Bioactive natural compounds obtained from arthropods

• Project/Area Number: 15580090
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Kyoto University
• Principal Investigator: MORI Naoki Kyoto University, Graduate School of Agriculture, Assistant Professor, 農学研究科, 助教授 (30293913)
• Project Period (FY): 2003 – 2005
• Project Status: Completed (Fiscal Year 2005)
• Budget Amount: ¥3,700,000 (Direct Cost: ¥3,700,000); Fiscal Year 2005: ¥800,000 (Direct Cost: ¥800,000); Fiscal Year 2004: ¥1,200,000 (Direct Cost: ¥1,200,000); Fiscal Year 2003: ¥1,700,000 (Direct Cost: ¥1,700,000)
• Keywords: volicitin / elicitor / induced resistance / pumiliotoxins / Dendrobatid alkaloids / atopic dermatitis / α-acaridial / house-dust mites / ヤケヒョウヒダニ

Research Abstract

1) Volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] is known as an insect-produced plant volatiles elicitor. In this study, the in vitro biosynthesis of volicitin was demonstrated for the first time by using gut tissues of Spodoptera litura larvae. The absolute configuration of the hydroxylinolenoyl moiety of volicitin was determined to 17-S in high enantiomeric excess in S.litura. Furthermore, N-linolenoyl-L-glutamine was only about 30% as active as volicitin. Among synthesized volicitin-related compounds, only glutamine conjugate induced the emission of volatile compounds from corn seedlings. On the other hand, we found uktraweak phton emissions from maize leaves damaged by Heilcovera armigera. Interestingly, the direct interaction between maize leaf cells and chemicals obtained from caterpillar regurgitants triggers the phton emissions.
2) Pumiliotoxins are very widely distributed in alkaloids-containing anurans from the neotropics. We demonstrated pumiliotoxin 237A, 251D and 8-deoxypumiliotoxin 193H from oribated mite extracts. It appears possible that some of the pumiliotoxins and related congeners found in extracts of various anurans have amite origin
3) Some particular substances obtained from mites, such as secretions from opisthonothal glands are suspected as one of antigens. We happened to find α-acaridial showed a positive reaction in patch tests for atopic dermatitis patients. In this study, we demonstrated that the female sex pheromone of Rhizoglyphus setosus (Astigmata : Acaridae) was identified as S-robinal, which is analogous to α-acaridial. Furthermore, we established the species-specific ITS sequence useful for the species identification of astigmatid mites and for studying low-level phylogenetic relationships.

