8.8 Hz, H-2′, H-6′), 7.35 (d, J = 8.5 Hz, H-3′, H-5′), 6.66 (dd, J = 17.7, 11.0 Hz, H-1″), 5.64 (dd, J = 17.7, 0.8 Hz, H-2″trans), 5.11 (dd, J = 11.0, 0.7 Hz, H-2″cis), 5.47 (d, J = 3.6 Hz, H-1), 3.56 (dd, J = 9.7, 3.7 Hz, H-2), 3.84 (t, J = 9.3 Hz, H-3), 3.42 (t, J = 9.4 Hz, H-4), 3.64 (ddd, J = 9.8, 4.7, 2.5 Hz, H-5), 3.73 (dd, J = 11.9, 2.5 Hz, H-6a), 3.68 (dd, J = 11.9, 4.7 Hz, H-6b); 13C NMR (50 MHz, MeOH-d4): δ 158.3 (C-1′), 118.1 (C-2′, C-6′), 128.3 (C-3′, C-5′), 133.4 (C-4′), 137.5 (C-1″), 112.4 (C-2″), 99.2 (C-1), 73.3 (C-2), 74.9 (C-3), 71.5 (C-4), 74.4 (C-5), 62.3 (C-6).

p-Ethylphenyl 2,3,4,6-Tetra-O-Acetyl-β-d-GlucopyranosideFootnote 6 (17)

HR-EI-MS m/z: 452.1654 [M]+, calculated for C22H28O10: 452.1682; [α]D −22.2 (CHCl3, c 1.0 g/dl, 20.7°C); IR ν max [cm−1] (neat), 1,751, 1,608, 1,510, 1,367, 1,221, 1,047; 1H NMR (600 MHz, CDCl3): δ 6.92 (d, J = 8.7 Hz, H-2′, H-6′), 7.12 (d, J = 8.7 Hz, H-3′, H-5′), 2.60 (q, J = 7.6 Hz, H-1″), 1.21 (t, J = 7.6 Hz, H-2″), 5.05 (d, J = 7.6 Hz, H-1), 5.26 (dd, J = 9.2, 7.5 Hz, H-2), 5.29 (t, J = 9.2 Hz, H-3), 5.17 (t, J = 9.5 Hz, H-4), 3.85 (ddd, J = 10.0, 5.3, 2.5 Hz, H-5), 4.29 (dd, J = 12.3, 5.3 Hz, H-6a), 4.17 (dd, J = 12.3, 2.4 Hz, H-6b), 2.08, 2.06, 2.05, 2.04 (s, CH 3C=O); 13C NMR (150 MHz, CDCl3): δ 154.9 (C-1′), 116.9 (C-2′, C-6′), 128.7 (C-3′, C-5′), 139.2 (C-4′), 28.0 (C-1″), 15.7 (C-2″), 99.3 (C-1), 71.1 (C-2), 72.7 (C-3), 68.2 (C-4), 71.8 (C-5), 61.9 (C-6), 170.5, 170.2, 169.3, 169.2 (C=O), 20.61, 20.55, 20.53, 20.50 (CH3C=O).

p-Ethylphenyl β-d-Glucopyranoside (18)

HR-FAB-MS m/z: 307.1156 [M + Na]+, calculated for C14H20O6Na: 307.1158; [α]D −65.4 (MeOH, c 1.0 g/dl, 19.9°C); IR ν max [cm−1] (neat), 3,335, 1,611, 1,511, 1,233, 1,070; 1H NMR (500 MHz, D2O): δ 6.96 (d, J = 8.5 Hz, H-2′, H-6′), 7.14 (d, J = 8.5 Hz, H-3′, H-5′), 2.49 (q, J = 7.6 Hz, H-1″), 1.06 (t, J = 7.5 Hz, H-2″), 4.96 (d, J = 7.6 Hz, H-1), 3.43 (dd, J = 9.4, 7.6 Hz, H-2), 3.48 (t, J = 9.1 Hz, H-3), 3.36 (t, J = 9.3 Hz, H-4), 3.48 (ddd, J = 9.9, 5.7, 2.0 Hz, H-5), 3.80 (dd, J = 12.3, 1.8 Hz, H-6a), 3.62 (dd, J = 12.4, 5.7 Hz, H-6b); 13C NMR (50 MHz, MeOH-d4): δ 157.1 (C-1′), 117.7 (C-2′, C-6′), 129.6 (C-3′, C-5′), 139.4 (C-4′), 29.0 (C-1″), 16.4 (C-2″), 102.5 (C-1), 74.8 (C-2), 77.9 (C-3)5, 71.3 (C-4), 78.0 (C-5)5, 62.4 (C-6).

