Identification of Volicitin-related Compounds from the Regurgitant of Lepidopteran Caterpillars

Mori, Naoki; Yoshinaga, Naoko; Sawada, Yoshitsugu; Fukui, Masato; Shimoda, Masami; Fujisaki, Kenji; Nishida, Ritsuo; Kuwahara, Yasumasa

doi:10.1271/bbb.67.1168

Cited by 51 publications

(51 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The absolute configuration of the hydroxylinolenic acid moiety of volicitin from the larvae of the three noctuid species, H. armigera, M. separata and S. litura, which are major agricultural pests in Japan, 7) was determined by HPLC. After methanolysis of volicitin purified from the larvae and conversion of the resulting ester with (R)-DBD-Pro-COCl, 14) the retention time of the natural volicitin derivative was compared with that of the (17S)-and (17R)-synthetic references (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Fatty acid-amino acid conjugates and related compounds 2,3) are also present in the oral secretions of other lepidopteran larvae. [4][5][6][7] Interestingly, recent studies have revealed that volicitin activated genes for the synthesis of terpenoids 8) and the nitrogen-containing metabolite indole in corn seedlings. 9) Fatty acid-amino acid conjugates in the oral secretions of two Manduca species elicited bursts in the production of jasmonic acid 5) and ethylene.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Absolute Configuration of Volicitin from the Regurgitant of Lepidopteran Caterpillars and Biological Activity of Volicitin-Related Compounds

Sawada

Yoshinaga

Fujisaki

et al. 2006

Bioscience, Biotechnology, and Biochemistry

Self Cite

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Absolute Configuration of Volicitin from the Regurgitant of Lepidopteran Caterpillars and Biological Activity of Volicitin-Related Compounds

Sawada

Yoshinaga

Fujisaki

et al. 2006

Bioscience, Biotechnology, and Biochemistry

Self Cite

View full text Add to dashboard Cite

“…In addition, the amounts of [ Fig. 5B) (Mori et al 2003;Yoshinaga et al 2010). Based on the composition of FACs in gut contents, synthetic purified Nlinolenoyl-L-glutamine and N-linoleoyl-L-glutamine were used to evaluate eliciting activity in soybeans.…”

Section: Quantification Of the Amounts Of [ 13 C 9 ]Flavonoids In Soymentioning

confidence: 99%

Inducible De Novo Biosynthesis of Isoflavonoids in Soybean Leaves by Spodoptera litura Derived Elicitors: Tracer Techniques Aided by High Resolution LCMS

et al. 2016

Self Cite

View full text Add to dashboard Cite

Isoflavonoids are a characteristic family of natural products in legumes known to mediate a range of plant-biotic interactions. For example, in soybean (Glycine max: Fabaceae) multiple isoflavones are induced and accumulate in leaves following attack by Spodoptera litura (Lepidoptera: Noctuidae) larvae. To quantitatively examine patterns of activated de novo biosynthesis, soybean (Var. Enrei) leaves were treated with a combination of plant defense elicitors present in S. litura gut content extracts and L-α-[ 13 C 9 , 15 N]phenylalanine as a traceable isoflavonoid precursor. Combined treatments promoted significant increases in 13 Clabeled isoflavone aglycones (daidzein, formononetin, and genistein), 13 C-labeled isoflavone 7-O-glucosides (daidzin, ononin, and genistin), and 13 C-labeled isoflavone 7-O-(6″-O-malonyl-β-glucosides) (malonyldaidzin, malonylononin, and malonylgenistin). In contrast levels of 13 C-labeled flavones and flavonol (4′,7-dihydroxyflavone, kaempferol, and apigenin) were not significantly altered. Curiously, application of fatty acid-amino acid conjugate (FAC) elicitors present in S. litura gut contents, namely N-linolenoyl-L-glutamine and N-linoleoyl-L-glutamine, both promoted the induced accumulation of isoflavone 7-O-glucosides and isoflavone 7-O-(6″-O-malonyl-β-glucosides), but not isoflavone aglycones in the leaves. These results demonstrate that at least two separate reactions are involved in elicitor-induced soybean leaf responses to the S. litura gut contents: one is the de novo biosynthesis of isoflavone conjugates induced by FACs, and the other is the hydrolysis of the isoflavone conjugates to yield isoflavone aglycones. Gut content extracts alone displayed no hydrolytic activity. The quantitative analysis of isoflavone de novo biosynthesis, with respect to both aglycones and conjugates, affords a useful bioassay system for the discovery of additional plant defense elicitor(s) in S. litura gut contents that specifically promote hydrolysis of isoflavone conjugates.

