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N-(18-Hydroxylinolenoyl)-l-Glutamine: A Newly Discovered Analog of Volicitin in Manduca sexta and its Elicitor Activity in Plants

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Abstract

Plants attacked by insect herbivores release a blend of volatile organic compounds (VOCs) that serve as chemical cues for host location by parasitic wasps, natural enemies of the herbivores. Volicitin, N-(17-hydroxylinolenoyl)-l-glutamine, is one of the most active VOC elicitors found in herbivore regurgitants. Our previous study revealed that hydroxylation on the 17th position of the linolenic acid moiety of N-linolenoyl-l-glutamine increases by more than three times the elicitor activity in corn plants. Here, we identified N-(18-hydroxylinolenoyl)-l-glutamine (18OH-volicitin) from larval gut contents of tobacco hornworm (THW), Manduca sexta. Eggplant and tobacco, two solanaceous host plants of THW larvae, and corn, a non-host plant, responded differently to this new elicitor. Eggplant and tobacco seedlings emitted twice the amount of VOCs when 18OH-volicitin was applied to damaged leaf surfaces compared to N-linolenoyl-l-glutamine, while both these fatty acid amino acid conjugates (FACs) elicited a similar response in corn seedlings. In both solanaceous plants, there was no significant difference in the elicitor activity of 17OH- and 18OH-volicitin. Interestingly, other lepidopteran species that have 17OH-type volicitin also attack solanaceous plants. These data suggest that plants have developed herbivory-detection systems customized to their herbivorous enemies.

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Acknowledgments

This study was partly supported by a Grant-in-aid for Scientific Research (nos. 23880014, 22380068 and 24120006) from the Ministry of Education, Culture, Sports, Science and Technology of Japan. NY was the recipient of Postdoctoral Fellowship for Research Abroad (no. 01212) from the Japan Society for the Promotion of Science for Young Scientists.

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Authors and Affiliations

  1. Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo, Kyoto, 606-8502, Japan

    Naoko Yoshinaga, Chihiro Ishikawa, Takako Aboshi & Naoki Mori

  2. Center for Chemical Ecology, Department of Entomology, Pennsylvania State University, University Park, PA, 16802, USA

    Irmgard Seidl-Adams & James H. Tumlinson

  3. Department of Agronomy, University of Wisconsin, Madison, WI, 53706, USA

    Elizabeth Bosak

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  1. Naoko Yoshinaga
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  2. Chihiro Ishikawa
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  3. Irmgard Seidl-Adams
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  4. Elizabeth Bosak
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  5. Takako Aboshi
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  6. James H. Tumlinson
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  7. Naoki Mori
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Correspondence to Naoko Yoshinaga.

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Supplemental Fig. 1

MS2 spectra of hydroxylinolenoyl-l-glutamine (OH-18:3-Gln) from Manduca sexta (A), Acherontia styx (B) and 17OH-volicitin from Spodoptera litura larval gut contents (C). Larval gut content of wild A. styx was prepared in the same way. (PPTX 106 kb)

Supplemental Fig. 2

GC/MS chromatogram of methyl acetoxylinolenate (M + 1-CH3COOH, m/z 291) derived from (A) 17OH-volicitin purified from Spodoptera litura larval gut contents, (B) 18OH-volicitin from Manduca sexta, and (C) synthesized 18OH-volicitin. (PPTX 71 kb)

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Yoshinaga, N., Ishikawa, C., Seidl-Adams, I. et al. N-(18-Hydroxylinolenoyl)-l-Glutamine: A Newly Discovered Analog of Volicitin in Manduca sexta and its Elicitor Activity in Plants. J Chem Ecol 40, 484–490 (2014). https://doi.org/10.1007/s10886-014-0436-y

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  • DOI: https://doi.org/10.1007/s10886-014-0436-y

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