p-Ethylphenyl 2,3,6,2′,3′,4′,6′-Hepta-O-Acetyl-β-Lactoside (19)

HR-FAB-MS m/z: 763.2396 [M + Na]+, calculated for C34H44O18Na: 763.2425; [α]D −22.4 (CHCl3, c 1.0 g/dl, 22.4°C); IR ν max [cm−1] (neat), 3,028, 1,751, 1,608, 1,508, 1,369, 1,219, 1,057; 1H NMR (600 MHz, CDCl3): δ 6.89 (d, J = 8.6 Hz, H-2″, H-6″), 7.10 (d, J = 8.7 Hz, H-3″, H-5″), 2.60 (q, J = 7.6 Hz, H-1″′), 1.20 (t, J = 7.6 Hz, H-2″′), 5.01 (d, J = 7.8 Hz, H-1), 5.16 (dd, J = 9.3, 7.8 Hz, H-2), 5.27 (t, J = 9.1 Hz, H-3), 3.89 (t, J = 9.4 Hz, H-4), 3.77 (ddd, J = 9.9, 5.8, 2.2 Hz, H-5), 4.50 (dd, J = 12.3, 2.6 Hz, H-6a), 4.15 (dd, J = 12.0, 5.6 Hz, H-6b), 4.51 (d, J = 8.0 Hz, H-1′), 5.13 (dd, J = 10.4, 7.9 Hz, H-2′), 4.97 (dd, J = 10.4, 3.5 Hz, H-3′), 5.36 (dd, J = 3.4, 1.0 Hz, H-4′), 3.90 (t, J = 7.1 Hz, H-5′), 4.13 (dd, J = 11.0, 6.8 Hz, H-6′a), 4.10 (dd, J = 11.2, 7.3 Hz, H-6′b), 2.16, 2.09, 2.08, 2.07, 2.06, 1.97 (s, CH 3C=O); 13C NMR (150 MHz, CDCl3): δ 154.8 (C-1″), 116.8 (C-2″, C-6″), 128.7 (C-3″, C-5″), 139.2 (C-4″), 28.0 (C-1″′), 15.7 (C-2″′), 99.0 (C-1), 71.5 (C-2), 72.8 (C-3), 76.2 (C-4), 72.7 (C-5), 62.0 (C-6), 101.0 (C-1′), 69.0 (C-2′), 70.9 (C-3′), 66.6 (C-4′), 70.7 (C-5′), 60.8 (C-6′) 170.41, 170.38, 170.3, 170.2, 170.1, 169.6, 169.0 (C= O), 20.9, 20.8, 20.67, 20.65, 20.62, 20.59, 20.50 (CH3C=O).

p-Ethylphenyl β-Lactoside (20)

1H NMR (300 MHz, pyridin-d 5 ): δ 7.26 (d, J = 8.7 Hz, H-2″, H-6″), 7.43 (d, J = 8.7 Hz, H-3″, H-5″), 2.64 (q, J = 6.8 Hz, H-1″′), 1.26 (t, J = 6.8 Hz, H-2″′), 5.73 (d, J = 7.5 Hz, H-1), 4.81–4.20 (overlapping signals H-2, H-3, H-4, H-6a, H-6b, H-2′, H-3′, H-4′, H-5′, H-6′a, H-6′b), 4.24 (ddd, J = 9.3, 6.3, 2.7 Hz, H-5), 5.31 (d, J = 8.1 Hz, H-1′); 13C NMR (75 MHz, pyridin-d 5 ): δ 156.7 (C-1″), 117.1 (C-2″, C-6″), 129.2 (C-3″, C-5″), 138.0 (C-4″), 28.3 (C-1″′), 16.2 (C-2″′), 102.0 (C-1), 74.6 (C-2), 76.8 (C-3), 81.8 (C-4), 76.8 (C-5), 61.9 (C-6), 105.9 (C-1′), 70.2 (C-2′), 72.6 (C-3′), 77.4 (C-4′), 75.3 (C-5′), 62.1 (C-6′).

p-(1″-Hydroxyethyl)-Phenyl 2,3,4,6-Tetra-O-Acetyl-β-d-GlucopyranosideFootnote 7 (Mixture of Epimers 21)