show abstract

“…Numerous studies have shown that this ingenious plant defense system is triggered by substances in the regurgitants of the herbivores. The best known of these plant volatile elicitors are the fatty acid amino acid conjugates (FACs) that first were identified from beet armyworm, Spodoptera exigua, larvae (3) but later also found in several other lepidopteran species (4)(5)(6)(7)(8) and other insects (9,10). Of the FACs, volicitin [N-(17-hydroxylinolenoyl)-L-glutamine], is the most active elicitor for seedlings of most cultivars of Zea mays (3,11,12).…”

mentioning

confidence: 99%

“…Of the other FACs often found in lepidopteran larvae, N-linolenoyl-Lglutamine is active in Z. mays and in several other species of plants on which it has been tested. FACs with negligible activity are glutamine conjugates with linoleic, oleic, and other minor fatty acids (6)(7)(8). Some lepidopteran species also contain glutamic acid conjugates, for example, tobacco hornworm Manduca sexta (11) and tomato hornworm M. quinquemaculata (13).…”

mentioning

confidence: 99%

Active role of fatty acid amino acid conjugates in nitrogen metabolism in Spodoptera litura larvae

Yoshinaga

Aboshi

Abe

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

View full text Add to dashboard Cite

Since the first fatty acid amino acid conjugate (FAC) was isolated from regurgitant of Spodoptera exigua larvae in 1997 [volicitin: N-(17-hydroxylinolenoyl)-L-glutamine], their role as elicitors of induced responses in plants has been well documented. However, studies of the biosyntheses and the physiological role of FACs in the insect have been minimal. By using 14 C-labeled glutamine, glutamic acid, and linolenic acid in feeding studies of Spodoptera litura larvae, combined with tissue analyses, we found glutamine in the midgut cells to be a major source for biosynthesis of FACs. Furthermore, 20% of the glutamine moiety of FACs was derived from glutamic acid and ammonia through enzymatic reaction of glutamine synthetase (GS). To determine whether FACs improve GS productivity, we studied nitrogen assimilation efficiency of S. litura larvae fed on artificial diets containing 15 NH4Cl and glutamic acid. When the diet was enriched with linolenic acid, the nitrogen assimilation efficiency improved from 40% to >60%. In the lumen, the biosynthesized FACs are hydrolyzed to fatty acids and glutamine, which are reabsorbed into tissues and hemolymph. These results strongly suggested that FACs play an active role in nitrogen assimilation in Lepidoptera larva and that glutamine containing FACs in the gut lumen may function as a form of storage of glutamine, a key compound of nitrogen metabolism.volicitin ͉ insect physiology ͉ plant defense ͉ glutamine ͉ insect-produced elicitors

show abstract

Identification of Volicitin-related Compounds from the Regurgitant of Lepidopteran Caterpillars

Cited by 51 publications

References 13 publications

Absolute Configuration of Volicitin from the Regurgitant of Lepidopteran Caterpillars and Biological Activity of Volicitin-Related Compounds

Absolute Configuration of Volicitin from the Regurgitant of Lepidopteran Caterpillars and Biological Activity of Volicitin-Related Compounds

Inducible De Novo Biosynthesis of Isoflavonoids in Soybean Leaves by Spodoptera litura Derived Elicitors: Tracer Techniques Aided by High Resolution LCMS

Active role of fatty acid amino acid conjugates in nitrogen metabolism in Spodoptera litura larvae

Contact Info

Product

Resources

About