Research Products

• [Journal Article] Ultraweak phton emission from herbivory-injured maize plants. (2006)
  • Author(s): Yoshinaga, N., Kato, K., Kageyama, C., Fujisaki, K., Nishida, R., Mori, N.
  • Journal Title: Naturwissenschaften 93 Pages: 38-41
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] A hemiterpene glucoside as a probing deterrent of the bean aphid, Megoura crassicauda, from a non-host vetch, Vicia hirsute. (2006)
  • Author(s): Ohta, N., Mori, N., Kuwahara, Y., Nishida, R.
  • Journal Title: Phytochemistry 67 Pages: 584-588
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Chemical ecology of astigamatid mites LXXXII. β-Acaridial as a female sex pheromone of the mold mite Tyrophagus putrescentiae(Acari : Acaridae). (2006)
  • Author(s): Maruno, G., Mori, N., Nishida, R., Kuwahara, Y.
  • Journal Title: Japanese Journal of Environmental Zoology 16 Pages: 167-173
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Ultraweak phton emission from herbivory-injured maize plants. (2006)
  • Author(s): Yoshinaga, N., Kato, K., Kageyama, C., Fujisaki, K., Nishida, R., Mori, N.
  • Journal Title: Naturwissen-schaften 93 Pages: 38-41
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] A hemiterpene glucoside as a probing deterrent of the bean aphid, Megoura crassicauda, from a non-host vetch Vicia hirsute (2006)
  • Author(s): Ohta, N., Mori, N., Kuwahara, Y., Nishida, R.
  • Journal Title: Phytochemistry 67 Pages: 584-588
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Chemical ecology of astigamatid mites LXXXII. β-Acaridial as a female sex pheromone of the mold mite Tyrophagus putrescentiae (Acari : Acaridae). (2006)
  • Author(s): Maruno, G., Mori, N., Nishida, R., Kuwahara, Y.
  • Journal Title: Japanese Journal of Environmental Zoology 616 Pages: 167-173
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Ultraweak photon emission from herbivory-injured maize plants. (2006)
  • Author(s): Yoshinaga, N., Kato, K., Kageyama, C., Fujisaki, K., Nishida, R., Mori, N.
  • Journal Title: Naturwissenschaften 93 Pages: 38-41
• [Journal Article] A hemiterpene glucoside as a probing deterent of the bean aphid, Megoura crassicauda, from a non-host vetch, Vicia hirsuta. (2006)
  • Author(s): Ohta, N., Mori, N., Kuwahara, Y., Nishida, R.
  • Journal Title: Phytochemistry 67 Pages: 584-588
• [Journal Article] In vitro biosynthesis of volicitin in Spodoptera litura. (2005)
  • Author(s): Yoshinaga, N., Morigaki, N., Mtauda, F., Nishida, R., Mori, N.
  • Journal Title: Insect Biochemistry and Molecular Biology 35 Pages: 175-184
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Identification of astigmatid mites using the second internal transcribed spacer (ITS2) region and its application for phyrogenetic study. (2005)
  • Author(s): Noge, K., Mori, N., Tanaka, C., Nishida, R., Tsuda, M., Kuwahara, Y.
  • Journal Title: Experimental and Applied Acarology 35 Pages: 29-46
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] S-Isorobinal as the female sex pheromone from an alarm pheromone-emitting mite, Rizoglyphus setosus. (2005)
  • Author(s): Mizoguchi, A., Murakami, K., Shimuzu, N., Mori, N., Nishida, R., Kuwahara, Y.
  • Journal Title: Experimental and Applied Acarology 36 Pages: 2405-2417
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Scheloribatid mites as the source of pumiliotoxins in dendrobatid frogs. (2005)
  • Author(s): Takada, W., Sakata, T., Shimano, S., Enami, Y., Mori, N., Nishida, R., Kuwahara, Y.
  • Journal Title: Journal of Chemical Ecology 31 Pages: 2405-2417
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Biosynthesis of neral in Carpoglyphus lactis (Acari : Carpoglyphidae) and detection of its key enzyme, geraniol dehydrogenase, by electrophoresis. (2005)
  • Author(s): Noge, K., Kato, M., Iguchi, T., Mori, N., Nishida, R., Kuwahara, Y.
  • Journal Title: Journal of the Acalorogical Society of Japan 14 Pages: 75-81
  • NAID: 10017093552
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] S-Isorobinal as the female sex pheromone from an alarm pheromone-emitting mite, Rizoglyphus setosus. (2005)
  • Author(s): Mizoguchi, A., Murakami, K., Shimizu, N., Mori, N., Nishida, R., Kuwahara Y.
  • Journal Title: Experimental and Applied Acarology 36 Pages: 107-117
• [Journal Article] Biosynthesis of neral in Carpoglyphus lactis (Acari : Carpoglyphidae) and detection of its key enzyme, geraniol dehydrogenase, by electrophoresis. (2005)
  • Author(s): Noge, K., Kato, M., Iguchi, T., Mori, N., Nishida, R., Kuwahara, Y.
  • Journal Title: Journal of Acarological Society of Japan 14 Pages: 75-81
  • NAID: 10017093552
• [Journal Article] In vitro biosynthesis of volicitin in Spodoptera litura (2005)
  • Author(s): N.Yoshinaga, N.Morigaki, F.Matsuda, R.Nishida, N.Mori
  • Journal Title: Insect Biochemistry and Molecular Biology 35 Pages: 175-184
• [Journal Article] Accumulation of HDMBOA-Glc is induced by biotic stresses prior to the release of MBOA in maze leaves (2004)
  • Author(s): A.Oikawa, A.Ishihara, C.Tanaka, N.Mori, M.TSuda, H.Iwamura
  • Journal Title: Phytochemistry 65 Pages: 2995-3001
• [Journal Article] Identification of α-acaridial as the female sex pheromone of Schwwiebea similis (Acari : Acaridae) (2004)
  • Author(s): K.Nishimura, N.Mori, K, Okabe, Y.Kuwahara
  • Journal Title: Jpan.J.Environ.Entomol.Zool. 15(2) Pages: 107-117
• [Journal Article] Neral as an alarm pheromone of the acarid mites, Oulenzia sp.(astigmata : Winterschmidtiidae) (2004)
  • Author(s): N.Shimizu, K.Noge, N.Mori, R.Nishida, Y.Kuwahara
  • Journal Title: J.Acarol.Soc.Jpn. 13(1) Pages: 57-64
• [Journal Article] Neral biosynthesis via the mevalonate pathway, evidenced by D-glucose-1-^<13>C feeding in Caloglypgus lactis and 13C Incorporation into other ophisthomotal gland exudates (2004)
  • Author(s): Morita, N.Mori, R.Nishida, N.Hirai, Y.Kuwahara
  • Journal Title: J.Pestic.Sci. 29 Pages: 27-32
• [Journal Article] Absolute configuration of volicitin from regurgitant of lepidopteran caterpillars and biological activity of volicitin-related compounds.
  • Author(s): Sawada, Y., Yoshinaga, N., Fujisaki, K., Nishida, R., Kuwahara, Y., Mori, N.
  • Journal Title: Bioscience, Biotechnology and Biochimistry (accepted)
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Absolute configuration of volicitin from regurgitant of lepidopteran caterpillars and biological activity of volicitin-related compounds.
  • Author(s): Sawada, Y., Yoshinaga, N., Fujisaki, K., Nishida, R., Kuwahara, Y., Mori, N.
  • Journal Title: Bioscience, Biotechnology and Biochimistry (accepted)
  • Description: 「研究成果報告書概要(欧文)」より