HR-CI-MS m/z: 469.1716 [M + H]+, calculated for C22H29O11: 469.1710; 1H NMR (500 MHz, CDCl3): δ 6.97 (d, J = 8.6 Hz, H-2′, H-6′), 7.31 (d, J = 8.6 Hz, H-3′, H-5′), 4.88 (q, J = 5.8 Hz, H-1″), 1.48 (d, J = 6.5 Hz, H-2″), 5.07 (d, J = 7.6 Hz, H-1)/5.07 (d, J = 7.4 Hz, H-1)Footnote 8, 5.27 (t, J = 9.1 Hz, H-2), 5.30 (t, J = 9.0 Hz, H-3), 5.17 (t, J = 9.4 Hz, H-4), 3.86 (ddd, J = 9.9, 5.3, 2.3 Hz, H-5), 4.29 (dd, J = 12.3, 5.2 Hz, H-6a), 4.17 (dd, J = 12.3, 2.2 Hz, H-6b)/4.17 (dd, J = 12.2, 2.2 Hz, H-6b)8, 2.08, 2.06, 2.05, 2.04 (s, CH 3CO); 13C NMR (125 MHz, CDCl3): δ 156.2 (C-1′), 117.06/117.04 (C-2′, C-6′)8, 126.7 (C-3′, C-5′), 140.9 (C-4′), 69.9/69.8 (C-1″)8, 25.23/25.22 (C-2″)8, 99.2 (C-1), 71.2 (C-2), 72.7 (C-3), 68.3 (C-4), 72.1 (C-5), 62.0 (C-6), 170.5, 170.2, 169.4, 169.3 (C=O), 20.7, 20.64, 20.63, 20.60 (CH3C=O).

p-(1″-Hydroxyethyl)-Phenyl β-d-Glucopyranoside (Mixture of Epimers 22)

HR-EI-MS m/z: 300.1198 [M]+, calculated for C14H20O7: 300.1209; IR ν max [cm−1] (neat), 3,367, 1,610, 1,510, 1,230, 1,068; 1H NMR (500 MHz, D2O): δ 7.00 (d, J = 8.8 Hz, H-2′, H-6′), 7.26 (d, J = 8.8 Hz, H-3′, H-5′), 4.75 (q, J = 6.5 Hz, H-1″), 1.32 (d, J = 6.5 Hz, H-2″), 4.98 (d, J = 7.5 Hz, H-1), 3.43 (dd, J = 8.9, 7.5 Hz, H-2), 3.48 (t, J = 8.9 Hz, H-3), 3.36 (dd, J = 9.8, 8.9 Hz, H-4), 3.48 (ddd, J = 9.8, 5.5, 2.4 Hz, H-5), 3.79 (dd, J = 12.4, 2.1 Hz, H-6a), 3.62 (dd, J = 12.4, 5.7 Hz, H-6b); 13C NMR (125 MHz, D2O): δ 156.7 (C-1′), 117.5 (C-2′, C-6′), 128.0 (C-3′, C-5′), 140.6 (C-4′), 70.10/70.06 (C-1″)8, 24.3 (C-2″), 101.1 (C-1), 73.8 (C-2), 76.9 (C-3), 70.3 (C-4), 76.4 (C-5), 61.4 (C-6).

p-(1″-Acetoxyethyl)-Phenyl 2,3,4,6-Tetra-O-Acetyl-β-d-Glucopyranoside (Mixture of Epimers 23)

HR-EI-MS m/z: 510.1736 [M]+, calculated for C24H30O12: 510.1737; 1H NMR (500 MHz, CDCl3): δ 6.99 (d, J = 8.7 Hz, H-2′, H-6′), 7.31 (d, J = 8.6 Hz, H-3′, H-5′), 5.86 (q, J = 6.5 Hz, H-1″), 1.51 (d, J = 6.5 Hz, H-2″), 5.08/5.07 (d, J = 7.6 Hz, H-1)8, 5.29 (dd, J = 9.3, 7.5 Hz, H-2), 5.32 (t, J = 9.1 Hz, H-3), 5.19 (t, J = 9.5 Hz, H-4), 3.87 (ddd, J = 10.0, 5.3, 2.5 Hz, H-5), 4.31 (dd, J = 12.3, 5.3 Hz, H-6a), 4.18/4.17 (dd, J = 12.3, 2.3 Hz, H-6b)8, 2.08/2.088, 2.06, 2.05, 2.05, 2.04 (s, CH 3CO); 13C NMR (125 MHz, CDCl3): δ 156.4 (C-1′), 116.9 (C-2′, C-6′), 127.57/127.55 (C-3′, C-5′)8, 136.7 (C-4′), 71.8 (C-1″), 22.1/22.0 (C-2″)8, 99.0 (C-1), 71.1 (C-2), 72.7 (C-3), 68.3 (C-4), 72.0 (C-5), 61.9 (C-6), 170.6, 170.3, 170.2, 169.4, 169.3 (C=O), 21.3, 20.7, 20.62, 20.60, 20.58 (CH3C=O).

