Isoflavonoids as insect feeding deterrents and antifungal components from root ofLupinus angustifolius

Lane, Geoffrey A.; Sutherland, O. R. W.; Skipp, R. A.

doi:10.1007/bf01020159

Cited by 64 publications

(39 citation statements)

References 26 publications

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“…With the provision that these studies were conducted using an artificial cell culture system, the marked coordinated increases in medicarpin and afrormosin levels in response to MeJA suggest that these compounds might have dual defensive roles against both insects and fungi. Antifungal activity and insect-feeding deterrence were found to be closely associated for several isoflavonoids from L. angustifolius (Lane et al, 1987). Afrormosin has been shown to be toxic to soybean loopers (Pseudoplusia includens; Caballero et al, 1986), and a large pool of afrormosin glucosides likely acts as a preformed insect deterrent (Wittstock and Gershenzon, 2002).…”

Section: Functions For Induced Isoflavonoids In Medicagomentioning

confidence: 99%

Metabolomics Reveals Novel Pathways and Differential Mechanistic and Elicitor-Specific Responses in Phenylpropanoid and Isoflavonoid Biosynthesis in Medicago truncatula Cell Cultures

et al. 2007

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High-performance liquid chromatography coupled to ultraviolet photodiode array detection and ion-trap mass spectrometry was used to analyze the intra-and extracellular secondary product metabolome of Medicago truncatula cell suspension cultures responding to yeast elicitor (YE) or methyl jasmonate (MeJA). Data analysis revealed three phases of intracellular response to YE: a transient response in mainly (iso)flavonoid metabolites such as formononetin and biochanin-A that peaked at 12 to 18 h following elicitation and then declined; a sustained response through 48 h for compounds such as medicarpin and daidzin; and a lesser delayed and protracted response starting at 24 h postelicitation, e.g. genistein diglucoside. In contrast, most compounds excreted to the culture medium reached maximum levels at 6 to 12 h postelicitation and returned to basal levels by 24 h. The response to MeJA differed significantly from that to YE. Although both resulted in accumulation of the phytoalexin medicarpin, coordinated increases in isoflavonoid precursors were only observed for YE and not MeJA-treated cells. However, MeJA treatment resulted in a correlated decline in isoflavone glucosides, and did not induce the secretion of metabolites into the culture medium. Three novel methylated isoflavones, 7-hydroxy-6,4#-dimethoxyisoflavone (afrormosin), 6-hydroxy-7,4#-dimethoxyisoflavone (alfalone), and 5,7-dihydroxy-4#,6-dimethoxy isoflavone (irisolidone), were induced by YE, and labeling studies indicated that the first two were derived from formononetin. Our results highlight the metabolic flexibility within the isoflavonoid pathway, suggest new pathways for complex isoflavonoid metabolism, and indicate differential mechanisms for medicarpin biosynthesis depending on the nature of elicitation.

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Section: Functions For Induced Isoflavonoids In Medicagomentioning

confidence: 99%

Metabolomics Reveals Novel Pathways and Differential Mechanistic and Elicitor-Specific Responses in Phenylpropanoid and Isoflavonoid Biosynthesis in Medicago truncatula Cell Cultures

et al. 2007

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“…Some natural products, for example, isoflavonoids and triterpenes, show activity against both microbial and insect challengers of the plants that produce them (9)(10)(11). Root-derived cell suspension lines of the model legume Medicago truncatula studied previously accumulated the isoflavonoid-derived pterocarpan phytoalexin medicarpin in response to treatment with yeast elicitor (YE), and triterpene saponins after exposure to the wound signal methyl jasmonate (MJ) (12)(13)(14).…”

mentioning

confidence: 99%

Different mechanisms for phytoalexin induction by pathogen and wound signals in Medicago truncatula

Naoumkina

Farag

Sumner

et al. 2007

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

171

157

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Cell suspensions of the model legume Medicago truncatula accumulated the isoflavonoid phytoalexin medicarpin in response to yeast elicitor or methyl jasmonate (MJ), accompanied by decreased levels of isoflavone glycosides in MJ-treated cells. DNA microarray analysis revealed rapid, massive induction of early (iso)flavonoid pathway gene transcripts in response to yeast elicitor, but not MJ, and differential induction by the two elicitors of sets of genes encoding transcription factors, ABC transporters, and ␤-glucosidases. In contrast, both elicitors induced genes encoding enzymes for conversion of the isoflavone formononetin to medicarpin. Four MJ-induced ␤-glucosidases were expressed as recombinant enzymes in yeast, and three were active with isoflavone glucosides. The most highly induced ␤-glucosidase was nuclear localized and preferred flavones to isoflavones. The results indicate that the genetic and biochemical mechanisms underlying accumulation of medicarpin differ depending on the nature of the stimulus and suggest a role for MJ as a signal for rapid hydrolysis of preformed, conjugated intermediates for antimicrobial biosynthesis during wound responses.glucosidase ͉ methyl jasmonate ͉ phytoanticipin ͉ cell culture ͉ elicitation

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“…and Cladosporium cladosporioides (Fres.). 40 Isoflavonoids (judaicin, judaicin-7-O-glucoside, 2-methoxyjudaicin, and maackiain) isolated from the wild relatives of chickpea act as antifeedant against Helicoverpa armigera (Hubner) at 100 ppm. Judaicin and maackiain were also found to be deterrent to S. littoralis and S. frugiperda, respectively.…”

mentioning

confidence: 99%

Mechanisms of plant defense against insect herbivores

War

Paulraj

Ahmad

et al. 2012

Plant Signaling & Behavior

1,611

1,129

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Isoflavonoids as insect feeding deterrents and antifungal components from root ofLupinus angustifolius

Cited by 64 publications

References 26 publications

Metabolomics Reveals Novel Pathways and Differential Mechanistic and Elicitor-Specific Responses in Phenylpropanoid and Isoflavonoid Biosynthesis in Medicago truncatula Cell Cultures

Metabolomics Reveals Novel Pathways and Differential Mechanistic and Elicitor-Specific Responses in Phenylpropanoid and Isoflavonoid Biosynthesis in Medicago truncatula Cell Cultures

Different mechanisms for phytoalexin induction by pathogen and wound signals in Medicago truncatula

Mechanisms of plant defense against insect herbivores

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