p-Vinylphenyl 2,3,4,6-Tetra-O-Acetyl-β-d-Glucopyranoside7 (24)

HR-EI-MS m/z: 450.1518 [M]+, calculated for C22H26O10: 450.1526; [α]D −20.8 (CHCl3, c 1.0 g/dl, 21.2°C); IR ν max [cm−1] (neat), 3,022, 1,755, 1,630, 1,606, 1,508, 1,367, 1,221, 1,047; 1H NMR (500 MHz, CDCl3): δ 6.95 (d, J = 8.7 Hz, H-2′, H-6′), 7.34 (d, J = 8.7 Hz, H-3′, H-5′), 6.66 (dd, J = 17.8, 10.9 Hz, H-1″), 5.65 (dd, J = 17.5, 0.7 Hz, H-2″trans), 5.19 (dd, J = 10.9, 0.7 Hz, H-2″cis), 5.08 (d, J = 7.5 Hz, H-1), 5.27 (dd, J = 9.1, 7.5 Hz, H-2), 5.30 (t, J = 9.0 Hz, H-3), 5.17 (t, J = 9.5 Hz, H-4), 3.86 (ddd, J = 10.0, 5.2, 2.5 Hz, H-5), 4.29 (dd, J = 12.3, 5.5 Hz, H-6a), 4.17 (dd, J = 12.3, 2.5 Hz, H-6b), 2.08, 2.06, 2.05, 2.04 (s, CH 3CO); 13C NMR (125 MHz, CDCl3): δ 156.4 (C-1′), 117.0 (C-2′, C-6′), 127.3 (C-3′, C-5′), 133.0 (C-4′), 135.8 (C-1″), 113.0 (C-2″), 99.1 (C-1), 71.1 (C-2), 72.7 (C-3), 68.3 (C-4), 72.0 (C-5), 61.9 (C-6), 170.5, 170.2, 169.3, 169.2 (C=O), 20.63, 20.58, 20.56, 20.54 (CH3C=O).

p-Vinylphenyl β-d-Glucopyranoside7 (25)

HR-EI-MS m/z: 282.1097 [M]+, calculated for C14H18O6: 282.1103; [α]D −81.5 (MeOH, c 1.0 g/dl, 21.0°C); IR ν max [cm−1] (neat), 3,318, 1,627, 1,606, 1,509, 1,245, 1,076, 1,046; 1H NMR (600 MHz, MeOH-d4): δ 7.04 (d, J = 8.5 Hz, H-2′, H-6′), 7.38 (d, J = 8.5 Hz, H-3′, H-5′), 6.66 (dd, J = 17.6, 10.9 Hz, H-1″), 5.64 (dd, J = 17.3, 0.9 Hz, H-2″trans), 5.11 (dd, J = 11.0, 0.9 Hz, H-2″cis), 4.90 (d, J = 7.6 Hz, H-1), 3.46–3.36 (overlapping signals, H-2, H-3, H-4, H-5), 3.89 (dd, J = 12.1, 2.0 Hz, H-6a), 3.68 (dd, J = 12.1, 5.6 Hz, H-6b); 13C NMR (150 MHz, MeOH-d4): δ 158.8 (C-1′), 117.7 (C-2′, C-6′), 128.3 (C-3′, C-5′), 133.5 (C-4′), 137.5 (C-1″), 112.4 (C-2″), 102.2 (C-1), 74.9 (C-2), 78.2 (C-3), 71.4 (C-4), 78.0 (C-5), 62.5 (C-6).

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Socolsky, C., Fascio, M.L., D’Accorso, N.B. et al. Effects of p-Vinylphenyl Glycosides and Other Related Compounds on the Oviposition Behavior of Ceratitis capitata . J Chem Ecol 34, 539–548 (2008). https://doi.org/10.1007/s10886-008-9440-4

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